📆 Day Trip Itinerary: Things to Do in Vineyard Haven for Martha's Vineyard Visitors during Winter (2025)
what to do during the off-season, tourist attractions, where to eat, and how to get to and from Tisbury, MA for a day-trip
Feeling a little cooped up and need a fun day trip? Come on over to Martha’s Vineyard! There’s plenty to do and see even in the Winter.
🗺️ MVacay’s Guide to Vineyard Haven
If you're planning a trip in the winter or spring, plan to catch the Steamship Authority Ferry from Woods Hole (which is in Falmouth, MA). You will have to park your car at a remote parking lot for the ferry (Palmer Ave), take a brief shuttle to arrive at the Woods Hole terminal. There, you can buy a ticket at the office or a mobile ticket (~$20 round trip) to get to the island.
The ferries leave about every hour or so throughout the day, and are occasionally cancelled due to weather or staffing issues, so I suggest checking the schedule on their mobile website on the morning of your trip to ensure they are running on time. Be sure to route to the parking lot and not the ferry terminal.
To clarify, you do not need to bring your car or have a reservation. I suggest coming as a walk-on passenger and spending your day within walking distance of the ferry terminal!
⭐ Some Background on Vineyard Haven
Vineyard Haven, officially known as Tisbury, MA, is one of the key gateways to Martha’s Vineyard, welcoming visitors through its bustling ferry terminal. With a rich history as a maritime center, the town has an active harbor year-round. Highlights include historic landmarks like the Martha’s Vineyard Museum and beloved institutions such as The Black Dog Tavern. Along its charming Main Street, visitors can enjoy boutique shops, cozy cafes, and local art galleries, while nearby beaches provide an escape.
Vineyard Haven in One Day - Things to Do
📍 Visit Tourist Attractions
Historic William Street: stroll and view old Captain’s homes constructed in the 1850s. While you won’t be able to go in them, the coastal charm is adorable for a leisurely walk.
Martha’s Vineyard Museum: interactive exhibits, island history, great for kids, beautiful lagoon view.
⛲ Stroll Through Downtown Vineyard Haven
Visit Vineyard shops like Black Dog, CB Stark, Bunch of Grapes, Green Room and Rainy Day.
Stop in Owen Park: a great scenic park including a kids’ playground, harbor view, a great place to observe docking boats.
🦞 Dining with Views + Great Seafood
Art Cliff Diner: a cozy popular option for breakfast and lunch
9 Craft Kitchen: A more upscale for great oysters and lobster
Other great year-round options include Waterside Market, Black Dog Tavern and Net Result
🌊 Lounge by the Beach
Owen Park Beach: minutes from the ferry, features shallow waters, both dog and kid friendly. Also includes public restrooms and a foot rinsing area.
🍦🍹 Grab a Treat or a Drink
First Light Cafe: within the MV Museum they offer fresh snacks when the museum is open
Catboat Coffee: a short walk from the ferry, this shop is loved by locals
🏨 Want to Stay the Night?
We love Nobnocket as a year-round option within walking distance:
📆 Itinerary:
Now that you know the main players - here’s how this could realistically look, leaving travel time on either side of the trip.
10:00 - Arrive, Park + Purchase round-trip ticket in Woods Hole.
10:15 - Depart Woods hole for Vineyard Haven
11:00 - Arrive in Vineyard Haven, walk down Main Street and browse the shops
12:15 - Eat Lunch at Art Cliff Diner
1:15 - Head over to MV Museum
2:45 - Walk to enjoy the view at Owen Park of ships coming in
3:00 - Grab a cocktail and oysters at 9 Craft Kitchen
4:00 - Venture on the docks near Black Dog Tavern to grab a t-shirt and pictures
4:15 - Walk back over to the Steamship Authority terminal to depart the island
FYI, we also have 10+ other weekend, week-long and day-trip itineraries:
Hours are subject to change, please check before going to any of these locations. If you’re into events and local markets don’t forget to check our Weekend Update before your visit.