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

Program No. 21005RJ
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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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.

What You'll Learn

  • 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
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Debra Levin
Debra Levin is an honors graduate of Penn State and a former teacher. Debra has led groups of seniors, students, nurses, veterinarians, and retired fire chiefs to name but a few. Back home in Boston, she spends time volunteering with the symphony, theaters, and an art museum, when not speed walking and playing Wordle.

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

Profile Image of Debra Levin
Debra Levin View biography
Debra Levin is an honors graduate of Penn State and a former teacher. Debra has led groups of seniors, students, nurses, veterinarians, and retired fire chiefs to name but a few. Back home in Boston, she spends time volunteering with the symphony, theaters, and an art museum, when not speed walking and playing Wordle.
Profile Image of Gayle Felix
Gayle Felix View biography
Gayle Felix has been a Road Scholar group leader since 2015. She grew up and raised her family outside of Boston and now resides in Hingham, Massachusetts. With a history/American studies degree from Boston University, she enjoys sharing the history of Boston and surrounding areas. Gayle has led programs in New England; Washington, DC; and other areas in the United States. Gayle enjoys being with her family and friends, biking, kayaking, golfing, and hiking. She especially enjoys traveling and meeting new people.
Profile Image of George Schmidt
George Schmidt View biography
George Schmidt has been leading groups along the East Coast – from Williamsburg to Boston – for over 15 years. He now focuses on Boston, Plymouth, Cape Cod, Martha’s Vineyard, and Nantucket. He has had an eclectic career, spending time in industry, academia, and being self-employed. George has traveled to over 100 countries and all seven continents. He is active in his hometown of Mashpee, where he has served on the Finance and School Committees, both of which he has had the privilege of chairing.
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!”
Profile Image of Ellie Rose
Ellie Rose View biography
Ellie Rose was born in Scotland and raised in Canada and the U.S. She had the privilege of being able to travel globally and has always brought her children with her. She worked for over 40 years for the Commonwealth of Massachusetts. When she retired, she knew she wasn’t ready to really stop working. Her passion was traveling and working with people, which led her to her current career.
Profile Image of Teri Contino
Teri Contino View biography
Teri Contino has over two decades' experience leading groups in New England. She was born in Boston, raised in Woodstock, NY, and vacationed on Cape Cod for much of her life. She returned to Boston after receiving an undergraduate degree from Cornell University and now lives in Newburyport, MA. Teri has always loved teaching, learning, travel, history, culture, books, theater, birds, and the ocean. She currently splits her time between travel, stage managing community theater, working in the garden, and staying close to the water.
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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.
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8 days
7 nights
16 meals
7 B 4 L 5 D
Check-In, Orientation, Welcome Dinner
Boston, MA
Hilton Boston Logan Airport

Activity note: Hotel check-in from 3:00 p.m.

Afternoon: 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.

Ferry to MV, Walk to Tabernacle, Introduction to Oak Bluffs
Oak Bluffs, Martha's Vineyard
Dockside Inn

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.

Exploring Martha’s Vineyard, Historic Edgartown
Oak Bluffs, Martha's Vineyard
Dockside Inn

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.

Nature Preservation, Vineyard Haven
Oak Bluffs, Martha's Vineyard
Dockside Inn

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.

Historic Cape Cod, Sandwich Glass Museum
Hyannis, MA
Hyannis Harbor Hotel.

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 drive to Hyannis for a visit to the Cape Cod Maritime Museum. Finally, we will drive to the hotel for check in.

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.

Exploring Nantucket, Whaling Museum
Hyannis, MA
Hyannis Harbor Hotel.

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.

Exploring Scenic Cape Cod & the Arts, Provincetown
Hyannis, MA
Hyannis Harbor Hotel.

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.

Program Concludes
Hyannis, MA

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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