The Best One Day itinerary for Martha’s Vineyard

Just like Nantucket, Martha’s Vineyard is a must see when exploring the Cape Cod peninsula of Massachuetts. This island really shines as a fantastic day trip from the cape for anyone who loves coastal beauty, unique architecture, vibrant main streets and one of a kind natural landscapes.

There is a lot to see and do on Martha’s Vineyard. You could easily spend a week exploring its six towns, relaxing on its beautiful beaches, and hiking around sand dunes. If you only have a day, you won’t be able to see it all, but this one-day itinerary for Martha’s Vineyard will help you make the most of your short time on the island.  

Arriving on the Island

The quickest way to get to Martha’s Vineyard is to take a fast ferry from Hyannis or Woods Hole port on Cape Cod. It takes about 45 minutes to an hour to reach the island from the Cape on a fast ferry.

Steamship Authority offers year-round service and Hy-line Cruises offers seasonal routes to Oak Bluffs and Vineyard Haven. 

There are other ferries and ports to get to Martha’s Vineyard, but for a day trip, you’ll want to take a fast ferry from Cape Cod to make the most of your time on the island. 

I always get to the island by 9 a.m. and take a 6-7 p.m. ferry back. I like having a full day to explore as much as I can. 

Getting around the island

The best way to explore Martha’s Vineyard on a day trip is by bike. The island is pretty big, a little too big to see it all by bike in a day, but I do not recommend a car, especially if you are visiting during high season. There is plenty to do by foot and bike on a day trip. I only recommend a car to explore the island if you are visiting for multiple days outside of high season as, car rentals, car ferries, and parking are costly during summer and visitor parking is extremely limited in summer.

You can also use the VTA bus system that offers routes all over the island. While the buses are reliable, they take time and prevent you from exploring on your own time. This option is best if you want to head up-island to a beach or the Aquannah cliffs and explore just one area for the day.

Ride shares such as Uber is available on the island but can be slow with long wait times, especially in summer. 

Step by Step Day Itinerary for Martha’s Vineyard

This itinerary is best for biking and starts in Oak Bluffs. 

When arriving at Martha’s Vineyard you’ll either land at Vineyard Haven or Oak Bluffs. I prefer Oak Bluffs since it’s a bit more lively with the most things to see and do and more bike rental options.

But no matter where you land on the Vineyard, this itinerary will work for you. 

Rent a bike

I suggest arriving by 9 a.m. since that is when the bike rentals open. During high season, rentals can sell out, so I always recommend renting a bike first. 

The best company to rent from is whichever one has bikes and is closest to the ferry port. Plan to spend around $40 a day on a bike rental, more if you rent an electric bike. There are some hills on the island, but nothing too intense, so a manual bike is all you need.

Bike to Edgartown

I love to start my day in Edgartown, which is about 6 miles or 30-40 minutes bike ride from Oak Bluffs. While biking down Beach Road to Edgartown, you’ll go over the Jaws Bridge, through Joseph Sylvia State Beach, and pass ponds, gorgeous homes, and rhe scenic coastline along the way.

Edgartown Lighthouse

Once in town, I love a pit stop at the Rosewater Market for a morning snack. 

Next, head to the Edgartown Lighthouse. There is a small park with benches and a dirt trail leading down to the lighthouse beach right along Water Street by the Harbor View Hotel. During certain times of the year, you can climb the lighthouse’s tower for magnificent views of the harbor.

Enjoy the atmosphere, watch the boats, and spot wildlife in the harbor.

Downtown Edgartown

After exploring the lighthouse, enjoy riding your bike around town through Main Street and the historic district, enjoying the beautiful homes and landmarks such as the Old Whaling Church and the Captain Benjamin Smith House built in 1780 (34 South Summer Street). 

Additional Historic Landmarks Include:

• Fisher-Bliss House (1832)
• Captain Holley House (c.1848)
• Harbor View Hotel (1891)
• Captain Morse House (1840)
• John Coffin House (1703)
• Baylies-Pease House (c.1845)

By this time, many of the boutiques should be open, which is perfect for anyone craving some retail therapy. Enjoy browsing the local shops for women’s fashion, jewelry, thoughtful gifts, and outdoor gear.

After a relaxing morning in Edgartown head back towards Oak Bluffs making your way to Tisbury for lunch.

East Chop Lighthouse

From Edgartown, bike back along Seaview Ave into Oak Bluffs to Chop Drive to go by the East Chop Lighthouse (Telegraph Hill). 

The route is along the ocean and offers scenic coastal views. The historic East Chop light is a fun stop along the way to Tisbury. It is in a park overlooking the ocean, with its grounds open to the public. 

Lunch

From the East Chop Lighthouse, take the scenic Beach Road towards Vineyard Haven for lunch.

I like to head to Tisbury (Vineyard Haven) for lunch. It is about a 45-minute bike ride from Edgartown. You can stop in Oak Bluffs instead, but I love the restaurants and low-key atmosphere of Tisbury more.

Beach Road, The Net Result, the Black Dog Tavern Fish MV, and Salvatore’s, if you like Italian are all good choices for lunch in Tisbury. 

If you decide to stop in Oak Bluffs for lunch, Lookout Tavern, Nancy’s Restaurant, or Offshore Ale Co. are all good options.

Explore Tisbury 

The town of Tisbury (Vineyard Haven) is pretty small, so it won’t take long to check out Main Street and walk around.

For a walk on the beach and views of the harbor, head to Owen Park Beach.

Biking to West Chop lighthouse (only 10 minutes from downtown Tisbury) through the residential streets is another lovely way to spend the afternoon. 

Explore Oak Bluffs

Once you have gotten your fill of Vineyard Haven, it is time to bike back to Oak Bluffs for the last part of the day. 

If you have time, check out the Martha’s Vineyard Museum in Tisbuy on the way back to Oak Bluffs.

I try to get to Oak Bluffs at least 2-3 hours before my ferry departs to enjoy the gingerbread cottages and walk into some of the local boutiques. 

Gingerbread Cottages

It is about a 20-minute bike ride from Tisbury to your next stop in Oak Bluffs, one of my favorite sites on the island, The Ginger Bread Cottages. 

These decorative Carpenter Gothic cottages are a must-see. The historic pastel color cottages are an iconic site on Martha’s Vineyard, with a history that begins in the 1800s, long before they were even built. 

The cottages are all privately owned now, but there is a Cottage Museum open to the public, offering more insight into these beautiful works of art.

Ocean Park and Circuit Ave

From the Gingerbread Cottages, bike along Ocean Ave, where you can enjoy more restored historic properties lining Ocean Park. Enjoy a break at Ocean Park and views of the Ocean.

While in Oak Bluffs, visit the oldest operating platform carousel in America, the Flying Horses Carousel, and save some time to check out the local boutiques along Circuit Ave. 

Return Bikes

Depending on the time, you may want to return your bike after viewing the Gingerbread Cottages, as it is easy to walk around downtown Oak Bluffs from the ferry port.

Catch the Return Ferry

Your trip to Martha’s Vineyard has ended, but I hope you enjoyed your day following this itinerary. 

This itinerary usually takes me around 8-9 hours, so it really is a full day. Check your pace during the day, and cut out what you need to so you don’t miss your ferry back to Cape Cod. 

Below are a few tips regarding this itinerary for Martha’s Vineyard. 

Additional Notes:

Download offline Google Maps for biking route directions. Service is mostly available but can be spotty in the more remote areas of the island.

If you have a late start to the day, after Edgartown, skip Tisbury and stay in Oak Bluffs for the rest of your day. There is more to see and do in this area, and it is better to do less and enjoy more than try to pack everything into one day. 

I recommend visiting Edgartown, Tisbury, and Oak Bluffs on your first visit to Martha’s Vineyard. With multiple visits, head to Aquinnah on the western part of the island to enjoy the cliffs overlook, Moshup Beach, and Gay Head Lighthouse. 

It is about 20 miles, or a 40-minute drive from Oak Bluffs to Aquinnah Cliffs Overlook. You can also bike the route, but it takes about two hours one way.  

In the high season, car parking is $30 daily at the Philbin Beach lot, (near Mosup Beach) no matter how long you park. There are a handful of free 90-minute parking spots for lighthouse viewing but in summer, these spots rarely open up. So it might be easiest to visit this area in the off-season.