Itinerary
- Day 1
Boston
You'll arrive in Boston and check into the Hyatt Regency in downtown, which puts you right near Faneuil Hall and Newbury Street. The afternoon is yours to walk around the South End or take a stroll along the Charles River Esplanade. Later this evening, you'll meet your Travel Director and the rest of the group for a welcome dinner with wine.
- Meals
- Dinner (Dinner with wine at 18:00, join your Travel Director for an opportunity to mingle with fellow guests)
Optional Activities
- Leisurely stroll through the charming South End
- Walk along the picturesque Charles River Esplanade
- Explore historic Faneuil Hall
- Browse fashionable Newbury Street
Landmarks/POIs Faneuil Hall Newbury Street Charles River Esplanade South End - Day 2
Boston to Plymouth
This morning starts with a guided walk along Boston's Freedom Trail where you'll see Boston Common and the Old State House while learning about America's independence. From there, you'll head to Plymouth and board the Mayflower II, a full-scale replica of the historic ship. Lunch at Plimoth Patuxet features traditional English and indigenous dishes, then a guide takes you through the settlement. The day ends at Pilgrim Hall Museum with a special focus on women's roles in Plymouth's history.
- Meals
- Breakfast, Lunch (Taste of Two Cultures lunch at Plimoth Patuxet Museum featuring traditional English fare and indigenous dishes including turkey sauced two ways, Naussamp cornmeal, Native stewed squash, Cheate bread with butter, colonial carrot soup, and mint tea with blueberries)
Included Activities
- Guided walk along Boston's Freedom Trail - Boston Common, Granary Burying Ground, Old State House
- Board Mayflower II full-scale replica ship
- Taste of Two Cultures lunch at Plimoth Patuxet featuring traditional English fare and indigenous dishes
- Guided tour of Plimoth Patuxet settlement exploring daily lives of early settlers and Wampanoag people
- MAKE TRAVEL MATTER Experience at Pilgrim Hall Museum focusing on women's roles in Plymouth colony
Landmarks/POIs Boston Common Granary Burying Ground Old State House Mayflower II Plimoth Patuxet Museums Pilgrim Hall Museum - Day 3
Cape Cod
You'll spend the day at Cape Cod National Seashore exploring the region's history from Wampanoag lands through maritime traditions. There's an option to join a guided walk through the Peaked Hill Bars Historic District dunes with a local expert who can talk about the ecology and artists of the area. By evening, you'll settle into historic Sandwich with a relaxed night ahead.
- Meals
- Breakfast
Optional Activities
- Guided excursion through Peaked Hill Bars Historic District dunes with Local Expert
Landmarks/POIs Cape Cod National Seashore Peaked Hill Bars Historic District - Day 4
Cape Cod to Nantucket
You'll take a ferry ride from Hyannis to Nantucket on Hy-Line Cruises. Once there, a local expert from the Nantucket Historical Association leads a walking tour through downtown, sharing stories about women who shaped the whaling industry and island life. After lunch, you have free time to walk around Nantucket's streets at your own pace before heading back to Hyannis on the return ferry.
- Meals
- Breakfast, Lunch
Included Activities
- Ferry ride from Hyannis to Nantucket aboard Hy-Line Cruises
- Notable Nantucket Women guided walking tour with Local Expert from Nantucket Historical Association
Optional Activities
- Self-guided exploration of Nantucket's downtown streets
Landmarks/POIs Nantucket downtown - Day 5
Martha's Vineyard
A morning ferry takes you to Martha's Vineyard, known for its beaches and charming harbor towns. You'll check out Oak Bluffs with its famous gingerbread cottages, visit the Flying Horses Carousel, and see State Beach from the Jaws film. A guide shares the island's history from whaling to modern tourism and tells you about Edgartown Harbor Lighthouse. Dinner at Bettini restaurant in your hotel features seasonal offerings from local farms, fishing boats, and foragers.
- Meals
- Breakfast, Dinner (Locally sourced dinner in a private dining space at Bettini Restaurant featuring seasonal offerings from local farms, fishing boats and foragers)
Included Activities
- Ferry to Martha's Vineyard
- Explore Oak Bluffs and gingerbread cottages
- Visit Flying Horses Carousel
- See State Beach
- Learn about Edgartown Harbor Lighthouse history
Landmarks/POIs Oak Bluffs Flying Horses Carousel State Beach Edgartown Harbor Lighthouse - Day 6
Newport
You'll arrive in Newport and check into the historic Hotel Viking in the heart of the coastal city. In the afternoon, you choose between two options: the Newport Car Museum with over 100 vehicles from the 19th and 20th centuries, or Green Animals Topiary Garden with sculpted shrubs dating back to 1872. Later, take a leisurely stroll through Newport's streets as evening settles in.
- Meals
- Breakfast
Optional Activities
- Visit Newport Car Museum featuring over 100 vehicles highlighting design and performance milestones from the 19th and 20th centuries
- Explore Green Animals Topiary Garden at Brayton House, the oldest topiary garden in the United States with over 80 sculpted shrubs maintained since 1872
Landmarks/POIs Newport Car Museum Green Animals Topiary Garden Brayton House - Day 7
Newport
Your morning begins with Newport's Ten Mile Drive, a scenic coastal route with public parks, historic landmarks, and ocean views. Next, you'll tour the Breakers, the grandest of Newport's summer cottages and a display of Vanderbilt wealth from America's Gilded Age. Later, a sunset sail aboard the Adirondack II, an 80-foot schooner, takes you across Newport Harbor and Narragansett Bay.
- Meals
- Breakfast, Dinner (Seafood dinner with wine in the evening to share highlights of your trip with fellow travellers)
Included Activities
- Ten Mile Drive scenic coastal route
- Visit the Breakers mansion
- Sunset sail aboard Adirondack II schooner
Landmarks/POIs The Breakers Newport Harbor Narragansett Bay Ten Mile Drive - Day 8
Newport to Boston
Your tour ends today. You'll say goodbye to fellow travelers and head to Logan International Airport for your flight, carrying memories of Boston's historic character, Cape Cod's beauty, and Newport's elegance.
Landmarks/POIs Logan International Airport
