Travel with the Chamber: Cape Cod & The Islands

June 6–12, 2026 | 7 Days

Overview

Step into a classic New England escape featuring charming seaside towns, iconic history, and scenic coastal landscapes. From historic Boston to the picturesque islands of Martha’s Vineyard and Nantucket, this thoughtfully curated tour blends culture, history, and leisure at a relaxed pace.

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Tour Highlights

• Guided Boston city tour and historic landmarks
• Plimoth Patuxet Museums, Mayflower II, and Plymouth Rock
• Martha’s Vineyard and Nantucket Island excursions
• Cape Cod National Seashore and cranberry bog visit
• Newport, Rhode Island and The Breakers Mansion
• Farewell New England lobster dinner

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What’s Included

• Roundtrip airfare from FAT
• 6 nights first-class hotel accommodations
• 9 meals including breakfasts and dinners
• Professional Tour Director
• Motorcoach transportation and hotel transfers
• Admissions and sightseeing per itinerary

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Tour Details

• Activity Level: Easy to Moderate
• Pricing starts at $3,675 per person, double occupancy
• Single supplement applies

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Full Itinerary:

Day 1 – Arrive Boston

Today fly to the historic city of Boston. Upon arrival, meet your Tour Director and transfer to your Boston-area hotel for a one-night stay. Enjoy a Welcome Drink this evening.

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Day 2 – Boston City Tour – Plymouth – Cape Cod

This morning enjoy a Boston City Tour featuring Boston Common, the Old State House, the Old North Church from where Paul Revere got the signal to start his famous ride, the Old South Meeting House, Beacon Hill, and Old Ironsides.

Visit the Faneuil Hall Marketplace, located in downtown Boston near the waterfront and originally gifted to the city in 1742. Later, depart Boston and travel to Plymouth.

Visit Plimoth Plantation, an accurate recreation of the Pilgrims’ 1627 village where costumed interpreters portray colony residents in this living history museum. Then celebrate the journey that brought the Pilgrims to the New World as you visit the Mayflower II, the 1620 ship reproduction recently renovated for the 400th Anniversary of the voyage.

Also see famous Plymouth Rock, the place where the Pilgrims first stepped ashore after an 66-day trans-Atlantic voyage. Later arrive at your hotel on Cape Cod for a five-night stay. Enjoy a Welcome Dinner this evening with your fellow travelers.

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Day 3 – Martha’s Vineyard

This morning enjoy a scenic ferry ride to famous Martha’s Vineyard, where little has changed since European settlers arrived early in the 17th century. The island’s resident population includes writers, artists, entertainers, and fishermen.

Your Martha’s Vineyard Tour includes the colorful Victorian cottages of Oak Bluffs, Edgartown with its stately houses built by whaling captains, pristine beaches, and colorful yacht harbors. Later return via ferry and back to your hotel.

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Day 4 – Cape Cod National Seashore – Cranberries – Provincetown

This morning travel along the Cape Cod National Seashore, dedicated in 1961 by President JFK, which features forty miles of pristine sandy beaches, marshes, ponds, and uplands supporting diverse species of wildlife dotted with lighthouses, cultural landscapes, and wild cranberry bogs.

Visit a traditional cranberry bog and learn about the harvesting of Cape Cod’s famous fruit. Later arrive in Provincetown, located on the tip of Cape Cod, which boasts a lively artist community, beautiful beaches, great restaurants, and charming shops. Enjoy some leisure time to relax, eat, and shop.

Late afternoon return to your Cape Cod hotel. Dinner is included this evening at a popular local restaurant.

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Day 5 – Newport, Rhode Island

Today visit Newport, Rhode Island, one of New England’s most delightful coastal cities and a longtime favorite vacation site of affluent socialites and yachting enthusiasts.

Enjoy a Newport City Tour and drive by the Touro Synagogue, the oldest synagogue in America, the International Tennis Hall of Fame, and the splendid estates along Bellevue Avenue. Marvel at the extravagant life-style of a bygone era with a guided tour of The Breakers Mansion, the Vanderbilt’s lavishly decorated turn-of-the-century mansion.

Then follow the “Ten-Mile Drive” along the magnificent rocky coast which boasts exquisite estates from the early 1900s.

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Day 6 – Nantucket Island

This morning board a ferry and cruise to scenic and historic Nantucket Island featuring a cobblestoned Main Street, unspoiled beaches, sea captains’ houses, and art galleries.

Enjoy a visit to the Nantucket Whaling Museum, including its rooftop observation deck overlooking the harbor and other exhibits showcasing island reflections from a time when Nantucket was the whaling capital of the world.

Enjoy some time at your own pace to shop or explore the yacht-filled harbor and waterfront. This afternoon board a ferry and return to your Cape Cod hotel. Tonight’s Farewell Dinner is a traditional New England lobster dinner.

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Day 7 – Cape Cod – Boston – Flight Home

Today transfer to the Boston airport filled with wonderful memories of your Cape Cod & the Islands tour.

Land-only rates do not include hotel transfers. Roundtrip air package includes hotel transfers.