What to do and see in Massachusetts, United States: The Best Boat Rentals

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.

We offer Charters aboard Indiscretion and also offer a food and beverage package which is quite exceptional! Fishing, Family, Corporate, and Fun Charters! Cruise away from Downtown Boston on your way to Hours of adventure on Historic Boston Harbor. Relax aboard a luxurious Classic 42' Post Sportfish with plenty of room for all, enjoy seeing the many historic sights and rich History of Boston Harbor and the Islands.snorkeling in crystal clear Harbor waters brimming with marine life, and do some sightseeing with so much to see in an always changing seascape! Meet up with your skipper for the day at the New England Aquarium dock and climb aboard a 42' Post Sportfish, setting your sights on discovery in the bountiful sunshine. Watch the crew toss off the mooring lines, settle into a comfy seat for the voyage ahead, and chat with your Skipper or First Mate about what you might see during your History-packed cruise.

Down Cape Charters & Boat Rentals is a family owned business located on the eastern shore of Pleasant Bay, the largest contiguous bay along the Cape Cod National Seashore. For the past 30 years we have established ourselves as the area’s leading source of watercraft rentals, charters and tours. Come, join us, and see Cape Cod the way it’s meant to be seen!

Arey's Pond Boat Yard has been teaching sailors on Little Pleasant Bay since 1964. We teach the majority of our lessons on our 14’ Arey’s Pond Catboats. Catboats are the traditional sailboats of Cape Cod. They are gaff rigged, very stable, and with only one sail, make perfect vessels for sailors of all ages and skill levels. All of our instructors are certified by US Sailing. Experienced sailors can rent one of our catboats for a day of exploration on pleasant bay.

Sailboat rentals, kayaks, stand-up paddle boards, lessons and tours in Chatham, Massachusetts, on the kid-friendly Ridgevale Beach. Family owned & operated for over 50 years in conjunction with the Ridgevale Beach Snack Bar, Chatham Sailboat Rentals offers water activities for all skill and age levels to be enjoyed on Buck's Creek and Nantucket Sound.

Jetties Sailing Center, which is run by Nantucket Community Sailing, offers rentals of SUP paddle boards, kayaks (single & double), and windsurfers. The Jetties Sailing Center also offers sailboat rentals in a variety of sizes and models. If you don't know how to sail, the Jetties Sailing Center also offers private sailing lessons in Rhodes 19s, Marshall Cat 15s, Sunfish, windsurfers, Lasers, the Hobie Getaway (and 420s per the Program Director's discretion)! Here's some background information about our organization: Nantucket Community Sailing actively supports the local community by offering youth scholarships and outreach programming. In 2017 we provided $81,500 in sailing scholarships and free community outreach programs. Nantucket Community Sailing additionally sponsors the Nantucket High School Sailing Team and works closely with many local non-profits to offer free sailing and water sports activities to youth and adult members of the Nantucket community!

With sensational skyline views and completely customizable options, the Boston Elite is Boston’s most innovative dining and entertainment experience. Work with our crew to create a totally unique event, and enjoy all the prestige of cruising Boston Harbor on your own private yacht.

Enjoy Salem from the water on a beautiful classic sailing yacht! The schooner When And If at Sunset Sail Salem is your chance to enjoy a relaxing sail on Salem Sound as the wind fills the sails and your captain and crew sail you away. Private and shared charters are the perfect way to experience the best of the North Shore, day or night all summer long. Let's go sailing!

The only Ocean sports company on Martha's Vineyard! We provide Parasailing, jet ski rentals, waterskiing, wakeboarding, tubing, kneeboarding, flyboard lessons, banana boating, tubing, and boat rentals. Come have a day on the water with us!

Join us aboard our luxurious 103’ Trilogy in cruising to one of our many destinations: Boston Harbor, Nantasket Beach, Georges Island, Spectacle Island and Little Brewster Island. Available for sunset cruises, 2-hr, 4-hr, half/full day excursions as well as weekends. We also offer Dockside Celebrations for groups up to 12. Features: Master Suite, 2 VIP Staterooms, Spa Pool Tub, SUP, & Water Toys.