Boston, Cape Cod & The Islands - Small Group
Tour Type: Regional
Brochure Type USA Canada Small Group 2026 v1
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous ? and learn about the area's past as a pirates' haven.
Authentic Dining
Brochure Type USA Canada Small Group 2026 v1
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous ? and learn about the area's past as a pirates' haven.
Authentic Dining
- Martha's Vineyard Indulge in a locally sourced dinner in a private dining space in Bettini Restaurant.
- 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.
- Boston At 1800, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
- Boston 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 t
- Boston Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
- 4 Dinner with Wine (DW)
- 7 Breakfast (B)
- Boston Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
- Boston 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 t
- Newport 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
- Newport Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
- Plymouth 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 W
- Boston 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 signi
- 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
- Sandwich 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.
- Nantucket 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
- 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
- Cape Cod 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 C
Call (781) 545-4281 for more information or to book today! Mention code 18824891
- Tour Operator
- Insight Vacations
- Offer
- Offer valid through 12/30/2024
- Duration
- 8 Days
- Escorted
- Escorted - Yes
| Day | Destination | Description |
| Day 1 | Boston | 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. Accommodations: Hyatt Regency, Boston |
| Day 2 | Boston | Historic Boston: Explore the city 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. See Bunker Hill Monument, Boston Common, Boston Public Garden, Trinity Church and Copley Square. Later, choose to visit the John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president, or tour Boston's oldest and largest Museum of Fine Arts, which is home to over 500,000 works of art, making it one of the largest art collections in the Americas. The rest of the day is at leisure. Accommodations: Hyatt Regency, Boston |
| Day 3 | Sandwich | 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. Accommodations: Dan'l Webster Inn and Spa, Sandwich |
| Day 4 | Sandwich | 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. Accommodations: Dan'l Webster Inn and Spa, Sandwich |
| Day 5 | Martha's Vineyard | Martha's Vineyard, a Presidential Paradise: Board a ferry this morning to Martha's Vineyard (seasonal). 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 dinner is sure to delight with the season's freshest offerings from local farms, fishing boats, foragers and markets. Accommodations: Harbor View Hotel Martha's Vineyard |
| Day 6 | Nantucket | 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 homes date back to its whaling days which also in?uenced 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. Accommodations: Hotel Viking, Newport |
| Day 7 | Newport | Newport, the Queen of Summer Resorts Relaxed Start: 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, 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 you join your fellow travelers for a Celebration Dinner at La Forge Casino Restaurant originally established in 1880. Accommodations: Hotel Viking, Newport |
| Day 8 | Boston | Back to Boston Relaxed Start: 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. Accommodations: |
- Disclaimer
- Twin prices are per person.
- These prices are correct at the time of the website going live, however are subject to confirmation at the time of booking.
- All tour information is correct at time of tours going live, however is subject to change, please confirm all details at time of booking.
- For full terms and conditions, please refer to our Conditions page.
- Hotel Class Key: D: Deluxe SF: Superior First Class F: First Class
