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Schooner & Sailboat Cruises in New England

To a great extent, much of New England history and culture is washed by the waters of the world’s oceans – from the arrival of the Mayflower on the shores of Cape Cod, MA in 1620 to the departures of whaling vessels from the docks of New Bedford, MA, to every corner of the world. An absolutely memorable New England adventure is a cruise along the region’s bays, coves, and rocky coasts on a schooner or other sailing vessel. Sailing ships along the coast – starting, at the northward tip, with the majestic windjammers of Maine -- offer cruises of a few hours to a few days.

A Schooner Cruise Along the New England Coast is the Height of an Authentic Adventure

With the wind at your back, schooners and other similar-sized vessels – variations include sloop, cutter, and ketch – carry you and your family and friends on a breezy coastal tour, with views of bustling harbors, fishermen at work, remote mansions, lighthouses, rocky shores and islands, seals, bald eagles, and other magnificent ships. A boat ride on a schooner is a wonderful and so-New England way to host a family reunion, wedding celebration, or simply an adventure among work friends. In most cases, the passengers can be involved and support the crew in a variety of ways like adjusting the sails (sometimes even taking control of the helm). As with any good tour, your captain and crew will describe the history of the area and most likely come up with a few salty tales of the sea, touching on real stories of wrecks, rum runners, and pirates. A schooner cruise could very well be the peak – and most authentic -- experience of your New England vacation.

Cocktail Cruise - Whistling Man Schooner Co. - Burlington, VT
Whistling Man Schooner Co.

1 College Street Burlington, VT, 05401 Phone: 802-825-7245

Ready for an adventure? Set sail aboard an historic sloop for a Lake Champlain cruise to remember

Set sail into an adventure when you book a cruise aboard the sloops of the Whistling Man Schooner Co. The two classic sailing sloops — the Friend Ship and the Wild Rose — sail out of Burlington, VT and cruise scenic Lake Champlain for two memorable hours. Book a private romantic sunset cruise for two, be part of a public cruise, or arrange for a tandem cruise with a dozen of your friends, family members or work colleagues. Public and private cruises — from three to 10 per day — depart daily May 15 through Oct. 11. The historic sloops, originally designed in 1904, are traditional wooden-rigged Friendship sloops known for being safe and sturdy. Bring your own snacks and drinks (the website has a curated list of favorite purveyors).
Sailing Cruise - Maine Windjammers - Camden, ME
Maine Windjammer Association

Sailing from Ports in Rockland and Camden, ME, 04843 Phone: Toll-Free: 800-807-9463

Windjammer association offers a variety of themed and non-themed cruises

When it comes to cruises, it’s all about variety with the nine members of the Maine Windjammer Association fleet. With accommodations for 16 to 31 guests, the vessels are ideal for private charters. And scheduled cruises include everything from grandparents/grandkids cruises to those for painters, photographers, lighthouse-lovers and wildlife enthusiasts. Join a cruise with an eye toward watching the Perseid meteor showers, or fall foliage; sign on to a yoga cruise or one celebrating craft beers or one where you’ll be part of the Great Schooner Race. Or, prepare to sit back and relax on a cruise with no itinerary except that dictated by the wind. Cruises feature fabulous home-cooked meals (including an on-shore lobster bake), and evening entertainment from music to games to storytelling.
Sailing Couple - A Morning in Maine - Rockland, ME
A Morning in Maine

3 Park Drive Rockland, ME, 04841 Phone: 207-691-7245

Learn about Penobscot Bay as you glide through it on board a 55-foot ketch

Spend a glorious morning in Maine — or an afternoon, or an evening — aboard the aptly named 55-foot ketch Morning in Maine as it sails on Penobscot Bay. During your two-hour cruise, you’ll learn about the beautiful bay’s natural and historic features. You’ll see seabirds and harbor seals, lighthouses and historic schooners, as you relax on deck. Or, if the spirit moves you, lend a hand with the sails or steering! In addition to regular cruises, Morning in Maine offers special sunset cruises; Science Under Sail cruises with a science educator (especially great for kids, who get to use real oceanographic equipment); and a trip to Monroe Island, ME, a six-hour adventure complete with scenic hikes, beach combing and lobster rolls. Private charters are available.
Sailboats Under the Bridge - America's Cup Charters - Newport, RI
America's Cup Charters

49 America's Cup Avenue Newport, RI, 02840 Phone: 401-849-5868

Board a legendary yacht at Newport Harbor and be prepared for breathtaking views

Cruises with America’s Cup Charters start in style, on the docks at beautiful, bustling Newport Harbor, RI. When you step onto your legendary yacht for a day cruise in Narragansett Bay or a customized charter cruise, that sense of style - as well as comfort - continues. Sail aboard the Weatherly, the 1962 Cup winner and one of only three surviving wooden America’s Cup defenders in the world; or the 1970 Cup contender Heritage, with its eye-catching varnished Sitka spruce hull; or the classic Gleam and Onawa. No sailing experience is required — you can help raise the sails, take a turn at the helm, or just sit back and enjoy the breathtaking views.
Smiling Cruise Group 500x250 - Argia Mystic Cruises - Mystic, CT
Argia Mystic Cruises

75 Steamboat Wharf Mystic, CT, 06355 Phone: 860-536-0416

Half-Day Sailing Adventures and Romantic Evening Sails

May through mid-October, choose a half-day or sunset sail aboard the sailing ship ARGIA! Discover islands, lighthouses, and traditional windjammer sailing, right from down-town Mystic, Connecticut. ARGIA accommodates up to 49 guests for public or private half-day or evening sails down the historic Mystic River to Fishers' Island Sound. Sail in smooth and protected waters aboard this Coast Guard licensed vessel.

Relax as you sail by scenic coastlines, take a turn at the helm, or help the crew hoist and trim the sails. Pack a picnic and a bottle of wine (or order snacks from us when you book) to make this excursion truly memorable.
Departures Daily (May thru mid-October) at:
  • 9:30am
  • Noon
  • 3:00pm (½ hr. earlier in October)
  • 6:00pm (½ hr. earlier after Labor Day, 1 hr. earlier in October)