Top 10 Outdoor Activities in Martha's Vineyard, Massachusetts (MA)

Private Sailing Charters in Edgartown on Martha's Vineyard aboard a traditional Cape Cod catboat.

This ever-changing environment still provides an important habitat for nesting shorebirds, and a sporting challenge for the fishermen who surfcast from this popular site.

COVID ALERT: WE ARE ONLY TAKING PRIVATE CHARTER RESERVATIONS ON OUR WEBSITE The boat "Plan Sea" is a newly remodeled down east luxury yacht. She seats 18 passengers on teak-trimmed, Sunbrella-cushioned furniture. The open deck and wet bar make Plan Sea the perfect party venue. You may rent (private charter) the entire boat(offered on our website). Public scheduled cruises are DISCONTINUED due to the pandemic. Activities include tours, transportation and parties. Cruises depart from Falmouth on Cape Cod and Martha's Vineyard. Sunset cruises are a great cocktail hour cruise out of Edgartown and Falmouth. Plan Sea boat cruises are a great activity for bridal parties, women's weekends, family reunions, couples and other groups to enjoy time on the water and learn about the history and sights around the Cape and Islands. We are a proud recipient of the TripAdvisor Certificate of Excellence. Cruises fill up fast during our short season, so book now.

Ahoy mateys! Join us as we set sail on a pirate's treasure hunt along the shores of beautiful and historic Oak Bluffs on the legendary island of Martha's Vineyard. On our custom pirate ship your kids will dress and talk like a pirate, assemble a treasure map, battle rival pirates with water cannons and hoist sunken treasure from the ocean floor! Once aboard the Sea Gypsy, we must work together to build a treasure map and determine our course. Along the way, we find a message in a bottle and discover that Stinky Pete, the Island’s smelliest pirate, has stolen the keys! We must raise the battle flag, fight off our enemy with water cannons, and steal back the keys to claim our treasure! The voyage culminates as we discover where "X" marks the spot...we must work as a team (heave-ho!) to raise the treasure chest from the ocean as it's heavy with sea water and sparkling booty. Every one of the crew will be rewarded for their efforts and take home their fair share of the loot. There’s singin’, dancin’, and drinkin’ of pirate grog as we sail back to port victorious in our spoils. You’ll be amazed how quickly the Pirate Adventures crew taps into the wonder of your child’s imagination. This wholesome, family-oriented cruise is perfect thing to do on a day trip, vacation, weekend or really just about anytime your are seeking a child-friendly and action-packed bunch of fun while on MV. There is a reason why Pirate Adventures is ranked high on a family’s vacation highlights. This isn’t a performance by actors - this is a highly interactive pirate experience where each of our trained crew makes sure your child is involved and engaged throughout the whole journey. It's a fun, unique, memory-making adventure cruise designed for families by a family (a pirate family of course).

Experience Martha's Vineyard sailing aboard our sleek, fast, classic sailboat with Master Mariner & ASA-Certified Sailing Instructor, Captain Wendy. Exploring the beauty & history of the area by sea is the perfect adventure for your Vineyard vacation. The picturesque coastline of lighthouses, historic homes, and beautiful beaches are just a few of the beloved sights of the area. Sail aboard M.S. Resolute with us!

All Star Bike Rentals has over 30 years in the bike rental industry on Martha’s Vineyard allowing us to provide the best bicycle rental service. With our experience we can offer you the best tips and advice for making your way around the Oak Bluffs, Vineyard Haven and other towns around the island so your trip is memorable on your bike. If you have any questions please don’t hesitate to call.

Our company offers customized private sightseeing tours of the island by boat, island hoping and private beach events. Boating on Martha's Vineyard has never been so affordable, tell us when you are visiting Martha's Vineyard and let us create an unforgettable cruising experience for you and your guests. Give us your budget, and we can help you create your own personalized cruising experience.

This Oak Bluffs beach and surrounding area of colorful gingerbread Victorian houses have strong links to African-American heritage on Martha's Vineyard, dating back to the Revolutionary War. The beach was the setting for a teenage romance movie called "The Inkwell."