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.
06:15AM Boston Hotels
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Please provide and present your order/invoice number, voucher+photo IDupon check-in.
Pickup time may differ from voucher start time. Confirm with operator afterbooking. Check “Meeting & Pick-up” for details. Arrive 5–10 mins early.
Late passengers: 10-min grace period. JUPITER LEGEND and CTOURHOLIDAYS is not liable for delays or missed connections.
Smoking prohibited on buses, attractions & hotels (fines may apply-$250+).
No pets allowed.
Leaving the group: Inform the guide and sign a form. No refunds for unusedportions.
Parking: Not available at the meeting point. Guests must arrange owntransportation.
Itinerary and vehicle may be adjusted due to weather, traffic, or otherconditions.Passengers may be transferred to another vehicle if needed.
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Boston, one of the oldest cities in the United States, is rich in history, culture, and education. Known for its significant role in the American Revolution and its prestigious universities, Boston offers a unique blend of historic charm and modern vibrancy.
A 2.5-mile (4 km) walking route that passes 16 locations significant to the history of the United States, including churches, meeting houses, burying grounds, museums, and historic markers.
Home to the Boston Red Sox, Fenway Park is the oldest ballpark in Major League Baseball and a must-visit for sports fans and history buffs alike.
America's oldest public park, Boston Common is a central gathering place for both locals and visitors, offering green spaces, walking paths, and seasonal activities.
One of the most comprehensive art museums in the world, the MFA houses nearly 450,000 works of art, ranging from ancient Egyptian to contemporary.
A group of islands in Boston Harbor offering outdoor recreation, historic sites, and stunning views of the city skyline.
A creamy, hearty soup made with clams, potatoes, onions, and sometimes bacon or salt pork. Boston-style clam chowder is typically made with milk or cream and is served with oyster crackers.
A buttered, toasted split-top roll filled with lobster meat, usually dressed with mayo or butter. Some versions include celery or other vegetables for added crunch.
A layered dessert consisting of sponge cake filled with custard or cream and topped with chocolate glaze. It's the official dessert of the Commonwealth of Massachusetts.
Boston is known for its fresh oysters, which can be found at many seafood restaurants and raw bars. They are typically served on the half-shell with various toppings or sauces.
This is the best time to visit Boston for pleasant weather and outdoor activities. The city is vibrant with festivals and outdoor events.
US Dollar (USD)
Eastern Standard Time (EST) (UTC-5) or Eastern Daylight Time (EDT) (UTC-4) during daylight saving time
120VV, 60HzHz
Boston is generally a safe city for travelers, with a low crime rate and a strong police presence. However, as with any major city, it's important to be aware of your surroundings and take precautions to ensure a safe and enjoyable visit. Some areas of the city, such as certain neighborhoods in Dorchester, Roxbury, and Mattapan, have higher crime rates and should be avoided, especially at night.
South Station, North Station
South Station, Logan Airport
The MBTA subway system is efficient and affordable, with four main lines (Red, Blue, Green, and Orange) connecting major attractions and neighborhoods.
Available • Apps: Uber, Lyft
Car, Bike, Scooter
A historic coastal city known for its connection to the Salem Witch Trials of 1692. Salem offers a mix of historic sites, museums, and waterfront activities.
Two historic towns that played significant roles in the American Revolution. Lexington and Concord offer a mix of historic sites, museums, and scenic walking trails.
A popular summer destination known for its beautiful beaches, charming coastal towns, and outdoor recreation. Cape Cod offers a mix of relaxation and adventure.
Price varies by option