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Travel AI

Ultimate 5-Day Martha's Vineyard Itinerary Itinerary

Last updated: 2024 Jun 14

Exploring Oak Bluffs

Morning

Start your Martha's Vineyard adventure with a delightful breakfast at Little House Cafe. Afterward, embark on the Oak Bluffs Martha's Vineyard GPS Smartphone Audio Tour to learn about the history and culture of this charming town while visiting iconic landmarks like the Flying Horses Carousel and the Gingerbread Cottages.

Afternoon

For lunch, savor the fresh catch of the day at Larsen's Fish Market. Follow it up with a fun-filled Oak Bluffs Martha's Vineyard Scavenger Hunt Experience, exploring hidden gems and enjoying the scenic views of the harbor.

Evening

As the sun sets, dine at the elegant The Red Cat Kitchen at Ken N' Beck, known for its innovative cuisine. Conclude your day with a leisurely stroll along the Oak Bluffs waterfront, taking in the sea breeze and the sound of the waves.

Bedtime

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Edgartown's History and Culinary Delights

Morning

Enjoy a delicious breakfast at The Black Dog Tavern, a Martha's Vineyard institution. Fuel up for the day before embarking on the Edgartown Self Guided (APP/GPS) Audio Historic Walking Tour. Explore the stately homes and learn about the whaling history of this picturesque village.

Afternoon

For lunch, head to Offshore Ale Co. and taste their craft brews alongside a hearty meal. Afterward, indulge in a private Martha´s Vineyard Private Scavenger Hunts, tailored to your interests and providing a unique way to discover Edgartown.

Evening

Dine at The Port Hunter, where the menu offers a blend of local flavors and global inspiration. After dinner, take a leisurely drive to the Aquinnah Cliffs to witness a breathtaking sunset over the colorful clay cliffs.

Bedtime

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Vineyard Haven's Sights and Sounds

Morning

Start your day with a sumptuous breakfast at ArtCliff Diner, known for its creative dishes. Post-breakfast, engage in the Martha's Vineyard Driving & Walking GPS-Guided Audio Tour, which will take you through the highlights of Vineyard Haven, including the historic sites and the picturesque harbor.

Afternoon

Grab a quick bite at Back Door Donuts, a local favorite for its delectable pastries. Then, spend your afternoon visiting the boutiques and art galleries of Vineyard Haven, with a special stop at the Martha's Vineyard Museum to delve into the island's rich history.

Evening

For dinner, enjoy the casual elegance of Alchemy Bistro & Bar, offering a menu filled with seasonal and local ingredients. Cap off the evening with a live performance at the Vineyard Haven's renowned performance venue, The Martha's Vineyard Playhouse.

Bedtime

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Nature and Relaxation in Falmouth

Morning

Cross over to the adjacent city of Falmouth and begin your day with a delightful breakfast at Name of a Falmouth Restaurant. Then, explore the pristine natural beauty of the area with a visit to the Woods Hole Science Aquarium and a leisurely walk through the Spohr Gardens.

Afternoon

Enjoy a delicious lunch at Name of a Falmouth Restaurant before immersing yourself in the rich maritime history of the region at the Woodshole Historical Museum. Afterward, take some time to relax on the beautiful Surf Drive Beach.

Evening

Dine at Name of a Falmouth Restaurant and savor the flavors of the local cuisine. Conclude your day with a tranquil sunset cruise, taking in the scenic views of the coastline and the surrounding waters.

Bedtime

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Culinary Tour of the Vineyard

Morning

Start your final day with a breakfast at Name of a Martha's Vineyard Restaurant, known for its delicious pastries. Then, take a Martha's Vineyard Food and Wine Lovers Experience Tour, visiting local farms, wineries, and culinary hotspots to sample the island's freshest flavors.

Afternoon

Enjoy a leisurely lunch at Name of a Martha's Vineyard Restaurant, where the menu is inspired by the bounties of the sea and the land. Spend the rest of your afternoon exploring the charming boutiques and art galleries of Name of a Martha's Vineyard Town.

Evening

For your final dinner on the island, indulge in the sophisticated ambiance and contemporary cuisine of Name of a Martha's Vineyard Restaurant. Raise a glass to a memorable trip and reminisce about your favorite moments on Martha's Vineyard.

Bedtime

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