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Massachusetts

On the Road: Cape Cod, Martha's Vineyard and Nantucket

Program No. 2100560MEADV-0219
In some of New England’s most idyllic seaside towns, discuss whaling history, Victorian architecture, influential artists and unique ecology with naturalists and local experts.

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Prefer to enroll or inquire by phone? 800-454-5768
Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.

DATES & PRICES

1 Bed (king or queen)
Comfortable accommodations with either one queen or one king bed.
Jun 7 - Jun 14, 2025
1 Bed (king or queen) 3,299
Jun 14 - Jun 21, 2025
1 Bed (king or queen) 3,549
Jun 21 - Jun 28, 2025
1 Bed (king or queen) 3,749
Sep 6 - Sep 13, 2025
1 Bed (king or queen) 3,549
Sep 13 - Sep 20, 2025
1 Bed (king or queen) 3,549
Sep 20 - Sep 27, 2025
1 Bed (king or queen) 3,549
Sep 27 - Oct 4, 2025
1 Bed (king or queen) 3,549
Oct 4 - Oct 11, 2025
1 Bed (king or queen) 3,549
Oct 11 - Oct 18, 2025
1 Bed (king or queen) 3,299

DATES & PRICES

1 Bed (king or queen)
Comfortable accommodations with either one queen or one king bed.
Jun 7 - Jun 14, 2025
1 Bed (king or queen) 4,219
Jun 14 - Jun 21, 2025
1 Bed (king or queen) 4,659
Filling Fast!
Jun 21 - Jun 28, 2025
1 Bed (king or queen) 4,949
Sep 6 - Sep 13, 2025
1 Bed (king or queen) 4,579
Sep 13 - Sep 20, 2025
1 Bed (king or queen) 4,579
Filling Fast!
Sep 20 - Sep 27, 2025
1 Bed (king or queen) 4,579
Sep 27 - Oct 4, 2025
1 Bed (king or queen) 4,579
Filling Fast!
Oct 4 - Oct 11, 2025
1 Bed (king or queen) 4,579
Filling Fast!
Oct 11 - Oct 18, 2025
1 Bed (king or queen) 4,129
This date is available to book as a private experience for your group!

At a Glance

Examine history and culture past and present on an exploration of Cape Cod, Martha's Vineyard and Nantucket. Learn how fishing and whaling brought about economic development and explore the diversity of Martha's Vineyard with regard to its iconic island lifestyle and traditions. Contrast the history and island life of the Vineyard to those of the island of Nantucket and discover the arts and culture of Cape Cod, as well as the natural beauty that inspires so many.
Activity Level
Keep the Pace
Walking up to 2 miles per day; standing in museums. Some unavoidable stairs in historic sites. Getting on and off coach.
Small Group
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.

Best of all, you’ll…

  • Learn about the historic role played by the region’s whaling history on a day trip to Nantucket.
  • Live the island life on Martha's Vineyard while learning about its history, diversity and unique Victorian architecture.
  • With a naturalist, study the unique ecology of the sand dunes of Cape Cod National Seashore.

General Notes

Program includes independent time to explore the city and several meals on your own. Group Leaders will provide directions for self-directed excursions. Suggestions for free-time activities provided in preparatory materials. All rooms in the Martha Vineyard hotel have only one queen-sized bed; therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please see lodging description for more information.
Featured Expert
All trip experts
Profile Image
Carol Carson
Carol “Krill” Carson is a marine biologist who has worked in the New England area since 1980. She spends her summers watching whales and studying the Northern Diamondback Terrapin, a threatened species of marsh turtle. In the fall, Krill and her team rescue marine wildlife that strand on Cape Cod. Krill is the founder and president of the New England Coastal Wildlife Alliance (NECWA), and the author of the book “My Friend Salt: The story of Salt, the most famous humpback whale in the world!”

Please note: This expert may not be available for every date of this program.

Profile Image of Carol Carson
Carol Carson View biography
Carol “Krill” Carson is a marine biologist who has worked in the New England area since 1980. She spends her summers watching whales and studying the Northern Diamondback Terrapin, a threatened species of marsh turtle. In the fall, Krill and her team rescue marine wildlife that strand on Cape Cod. Krill is the founder and president of the New England Coastal Wildlife Alliance (NECWA), and the author of the book “My Friend Salt: The story of Salt, the most famous humpback whale in the world!”
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
Program
At a Glance
Duration
8 days
Program Begins
Boston, MA
Program Concludes
Hyannis, MA
Group Type
Small Group
Meals
16 | 7B | 4L | 5D |
Activity Level
Examine history and culture past and present on an exploration of Cape Cod, Martha's Vineyard and Nantucket. Learn how fishing and whaling brought about economic development and explore the diversity of Martha's Vineyard with regard to its iconic island lifestyle and traditions. Contrast the history and island life of the Vineyard to those of the island of Nantucket and discover the arts and culture of Cape Cod, as well as the natural beauty that inspires so many.)
Best of all, you'll...
  • Learn about the historic role played by the region’s whaling history on a day trip to Nantucket.
  • Live the island life on Martha's Vineyard while learning about its history, diversity and unique Victorian architecture.
  • With a naturalist, study the unique ecology of the sand dunes of Cape Cod National Seashore.
General Notes
Program includes independent time to explore the city and several meals on your own. Group Leaders will provide directions for self-directed excursions. Suggestions for free-time activities provided in preparatory materials. All rooms in the Martha Vineyard hotel have only one queen-sized bed; therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please see lodging description for more information.
Featured Expert
Profile Image
Carol Carson
Carol “Krill” Carson is a marine biologist who has worked in the New England area since 1980. She spends her summers watching whales and studying the Northern Diamondback Terrapin, a threatened species of marsh turtle. In the fall, Krill and her team rescue marine wildlife that strand on Cape Cod. Krill is the founder and president of the New England Coastal Wildlife Alliance (NECWA), and the author of the book “My Friend Salt: The story of Salt, the most famous humpback whale in the world!”
Please Note:
This expert may not be available for every date of the program
Activity Level
Keep the Pace
Walking up to 2 miles per day; standing in museums. Some unavoidable stairs in historic sites. Getting on and off coach.
Small Group (13 to 24)
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.
Suggested Reading List
View Full List (20 Books)
You can also find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
HAVE QUESTIONS?
Prefer to enroll or inquire by phone?
We can help. Give us a call, and we can answer all of your questions!
Call 800-454-5768
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
Duration
8 days
7 nights
What's Included
16 meals | 7B | 4L | 5D |
1 expert-led lecture
11 expert-led field trips
An experienced Group Leader
7 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
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Activity Note
Hotel check-in from 3:00 p.m.
Afternoon:
Program Registration. After you check in and have your room assignment, join us at the Road Scholar table to meet the Group Leader and confirm orientation time and place. Orientation. The Group Leader will greet everyone with a warm welcome and lead introductions. We will review the up-to-date program schedule and any changes, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer any questions you may have. Everyone will be responsible for their own luggage, with some assistance available. Transportation will be provided by a variety of vehicles including (but not limited to) ferries, private and taxi vans, motor coaches, and “safari” style trucks. Periods in the schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. On the Road programs are journeys that take participants to multiple study sites in a region with a number of overnight stays. Lectures, talks, discussions, field trips, and on-board commentary amplify the program theme. Some journeys involve great distances and may take hours, others are much shorter. Long or short, On the Road journeys are learning experiences that make the most of our time together.
Dinner:
At the hotel
Evening:
At leisure. Continue getting to know your fellow participants, settle in, and get a good night’s rest for the day ahead, including morning check out.
Activity Note
Climbing up and down stairs between ferry walk on level and passenger level. Walk with luggage from the ferry port to the hotel, about 1/3 of a mile on a flat, paved sidewalks. A taxi will carry luggage for any participants who have difficulty carrying their suitcase. Walk through the Camp Meeting Association grounds is up to 1 mile; standing for about 1 hour; flat pavement.
Breakfast:
At hotel
Morning:
After checking out of the hotel, we will board a motorcoach and drive to Woods Hole in the town of Falmouth, Massachusetts, on the far southwest corner of Cape Cod. There we will board the ferry to Oak Bluffs on Martha's Vineyard. The ferry crosses the 7 miles between the mainland and the island in approximately 45 minutes. The vessels of the Steamship Authority — a lifeline to the Islands — are functional with basic amenities.
Lunch:
On the ferry we’ll have boxed lunches.
Afternoon:
Arriving at the Oak Bluffs ferry terminal, as a group we will walk to our hotel before our field trip. The hotel will provide transport for our luggage. We’ll then be off on a walk with the Group Leader to the Oak Bluffs Camp Meeting Association and the historic Tabernacle at its center. Led by a resident docent, we’ll walk through the campground to learn about the “gingerbread” cottages and the residents who carefully maintain and decorate them. What we see today grew out of Methodist camp meetings that began in 1835.
Dinner:
Plated meal at a local restaurant.
Evening:
At leisure. You might like to set off on your own and walk back through the campground, relax on the green of one of Oak Bluffs many parks, or just watch boats in the marina set out to sea.
Activity Note
Getting in/out of vans; walking up to 1.5 mile; standing for about 1 hour.
Breakfast:
At a local restaurant.
Morning:
Accompanied by resident experts, we’ll set out in vans to explore the island of Martha’s Vineyard. Take in the scenic up-Island country-side, passing through the historic farming towns of West Tisbury and Chilmark. Catch glimpses of centuries old stone walls, views to the Atlantic shoreline, grazing livestock, rolling hills and historic homesteads in Chilmark and the picturesque secluded fishing village of Menemsha. Stop at the multi-colored clay cliffs at Aquinnah. We’ll end the morning in Edgartown. The remainder of the early afternoon is free for independent exploration.
Lunch:
On your own to enjoy what you like.
Afternoon:
We’ll regroup and stroll Edgartown’s narrow brick paths with a local to learn about the history and evolution of the town, from colonial settlement to busy whaling port.
Dinner:
This meal has been excluded from the program cost and is on your own to enjoy what you like.
Evening:
At leisure.
Activity Note
Walking up to 2 miles, standing up to 2 hours with breaks; Bring water bottle, hat, sunscreen. Field trips operate rain or shine except during thunderstorms and extreme wind conditions.
Breakfast:
At a local restaurant.
Morning:
Weather dependent, we'll transfer via taxi vans from Oak Bluffs to a local nature preservation. There, we'll take a guided tour of the nature preservation from a local expert. Learn about the ecosystems and how they are unique to Martha's Vineyard. After, we'll take taxi's to the busy harbor town of Vineyard Haven.
Lunch:
Plated meal at a local restaurant.
Afternoon:
After lunch we will depart on foot for the Martha's Vineyard Museum which houses a collection of exhibits related to the islands history. Back in Vineyard Haven there will be time for independent exploration to stroll through the old wharf, shipyard, historic district, art galleries, and quiet lanes.
Dinner:
On your own to enjoy what you like. You are welcome to remain in Vineyard Haven or return to Oak Bluff.
Evening:
At leisure.
Activity Note
Total walking distance for the day is up to 2 miles. Each person is responsible for his/her own luggage getting on and off the ferry; 45 minute ferry crossing; total drive distance is 40 miles.
Breakfast:
At a local restaurant.
Morning:
Say goodbye to Martha's Vineyard as we depart by taxi for the ferry terminal at Vineyard Haven. The ferry crosses back to Woods Hole on the mainland. Enjoy a scenic drive on the Cape from Woods Hole to our final destination of Hyannis, MA. Although just one of seven villages in the town of Barnstable, Hyannis is the hub of commercialization on Cape Cod and referred to by some as the "Capital of the Cape". En route we will stop to experience a few of the gems of Upper and Mid Cape Cod.
Lunch:
At a local seafood shack in Sandwich, MA, with many options available.
Afternoon:
Settled in 1637 and incorporated as a town just two years later, Sandwich boasts its status as the oldest town on Cape Cod. First, we will visit the Sandwich Glass Museum for a glass blowing demonstration and see how the museum has promoted a broad understanding and appreciation of Sandwich town history, with particular emphasis on the unique contribution of the glass industry to the local community. Afterwards, we will take a short walk to visit the Dexter Grist Mill and explore the grounds around Shawme Pond with commentary from a local expert. Thomas Dexter built the first grist mill on this site in 1654 so that the inhabitants of the village of Sandwich would not have to grind their own corn for cornmeal, their staple food. Finally, we will drive the rest of the way to Hyannis and check into the hotel.
Dinner:
Plated meal at a local restaurant.
Evening:
At the local restaurant, enjoy a lecture by a local expert on the history of Cape Cod.
Activity Note
The Ferry to Nantucket is located a few walkable blocks from the hotel. Activities on the island require walking up to 2 miles (about 1.5 hours).
Breakfast:
At hotel
Morning:
This morning we will head to the nearby terminal and board the ferry to Nantucket. Upon disembarking, meet a local expert from the Nantucket Historical Association for a narrated walk through the town center. See the architecture and hear the stories of the houses and the families that lived in them to illustrate the island’s history.
Lunch:
On your own to explore local fare in Nantucket.
Afternoon:
Enjoy a self-guided field trip to the Nantucket Whaling Museum. Housed in a restored 1847 candle factory, a 46-foot sperm whale skeleton floats suspended from the ceiling above many other attractions. Enjoy the views Nantucket harbor from the rooftop observation deck. Put the information you learned on the morning walk and at the Museum to use as you delve deeper into locales of your choosing. Take some time on your own to go “laning” (walking the lanes of the historic district of Nantucket) and explore independently before returning on the ferry to Hyannis.
Dinner:
At a local restaurant.
Evening:
At leisure. Take this opportunity to walk along Main Street Hyannis.
Activity Note
This is a full day of motorcoach exploration with frequent stops; one way distance 50 miles— 75-90 minutes drive time; 4-wheel driving on soft but bumpy sand dunes.
Breakfast:
At hotel
Morning:
Departing from the hotel via motorcoach we will have a full day exploration of Cape Cod, all the way to the tip of the cape in Provincetown. We will embark on an educational cruise with an expert naturalist to Monomoy Island, a barrier island that is home to thousands of seals, birds and other wildlife.
Lunch:
At a local restaurant.
Afternoon:
Next, we will go off-roading with local experts through the sand dunes of Cape Cod National Seashore in specially-authorized four-wheel-drive Jeeps. You will begin this adventure in Provincetown or “P-town,” as the locals call it. Sitting on the outermost part of the cape, P-town has some interesting history— Did you know that the Pilgrims, before settling in Plymouth, first landed in Provincetown? Today it has become known for its lively art scene that enhances the culture of the rest of Cape Cod, while highlighting the unique ambiance that is P-Town.
Dinner:
At a favorite local restaurant that highlights the unique atmosphere of Provincetown.
Evening:
Return to Hyannis and prepare for departure in the morning.
Activity Note
Transfer departs Hyannis at 8:30 a.m. to Boston Logan International Airport. Please do not schedule flights before 12:30 p.m. Hotel check-out time is 11:00 a.m.
Breakfast:
At hotel.
Morning:
This concludes our program. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!
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MEALS
16 Meals
7 Breakfasts
4 Lunches
5 Dinners
The following choices may be available when requested in advance: Vegetarian, Gluten Free, Low Fat, Low Salt
LODGING
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Showing Lodging For:
Oct 11, 2025 - Oct 18, 2025
  • Oct 11, 2025 - Oct 18, 2025
  • Jun 07, 2025 - Jun 14, 2025 (Boston, MA to Hyannis, MA)
  • Jun 14, 2025 - Jun 21, 2025 (Boston, MA to Hyannis, MA)
  • Jun 21, 2025 - Jun 28, 2025 (Boston, MA to Hyannis, MA)
  • Sep 06, 2025 - Sep 13, 2025 (Boston, MA to Hyannis, MA)
  • Sep 13, 2025 - Sep 20, 2025 (Boston, MA to Hyannis, MA)
  • Sep 20, 2025 - Sep 27, 2025 (Boston, MA to Hyannis, MA)
  • Sep 27, 2025 - Oct 04, 2025 (Boston, MA to Hyannis, MA)
  • Oct 04, 2025 - Oct 11, 2025 (Boston, MA to Hyannis, MA)
  • Oct 11, 2025 - Oct 18, 2025 (Boston, MA to Hyannis, MA)
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
1 night
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
3 nights
Location: Oak Bluffs
The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. Many of our guest rooms and suites feature commanding views of the Oak Bluffs Harbor, and the patio furniture on our porches that span the length of both the front and back of the building provide ample space to take in some sunshine, enjoy the sunset, or people-watch to your heart’s content. **Please note, there are no elevators at this hotel and guest rooms span throughout three floors. Participants must be able to walk up three flights of exterior stairs. We cannot guarantee requests for 2 beds in room at the Martha Vineyard Hotel, Dockside Inn. Almost all of the rooms have one queen-sized bed. There are very limited number of rooms with 2 beds (some two bedded rooms are 1 queen bed and 1 queen or twin sleeper sofa); therefore, we cannot offer roommate matching services on this program or guarantee 2 bed room requests. Please be prepared to share a bed with your roommate on this program.
3 nights
Location: Hyannis
The Hyannis Harbor Hotel is situated in the heart of the Hyannis waterfront, overlooking the Hy-Line Ferry Service to Nantucket and Martha’s Vineyard. Recently renovated, the hotel has a New England nautical theme.
Participant Reviews
4.72
Based on 30 Reviews
Sort By:
Charles – Class of 2014 | Atlanta, GA
This is another of the many excellent trips Road Scholar provides. This area was new to me and I felt we left with a very good understanding of the history, geography, and local flavor. Area vendors, residents were friendly and engaging. Much more "down to earth" than I imagined it to be - not just a sanctuary for the "rich and famous".
— Review left October 21, 2024
Richard – Class of 2021 | Hudson, OH
You WILL learn much on this Road Scholar trip. Many times I found myself saying, “I didn’t know that!”
— Review left October 14, 2024
Stephen – Class of 2017 | Park Ridge, IL
Great trip to an area I had not been before.
— Review left October 5, 2024
Michael – Class of 2013 | Silver Spring, MD
There was a lot to enjoy. I'd never been to Nantucket and was on Martha's Vineyard more than 40 years ago. Our program was near the end of the season, but most places were still open and crowds were less than high season. Don't overpack in case a hotel does not have an elevator.
— Review left October 3, 2024
Barry – Class of 2010 | Lincoln, CA
An excellent program--highly recommended!
— Review left October 2, 2024
Deborah – Class of 2015 | Langhorne, PA
Learned about a part of the USA we hadn't experienced.Presenters were all terrific and enjoyed sharing their knowledge The weather can have a big influence on some of the activities/programs and going off script can happen, so be prepared to be flexible. It was still a great experience and very glad we went.
— Review left September 26, 2024
Phyllis | Saratoga, CA
Road Scholars has a wonderful variety of trips and excursions.
— Review left September 24, 2024
Patricia – Class of 2024 | Johnson City, TX
I am so glad that I got to explore this area of the United States. It's been on my bucket list for a long time. Gayle Felix was an outstanding tour guide. Her knowledge of the area was vast and her organizational skills were amazing. I so appreciate her encouraging exploration on our own as I have to say that the pace of the trip (especially the first few days) was much slower than I prefer. This was my first Road Scholar trip so I can't make any comparisons in that regard. This is a great way to see this area.
— Review left September 17, 2024
Carol – Class of 2003 | Altamont, NY
Wonder if any of the others on our trip would have liked to see the Wampanoag Museum. It might enhance our understanding of the Native American experience of the past and the furred.
— Review left July 8, 2024
Barbara – Class of 2018 | Exeter, NH
I believe I left something off the evaluation. The evening with Krill Carson was wonderful! She was dynamic and gave the whale hunting character of the area a whole, new perspective. As humans continue to invade and spoil the animal habitats, the work she and others do becomes more and more important. Thank you for including the evening with Krill in our trip.
— Review left June 15, 2024
This participant did not give a star rating.
Angela – Class of 2022 | Supply, NC
Visiting Martha's Vineyard/Nantucket/Cape Cod was something I'd wanted to do for some time. All the educational portions were good but I would have liked a little more time in each venue. Overall I recommend this tour
— Review left June 10, 2024
Nancy – Class of 2007 | Cincinnati, OH
I highly recommend this program. The towns visited on Martha’s Vineyard, Cape Cod and Nantucket were all unique. The seal watch tour and sand dunes tour were really great. The accommodations and included meals were good. Several interesting museums were visited. Our tour director George Schmidt was one of the best I have encountered on Road Scholar trips. He arranged for several additional interesting stops due to his knowledge of the area.He kept the tour running smoothly. Definitely travel before Columbus Day as restaurants and shops start shutting down for the season then.
— Review left October 8, 2023
Laura – Class of 2014 | Springhill, TN
This was a great introduction to this part of the world. I loved this trip so much, I went on it twice!!
— Review left October 1, 2023
Wendy – Class of 2015 | Shaker Heights, OH
Fun and interesting trip. Cheryl is an outstanding group leader!
— Review left June 11, 2023
Mary – Class of 2011 | Topeka, KS
Very enjoyable trip. Our leader was very good. Met great people in the group
— Review left October 20, 2022
Alexandra – Class of 2017 | Seal Beach, CA
On the Road:Cape Cod, Martha's Vineyard and Nantucket was a fantastic tour and our tour guide George did a great job! I have never traveled to this area before and I enjoyed experiencing and learning about this beautiful area. It was great fun!
— Review left October 9, 2022
Kenneth – Class of 2000 | Whitesboro, NY
We saw a lot of Cape Cod that we never saw before.
— Review left September 22, 2022
Beverly – Class of 2014 | Rogersville, MO
This was a great way to visit three places that are not easy to get to. Enjoyed seeing all three and learning about the uniqueness of each of them. Gayle Felix is a superb group leader.
— Review left September 18, 2022
Karen – Class of 2019 | Largo, FL
This trip is a great value for visiting Cape Cod and Martha's Vineyard, with a visit of just a few hours on Nantucket and an hour or so of free time in Provincetown. It was a good immersion into the local culture and history. The pre- & post-busy-season tour dates made the weather comfortable & the locations we visited were not crowded.
— Review left June 23, 2022
Patrick – Class of 2018 | Pingree Grove, IL
George our guide for great. Even when problems arose he stepped upped, corrected the issue (many times with a sense of humor) and we were back on track as if nothing happen.
— Review left June 12, 2022
Cheryl – Class of 2016 | Honolulu, HI
This is a wonderful program, made all the more enjoyable because of our fabulous tour guide, Gayle. Highlights include strolling through charming small towns, climbing to the top of a historic lighthouse, gaining insights about President Kennedy, snapping photos of seals on a coastal cruise and savoring delicious seafood meals at restaurants local residents love. If you're a shopaholic, be aware a good number of stores close after Columbus Day.
— Review left October 20, 2021
Lois – Class of 2020 | Louisville, KY
This program gives you a perspective of life on Martha's Vineyard, Nantucket and Cape Cod. You will enjoy the splendor and individuality of this beautiful east coast living.
— Review left October 19, 2021
Stephen – Class of 2017 | Georgetown, TX
The program, led by Gayle, was informative, fun, and very educational. Our leader was outstanding. Fellow participants were fun and the people hired to enhance our experience were all terrific. I would recommend this program to anyone EXCEPT I would never take this program after Columbus Day.
— Review left October 17, 2021
Therese – Class of 2019 | Chicago, IL
Don't miss this trip! Road Scholar takes the work out of transporting you from place to place in the Cape Cod area! Such a breathtaking area of the country! Quaint small towns on the coast, island hopping by ferry, and an abundance of seafood! Loved all the tours, especially because of our lovely tour guide Gayle! As a native to the area she was able to provide us with an insider's perspective! Plan on being flexible during covid and with unpredictable weather! At the conclusion of the trip you will want to a "Washed Ashore". A non-native who decides to stay forever!
— Review left October 10, 2021
Linda – Class of 2013 | Odenton, MD
On the Road: Cape Cod, Martha’s Vineyard and Nantucket is a spectacular tour which provides knowledge and views I would never have known about. I can highly recommend this for an in-depth discovery of our founding fathers. You will see areas where the public is not always able to enjoy. The entire trip was enjoyable.
— Review left September 19, 2021
Roz – Class of 2004 | Bridgeville, PA
Well informed, engaging leader. Organized and well planned out program.
— Review left July 1, 2019
Rita – Class of 2012 | Pittsburgh, PA
Beautiful areas of the country and interesting history. Wonderful leader and fellow participants!
— Review left June 30, 2019
Sondra – Class of 2009 | Montrose, NY
I highly recommend this program for anyone who wants an in-depth experience of Cape Cod & the 'islands.' The area is beautiful, historic and varied. The program is so well planned that not a moment is wasted.
— Review left June 23, 2019
Phyllis – Class of 2019 | Miami, FL
Great itinerary and guide. This covered some wonderful places and each day was packed with enjoyable and interesting things to see.
— Review left June 23, 2019
Gerald – Class of 2017 | Tampa, FL
Always wanted to visit Cape Cod. Can’t imagine a better way to have done than with Road Scholar and Ruth Bennett
— Review left June 8, 2019





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