5 Days of Martha's Vineyard Magic Itinerary

Begin your second day with a visit to Mytoi Japanese Garden in Chappaquiddick. This serene garden offers a peaceful retreat with its beautiful landscapes, koi ponds, and walking paths. It's an ideal spot for relaxation and reflection. Afterward, have breakfast at ArtCliff Diner, known for its creative breakfast dishes and cozy ambiance.

Head over to Martha's Vineyard Museum in Vineyard Haven for an afternoon filled with history and culture. The museum showcases exhibits on the island's whaling history, maritime heritage, and local art. It's an excellent place to gain insight into Martha's Vineyard's rich past. For lunch, stop by Net Result, where you can savor fresh seafood while enjoying views of the harbor.

Spend your evening at Menemsha Beach to witness one of Martha's Vineyard’s most famous sunsets. This quaint fishing village offers a perfect backdrop for an unforgettable sunset experience. Bring along some snacks from Menemsha Fish Market or grab dinner there after sunset; their clam chowder is highly recommended.

Kick off your third day with a bike ride along Martha’s Vineyard’s scenic bike paths starting from Edgartown towards Katama Beach (South Beach). The ride offers stunning coastal views and is suitable for all skill levels. Rent bikes from MV Bike Rentals if needed before heading out on this adventure! Enjoy breakfast at Espresso Love, known for its great coffee and pastries.

In the afternoon, embark on a sailing excursion from Oak Bluffs Harbor aboard one of the local charter boats such as Mad Max or When And If Schooner (ensure prior booking). Sailing around Martha’s Vineyard provides unique perspectives of its coastline that you won’t get from land-based activities! Have lunch onboard or back at Oak Bluffs at Coop de Ville which serves excellent seafood platters.

Conclude your adventurous day by exploring Circuit Avenue in Oak Bluffs – it’s bustling with shops selling everything from souvenirs to high-end fashion items! As night falls enjoy dinner at Sweet Life Cafe which offers an elegant dining experience featuring seasonal menus crafted using local ingredients.

Start your fourth day with a visit to the Martha's Vineyard Camp Meeting Association in Oak Bluffs. This historic site is home to the famous gingerbread cottages and the Tabernacle, a large iron structure used for religious meetings and concerts. The colorful cottages are a photographer's dream, and the area is steeped in history. For breakfast, head to Betty's Breakfast Nook, known for its hearty breakfast options and friendly atmosphere.

In the afternoon, take a trip to the Polly Hill Arboretum in West Tisbury. This beautiful botanical garden features a diverse collection of plants from around the world, set in a serene landscape perfect for a leisurely stroll. It's an excellent spot for nature lovers and those looking to unwind. For lunch, stop by 7a Foods, a local favorite offering delicious sandwiches and baked goods made with fresh, local ingredients.

As evening falls, make your way to Vineyard Haven for some evening entertainment at the Martha's Vineyard Playhouse. Catch a live performance or film screening at this charming venue that showcases local talent and productions. Before the show, enjoy dinner at The Black Dog Tavern, which offers classic New England fare with stunning harbor views.

South Beach is your destination for this final morning on Martha’s Vineyard. Known for its wide sandy shores and great waves, it’s perfect for sunbathing or taking a refreshing dip in the ocean. Enjoy breakfast at Little House Cafe before heading out; their breakfast burritos are particularly popular.

Aquinnah Cultural Center awaits you in the afternoon where you can learn about the rich history of the Wampanoag Tribe of Gay Head (Aquinnah). The center offers exhibits on tribal history, culture, and contemporary life – providing an insightful experience into one of America’s Native communities. Have lunch at Chilmark Tavern which serves up delicious farm-to-table dishes.

Menemsha Sunset will be your final stop on this journey as you return to Menemsha Beach one last time to catch another breathtaking sunset – perhaps even more spectacular than before! End your trip with dinner at Beach Plum Inn & Restaurant, known for its romantic setting and exquisite cuisine made from locally sourced ingredients.