Itinerary
- Day 1
Boston
You'll arrive in Boston and check into the Hyatt Regency downtown, which puts you right near Faneuil Hall and Newbury Street. The afternoon is yours to explore the South End or take a walk along the Charles River Esplanade if you prefer something quieter. Later this evening, you'll meet your Travel Director and the other guests for a welcome dinner with wine.
- Meals
- Dinner (Dinner with wine at 18:00, join your Travel Director for a welcome reception with fellow guests)
- Accommodation
- Hotel (Hyatt Regency, Boston)
Included Activities
- Dinner with wine and welcome reception with Travel Director and fellow guests
Optional Activities
- Stroll through the charming South End
- Walk along the Charles River Esplanade
- Visit Faneuil Hall
- Explore Newbury Street
Landmarks Faneuil Hall Newbury Street South End Charles River Esplanade 
- Day 2
Boston to Plymouth
Start following the Freedom Trail to see Boston Common, the Granary Burying Ground, and the Old State House. After that, you'll head to Plymouth to walk aboard the Mayflower II replica and check out the Pilgrim Hall Museum where someone from a Mayflower descendant family shares insights. The day wraps up at Plimoth Patuxet Museums where you can walk through recreated 1600s English village and Wampanoag homesite settings.
- Meals
- Breakfast
- Accommodation
- Hotel (Dan'l Webster Inn and Spa, Sandwich)
Included Activities
- Guided tour of Freedom Trail with Travel Director
- Visit Boston Common
- Visit Granary Burying Ground
- Visit Old State House
- Board the Mayflower II replica ship
- Guided visit to Pilgrim Hall Museum led by Mayflower descendant
- Walk through Plimoth Patuxet Museums - reconstructed 1600s English village and Wampanoag homesite
Landmarks Boston Common Granary Burying Ground Old State House Mayflower II Pilgrim Hall Museum Plimoth Patuxet Museums - Day 3
Cape Cod
You'll spend the day on Cape Cod exploring the maritime heritage and learning about the Wampanoag people, European settlement, fishing traditions, and the region's history. There are windswept shores, sand dunes, historic lighthouses, and fishing villages to see along Cape Cod's National Seashore.
- Meals
- Breakfast
- Accommodation
- Hotel (Dan'l Webster Inn and Spa, Sandwich)
Included Activities
- Explore Cape Cod's National Seashore with focus on cultural themes including Wampanoag history, European settlement culture, fishing and life-saving traditions, and communication technology
Landmarks Cape Cod National Seashore 
- Day 4
Hyannis to Nantucket
Board a ferry from Hyannis to Nantucket in the morning and walk the cobblestone streets past preserved historic homes from the island's whaling days. You'll learn how the whaling industry shaped the island's economy and society, then hear stories about seafaring adventures. The ferry back to Hyannis leaves in the evening.
- Meals
- Breakfast
- Accommodation
- Hotel (Dan'l Webster Inn and Spa, Sandwich)
Included Activities
- Ferry passage to Nantucket from Hyannis
- Walk through historic downtown Nantucket
- Explore Nantucket's whaling history and impacts on island economy, social and racial development
- Ferry return to Hyannis
Landmarks Nantucket - Day 5
Hyannis to Martha's Vineyard
Take the morning ferry to Martha's Vineyard and head to Oak Bluffs to see the iconic gingerbread cottages and the Flying Horses Carousel, the oldest operating platform carousel in America. You'll check out State Beach, which became famous from the film Jaws, and learn about Edgartown harbor lighthouse. Later, you'll have dinner at Bettini Restaurant, which sources ingredients locally.
- Meals
- Breakfast, Dinner (Indulge in a locally sourced dinner in a private dining space in Bettini Restaurant)
- Accommodation
- Hotel (Harbor View, Martha's Vineyard)
Included Activities
- Ferry passage to Martha's Vineyard from Hyannis
- Explore Oak Bluffs with Local Expert and visit Gingerbread Cottage Museum
- Visit the Flying Horses Carousel
- See State Beach
- Learn about Edgartown harbor lighthouse history
- Locally sourced dinner at Bettini Restaurant in private dining space
Landmarks Oak Bluffs Flying Horses Carousel State Beach Edgartown Harbor Lighthouse Bettini Restaurant - Day 6
Newport
You'll settle into the Hotel Viking in Newport and then have time to personalize your afternoon. Choose between the Newport Car Museum with over 100 vehicles on display or the Green Animals Topiary Garden at Brayton House, where sculpted shrubs have been shaped since 1872. This evening, take a casual stroll through Newport's streets.
- Meals
- Breakfast
- Accommodation
- Hotel (Viking, Newport)
Included Activities
- Choose between: Newport Car Museum (over 100 vehicles highlighting design and performance milestones) OR Green Animals Topiary Garden at Brayton House (oldest topiary garden in America with 80+ sculpted shrubs)
Optional Activities
- Leisurely stroll through Newport's vibrant streets
Landmarks Newport Car Museum Green Animals Topiary Garden Brayton House - Day 7
Newport
Your day starts with the Ten Mile Drive, a scenic coastal route through Newport with public parks and historic landmarks. Next, you'll tour the Breakers to see the Vanderbilt mansion and Gilded Age wealth on display. Then you'll board the Adirondack II schooner for a sail through Newport Harbor and Narragansett Bay, passing historic homes and learning about seafaring and pirate history. Dinner tonight is at La Forge overlooking the International Tennis Hall of Fame.
- Meals
- Breakfast, Dinner (Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savouring a freshly prepared meal)
- Accommodation
- Hotel (Viking, Newport)
Included Activities
- Drive the scenic Ten Mile Drive
- Visit the Breakers mansion
- Sail aboard the Adirondack II schooner through Newport Harbor and Narragansett Bay
- Seafood dinner with wine at La Forge overlooking International Tennis Hall of Fame
Landmarks Ten Mile Drive The Breakers Adirondack II Newport Harbor Narragansett Bay International Tennis Hall of Fame La Forge 
- Day 8
Newport to Boston
You'll say goodbye to your fellow travelers and transfer to Logan International Airport to head home. You're taking with you memories from Boston's historic sites, Cape Cod's coastal beauty, and Newport's elegant charm.
- Meals
- Breakfast
Included Activities
- Transfer to Logan International Airport
Landmarks Logan International Airport
