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America’s Best Sailing Adventures

Kevin Steele

North America’s lakes and oceans are a playground for sailing companies and small charter cruise ships that provide exciting itineraries, sailing certifications, and unique land excursions like kayaking, snorkeling, and hiking. From New England to Hawaii, here are 15 one-of-a-kind sailing experiences.—Kristen Oliveri

Courtesy Schooner J&E Riggin
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Schooner J&E Riggin

WHERE: Maine

This Windjammer offers unique and thoughtful itineraries for those looking to explore the beautiful coast of Maine. Guests can choose from a variety of three-, four-, or six-day sailings focusing on Maine lighthouses and lobster dinners, fall foliage tours, or Maine quilting cruises, among others. Guests are treated to home-cooked, comfort food dishes made exclusively with local produce from chef Annie Mahle’s own garden. With most itineraries, guests are also treated to an off-the-boat lobster bake.

PLAN YOUR TRIP: Visit Fodor’s Maine Guide

Dustin Ryan
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Charleston Sailing Charters

WHERE: South Carolina

Take a sail around Charleston, South Carolina, on Charleston Sailing Charters, a sailing yacht that can accommodate up to four guests for overnight and extended stays as well as intimate special events such as proposals or weddings. Guests can spend a night out on the town in Charleston before heading back to the boat to sleep. Sailing destinations can include the Bohicket marina near Kiawah Island on Seabrook Island or Nassau in the Bahamas on longer sails.

PLAN YOUR TRIP: Visit Fodor’s Charleston Travel Guide

Jerryway |
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Alaska Adventure Sailing

WHERE: Alaska

The majestic state of Alaska is the ideal destination for a sailing adventure out on the open water. This sailing company can customize itineraries throughout southeast Alaska, where guests can get the once-in-a-lifetime chance to sail by a glacier, as well as participate in adventurous excursions such as humpback whale-watching, skiing and snowboarding, rock climbing, or a soak in a natural hot spring.

PLAN YOUR TRIP: Visit Fodor’s Alaska Travel Guide

Jerry Bryant
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Hawaii Sailing Adventures

WHERE: Hawaii

For those looking to charter a private sailboat around the beautiful islands of Hawaii, look no further than Hawaii Sailing Adventures. These catamaran sailboats venture across Kauai, Maui, Niihau, Lanai, Molokai, Honolulu, Waikiki, Oahu, and Kaneohe Bay, as well as the Big Island, the Napali Coast, and Kohala Coast. Each adventure can be customized to include a variety of activities such as snorkeling, kayaking, fishing, or venturing ashore to local restaurants.

PLAN YOUR TRIP: Visit Fodor’s Top Attractions in Hawaii

Kevin Steele
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Santa Barbara Sailing

WHERE: California

The picturesque city of Santa Barbara, California, is home to Santa Barbara Sailing, a company providing instructional sailing vacation trips. The main offering is their eight-day “live aboard” package catering to sailing novices or passengers with basic knowledge looking to take their skills to the next level. Guests are able to achieve the first three levels of the American Sailing Association (ASA) certification as well as become a Bareboat Charterer certified to sail global day charters.

PLAN YOUR TRIP: Visit Fodor’s Santa Barbara Guide

Ted Dillard
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Maine Windjammer Cruises

WHERE: Maine

Maine Windjammer Cruises is steeped in rich history, dating back to 1936, when the fleet was used as cargo schooners. Today, they have been transformed to showcase all-inclusive sailing cruises along the coast of Maine with an eye on sustainability. They serve only local fish and produce while aboard and rely on wind to power their vessels. Accommodations are rustic and authentic and ports of call vary, depending on sailing conditions.

PLAN YOUR TRIP: Visit Fodor’s Portland Guide and Fodor’s Kennebunk and Kennebunkport Guide

J. Carey
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Mystic Whaler Cruises

WHERE: Connecticut

This cruise organization couples 19thcentury charm with modern amenities in order to show their guests the natural beauty of Connecticut. The Mystic Whaler, which can accommodate up to 31 guests for one- to five-day tours, is a reproduction of a late 19th-century coastal cargo schooner, designed and built for passenger trade in 1967. Guests can enjoy the intimate furnishings of the boat, complete with Italian oak floors, fir wainscoting, and mahogany accents.

PLAN YOUR TRIP: Visit Fodor’s New Haven, Mystic and the Coast Travel Guide

Leesniderphotoimages |
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Blount Small Ship Adventures


Blount Small Ship Adventures began in the 1960s when Luther Blount started building small ships where his friends could get a sailing experience coupled with the comfort of traveling on a friend’s private yacht. While bigger than a sailboat, the appeal of these vessels is that they have retractable pilot houses that enable them to sail beneath low bridges and transit locks. This allows guests to have unique experiences sailing and exploring areas like the Erie Canal.

PLAN YOUR TRIP: Visit Fodor’s Erie Canal Village Review

Littleny |
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Florida Keys Sailing

WHERE: Florida

Arguably one of the best ways to see the Florida Keys is aboard a beautiful sailboat. The Florida Keys Sailing group offers longer adventures for experienced sailors and shorter trips for novice sailors looking to hone their skills. Guests can dive into activities including swimming and snorkeling or indulge in a dinner under the stars or on land at a tiki hut in the Keys. Ships in their fleet like the Catalina and the Irwin have air conditioning.

PLAN YOUR TRIP: Visit Fodor’s Florida Keys Travel Guide

Billy Black
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WHERE: Canada & Worldwide

This large-scale sailing company with adventures all over the world offers itineraries throughout Vancouver. While the itineraries can change whether it’s a bareboat charter or a skipper charter, they often include activities such as hiking, snorkeling, and kayaking. While aboard, guests sail through the dramatic scenery and wildlife of the Pacific Northwest.

PLAN YOUR TRIP: Visit Fodor’s Vancouver Travel Guide

Stevengaertner |
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Great Lakes Cruising Company

WHERE: Michigan

As the only cruise company specializing in sailing the Great Lakes, the Great Lakes Cruising Company consists of a fleet of small cruise ships, topping out at 200 guests that offer tours and itineraries sailing from Chicago to Toronto. Trips showcase the largest freshwater ecosystem in the world and offer a variety of land excursions.

PLAN YOUR TRIP: Visit Fodor’s Michigan Guide

Courtesy of Newport Beach Sail
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Newport Beach Sail

WHERE: California

At the Newport Beach Sailing School in California, travelers can choose from three-, five-, or seven-day “learn to sail vacations” aboard a Hunter sailboat. The adventures, while educational (participants can receive American Sailing Association credits), are also paired with recreational activities including kayaking, bike riding, and gondola rides.

PLAN YOUR TRIP: Visit Fodor’s Newport Beach Guide

Jonathange |
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Sailboat Charters of Miami

WHERE: Florida

This boutique sailing company offers sailing vacations to the Florida Keys as well as Bimini in the Bahamas. Guests can angle for local fish or anchor in remote destinations for snorkeling and water activities. In addition, they offer special occasion sailings, such as a seven-day honeymoon charter with a custom itinerary.

PLAN YOUR TRIP: Visit Fodor’s Top Things to Do in Miami Guide

Capt. Blain AndersonS/V BOB Sound Sailing – Sail Alaska​
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WHERE: Alaska

There’s no better way to see the beautiful landscape and wonders of Alaska than aboard the sailing vessel BOB, a wing-keeled 1993 Catalina/Morgan 50 that can accommodate up to six people. Trips depart from Sitka, Petersburg, or Juneau. Each trip sails to the Tongass National Forest as well as the Glacier Bay National Park.   

PLAN YOUR TRIP: Visit Fodor’s Alaska Tips and Resources