Martha’s Vineyard, the charming island south of Cape Cod, offers a perfect escape for day-trippers seeking a blend of natural beauty, small-town charm, and coastal elegance. While some visitors opt for longer stays, it’s entirely possible to experience the island’s magic in just one day. This flexible itinerary starts with a morning in Vineyard Haven and then gives you the option to spend your afternoon in either Oak Bluffs or Edgartown, allowing you to tailor your experience to your preferences.
Morning: Arrival & Vineyard Haven
7:30 AM – 8:30 AM: Ferry Departure Begin your day by catching an early morning ferry from Woods Hole. The ferry ride itself is part of the experience, offering stunning views of Nantucket Sound as you approach the island. The ferry with the most time options departs from Woods Hole and arrives in Vineyard Haven. There are also some ferries with limited, seasonal options from Hyannis and Falmouth to Oak Bluffs.
8:30 AM – 9:15 AM: Breakfast in Vineyard Haven
Upon arrival in Vineyard Haven (also known as Tisbury), head to a local café for a hearty breakfast. Consider dining at Mocha Mott’s for coffee and pastries, Black Dog Bakery for fresh baked goods, or Waterside Market for a more substantial breakfast.
9:15 AM – 12:00 PM: Explore Vineyard Haven Thoroughly After breakfast, discover the understated charm of Vineyard Haven:
- Visit the Martha’s Vineyard Museum, featuring fascinating exhibits on island history, shipwrecks, and culture
- Stroll down Main Street to browse the unique shops, including Bunch of Grapes Bookstore, an island institution
- Explore the working harbor and Owen Park Beach for beautiful waterfront views
- Walk along the Vineyard Haven harbor with views of the ferry terminal and visiting yachts
Afternoon: Choose Your Adventure For the afternoon portion of your day trip, choose between two distinctive Martha’s Vineyard towns: the vibrant, eclectic Oak Bluffs or the elegant, historic Edgartown.
Option 1: Afternoon in Oak Bluffs 12:00 PM – 12:30 PM: Transit to Oak Bluffs Take the #13 VTA bus from Vineyard Haven to Oak Bluffs (approximately 10-15 minutes) or rent a bicycle for more flexibility. The free ride offers lovely coastal views along the way.
12:30 PM – 2:00 PM: Lunch and Initial Exploration
- Enjoy lunch at Nancy’s or Lookout Tavern for seafood with a view
- Begin your exploration of this vibrant town
2:00 PM – 5:00 PM: Oak Bluffs Experience Oak Bluffs offers a unique blend of Victorian charm and lively atmosphere:
- Visit the iconic gingerbread cottages of the Martha’s Vineyard Camp Meeting Association and tour the Cottage Museum to learn about the history of these unique structures
- Stroll through Ocean Park with its Victorian gazebo and sweeping harbor views
- Take photos of and perhaps ride the Flying Horses Carousel, the nation’s oldest operating carousel
- Explore Circuit Avenue shops for souvenirs and treats
- Relax at Inkwell Beach for some seaside downtime
Option 2: Afternoon in Edgartown
12:00 PM – 12:30 PM: Transit to Edgartown Take the #13 VTA bus from Vineyard Haven to Edgartown (approximately 30 minutes) or rent a bicycle for more flexibility.
12:30 PM – 2:00 PM: Lunch and Initial Exploration Edgartown exudes New England coastal elegance:
- Enjoy lunch at The Seafood Shanty with harbor views, or grab a lobster roll from Among the Flowers Café
- Begin your exploration of the historic town center
2:00 PM – 5:00 PM: Edgartown Experience Dedicate your afternoon to experiencing Edgartown’s historic charm:
- Walk down North Water Street to admire the stately sea captain’s homes
- Visit the Edgartown Harbor Lighthouse at the end of North Water Street
- Tour the Old Whaling Church and Vincent House & Gardens for local history
- Browse the boutique shops along Main Street and the surrounding area
- Take the short On Time Ferry to Chappaquiddick Island just to say you’ve been there
- Relax at Lighthouse Beach or walk the harbor promenade
Evening: Dinner and Departure 5:00 PM – 6:30 PM: Pre-Departure Relaxation and Dinner Depending on which town you chose for your afternoon:
- In Oak Bluffs: Enjoy dinner at Offshore Ale Company, a local brewpub
- In Edgartown: Try The Port Hunter for contemporary fare
- In Vineyard Haven (if you return): Dine at Beach Road Restaurant
6:30 PM – 7:30 PM: Return Ferry Catch an evening ferry back to the mainland, taking one last opportunity to soak in the island views. Then return to your cozy room at Brewster By The Sea Inn.
Tips for Maximizing Your Day Trip
- Check ferry schedules in advance and book tickets early, especially during peak season.
- Use the Martha’s Vineyard Transit Authority (VTA) buses to get around efficiently.
- Wear comfortable walking shoes as you’ll cover considerable ground.
- Pack layers as island weather can change quickly, even in summer.
- Bring sunscreen, water, and snacks for beach time and explorations.
- Many Martha’s Vineyard attractions are seasonal so check hours in advance.
Frequently Asked Questions How do I get to Martha’s Vineyard from Brewster on Cape Cod? From Brewster By The Sea Inn you’ll need to:
- Drive approximately 50-60 minutes (35 miles) to the Woods Hole Ferry Terminal in Falmouth
- Park in one of the Steamship Authority’s off-site lots (follow signs for ferry parking)
- Take their shuttle to the ferry terminal
- Board the ferry to Martha’s Vineyard (either Oak Bluffs or Vineyard Haven, depending on the season)
How far away is Martha’s Vineyard? Martha’s Vineyard lies approximately:
- 7 miles off the southern coast of Cape Cod
- The ferry ride from Woods Hole to Vineyard Haven takes about 45 minutes
- From Brewster specifically, expect a total travel time of about 2-2.5 hours (driving to Woods Hole plus ferry)
Is a car necessary for a day trip to Martha’s Vineyard? No, a car is not necessary for a day trip to Martha’s Vineyard and can actually be inconvenient for several reasons:
- Ferry reservations for vehicles are difficult to secure, especially in summer
- Car ferry tickets are expensive (over $100 round-trip for a standard vehicle)
- Parking in towns can be challenging and costly
- The island has an excellent public transportation system (VTA buses) connecting all major points of interest
- Bicycle rentals are readily available near ferry terminals
- Taxis and rideshare services operate throughout the island
- The main towns are pedestrian-friendly with most attractions within walking distance
For a day trip, taking the passenger ferry and using alternative transportation on the island is the most practical approach.
How many towns are on Martha’s Vineyard? Martha’s Vineyard comprises six distinct towns:
- Edgartown – Known for its whaling history and elegant white-painted homes
- Oak Bluffs – Famous for gingerbread cottages and vibrant atmosphere
- Vineyard Haven (Tisbury) – The main port and a year-round community
- West Tisbury – Rural center with agricultural heritage
- Chilmark – Rolling hillsides and stone walls with exclusive beaches
- Aquinnah – Home to dramatic cliffs and Wampanoag tribal lands
Many visitors find themselves planning return trips to discover more of what Martha’s Vineyard has to offer.
