Explore Cape Cod National Seashore, a protected stretch of Outer Cape coastline defined by Atlantic beaches, shifting dunes and lighthouses. At the Salt Pond Visitor Center, look across Salt Pond and Nauset Marsh and discover exhibits that deepen the coastal views.

Displays examine Wampanoag heritage, fishing, maritime travel and the lifesaving stations that once served this exposed shore. Together, the scenery and stories reveal how the Atlantic has shaped Cape Cod’s communities and livelihoods.

Sail from Hyannis to Nantucket and walk through the island’s historic downtown, where cobblestone streets and preserved houses recall its seafaring past. Learn how the whaling industry brought wealth to the island and how its decline reshaped local life.

The walk also considers the rise of tourism and the ways economic change affected Nantucket’s social and racial history. Explore the island beyond its postcard streets, connecting its carefully preserved architecture with the people and industries behind it.

• 4 Dinner (D)
• 7 Breakfast (B)

• Experience enhanced hygiene protocols to align with the latest guidance following COVID-19. All Travel Directors and Drivers have completed training in enhanced well-being and hygiene protocols.
• We only work with establishments we are confident will consistently adhere to our high well-being standards, which include hotels, restaurants and sight-seeing venues.
• Hand sanitizer is freely available on board for you to use throughout the day.

• Provincetown: At the tip of Cape Cod, Provincetown combines maritime history with one of America’s most distinctive arts communities. The Pilgrims first landed here in 1620 before continuing to Plymouth, while the Pilgrim Monument still marks that story today. Explore Commercial Street, where galleries, independent shops and cafes reflect a town long shaped by fishing, creativity, tourism and the sea today.
• Martha’s Vineyard: Discover Oak Bluffs, where Ocean Park faces a working harbor filled with ferries, fishing boats and sailboats. See the Flying Horses Carousel, the oldest continuously operating carousel in the U.S., with its original hand-carved horses, and explore streets lined with Victorian inns, independent shops and cafes that reveal the town’s long history as a summer resort.
• Explore the Martha’s Vineyard Camp Meeting Association with your Local Expert and discover more than 300 colorful Victorian cottages. What began in 1835 as a Methodist summer gathering of worshippers living in tents evolved into an extraordinary collection of Carpenter Gothic homes, known for their intricate ‘gingerbread’ woodwork, decorative porches and brightly painted facades surrounding the historic Tabernacle.
• Newport: Meet your captain and jump onboard the Madeline, a 72-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. 
• Newport: Enjoy a visit to one of Newport’s renowned landmarks, The Vanderbilt’s Breakers Mansion.

Insight Vacations

• Top-rated dining, from farm-to-table to local restaurants
• Deluxe coach travel
• 4 & 5-star stays

Walk Boston’s Freedom Trail with your Travel Director and trace the events that shaped American independence. See Boston Common, Granary Burying Ground and the Old State House, where landmarks of civic life and revolution stand within a compact historic district.

The Granary Burying Ground is the resting place of Samuel Adams and other revolutionary figures. At the Old State House, hear how the Boston Massacre of 1770 became a turning point in colonial resistance.

Meet your Travel Director and fellow travellers over dinner with wine in Boston. This hosted gathering offers a relaxed introduction to the people sharing your journey and a chance to ask questions about the places ahead.

Set in a city known for its historic neighbourhoods and lively dining scene, the evening brings everyone together around the table. Share a first taste of Boston’s hospitality while getting to know your travelling companions.

Step aboard Mayflower II in Plymouth, a full-scale reconstruction of the ship associated with the English settlers’ 1620 Atlantic crossing. Explore the vessel’s compact spaces and consider the conditions faced by those who travelled aboard the original Mayflower.

Built using historical research, the ship makes the scale of a 17th-century ocean voyage tangible. Its setting on the Plymouth waterfront also offers a place to reflect on the arrival’s lasting consequences for Indigenous communities and colonial New England.

Explore Pilgrim Hall Museum with a Mayflower descendant in Plymouth. View original 17th-century artefacts and possessions associated with the Mayflower passengers while hearing personal stories behind the early Plymouth Colony.

Founded in 1824, Pilgrim Hall is America’s oldest continuously operating public museum. The guided visit connects surviving objects with the people who used them, offering a more personal understanding of this chapter of colonial history. The experience supports education through the museum’s work.

Explore the recreated Wampanoag homesite and 17th-century English village at Plimoth Patuxet Museums in Plymouth. Walk among timber-framed houses and heritage crops, and observe traditional skills that illuminate daily life in the region.

The open-air exhibits present distinct Wampanoag and English perspectives rather than a single founding story. See details such as dugout canoes and period building techniques while learning about the communities connected to Patuxet, the Indigenous place on which Plymouth was established.

Explore Provincetown’s Commercial Street at the tip of Cape Cod, where galleries, independent shops and cafés reflect a long-established creative community. Take in the town’s working waterfront and the atmosphere of a place shaped by fishing and the sea.

The Pilgrims first landed at Provincetown in 1620 before continuing to Plymouth, a history commemorated by the Pilgrim Monument. Its maritime past and artistic identity sit side by side in this distinctive Outer Cape town.

Visit the Gingerbread Cottage Museum in Oak Bluffs and explore the Martha’s Vineyard Camp Meeting Association with a Local Expert. See colourful Carpenter Gothic cottages, decorative porches and intricate woodwork surrounding the historic Tabernacle.

The neighbourhood began as a Methodist summer camp in 1835, when worshippers stayed in tents; more than 300 Victorian cottages now express its evolution. Your visit reveals the origins of Oak Bluffs’ gingerbread architecture and the community traditions preserved within it.

Discover Martha’s Vineyard on an island orientation that takes in Oak Bluffs and coastal landmarks, including State Beach. See how harbour towns, beaches and longstanding summer communities give different parts of the island their character.

In Oak Bluffs, Victorian streets meet a working harbour of ferries, fishing boats and sailboats. State Beach offers a contrasting sweep of shoreline and is familiar to filmgoers from Jaws, which was filmed on Martha’s Vineyard.

Dine at Bettini, the signature restaurant of the historic Harbor View Hotel in Edgartown. Enjoy a seasonal meal shaped by locally caught seafood, produce from island farms and ingredients gathered by foragers.

Named for a family with longstanding Martha’s Vineyard maritime ties, Bettini places the island’s food traditions at the centre of the table. Taste the connection between land and sea through dishes that reflect the fishermen and growers supplying the kitchen.

Choose to visit the Newport Car Museum, where more than 100 vehicles trace developments in automotive design and performance. Explore a collection spanning the sculpted lines of mid-century Cadillacs and models such as the Ford GT, Porsche 911 and Corvette Stingray.

Housed in a repurposed missile plant, the museum presents cars as works of engineering and design. This is one of two included Insight Choice activities in Newport; travellers may choose it instead of Green Animals Topiary Garden.

Choose to explore Green Animals Topiary Garden at Brayton House in Newport. Wander seven coastal acres planted with more than 80 sculpted shrubs, including animal figures and geometric forms.

Established in 1872, it is America’s oldest topiary garden, shaped and maintained by generations of gardeners. The living collection offers a close look at horticultural craft on Rhode Island’s historic shoreline. This is one of two included Insight Choice activities; travellers may choose it instead of the Newport Car Museum.

Follow Newport’s Ten Mile Drive along the Rhode Island coast for views of the ocean, public parks and historic landmarks. The scenic route introduces the seaside setting that drew wealthy families to Newport as a summer resort.

Watch for the contrast between open shoreline and the grand estates associated with America’s Gilded Age. Take in Newport’s coastal landscape while gaining a sense of how its natural beauty became part of the city’s enduring appeal.

Visit The Breakers, the grandest of Newport’s celebrated summer cottages and a former residence of the Vanderbilt family. Explore the mansion’s lavish interiors for a close look at the scale and style of elite summer life during America’s Gilded Age.

Built in the 1890s for Cornelius Vanderbilt II, the house was designed to convey wealth through its architecture and decoration. Its oceanfront setting makes the contrast between private luxury and coastal grandeur especially striking.

Sail aboard the schooner Madeline through Newport Harbor and Narragansett Bay. From the water, look toward nearby islands, historic buildings and the shoreline homes associated with Newport’s wealthy summer residents.

Your captain brings the surrounding coast into focus with stories of the area’s maritime past, including its links to piracy. The schooner’s open-deck perspective offers a distinctive way to experience Newport’s harbour and seafaring heritage.

Gather for dinner at La Forge in Newport and share the experiences of your journey over a meal with wine. The restaurant overlooks the International Tennis Hall of Fame, placing the evening in the heart of the seaside city.

Newport’s harbour, historic estates and sporting traditions give this gathering a distinctive setting. Enjoy a freshly prepared seafood dinner and conversation with fellow travellers in a city whose coastal character has been a draw for generations.

Explore the dunes surrounding Provincetown on an optional excursion into the Outer Cape’s coastal landscape. The activity offers a closer view of the sand formations that help define this exposed stretch of Cape Cod.

Wind, tides and coastal vegetation continually reshape the dunes, creating a landscape distinct from Provincetown’s busy streets and waterfront. This experience is at additional cost and bookable on tour; the tour information does not specify the excursion’s route or mode of travel.