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Boston, Cape Cod and the Islands

8 Day Tour from Massachusetts to Rhode Island | Operated by InsightVacations

  • 8 Days

  • 1 Country

    United States
  • 6 Cities

    Boston, Sandwich, Cape Cod, Martha's Vineyard, Nantucket, Newport
  • 11 Meals

    4 Dinner with Wines, 7 Breakfasts
  • Pace: Comfortable

    Mainly 2–3-night stays in each location. Comfortable travel days with numerous stops. Requires 1-3 miles of walking per day that might involve some uneven surfaces, such as cobblestones and stairs.

Trip Itinerary

Day 1: Boston, the Cradle of Liberty

Welcome to Boston, described by many as the most European city in the U.S., you can expect a thriving art scene, delicious variety of seafood delicacies and plenty of charm. Arrive to the Hyatt Regency Boston, just steps from Boston's most desirable area-attractions such as the Boston Common, Faneuil Hall, and Boston's famous shopping destination, Newbury Street. A 10-to-15 minute walk will bring you to the South End, Back Bay or the Charles River Esplanade. At 18:00, join your Travel Director for a Welcome Dinner with wine and an opportunity to mingle with fellow guests.

Hotel: Hyatt Regency Boston
Included Meals: Dinner with Wine
Authentic Dining: Dinner in Boston At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
Notes
Day 2: Historic Boston

Explore the city with your Travel Director and learn about the city's transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Sights include Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhoods of Back Bay and historic North End, otherwise known as Boston’s Little Italy. Make sure you try the neighborhood's famous cannoli and grab yourself some of the best espresso in town. Later, choose to visit Fenway Park, America's oldest baseball stadium and home of the Boston Red Sox or tour The John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president. The rest of the day is free to pursue your own interests.

Hotel: Hyatt Regency Boston
Included Meals: Breakfast
Top Rated Highlights: Historic Boston Freedom Trail Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy. 
Insight Choice: Fenway Park Tour Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
Insight Choice: Visit the Museum of Fine Arts Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
Notes
Day 3: Pilgrim Heritage and on to Sandwich

This morning, discover Plymouth's history at the first pilgrim settlement. Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Join a MAKE TRAVEL MATTER® Experience as you visit the Plimoth Patuxet museum. This living memorial is dedicated to preserving the histories of the Native and English inhabitants of this region and educating the public on early settlers and the Wampanoag People in an immersive and engaging environment. Later you'll get to know the Cape more intimately as you make your way to the coastal haven of Sandwich. This afternoon, discover the art and science of glass making at Sandwich Glass Museum where you can watch glassblowers in action and explore exhibits spanning over three centuries. Enjoy a dinner back at your hotel later this evening featuring local favorites.

Hotel: Dan'l Webster Inn and Spa
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Visit the Pilgrim Hall Museum in Plymouth Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
Make Travel Matter: Plimoth Patuxet Museum Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.
Top Rated Highlights: Visit the Sandwich Glass Museum View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century. 
Notes
Day 4: Explore Cape Cod

Head out to Salt Pond on Cape Cod's National Seashore and learn about the natural wonder and human history represented on the Cape, from its First People and European settlement to modern lifestyles and communication technology. An optional experience on the Sand Dunes of the National Seashore may present itself later today. Roll through the Dune Shacks of Peaked Hill Bars Historic District, catching sight of Pilgrim Lake and the famed artists’ dune shacks while Local Experts share the history and ecology of these striking and inspiring dunes. 

Hotel: Dan'l Webster Inn and Spa
Included Meals: Breakfast
Top Rated Highlights: Cape Cod National Seashore Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
Notes
Day 5: Martha's Vineyard, a Presidential Paradise

Board a ferry this morning to Martha's Vineyard. Home to pristine sandy beaches, outdoor attractions and heavenly harbor towns, this summer hangout is no stranger to presidential visits. The island has hosted the Clintons and the Obamas, while the former U.S. First Lady, Jacqueline Kennedy Onassis, maintained a home here. After disembarking, make your way to Oak Bluffs, known for its rainbow-colored, gingerbread-like cottages with gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here. Get acquainted with the island, before reaching your hotel. Tonight's Sea-to-Table dinner is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.

Hotel: Harbor View Hotel
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Visit Oak Bluffs in Martha's Vineyard After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here. 
Authentic Dining: Dinner at Martha's Vineyard Tonight's Sea-to-Table dinner at Menemsha Room is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.
Notes
Day 6: Nantucket Island

Depart Martha's Vineyard in style on a high-speed catamaran for the picturesque island of Nantucket. Not only has it retained the charm of a bygone era, it is one of the most exclusive coastal communities in the U.S. During your visit, take in the beauty of the antique cobblestone streets, lined with high- end boutiques and breathtaking architecture during a guided walking tour. The simple homes date back to its whaling days which also influenced much of the culture on the island. In the past, the style of home directly correlated to a whaler's ranking. Return to the mainland in the evening to relax at your luxurious hotel.

Hotel: Hotel Viking Newport
Included Meals: Breakfast
Top Rated Highlights: Downtown Nantucket Walking Tour Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.
Notes
Day 7: Newport, the Queen of Summer Resorts

This morning, you'll enjoy a visit to The Breakers, a Gilded Age mansion and summer residence of Cornelius Vanderbilt II. The 70-room estate is the grandest of Newport's summer cottages. Today, it is a National Historic Landmark that serves as a symbol of the Vanderbilt family's social and financial pre-eminence in the Gilded Age. This afternoon, we sail around Newport Harbor aboard the Rum Runner II cruising by Newport mansions and former speakeasies, lighthouses, islands, and many other points of interest along the waterfront. Our journey through New England is almost at its end, but not before we join our fellow travelers for a Celebration Dinner at La Forge Casino Restaurant originally established in 1880.

Hotel: Hotel Viking Newport
Included Meals: Breakfast, Dinner with Wine
Insight Experiences: Visit Newport and Cruise Onboard the Adirondack II Jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity. 
Authentic Dining: Dinner in Newport Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
Insight Experiences: Breakers Mansion Visit Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
Notes
Day 8: Back to Boston

It's time to say goodbye to your fellow travelers as you return to Boston. For those heading home there will be complimentary transfers to Boston Logan International Airport, arriving at 12:00. Alternatively, you may return to the Hyatt Regency Boston if you wish to extend your stay.

Included Meals: Breakfast
Notes
This itinerary is for reference only. Upon booking with GET, guests will receive tour documents which will list all confirmed hotels and itineraries based upon the guest's departure date.

Price Includes

Dining Summary
  • - 4 Dinner with Wines (DW)
  • - 7 Breakfasts (B)
Authentic Dining
  • At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
  • Tonight's Sea-to-Table dinner at Menemsha Room is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.
  • Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
Top Rated Highlights
  • Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy. 
  • Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
  • View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century. 
  • Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
  • After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here. 
  • Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.
Insight Choice
  • Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
  • Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
Make Travel Matter
  • Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.
Insight Experiences
  • Jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity. 
  • Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.

Optional Experiences

Optional Experiences are subject to change. Your Travel Director will supply you with a final list of Optional Experiences available on your trip. Optional Experiences cannot be booked online; they can be purchased during your trip through your Travel Director.

Art's Sand Dune Tours (Available on Day 4)

Art’s Dune Tours provides an off-road tour experience to our family of visitors through the heart of the National Historic District of the Cape Cod National Seashore Park. Our knowledgeable tour guides will share the history and ecology of these beautiful and unique dunes that have inspired so many fine artists and writers.

Adult Price: $42 Child Price: $42