5 Days Complete Itinerary to Martha’s Vineyard

Planning a trip to Martha’s Vineyard is an exciting endeavor! Here’s a suggested itinerary to help you make the most of your time on the island:

Day 1: Arrival and Explore Vineyard Haven

  • Arrive at Martha Vineyard either by ferry from Woods Hole or by plane into Martha’s Vineyard Airport.
  • Check into your accommodation. Options range from cozy bed and breakfasts to luxurious hotels.
  • Explore Vineyard Haven, one of the island’s main towns. Visit the Vineyard Haven Harbor, stroll along Main Street to check out shops and galleries, and grab a bite to eat at one of the local eateries.
  • In the evening, enjoy a relaxing dinner at a waterfront restaurant like The Black Dog Tavern.

Day 2: Oak Bluffs and Edgartown

  • Start your day with breakfast at one of Vineyard Haven’s charming cafes.
  • Take a bus or rent a bike to Oak Bluffs. Explore the colorful gingerbread cottages at the Oak Bluffs Campground, visit the Flying Horses Carousel (the oldest operating carousel in the United States), and relax on the beautiful Inkwell Beach.
  • In the afternoon, head to Edgartown, known for its elegant historic homes and upscale shops. Visit the Edgartown Lighthouse for picturesque views of the harbor and explore the shops and art galleries along Main Street.
  • Enjoy dinner at one of Edgartown’s fine dining restaurants, such as Alchemy or The Terrace at The Charlotte Inn.

Day 3: Aquinnah and Chilmark

  • Rent a car or join a guided tour to explore the western part of the island.
  • Drive to Aquinnah to see the iconic Gay Head Cliffs, which offer breathtaking views of the ocean and colorful clay cliffs. Visit the Gay Head Lighthouse and learn about the area’s Native American history at the Aquinnah Cultural Center.
  • Stop by the quaint town of Chilmark and explore its scenic beauty. Visit the Chilmark General Store for lunch and grab some snacks for a picnic later in the day.
  • Spend the afternoon relaxing on Lucy Vincent Beach or exploring Menemsha, a picturesque fishing village known for its sunsets.
  • Have dinner at one of the seafood shacks in Menemsha and watch the sunset over the harbor.

Day 4: Outdoor Activities

  • Start your day with a morning hike or bike ride along one of Martha’s Vineyard’s scenic trails. Some popular options include the Menemsha Hills Trail and the Katama Airfield Trail.
  • Alternatively, you can spend the morning kayaking or paddleboarding in one of the island’s many ponds or coastal areas.
  • In the afternoon, visit one of Martha’s Vineyard’s farms for a tour and some fresh produce. The Morning Glory Farm in Edgartown is a popular choice.
  • Enjoy a leisurely dinner at a farm-to-table restaurant like State Road Restaurant in West Tisbury, which offers delicious seasonal cuisine.

Day 5: Departure

  • Enjoy a leisurely breakfast at your accommodation or one of the island’s cafes.
  • Depending on your departure time, you may have some free time to explore any sights or activities you may have missed.
  • Depart Martha’s Vineyard, either by ferry or plane, with fond memories of your island getaway.

Remember to check the ferry or flight schedules in advance and make any necessary reservations, especially during peak season. Also, keep an eye on the weather forecast and pack accordingly for outdoor activities. Enjoy your trip to Martha’s Vineyard!

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