• 4 Dinner (D)
• 7 Breakfast (B)

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

• Boston: At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
• Martha’s Vineyard: Dine at Bettini, the signature restaurant of the historic Harbor View Hotel in Edgartown, where Martha’s Vineyard’s culinary traditions take centre stage. Savour locally caught seafood, seasonal produce and ingredients sourced from island fishermen and farmers. Named for the Bettini family, longtime island residents with strong maritime connections, the restaurant also reflects the Vineyard’s enduring relationship with the sea.
• Newport: 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.

• Newport: A striking destination for design lovers and motoring enthusiasts alike, this museum reimagines the automobile as a canvas for innovation. Housed in a repurposed missile plant, its collection features over 100 cars, from the sculpted lines of mid-century Cadillacs to performance icons like the Ford GT, Porsche 911 and Corvette Stingray. Each car is selected for its impact on design, engineering and culture. 
• Newport: Established in 1872, this is America’s oldest topiary garden, where horticultural craftsmanship meets imaginative design. Set on seven coastal acres, the collection includes more than 80 sculpted shrubs, from giraffes and elephants to intricate geometric forms. Maintained by generations of gardeners, it remains a living work of art on Rhode Island’s historic shoreline. 

• 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.

Explore America’s origin stories as you step aboard Mayflower II, a faithful replica of the 1620 vessel. Continue with a guided visit to Pilgrim Hall Museum, viewing original 17th-century possessions while hearing a Mayflower descendant illuminate the human narratives behind the voyage and settlement.

Walk through Plimoth Patuxet Museums to encounter a Wampanoag homesite and a recreated 17th-Century English Village. This MAKE TRAVEL MATTER experience supports Quality Education, deepening understanding of both Indigenous lifeways and colonial history through research-based interpretation.

Journey through the Cape Cod National Seashore, where beaches and wind-brushed dunes meet lighthouse-dotted horizons. At the Salt Pond Visitor Center, take in wide views across Nauset Marsh and explore exhibits on Wampanoag heritage, lifesaving stations, and the peninsula’s enduring relationship with the Atlantic.

Experience Provincetown, a harbor town renowned for its artistic spirit and maritime grit. Stroll Commercial Street, note the hilltop Pilgrim Monument, and feel the creative energy that has drawn writers, painters, and performers to the Cape’s far tip.

Sail by ferry to Nantucket, approaching sandy spits and a snug harbor lined with cedar-shingled wharves. On foot, follow cobbles past cobblestone streets, picket fences, and weathered captains’ homes that speak to the island’s 19th-century maritime wealth.

Hear how Quaker roots and the rise—and decline—of the whaling industry shaped community life, architecture, and global connections. Today’s boutiques, galleries, and cafés occupy buildings once tied to far-flung voyages, preserving character while embracing a quieter coastal rhythm.

Discover Oak Bluffs with a Local Specialist and explore the Martha’s Vineyard Camp Meeting Association, a neighborhood of whimsical gingerbread cottages clustered around the iron-and-wood Tabernacle. Hear how an 1830s Methodist retreat evolved into a colorful village celebrated for its Carpenter Gothic craft.

Gain a wider perspective on an orientation drive that traces beaches and harbors, including film-famous State Beach. Coastline vistas, lighthouses, and story-rich towns reveal an island shaped by seafaring traditions, summer culture, and tight-knit year-round communities.

Gather in the heart of the city to meet your Tour Director and fellow travelers over a convivial welcome dinner with wine. Share first impressions of Boston as you settle into an elegant evening that sets a relaxed, sociable tone for the journey.

Learn helpful tips for navigating New England’s coastal towns and historic districts while sampling regional flavors. This hosted welcome is designed to connect the group and frame the days ahead with insight and ease.

Savor a sea-to-table dinner at Bettini, the signature restaurant of the storied Harbor View Hotel in Edgartown. Seasonal menus spotlight island fishermen’s catch, heirloom produce, and ingredients gathered by local foragers, paired with thoughtful wine selections.

Dine in refined coastal style with harbor and lighthouse vistas that celebrate island hospitality. The setting, cuisine, and conversation capture the Vineyard’s enduring connection to the sea and its farms.

Follow the famed Ten Mile Drive past rugged headlands, surf-swept coves, and lawns that meet the Atlantic coastline. This panoramic route threads through Ocean Drive and Bellevue Avenue, revealing parks, promenades, and cliff-top viewpoints.

Admire Gilded Age mansions built as summer stages for America’s industrial titans, and hear how Newport earned its title as the Queen of Summer Resorts. Sea air, stone walls, and sail-filled bays frame a classic New England seascape.

Step inside The Breakers, the Vanderbilt family’s most spectacular “summer cottage,” and encounter Gilded Age opulence at palatial scale. Marble, mosaics, and gilding adorn the Great Hall, while ocean-facing terraces open to salt-tinged breezes.

Designed by Richard Morris Hunt in an Italian Renaissance style, The Breakers fuses art, technology, and social history. Explore rooms that reveal the rhythms of seasonal entertaining and the staff’s behind-the-scenes mastery that made such grandeur possible.

Catch the wind and sail aboard the schooner Madeline, a classic 72-foot wooden vessel gliding through Newport Harbor and Narragansett Bay. Watch lighthouses, yacht clubs, and fortifications slip by as gulls wheel over sunlit swells.

Crew narratives evoke Newport’s privateers, regattas, and pirates’ haven lore. Canvas creaks, rigging hums, and sea breezes frame a maritime perspective on the mansions and headlands that define this storied coastline.

Visit the Newport Car Museum, where a repurposed missile plant stages automotive icons as sculpture and speed. Galleries showcase design and performance milestones—from mid-century Cadillacs to Ford GTs, Porsche 911s, and Corvette Stingrays.

Curated stories connect engineering breakthroughs with culture, film, and fashion. This is an included choice experience in Newport—select it if your passions lean toward sleek lines, V-8 burble, and the craft of motion.

Explore Green Animals Topiary Garden, the oldest topiary garden in the United States, where hedges become living sculpture. Across seven coastal acres, spot giraffes, elephants, and intricate geometric forms, all shaped by generations of dedicated gardeners.

Historic pathways and bay views frame horticultural whimsy and precision in equal measure. This is an included choice experience in Newport—perfect for design lovers, photographers, and anyone drawn to artistry in nature.

Join a guided dune tour across the Province Lands, where shifting sands, beach grass, and ocean light frame the simple historic dune shacks once favored by writers and painters. Learn how wind and tide continually sculpt this protected landscape.

Natural-history insights and art-colony lore bring the Outer Cape to life as you rumble over sandy tracks. This is an additional cost experience, bookable on tour, ideal for photographers and nature enthusiasts.

Walk the red-brick path of the guided walking tour along Boston’s storied Freedom Trail. Trace the nation’s early steps toward liberty as you pass Boston Common, the tree-shaded Granary Burying Ground, and the Old State House, where the Boston Massacre ignited revolutionary fervor.

Hear how patriots, printers, and protesters shaped a port town into a cradle of independence. Brick townhouses, steeples, and the city’s modern skyline frame poignant sites that connect colonial-era drama with today’s vibrant downtown.

Insight Vacations