10 Boat Tours & Water Sports in Cape Ann That You Shouldn't Miss

Cape Ann Whale Watch in Gloucester, Massachusetts provides guaranteed whale sightings for every whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester deemed one of the "Top 5 Whale Watching Destinations in the World" by the World Wildlife Fund due to the wide variety of whale species whom migrate to the coast of Gloucester, Massachusetts every year to feed on the abundant natural resources. We provide the best whale watching in New England as it's an awe-inspiring experience which every human being should have the opportunity to appreciate. We make it a very special event. For over 35 years, Cape Ann Whale Watch has been dazzling whale watching enthusiasts with sightseeing tours aboard the largest, fastest and most elegant whale watching vessel in Massachusetts, north of Boston, Massachusetts aptly named "The Hurricane II" due to its immense size and speed as it descends upon its destination. Cape Ann Whale Watch's patrons have the opportunity to spend a lot more time with the whales than with other whale watching companies in Gloucester MA since "The Hurricane II" gets to the whales' feeding grounds with much more expediency as well as traveling home faster, therefore more time is actually spent observing whales including but not limited to Humpback Whales, Minke Whales, Northern Right Whales, Pilot Whales, Northern Right Whales, Sperm Whales, Sei Whales, Blue Whales (The Largest Whales in the Seven Seas yet seldom seen around Gloucester MA), Fin Whales, Atlantic White Sided Dolphins, Harbor Porpoises and whole host of other fascinating marine creatures as we deliver the best whale watching excursion in Massachusetts. "The Hurricane II" boasts 115 ft length with over 400 ft of whale watching room from the railings of the upper and lower observation decks for optimum whale watching conditions. There is a heated, furnished indoor cabin with a full service galley serving hot meals, snacks and cold beverages as well as a fully stocked bar with local brews, popular beer, wine and mixed drinks. Cape Ann Whale Watch is truly the finest whale watching tour in the Boston MA area offering the highest level of quality, comfort and service at the cheapest, most affordable price suitable for any family entertainment budget whether on vacation or a day trip. We offer AAA discounts on the adult tickets. We also offer reduced rates for seniors, children and military families. We go where the whales go. Our vessels communicate with each other as to the location of whales so we will go anywhere to see them on the North Shore or South Shore of Massachusetts including off the coast of Boston, Massachusetts: Salem MA, Newburyport, Cape Cod, Hampton NH, Rowley, Rockport MA, Danvers, Peabody, Swampscott, Revere, Winthrop or wherever else the whales may roam.

Trip Advisor's #1 of 26 Tours in Gloucester, 7 Seas Whale Watch has had the privilege of introducing thousands of passengers to the many species of whales and marine wildlife that inhabit the waters from Cape Ann and out to the Stellwagen Bank Marine Sanctuary. Our trips run from mid-April to mid-October and are designed to educate, inspire and provide a deeper understanding and appreciation of our fragile marine environment. We are a family business – Three generations of career captains have worked from this very dock for more than 7 decades. We have a love and respect for the marine environment and a passion for providing the best possible customer experience for you and your family. We look forward to seeing you on the water.

Picture yourself relaxing on the deck of this beautiful 65- foot schooner as she sails out of Gloucester harbor on a light southwesterly breeze. Join us for a two-hour sail and get a taste for what it was like to sail on a fishing schooner a hundred years ago. Help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester's coastline. Some of our weekend public sails feature music. We offer group rates. And we specialize in private charters for weddings, corporate entertainment, teambuilding, birthdays and more. The Lannon is a great place for a party!

Connemara Bay Charters offers lobsterbake cruises, saltwater fishing, lobstering, and scenic charters in and around the waters off Cape Ann, Massachusetts (including Gloucester, Rockport, Manchester and Ipswich). The Connemara Bay is a 37-foot traditional, “Down East”-style Maine-built boat with plenty of deck space to accommodate up to six passengers. All charters are captained by Kevin O’Maley, a native of Gloucester with a lifetime of experience fishing, lobstering and boating in North Shore waters.

Fishing Charter Service, I specialize in stripers, bluefish, cod and haddock. You have the chance to catch a trophy fish minutes from the dock in my 25 foot boat. It has an electric head and cabin for protection from the elements. I have all the USCG safety requirements and Furuno RADAR Chart plotter, Fish Finder. I supply the rod and reels, so give me a call for a fun day out on the water.

We provide scuba diving charters services to many off-shore locations from Marblehead Massachusetts to the Isle of Shoals in the Gulf of Maine. Most dive charters are 1/2 days mornings and afternoons. See our yearly schedule which is posted on our website and details and other additional information about our services.

The Karen Lynn fishing charters of Gloucester MA is New England's premier sport fishing charter boat, specializing in Bluefin Tuna, Monster Striped Bass, Cod and Haddock, and Sharks.

Windfall, our elegant 49-foot sailing vessel, is available for day or overnight sailing charters.We dock for the summer season (June–October) in historic Gloucester, MA, in Smith's Cove, within walking distance to the famed artist colony of Rocky Neck. Summer charters are also available out of Boston or any accessible New England port. Or, use Windfall as your floating B&B (Boat & Breakfast dockside) while visiting the lovely Cape Ann region. In autumn we head south to go sailing in the beautiful, sunny Bahamas from late February through May. Meet us at our base of operation, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas. We practice all state and local covid-19 sanitation guidelines.

Come sailing aboard The Frayed Knot moored in Manchester-by-the-Sea, MA, a beautiful picturesque harbor located on the historic North Shore. We are a family run business offering sail charters or lessons for all levels of experience and ages. Our offerings include day sails (up to 10 guests), overnight sails (4 guests), lessons (private or group), private parties, birthdays, anniversaries, reunions, corporate and client events, romantic sails - engagement, honeymoon, bachelor/bachelorette parties and more. It can be a hands-on experience or just sit back, relax, and enjoy the scenery. It will truly be an experience you won't forget!

We are a full-service stand up paddleboard and surf company. We offer lessons, tours, rentals, sup yoga, kids camps, sales, SUP Surf lessons, kids surf nights, and more. In 2010, we began our operation on Pavilion Beach in Gloucester, MA (Now on-site at the Beauport Hotel). Since then, we have opened two more on-water locations (Essex River-Essex Marina and Long Beach-Cape Ann Motor Inn). With the rental of 2 of more boards, we offer our clients free delivery and pick-up anywhere on Cape Ann. Whatever your paddle and surf needs are, we've got you covered! We look forward to getting you on the water or seeing you in the Board Barn soon. We are open 7-days a week in the summer and on weekends (and by appointment) during the spring + fall.