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Best sailing destinations in North America

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Newport (Rhode Island)
Coastal charm meets historic elegance in Newport
8.8
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.
Highlights:
  • 🦞 Savor fresh lobster rolls at a waterfront shack
  • 🏰 Tour historic mansions like The Breakers
  • 🏖️ Climb Cliff Walk for breathtaking ocean vistas
San Juan Islands
Remote islands where glaciers meet turquoise seas
8.9
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.
Highlights:
  • 🥾 Hike to scenic viewpoints in Admiralty Island
  • 🚣‍♂️ Kayak through calm waters of Lake Clark
  • 🏰 Explore historic Fort William Henry ruins
Anguilla
Pristine beaches and turquoise waters
7.8
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.
Highlights:
  • 🐠 Snorkel with colorful reef fish at Little Bay
  • ⛵ Sail around the island’s turquoise waters on a catamaran
  • 🏖️ Relax on the powdery white sands of Shoal Bay
British Virgin Islands
Pristine sailing paradise with beaches
8.2
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.
Highlights:
  • 🐠 Snorkel over coral gardens in the crystal waters of Norman Island
  • 🏞️ Swim through the massive granite boulders at The Baths
  • ⛵ Sail between Tortola, Virgin Gorda, and Anegada islands
Saint Barthélemy
Luxury Island with Caribbean Charm
8.6
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.
Highlights:
  • 🐠 Discover marine life in the Nature Reserve marine zone
  • ⛰️ Hike to the summit of Morne du Vitet
  • 🏖️ Relax on the idyllic Colombier Beach
U.S. Virgin Islands
Caribbean Paradise with U.S. Convenience
8.3
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.
Highlights:
  • 🥾 Hike the scenic Reef Bay Trail and visit ruins
  • 🤿 Snorkel the vibrant coral reefs at Trunk Bay
  • 🏖️ Relax on the white sands of Magens Bay Beach
Great Exuma Island
Crystal clear waters and tranquility
7.9
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.
Highlights:
  • 🤿 Snorkel at Thunderball Grotto from the James Bond film
  • ⛵ Sail through the crystal-clear waters of the Exuma Cays
  • 🐷 Swim with the famous Exuma pigs at Pig Beach
Antigua and Barbuda
Tropical paradise with pristine beaches
7.6
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.
Highlights:
  • 🏰 Explore historic Nelson’s Dockyard in English Harbour
  • 🤿 Snorkel among vibrant coral reefs at Cades Reef
  • 🌸 Relax on the famous pink sands of Barbuda Beach
Bermuda
Pink sands and turquoise waters
8.4
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.
Highlights:
  • 🤿 Snorkel around vibrant coral reefs in Tobacco Bay
  • 🕳️ Explore the Crystal Caves and marvel at limestone formations
  • 🌸 Relax on the stunning pink sands of Horseshoe Bay Beach
Guadeloupe
Caribbean Gem with French Flair
7.6
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.
Highlights:
  • 🏖️ Relax and swim on the pristine beaches of Sainte-Anne
  • 🤿 Snorkel or dive at the Réserve Cousteau marine park
  • 🏞️ Hike to the stunning waterfalls in Guadeloupe National Park
Rhode Island
Coastal Charm and Historic Delights
7.3
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.
Highlights:
  • 🔥 Experience the WaterFire art installation in Providence
  • 🏰 Tour the opulent Gilded Age mansion The Breakers
  • 🌊 Walk the scenic Newport Cliff Walk coastline
Saint Vincent and the Grenadines
One destination, 32 islands, countless possibilities
7.6
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.
Highlights:
  • 🏰 Explore Fort Charlotte with panoramic Kingstown views
  • 🏖️ Relax on the pristine beaches of Tobago Cays
  • 🌋 Hike to the crater of La Soufrière volcano
St. Martin
Dual-Nation Beaches, Cuisine and Culture
7.8
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.
Highlights:
  • 🏖️ Relax on the pristine sands of Orient Bay Beach
  • 🥾 Hike to the highest point at Pic Paradis
  • ✈️ Watch planes land at the famous Maho Beach
Saint Lucia
Tropical paradise with volcanic mountains
7.5
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.
Highlights:
  • 🐠 Snorkel the colorful reefs of Anse Chastanet
  • 🫧 Soak in the volcanic Sulphur Springs mud baths
  • ⛰️ Climb the majestic Pitons for breathtaking island views
Martinique
Tropical Charm and French Flair
7.5
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.
Highlights:
  • 🏙️ Wander through colorful streets of Fort-de-France
  • 🏖️ Swim in crystal-clear waters at Les Salines Beach
  • 🌋 Hike to the summit of Mount Pelée volcano
Martha's Vineyard
Quaint New England by the Sea
7.5
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.
Highlights:
  • 🚴‍♂️ Cycle the scenic coastal route between Edgartown and Katama Beach
  • 🏡 Stroll through the colorful gingerbread cottages in Oak Bluffs
  • 🌅 Watch the sunset from the Gay Head Cliffs in Aquinnah
Maine
Lobsters, Lighthouses and Lush Landscapes
8.0
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.
Highlights:
  • 🏖️ Visit the Portland Head Light, Maine’s iconic lighthouse
  • 🦞 Eat a freshly steamed lobster at a coastal shack
  • 🌄 Watch the sunrise from Cadillac Mountain in Acadia National Park
Maryland
Historic Charm and Chesapeake Bay
7.2
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.
Highlights:
  • 🏰 Tour Fort McHenry, birthplace of the national anthem
  • 🦀 Try blue crab at a Baltimore Inner Harbor restaurant
  • ⚓ Explore the historic waterfront and U.S. Naval Academy in Annapolis
Fort Lauderdale
Venice of America's Sunny Shores
7.4
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.
Highlights:
  • 🏡 Tour the historic Bonnet House Museum and Gardens
  • 🏖️ Relax and sunbathe on Fort Lauderdale’s sandy beaches
  • 🛍️ Stroll lively Las Olas Boulevard’s shops and eateries
Antigua
365 beaches and turquoise waters
7.8
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.
Highlights:
  • 🌅 Hike to Shirley Heights for sunset and steel drum music
  • 🏖️ Relax on the pristine sands of Dickenson Bay Beach
  • ⚓ Explore historic Nelson’s Dockyard, a UNESCO site
Grenada
The Spice Isle's Hidden Charms
7.6
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.
Highlights:
  • 🌿 Hike through Grand Etang National Park’s lush rainforest
  • 🤿 Dive to explore the underwater sculptures at Molinière Bay
  • 🏖️ Relax on the powdery white sands of Grand Anse Beach
Belize
Tropical paradise with diverse ecosystems
7.0
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.
Highlights:
  • ⛵ Sail between tropical cayes across the Belize Barrier Reef
  • 🏛️ Explore ancient Mayan ruins at Xunantunich and Caracol
  • 🤿 Dive or snorkel the breathtaking Great Blue Hole
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