Best sailing destinations in North America
Best sailing destinations in North America
Protected island passages and historic coastal sound networks in North America
Warm island chains in the Caribbean anchor much of the region's sailing reputation, with reliable trade winds and a high concentration of sheltered anchorages within short distances of each other. A rockier coastline further north offers a considerably different, colder sailing tradition.
The destinations on this list range from warm-water Caribbean routes built specifically around charter tourism to colder coastal sailing further north with a longer, more traditional maritime history. Conditions and required experience vary considerably between the two.
Booking well ahead for Caribbean peak season matters considerably, since the best boats and routes fill up months before winter arrives. Local charter companies can advise on which anchorages stay quietest. Packing reef-safe sunscreen also matters considerably given the sensitivity of the surrounding marine environment.
Lists by region
Archipelago in United States
San Juan Islands
Remote islands where glaciers meet turquoise seas
Compared with the open Pacific coast, the San Juan Islands have sheltered waters between more than 170 named islands, so sailors anchor in quiet coves with views of Mount Baker. Orcas, harbour seals and bald eagles are often seen while the marinas at Friday Harbor and Roche Harbor are a short sail apart.
Outer Territory in United Kingdom
British Virgin Islands
Pristine sailing paradise with beaches
Sailors on Jost Van Dyke swim ashore from anchored boats to the Soggy Dollar Bar, which is said to be the birthplace of the Painkiller rum drink. The islands are close together, so charter boats sail from one sheltered anchorage to the next in a few hours, passing The Baths on Virgin Gorda.
Island in United States
Martha's Vineyard
Quaint New England by the Sea
July and August are the busy sailing months around Martha's Vineyard, when yachts fill the harbours of Edgartown and Vineyard Haven and race weekends take place on Nantucket Sound. Sailors visit Menemsha, a fishing village, to eat lobster rolls on the dock and watch the sun set.
State/Prefecture in United States
Rhode Island
Coastal Charm and Historic Delights
The Herreshoff Manufacturing Company in Bristol built several America's Cup winning yachts between 1893 and 1920 while the Herreshoff Marine Museum there still has classic wooden boats on display. Narragansett Bay has more than 30 islands, while Block Island, 13 miles offshore, has cliffs and a protected harbour.
Island in Bahamas
Great Exuma Island
Crystal clear waters and tranquility
Stocking Island, a thin strip of land that shelters the harbour at Georgetown, has a beach bar called Chat n Chill and coves where hundreds of cruising boats anchor each winter. A short sail north, the Exuma Cays have swimming pigs on Big Major Cay and clear shallow water.
State/Prefecture in United States
Maryland
Historic Charm and Chesapeake Bay
Compared with open ocean sailing, the Chesapeake Bay is a sheltered bay with hundreds of creeks, so sailors anchor in quiet coves and stop at crab houses in towns such as St Michaels. In Annapolis, home of the US Naval Academy, sailors race on Wednesday nights and gather in October for the sailboat show.
State/Prefecture in United States
Maine
Lobsters, Lighthouses and Lush Landscapes
Maine has thousands of islands and a coastline of more than 3,000 miles when bays and inlets are counted. In Penobscot Bay, windjammers, old style sailing schooners, leave from Camden and Rockland on trips of a few days while sailors anchor in quiet coves with lighthouses, ospreys, seals and lobster boats.
Outer Territory in United States
U.S. Virgin Islands
Caribbean Paradise with U.S. Convenience
Trunk Bay on St John has an underwater snorkelling trail with signs that name the fish and coral, in a national park that covers about 60 percent of the island. Sailors pick up moorings in quiet bays while St Thomas has a deep harbour that was a Danish trading port in the 1600s.
City in United States
Fort Lauderdale
Venice of America's Sunny Shores
Like a Venice with palm trees, Fort Lauderdale has about 300 miles of waterways with canals lined by yachts at back yard docks. Each autumn sailors gather for the Fort Lauderdale International Boat Show while the Bahamas are only a day's sail across the Gulf Stream.
Outer Territory in United Kingdom
Bermuda
Pink sands and turquoise waters
The Newport Bermuda Race, a 635 mile ocean race first held in 1906, ends in Bermuda every two years in June, when hundreds of sailors fill the docks of the Great Sound. The islands also have pink sand beaches and calm harbours where the America's Cup was sailed in 2017.
Outer Territory in France
Martinique
Tropical Charm and French Flair
Martinique makes its rum from fresh sugar cane juice instead of molasses, a style called rhum agricole, so sailors often tour a distillery before a punch on the dock. Le Marin on the south coast has a big charter base, while boats anchor off Saint Pierre, a town destroyed by Mount Pelee in 1902.
Country
Saint Vincent and the Grenadines
One destination, 32 islands, countless possibilities
Boatbuilders on Bequia still make wooden sailing boats by hand, while each Easter the island holds a regatta where traditional boats race beside visiting yachts. Sailors in the Grenadines hop between small islands to reach the Tobago Cays, a marine park where turtles swim in shallow turquoise water.
Outer Territory in United Kingdom
Anguilla
Pristine beaches and turquoise waters
Sandy Island, a tiny sand cay with a few palm trees and a beach bar, is a short sail from Road Bay on Anguilla. The flat coral island has more than 30 beaches, while sailors race traditional wooden sloops, the national sport, in regattas each August.
Country
Antigua and Barbuda
Tropical paradise with pristine beaches
The calls of frigatebirds are part of Codrington Lagoon on Barbuda, where boaters cross a shallow channel to see one of the largest colonies of these seabirds in the world. Sailors then anchor off a long pink sand beach while Antigua, the larger island, is a day sail to the south.
Country
Saint Lucia
Tropical paradise with volcanic mountains
Gros Piton and Petit Piton, two volcanic spires about 2,600 and 2,400 feet high, rise straight from the sea on the southwest coast of St Lucia, where sailors tie up to moorings between them. In December boats finishing the Atlantic Rally for Cruisers sail into Rodney Bay after crossing from the Canary Islands.
City in United States
Newport (Rhode Island)
Coastal charm meets historic elegance in Newport
Newport was the home of the America's Cup yacht races from 1930 to 1983, while today the harbour still has racing yachts under sail past Fort Adams. Mansions from the Gilded Age stand along Cliff Walk, a path above the sea, while the town is the start of the Newport Bermuda Race.
Overseas Territory in France
Saint Barthélemy
Luxury Island with Caribbean Charm
Fresh baguettes and superyachts lined up along the harbour are part of Gustavia, the small capital of St Barth, where French bakeries and cafes sit beside luxury shops. Each March crews of giant sailing yachts race around the island in the St Barths Bucket Regatta.
Island in Antigua and Barbuda
Antigua
365 beaches and turquoise waters
Nelson's Dockyard in English Harbour was a Royal Navy base in the 1700s while today it is a marina and UNESCO World Heritage site with Georgian buildings. Racing yachts crowd the bays during Antigua Sailing Week, held each spring since 1967, while the island has hundreds of coves for anchoring.
Country
Belize
Tropical paradise with diverse ecosystems
Off the Caribbean coast of Central America, Belize has a barrier reef about 190 miles long with hundreds of small islands called cayes. Sailors hop from Caye Caulker to Glover's Reef, where snorkellers swim over coral in calm water, while divers visit the Great Blue Hole, a sinkhole 407 feet deep.
Outer Territory in France
Guadeloupe
Caribbean Gem with French Flair
The smell of grilled fish and spiced Creole cooking drifts across the harbour at Terre de Haut in Les Saintes, an island group south of Guadeloupe with a horseshoe bay ringed by green hills. Snorkellers sail to Pigeon Island, a marine reserve made famous by Jacques Cousteau.
Country
Grenada
The Spice Isle's Hidden Charms
Grenada was settled by the French in the 1650s and later taken by the British, while the island is still called the Spice Isle for the nutmeg and cinnamon grown on its hillsides. It lies south of the usual hurricane track, so cruising boats stay in bays such as Prickly Bay in summer.
Island
St. Martin
Dual-Nation Beaches, Cuisine and Culture
In early March hundreds of sailboats race around the island in a big regatta that has been held since 1981, when sailors fill the bars of Simpson Bay with music. The island is shared by French Saint Martin and Dutch Sint Maarten while the Simpson Bay Lagoon is a protected anchorage opened by drawbridges.
Other lists you may like
Discover
Best sailing destinations in Africa
East African coastlines and remote Indian Ocean island chains anchor much of Africa's sailing tourism, with warm water and a string of islands well suited to multi-day charters.…
Read more
Discover
Best sailing destinations in Asia
Andaman Sea waters and island chains further east anchor much of Southeast Asia's sailing scene, combining limestone island scenery with generally warm, manageable sailing…
Read more
Discover
Best sailing destinations in Europe
Mediterranean island chains anchor much of Europe's sailing tourism, both offering hundreds of sheltered anchorages within manageable distances of each other, supported by decades…
Read more
Discover
Best sailing destinations in Oceania
A reef-sheltered island group off Australia's coast anchors much of the region's sailing tourism, offering sheltered, reef-protected waters well suited to both bareboat and…
Read more
Discover
Best sailing destinations in South America
Southern Chile's fjords offer some of the most dramatic, demanding sailing anywhere on earth, cutting through glacier-fed channels far from any major town. A warmer Atlantic…
Read more
Discover
Top sailing destinations and yachting routes
A good sailing destination needs the right combination of wind, protected anchorages and enough islands or coastline variety to make a multi-day route interesting rather than…
Read more
What other users say about travelfilters
“travelfilters made it easy for me to find ski areas and compare what else they offer, so that I could find the best place for my personal travel style.”
Chris
Snowboarding & Onsen trip to Japan
“I love how transparent the data feels. There is no pushy upsell, just honest information and settings I can tune to my own travel style.”
Maria
After booking her 2027 winter escape
“The level of detail for each destination and how well those are displayed, make planning feel confident instead of overwhelming.”
Mina
Planned a week in New York City
“We used travelfilters for our planning from start to end. The trip turned out even better than expected, thanks to all their tools and customisation options.”
Allan & Etienne
Trip to Japan to see autumn foliage
“Thanks to travelfilters, I found some hidden gems to see. Being able to filter for exactly your interests is a game changer for my travel planning.”
Michael
Tour through the old cities of Northern Italy
“The customizable filters helped me find a quiet beach town with good wifi and low season crowds in under five minutes.”
Diego
Weekend Escape to Llanes, Spain
“The airport connection map saved me hours by showing good flight options from my home airport to lesser-known cities.”
Nguyen
Planning a 2027 trip to France
“The website is clean, fast and focused on the search itself, which makes travelfilters feel more like a professional tool than an ad-heavy booking site.”
Hassan
Christmas Market trip, Germany
