Leave Boston behind and set out on a full-day journey to Martha’s Vineyard, one of New England’s most beloved islands. This experience blends ocean walks, charming seaside towns, and authentic working harbors. Highlights include a full walk along the Marginal Way, time to explore Kennebunkport, lunch and free time in Portland’s historic Old Port, and a visit to Portland Head Light, one of the most photographed lighthouses in the country. With dramatic coastal views, fresh seafood options, and thoughtfully paced stops, this trip captures the essence of southern Maine in a single, effortless day!
Depart Boston and head toward Cape Cod, leaving the city behind as the landscape shifts to beaches, waterways, and coastal towns.
One of the most important man-made waterways in the world, the canal offers scenic views and marks the transition into classic Cape Cod territory.
A charming coastal town near Woods Hole, Falmouth sets the tone for island travel with harbor views and relaxed seaside energy.
Island Queen Ferry (35 Minutes): Board the ferry for a smooth crossing to Martha’s Vineyard, enjoying fresh sea air and open-water views as anticipation builds.
Cruise across the sound, a defining part of the Vineyard experience and a chance to appreciate the region’s maritime character.
Arrive in one of the island’s most vibrant towns, known for its harbor, beaches, and colorful Victorian architecture.
Walk among the iconic gingerbread cottages arranged around a historic tabernacle, a uniquely preserved community that defines Oak Bluffs’ identity.
Visit the nation’s oldest operating carousel, a nostalgic landmark that has delighted visitors for generations.
Explore this elegant harbor town featuring white clapboard homes, historic streets, and views of one of the island’s most picturesque ports.
Set atop colorful clay cliffs, this lighthouse offers dramatic views of the Atlantic and represents the island’s natural and cultural heritage.
A scenic stop near Woods Hole, this lighthouse overlooks Vineyard Sound and provides a final coastal highlight before departing the island area.
Return to the mainland area via Woods Hole, a key maritime hub connecting Cape Cod to the islands.
Relax on the drive back to Boston, wrapping up a day that blends island charm, ocean travel, and classic New England scenery.
For a full refund, cancel at least 24 hours before the scheduled departure time.
You can cancel up to 24 hours in advance of the experience for a full refund.
Your guide to the flawless travel experience