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If your ferry ride is the only time you spend on the water while visiting Martha’s Vineyard, you’re missing out. Practically every water sport you can think of—from the traditional to the new and exotic—is available on these shores. We’ve rounded up our favorite island water sports below, with tips on where to rent gear and get your feet wet.

 

Island Water Sports - sunset on the water

 

Island Water Sports Near Edgartown

For island water sports that take a bit of practice, like stand-up paddleboarding, the sheltered flat waters of Sengekontacket Pond and Majors Cove are a perfect place to play. Inland from the sparkling sands of Joseph Sylvia Beach (that’s State Beach to islanders), you can’t miss this area as you cross the Jaws Bridge halfway between Edgartown and Oak Bluffs. We recommend Island Spirit Kayak in Oak Bluffs for kayaks and paddleboards. They’re conveniently located right on an inlet between the beach and the pond, so you can choose to explore the coastline or take it easier inland.

 

Further up the road, on Oak Bluffs Harbor, Martha’s Vineyard Oceansports offers a full array of motorized island water sports at surprisingly reasonable rates. This is the spot to rent a jet ski or go parasailing. MV Oceansports is also one of very few shops in the northeastern US to offer flyboarding. If you haven’t heard of this sport, imagine wakeboarding 15 feet up in the air. It’s not as scary as it sounds and it’s surprisingly easy to get the hang of. Instructors Kevin and Gene became some of the first pros at this island water sport when it was invented in the early 2010s, so you’ll be in good hands if you give it a go.

 

Both of these island water sports shops are easily accessible by Vineyard Transit Authority bus during the warmer months.

 

Up-Island Water Sports

rowboats on the beach Martha's Vineyard
Photo: Doug Kerr via Flickr

If you want to hang ten on the west coast—of Martha’s Vineyard, that is—take a day trip up-island and visit either Aloha Paddle in Aquinnah or Book-a-Boat in Menemsha. Though it’s a bit further away from Edgartown, you’ll share these waters with fewer fellow paddlers and take in views you can’t find anywhere else.

 

Aloha is 100% stand-up paddleboarding, with lessons, tours, and rentals available daily. Their kids’ programs make planning a family outing easy. Already got some experience? Challenge yourself with a SUP yoga class or paddle out on the open water to see the famous Gay Head cliffs from a totally new point-of-view.

 

Want to try your luck with the rod and reel without hiring a Martha’s Vineyard fishing charter? Book-a-Boat has a full selection of sailboats, sunfish, and motorized fishing boats, with kayaks and paddleboards available as well. Like their hometown of Menemsha, Book-a-Boat is a little old-fashioned—they prefer to make reservations over the phone to ensure you get exactly what you’re looking for.

 

Island Water Sports in Vineyard Haven

In the middle of the island’s north shore, where the Steamship Authority ferries come and go like clockwork, Vineyard Haven’s Wind’s Up natural watersports shop doubles as a great place to pick up forgotten essentials: they stock high-quality bathing suits, sunglasses, hats, and other supplies along with their rental fleet of kayaks, canoes, SUPs, and surfboards. This is an easy place to pick up rentals on your way to Edgartown from the ferry—just tell your taxi driver to take the scenic route (Beach Road, which is well worth the extra few minutes for its ocean views) and stop on the way.

 

After you explore Martha’s Vineyard by water, you’ll need a cozy place to stay on land—all of us at Vineyard Square, in the heart of downtown Edgartown, would love to welcome you and help plan your adventures.

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Engage in a Martha’s Vineyard Shopping Escapade
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Embark on a Self-Guided Martha’s Vineyard Lighthouse Tour
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Planning a solo beach vacation to an island might sound isolating, but for the growing number of visitors who prefer to explore Martha’s Vineyard alone, that doesn’t have to be the case. In fact, traveling alone gives you the freedom to have as much or as little social time as you want, with the added perks of making your own schedule and doing—for once—exactly what you want to do. People of all ages, in all different situations, are turning to solo travel as a way to break up daily routines, recharge, and even plot life’s next big moves. If you’re ready to hop the ferry to Martha’s Vineyard with no entourage in sight, this guide is for you.

 

Solo beach vacation on Martha's Vineyard--swimming alone

 

Best Martha’s Vineyard Beaches for Solo Travelers

Choosing the best beach depends a bit on what kind of solo beach vacation you’re after. For maximum seclusion with drop-dead gorgeous scenery and no development in sight, East Beach on Chappaquiddick—accessed via the tiny ferry in Edgartown—is your best bet. With seven miles of shoreline, you’re sure to find a spot away from others on this east-facing barrier beach. For more company, pitch your umbrella in the soft white sand of South Beach, also known as Katama Beach.

 

Where to Walk

For a great solo stroll, we like Poucha Pond, or really anywhere else on Chappaquiddick. This tiny island is less densely populated than the mainland of Martha’s Vineyard, so a little bit of wandering around there pays dividends in serenity. Consider taking a bicycle over on the ferry and spending the better part of an early morning peddling around. To get outside and learn about local flora and fauna with a group, check out the Felix Neck Wildlife Sanctuary’s adult classes.

 

Bad Martha Brewery patio with cornhole and live musicFood, Drinks, and New Friends

After a day in the sun and sand, round out your solo beach vacation with some local seafood and libations. Mid-to-late afternoon is a great time to meet new friends at Bad Martha Beer, one of our favorite local breweries. Food is scarce here, but the back patio has cornhole and live music and the farmhouse-style tasting room is surrounded by a beautiful garden nursery. The Wharf is where Edgartown’s nightlife happens, with casual dinner service giving way to a lively bar scene with DJs and live bands. For a quieter, more upscale experience, consider Atria, whose top-notch local menu changes nightly.

 

Where to Stay for Your Solo Beach Vacation

For an affordable place to stay near all of the above activities, we recommend choosing between the towns of Edgartown and Oak Bluffs. Oak Bluffs skews a little younger and wilder, while Edgartown is better for a more relaxing solo beach vacation—it’ll still be hopping during the day and evening, but it’s quieter late at night. To truly avoid crowds, plan your solo beach vacation for the spring or fall. The weather is often surprisingly lovely, but the scores of summer visitors are back home at work and school.

 

If you’re leaning toward Edgartown, we’d love to welcome you to the heart of downtown at Vineyard Square. The rates for our cozy rooms are especially solo-traveler friendly, and they include an array of amenities to make your trip easier to manage on your own: a house-made continental breakfast in-season, access to our fitness center, complimentary bicycles, beach chairs and umbrellas to borrow, as well as access to our fourth-floor veranda with stunning views of Edgartown Harbor.

Soak in the Sunshine at the Best Martha’s Vineyard Beaches
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Cycle Around on the Best Martha’s Vineyard Bike Rentals
Play a Round at Martha’s Vineyard’s Best Golf Courses
Engage in a Martha’s Vineyard Shopping Escapade
Enjoy a Pint from the Best Martha’s Vineyard Breweries
Embark on a Self-Guided Martha’s Vineyard Lighthouse Tour
Visit the Best Martha’s Vineyard Art Galleries in Edgartown

Whether you’re looking to catch that one fish you’ll tell your grandkids about someday or teach those same grandkids how to bait a hook, head for the legendary waters surrounding Martha’s Vineyard. Take your pick among our favorite Martha’s Vineyard fishing charters—you’ll find options for any budget, experience level, and age range.

 

Fishing boats at Menemsha, Martha's Vineyard
Photo: Ernest McGray, Jr. via Flickr

 

Family Deep Sea Fishing on the MV Skipper

In the Skipper‘s 30 years at sea, Captain John Potter has helped thousands of kids catch their very first fish. He knows exactly when and where the fish will be feeding, and shares pointers and stories with a smile. Potter and his crew go the extra nautical mile to make this our favorite Martha’s Vineyard fishing charter for first-timers, families, and all-around fun. Unlike other outfits, the Skipper offers affordable individual rates in addition to private charters. It’s no wonder they’ve been reeling in Best of the Vineyard awards for decades.

 

Menemsha Blues Charters

For experienced anglers willing to make the short trip up-island, head over to Menemsha Blues Charters. This fishing charter departs from one of the island’s least-developed fishing towns, then sails past the clay cliffs of Aquinnah and into waters full of striped bass, bluefish, and other island favorites. Captain Boyd’s vessel, the Mary Sea, is available for half-day and full-day charters at a flat rate.

 

Tomahawk Charters

Striped bass
Photo: Chesapeake Bay Program via Flickr

Captain Buddy Vanderhoop combines Native American fishing tradition with modern technology to help his clients catch especially large fish. A member of the Aquinnah Wampanoag Tribe, Vanderhoop harvests baitfish from the tribe’s natural herring fishery. His boat, the Tomahawk, is Martha’s Vineyard’s fastest fishing vessel, which means you’ll spend less time traveling to and from the fishing area and more time casting. It also allows Vanderhoop to access areas that would normally be impractical for a day trip. For a great story on this Martha’s Vineyard fishing charter, be sure to ask Captain Vanderhoop about his family’s whaling history.

 

Done Deal Charters

Done Deal Charters will pick you up from your preferred island location for a fully customized Martha’s Vineyard fishing adventure. The Done Deal can travel up to 300 miles on one tank of fuel and uses state-of-the-art electronics to find fish. On this high-tech fishing charter, we like our odds of bringing home a big one.

 

North Shore Charters

North Shore Charters tailors each trip to the group’s ability level, so it’s another great option for beginners and families. That said, we know plenty of experienced fishermen who swear by North Shore as well. The island’s oldest charter fishing outfit offers both in-shore and off-shore trips.

 

Edgartown Charter Fishing with Wayfarer Charters

Captain Jerome has been our neighbor for years—he was principal of the local school, and serves as president of the Martha’s Vineyard Striped Bass and Bluefish Derby. When he’s not leading fishing charters on the Wayfarer, he teaches aspiring captains the tricks of his trade. If you’re staying at Vineyard Square, a five-minute stroll will bring you right to Edgartown Harbor—in the time you would have spent traveling to another charter, catch some extra sleep or grab early morning breakfast at Dock Street Coffee Shop.

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Cycle Around on the Best Martha’s Vineyard Bike Rentals
Play a Round at Martha’s Vineyard’s Best Golf Courses
Engage in a Martha’s Vineyard Shopping Escapade
Enjoy a Pint from the Best Martha’s Vineyard Breweries
Embark on a Self-Guided Martha’s Vineyard Lighthouse Tour
Visit the Best Martha’s Vineyard Art Galleries in Edgartown

Trying to fit the whole Cape-and-Islands experience into one vacation? We recommend building a Nantucket day trip into a longer stay on Martha’s Vineyard. The Vineyard is considerably larger, with multiple distinct towns and things to do, whereas Nantucket’s action is more concentrated in one downtown area — perfect for a day trip. Martha’s Vineyard lodging is also more abundant and tends to be more reasonably priced. Still, our neighbors on Nantucket share a sense of island life all their own. Check out these tips for a Nantucket day trip, hop on the ferry, and experience the island next door.

 

Arriving in Nantucket harbor for a Nantucket Day Trip
Photo: Bob P.B. via Flickr

 

Nantucket Day Trip Transportation

Unless you’re among the world’s small cohort of private yacht owners, getting across the Sound for your Nantucket day trip takes a little planning. Hy-Line Cruises runs ferry service back and forth — hop the first one from Oak Bluffs in the morning and heading back in the evening just before dinner time.

 

Once you’re on land, you’ve got a couple of options for getting around. For a first-time visit, simply strolling around Nantucket town is more than enough to fill a day. If you do want to venture further away to popular spots like Cisco Brewers or Sankaty Head Lighthouse, Easy Riders Bike Rentals is your ticket. Nantucket is only about 14 miles long and five miles wide, so two wheels and some leisurely pedaling will serve you well.

 

Nantucket Day Trip Activities

Sip a cocktail by the water, shop the boutiques in town, or get little lesson in Nantucket history. The world is your oyster.

 

Murray's Toggery Shop
Photo: Ethan Oringel via Flickr

Nantucket Shopping

Downtown Nantucket is packed with shops and boutiques — some storefronts change with the tides of fashion while other mainstays have been around for decades. Murray’s Toggery Shop is one of those classics, as essential to Nantucket style as Vineyard Vines is to our home island. Come back sporting a pair of Nantucket Reds and we’ll know your trip was a success. For more ACK shopping hotspots, check out the Nantucket Chamber of Commerce‘s complete list.

 

Nantucket Historic Sites

If you see one historic site on your Nantucket day trip, make it the Nantucket Whaling Museum. This museum offers an astounding look at the industry that made both Martha’s Vineyard and Nantucket commercial hotbeds some 200 years ago. Highlights include the 46-foot skeleton of a real sperm whale and a restored candle factory that occupied the building in the mid-1800s. Before you leave the museum, head up to the rooftop observation deck for stunning views of Nantucket harbor. Your hosts at the museum desk can also direct you to a number of other properties entrusted to the Nantucket Historical Association, including the Old Mill, the Jethro Coffin House, and the Old Gaol.

 

Nantucket Food & Drink

No day trip to Nantucket would be complete without sampling some of the island’s cuisine for lunch. Cru, located right on the harbor, is one of the hottest places to see and be seen. Get fancy, grab a cocktail, and start shucking at this upscale raw bar. For more casual fare, try Black-Eyed Susan’s and Centre Street Bistro.

 

Where to Stay

Ready to plan your inter-island adventure? We’d love to make Vineyard Square your home base. Our modern, beachy accommodations and homemade continental breakfast in the heart of downtown Edgartown make traveling, sightseeing, and relaxing as easy as can be.

Soak in the Sunshine at the Best Martha’s Vineyard Beaches
The Top 7 Edgartown, MA Restaurants for Seafood Lovers
Cycle Around on the Best Martha’s Vineyard Bike Rentals
Play a Round at Martha’s Vineyard’s Best Golf Courses
Engage in a Martha’s Vineyard Shopping Escapade
Enjoy a Pint from the Best Martha’s Vineyard Breweries
Embark on a Self-Guided Martha’s Vineyard Lighthouse Tour
Visit the Best Martha’s Vineyard Art Galleries in Edgartown

There’s no need to boost the saturation in these vacation snapshots — nature’s paintbrush gifts us sunsets that are nothing short of vibrant. You only have so long to enjoy the show, so if you have your heart set on catching this classic island photo op then you need to be in the right place at the right time. Whether that place is perched atop a lighthouse or out on the water, these Martha’s Vineyard sunset spots are guaranteed to set your sights ablaze on either side of the island.  

 

Four Ways to Set Your Sights on a Martha’s Vineyard Sunset

Menemsha Sunset Martha's Vineyard
Menemsha Sunset | Photo: Massachusetts Office of Travel & Tourism via flickr (CC BY-ND 2.0)

 

Menemsha Public Beach

Between a charming village vibe and unobstructed water views, Menemsha is easily the most favored haven for enjoying end-of-day colors between locals and visitors alike. Stop by Larsen’s Fish Market or Menemsha Fish Market to grab some succulent seafood to-go before you claim your front-row seat on the shoreline. No matter how many people begin to pack up, be sure to stick around after the sun sinks below the horizon. Trust us, this is when the most vivid colors show their cards and you won’t want to catch them from your rearview mirror.

 

Aquinnah Cliffs

An already Instagram-famous photo location by day, the red clay Aquinnah Cliffs are even more beautiful when a blue sky is swapped out for a multicolored one. For one fail-proof vantage point, head to the Aquinnah Cliffs Overlook for a full sunset viewing package of the water, cliffs, and lighthouse. If you happen to swing by on a Thursday evening, opt for an even better view overlooking the beach from within the Gay Head Lighthouse itself.

 

East Chop Lighthouse

If you can’t squeeze a trip to the Wild West (as far as the Vineyard is concerned), stick closer to our corner for equally pleasing Martha’s Vineyard sunset sightings. Pay a visit to our neighbor, Oak Bluffs, to watch the colorful gradient from the East Chop Lighthouse. Sunday evening visitors have the advantage of viewing the sky from the lighthouse interior, but the views are just as grand if you’re watching them surround the stoic structure.

 

By Water on Edgartown Harbor

To truly feel like you’re right in the center of the action, set sail on a sunset cruise with Plan SeaBring aboard supper on-the-fly from your favorite Edgartown restaurant — this crew happily invites you to pack a snap and drink of your choosing. While you watch the purples, pinks, and oranges reflect off the water, the chatty cruise crew will drop fun facts and tales about the buildings and scenic views that the boat passes by.

 

Aquinnah Martha's Vineyard Sunset
Sunset in Aquinnah | Photo: Massachusetts Office of Travel & Tourism via flickr (CC BY-ND 2.0)

Want to catch the sunset but only have five minutes? For Vineyard Square Hotel guests, it’s as easy as running up to our shared fourth-floor harbor view veranda for an exclusive viewing of the radiant sky set above Edgartown’s rooftops. Be sure to swing by the front desk for even more sunset spot secrets or to share your own discoveries. We never get sick of a good sunset photo on this island!

Soak in the Sunshine at the Best Martha’s Vineyard Beaches
The Top 7 Edgartown, MA Restaurants for Seafood Lovers
Cycle Around on the Best Martha’s Vineyard Bike Rentals
Play a Round at Martha’s Vineyard’s Best Golf Courses
Engage in a Martha’s Vineyard Shopping Escapade
Enjoy a Pint from the Best Martha’s Vineyard Breweries
Embark on a Self-Guided Martha’s Vineyard Lighthouse Tour
Visit the Best Martha’s Vineyard Art Galleries in Edgartown