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 repetitive. The places that have built serious sailing culture tend to offer all three, along with the charter fleets and marinas to support it.
The routes on this list range from classic island-hopping itineraries with centuries of maritime history to more remote coastal routes that demand greater self-sufficiency. Some are easy for less experienced sailors. Others require real skill and proper weather judgement. Local charter companies can also advise on which anchorages tend to get crowded and which stay quiet even during peak season.
Seasonal wind patterns determine almost everything about a sailing trip's success and choosing the right months separates a smooth passage from a difficult one.
The Glenan Islands have white sand beaches and turquoise water off Brittany's south coast. A sailing school on the main island has taught students since 1947. Tides rise and fall up to about 12 metres in some bays. The Brest maritime festival gathers hundreds of old ships every four years.
Barbuda's Codrington Lagoon has one of the largest frigate bird colonies in the Caribbean. Boats take visitors through the shallow water to see the nesting birds. Sailors reach Barbuda from Antigua on a day sail. Pink sand beaches run for miles along the island's south coast.
The Marlborough Sounds have about 1,500 kilometres of coastline made of drowned river valleys. Sailors move between quiet bays and forested hills in short hops. Picton, at the head of Queen Charlotte Sound, is a busy ferry port. Green lipped mussel farms line the water near the town of Havelock.
Raiatea and Tahaa, two islands in the Society group, share one coral reef and lagoon. Sailors circle both islands inside the reef in calm water. Charter boats leave from Raiatea for weeklong trips among the islands. Visitors can tour vanilla farms on Tahaa by small boat.
Port Vauban is one of the largest yacht harbours in the Mediterranean. A row of superyachts called Billionaires' Quay lines the western wall. Visitors can walk the ramparts of Fort Carre and watch boats glide in. Each September a yacht show fills the harbour with sleek sailboats and motor yachts.
Locals perform the Moreska sword dance in the walled old town each summer. Sailors tie up in the harbour beneath the cathedral tower. The Peljesac Channel nearby has steady afternoon winds that fill the sails. Lumbarda has sandy beaches and vineyards that make Grk white wine.
The Route du Rhum race ends in Pointe a Pitre after 3,500 miles across the Atlantic. Solo sailors leave Saint Malo in France every four years. Visitors can sail to the Iles des Saintes, a small island group with red roofed houses. Snorkellers can visit the Cousteau Reserve near Pigeon Island.
Every November hundreds of boats leave Las Palmas in the Atlantic Rally for Cruisers. The rally sails about 2,700 nautical miles to Saint Lucia in the Caribbean. Visitors can watch the start from the marina and see crews wave. Boats fill the docks for weeks as sailors stock food and fix rigging.
The Family Island Regatta in April races old style wooden sloops in George Town. It began in 1954 and draws large crowds to Elizabeth Harbour. Sailors anchor near Stocking Island to swim in calm turquoise water. Hikers can climb Hamburger Hill for a view over the harbour.
A short crossing leads from Kos to Bodrum in Turkey. Ruins of the Asklepion, an ancient healing centre, sit on a hill above town. Boats can sail south to Nisyros, an island with a walkable volcano crater. Kalymnos, north of Kos, is known for its sponge divers.
The Hole in the Rock, a natural arch at Piercy Island, is big enough for boats to sail through. The bay has 144 islands with sheltered coves and quiet anchorages. Bottlenose dolphins swim beside boats in the calm water. Historic Russell, once a whaling port, has cafes near the ferry pier.
Whitehaven Beach has seven kilometres of soft white silica sand. The sand stays cool underfoot even on hot summer days. Sailors anchor at Tongue Bay and hike to a lookout over the swirling water at Hill Inlet. Hamilton Island Race Week draws hundreds of yachts each August.
The Ionian Sea around this island has light winds that suit new sailors. Small islands such as Paxos and Antipaxos lie a short sail to the south. Sailors tie up in Gaios and eat fresh fish at waterfront tavernas. The old town of Corfu is a UNESCO site with Venetian forts.
In 1983 the Australian yacht Australia II won the America's Cup off Newport. That win ended 132 years of American victories in the race. Visitors can join a sail on a classic wooden yacht from the harbour. Mansions from the Gilded Age line the shore near Brenton Point.
The Pakleni Islands lie a short sail from Hvar town. Pine trees shade small beaches and coves on these rocky islets. Sailors tie up at Palmizana and eat in restaurants above the water. A fortress on the hill above town gives views of the anchored boats.
Simpson Bay Lagoon is a huge sheltered harbour shared by hundreds of yachts. Drawbridges open for boats several times a day for the crowds. The Heineken Regatta fills Great Bay with racing boats each March. One island holds two countries, French Saint Martin and Dutch Sint Maarten.
The Royal Swedish Yacht Club, founded in 1830, has its summer base at Sandhamn. Each summer a large race around Gotland starts from these waters. Sailors follow marked channels through bare granite islands and pine forests. Wooden ferries and small boats serve the smaller islands.
The Trofeo Princesa Sofia regatta fills Palma Bay with racing boats each spring. The Real Club Nautico de Palma hosts crews and judges on the seafront. Visitors can watch from Paseo Maritimo and eat tapas at nearby bars. The huge Gothic cathedral La Seu rises beside the harbour walls.
The Route du Rhum race starts here every four years in early November. Crews sail solo across the Atlantic to the island of Guadeloupe. Visitors can walk the granite ramparts and watch boats leave the port. At low tide the sea drops far enough to reach islands on foot.
Rodney Bay is the finish point for the Atlantic Rally for Cruisers each December. Crews cross the line after about three weeks at sea. Visitors can greet them on the dock with fruit and rum punch. The twin Pitons rise from the sea south of the bay.
The caldera bay was formed by a huge volcanic eruption around 1600 BC. Boats anchor near Thirasia, a quiet island on the western side of the bay. Sailors swim in the warm sulphur water of the hot springs near Palea Kameni. Sunset sails pass white villages on the cliff tops.
The America's Cup began here in 1851 when the schooner America beat British yachts. The race course circled the island off England's south coast. Cowes Week in August fills the Solent with racing boats. Visitors can watch from the seafront at Cowes or from a ferry.
The tall ship Shenandoah sails from Vineyard Haven harbour each summer. It was built in 1964 as a copy of an old schooner. Visitors can join a day sail and help haul the ropes. Edgartown, on the eastern shore, has captains' houses beside the yacht club.
Cabrera Archipelago National Park lies off the south coast in the Balearic Sea. Sailors must reserve a permit and a mooring before visiting. Clear water there is ideal for snorkelling among schools of fish. Boat trips reach Sa Calobra, where a narrow gorge opens to a pebble beach.
The Sydney to Hobart yacht race finishes at Constitution Dock in Hobart. Crowds gather around the dock in late December to greet the arriving crews. The Australian Wooden Boat Festival fills the docks every two years. Sailors can then explore the D'Entrecasteaux Channel and Bruny Island.
Admiral Andreas Miaoulis, born on Hydra, led Greek ships against the Ottomans in the 1820s. Ship captains from the island built grand stone mansions with their wealth. Sailors tie up at the horseshoe harbour and walk to cafes. Day sails link Hydra with Poros and Spetses in the Saronic Gulf.
Porto Montenegro in Tivat is a marina for superyachts on the Bay of Kotor. Narrow Verige Strait, about 340 metres wide, links the inner and outer bay. Sailors pass Perast and its two small islands with churches. Mountains rise steeply on all sides of the water.
One destination, 32 islands, countless possibilities
Tobago Cays Marine Park has five small uninhabited islands ringed by a horseshoe reef. Green sea turtles feed in the shallow seagrass near the anchorage. Snorkellers can swim beside the turtles in calm turquoise water. Bequia holds an Easter regatta each spring for traditional wooden boats.
Three limestone sea stacks called the Faraglioni rise from the water off the coast. Small boats can pass through the arch of the middle stack. Sailors anchor nearby to swim in deep blue water and eat lunch on deck. A slow sail around the whole island takes only a morning.
Diamond Rock, a tall stone in the sea, was once commissioned as a British warship. The Royal Navy placed cannons on it in 1804 to block French ships. Sailors can moor at Le Marin and swim at Sainte Anne beach. Each summer traditional yole boats race around the island.
Vavau in northern Tonga has dozens of islands close together in sheltered water. Humpback whales arrive with their calves from July to October. Visitors can slip into the water near them with licensed guides. Swallows Cave has a blue glow inside for snorkellers who enter by boat.
Kornati National Park has 89 islands and islets, mostly bare and rocky. Most lie just a few hours by sail from the town marina. Sailors anchor in quiet coves and dine at small family konobas. St James Cathedral in the old town is built entirely of stone.
The St Barth Bucket Regatta draws superyachts to Gustavia each March. Boats race in close pairs near shore in a friendly contest. Visitors can watch from the harbour and see the masts of huge sailboats. Gustavia has red roofs and Swedish street names from its past.
Hurricane Hole on St John has quiet mangrove bays inside a national monument. Boat owners tie up in the bays to shelter from storms. Trunk Bay has an underwater trail with signs for snorkellers. Virgin Islands National Park covers about 60 percent of St John.
Les Voiles de Saint Tropez gathers classic wooden yachts each late September. Old racing boats from the early 1900s sail close together in the bay. Visitors can watch from the harbour wall and chat with crews. Pampelonne beach has long sand and beach clubs just beyond the point.
A lagoon circles Mount Otemanu, an old volcano that rises 727 metres. Sailors anchor on the calm side of the reef and swim with rays. Small islets called motus have white sand and palm trees. Sharks and manta rays glide through the passes to the open sea.
Painted Venetian houses in Fiskardo survived the earthquake of 1953. Yachts tie stern to the quay in the small harbour beside the cafes. Sailors can cross to Ithaca, the home island of Odysseus, in a few hours. Myrtos Beach has white pebbles and bright blue water.
Christopher Columbus stopped at La Gomera in 1492 before crossing the Atlantic. Steady trade winds still push sailors west from these islands each winter. Marinas on Tenerife and Gran Canaria stock up boats for ocean trips. Many crews spend several weeks preparing here before heading to the Caribbean.
Es Vedra, a jagged rock about 380 metres tall, rises from the sea off the southwest coast. Boats anchor nearby and crews swim in deep blue water. Cala d'Hort has a small beach facing the rock at sunset. Ferries and sailing yachts both make the short crossing to Formentera.
Mindelo, on Sao Vicente island, is a busy stop for boats crossing the Atlantic. Its marina fills with crews in November and December. Live morna music, the island's slow blues style, plays in waterfront bars. Steady northeast winds make the channels between islands good for sailing.
English Harbour has Nelson's Dockyard, a Georgian naval base listed by UNESCO in 2016. Antigua Sailing Week fills the bay with racing yachts each spring. Visitors can walk up to Shirley Heights at sunset and watch boats return. Classic wooden yachts race here in April in a separate regatta.
Ses Illetes beach has white sand and clear water that looks like a lagoon. Boats anchor over sand between patches of seagrass that fish use for shelter. Mooring buoys protect the seagrass, which keeps the water clear. The island is a short sail south of Ibiza.
Sailors crossing the Atlantic paint pictures on the marina walls at Horta on Faial. Sailors believe the art brings good luck on the next leg. Peter Cafe Sport, a bar on the waterfront, is the classic meeting place for crews. Sperm whales and dolphins often swim near boats in the channel to Pico.
Windjammer schooners have sailed from Camden and Rockland on multiday trips since the 1930s. The old wooden ships visit small islands and quiet coves in Penobscot Bay. Guests can help raise sails and eat lobster on a beach. Fog often rolls in and cools the morning air.
Annapolis, on the Chesapeake Bay, hosts big sailboat and powerboat shows each October. Midshipmen at the Naval Academy train on sailing yachts in the harbour. Visitors can sail on a skipjack, a traditional oyster boat, on the bay. The skipjack is the official boat of Maryland.
A cable car and about 588 steps climb from the old port to town. Boats anchor below the cliffs in the sunken volcano crater. Small boats leave the old port for the volcano crater on Nea Kameni. Cruise ships and small yachts share the deep bay below the cliffs.
The Belize Barrier Reef runs about 300 kilometres along the coast of Central America. Sailors hop between small sandy islands called cayes in shallow blue water. Snorkellers can swim at Hol Chan Marine Reserve near Ambergris Caye. Glover's Reef, a ring shaped atoll, sits farther offshore with quiet anchorages.
Thousands of small islands and rocks lie between Finland and Sweden here. The four masted barque Pommern, built in 1903, is a museum ship in Mariehamn. Sailors follow short channels between islands with red painted fishing huts. Ferries and cyclists share the tiny bridges and roads on land.
Racing wooden sloops, built by hand, are the national sport on this small island. Big races run each August during the summer festival, drawing crowds to the beaches. Visitors can anchor at Sandy Ground and watch practice runs near shore. Prickly Pear Cays, a short sail north, have quiet white beaches.
Stromboli's volcano erupts every 15 to 20 minutes, lighting the night sky with red sparks. Seven volcanic islands lie close together off the north coast of Sicily. Sailors can anchor near Stromboli after dark and watch the glowing lava trail. Salina and Lipari offer sheltered harbours and small restaurants serving caper salad.
Traditional wooden boats called dhonis carry visitors between the coral atolls of this island nation. Their curved bows and simple designs have been used for centuries. Guests can snorkel over reefs and sleep on the boat deck. Sand banks appear at low tide for picnics far from shore.
Croatia has over a thousand islands and many of them lie off this coast. Vis, a remote island, was closed to foreign visitors until 1989. Boats can visit the Blue Cave on nearby Bisevo island. Charter yachts leave from Split each Saturday for week long trips.
Sir Francis Drake Channel is a sheltered strip of water bordered by islands. Boats hop from island to island in short daylight sails. The Baths on Virgin Gorda are giant granite boulders that form cool pools. Norman Island has caves where legend says pirates hid treasure.
The Monaco Yacht Show fills Port Hercule with superyachts each September. Superyachts tie up beneath the Prince's Palace and the casino. Farther along the coast, sailors can stop in Nice and the deep bay at Villefranche. Cannes, Antibes and Saint Tropez are all a day's sail apart.
The King's Cup Regatta has raced off Phuket each December since 1987. Boats sail on to Phang Nga Bay, where limestone towers rise from green water. Kayakers paddle into sea caves and lagoons near James Bond Island. Chalong Bay is a busy anchorage with restaurants along the pier.
The Newport Bermuda Race covers 635 nautical miles and is held every two years. The 2017 America's Cup took place in Bermuda's Great Sound. Visitors can watch sailboats from the ferry or from the old Royal Naval Dockyard. Pink sand beaches and a large reef ring the island.
Each October a huge boat show fills several marinas with yachts and sailboats. Canals lined with waterfront homes and private docks wind through the city. Visitors can take a water taxi to restaurants and beaches. Many yachts stop here for repairs and supplies before Caribbean trips.
Mahon harbour is a deep natural inlet about five kilometres long. Sailors glide in past old forts and white painted houses on the cliffs. Calas such as Macarella and Macarelleta have pale sand and clear water. The whole island has been a UNESCO Biosphere Reserve since 1993.
Two bronze deer stand on columns at the entrance of Mandraki harbour. Fort St Nicholas, built by the Knights in the 1400s, guards the mole. Sailors can tie up beside old windmills along the sea wall. Symi, a small island with pastel houses, is a short sail north.
The Strait of Bonifacio, between Corsica and Sardinia, is known for strong winds. White limestone cliffs rise above the old citadel town of Bonifacio. Sailors can enter its narrow harbour and tie up beside the fishing boats. The Lavezzi Islands nearby have granite rocks and clear turquoise water.
Orcas pass through Haro Strait, west of San Juan Island, from May to September. Sailors can watch the whales from a safe distance under the rules. Friday Harbor is the main town with a busy ferry dock and marina. Small islands offer state park docks and quiet anchorages.
The Royal Langkawi International Regatta brings racing yachts each January or February. The island group has 99 islands, many with mangrove creeks and caves. Boats visit Kilim Geoforest Park to see eagles and limestone rocks. Telaga Harbour and Rebak Marina shelter yachts near the west coast.
An underwater sculpture park in Molinere Bay has statues of people standing in a circle. Divers and snorkellers can see coral and fish gathering on the statues. Sailors anchor at Hog Island for beach barbecues on Sundays. Carriacou, a quiet island, sits a day sail to the north.
Wooden dhows with triangular sails carry passengers around Stone Town at sunset. Builders at Nungwi still shape the wooden hulls by hand with simple tools. Visitors can take a dhow to Prison Island to see giant tortoises. Mnemba Atoll has coral gardens and dolphins for snorkellers.
Gulets, wide wooden sailing boats, take guests on blue cruises along this Turkish coast. Trips visit the Twelve Islands and Butterfly Valley. Guests sleep on deck or in small cabins and swim from the boat. Oludeniz, a nearby lagoon with white sand, is a popular stop.
Naoussa is a fishing harbour with a small Venetian fort at the entrance. Colourful fishing boats float beside cafes and octopus drying on lines. Strong meltemi winds blow in summer and attract kite surfers to Pounda. Sailors can day trip to Antiparos and its cave.
Block Island lies about 13 miles off the coast of Rhode Island. Great Salt Pond is a busy harbour with a large field of moorings. Sailors can bike to Mohegan Bluffs and its tall clay cliffs. Narragansett Bay nearby holds more than thirty islands and quiet coves.
The Amedee Lighthouse was built in Paris and shipped in pieces to a tiny islet. Boats from Noumea reach the islet in under an hour. Visitors can climb 247 steps to the top for views of the reef. Sea turtles and sea snakes swim in the clear shallow water.
The Bazaruto Archipelago has five islands with tall sand dunes and clear blue water. Wooden dhows with triangular sails carry visitors from island to island. Snorkellers can see rays and reef fish near the island of Magaruque. Dugongs graze in the seagrass near the coast.
Procida, an island near Naples, has a fishing harbour lined with pink and yellow houses. The harbour, called Marina Corricella, has small boats tied along the quay. Sailors can visit Ischia and Capri on the same trip. Volcanic Ischia has hot springs that warm the seawater near the shore.
An Ottoman castle from 1522 overlooks the harbour and old bazaar. Gulets, wide wooden sailing boats, leave for Blue Voyage cruises along the coast. Pine covered mountains surround the bay and shade quiet anchorages. Sailors can explore the Bozburun Peninsula and its small fishing villages.
A floating bridge links the island to the mainland across a narrow canal. The bridge swings open for boats at set times each day. Sailors can moor at Nidri and take a short trip to Meganisi island. Porto Katsiki has tall white cliffs above turquoise water.
The Lerins Islands lie just offshore with pine forests and quiet coves. Ile Sainte-Marguerite has a fort where the Man in the Iron Mask was held. Sailors anchor off the islands to swim and have lunch on deck. The Cannes Yachting Festival fills the old harbour each September.
The La Maddalena Archipelago has dozens of granite islands with pink sand beaches. Park rules limit boats to protect the seagrass and beaches. Sailors anchor at Budelli to view Spiaggia Rosa from the water. Cala Coticcio on Caprera has clear water and fine white sand.
Boats leave Mahe for Praslin and La Digue in the trade winds. Praslin has the Vallee de Mai forest with giant coco de mer palms. La Digue has granite boulders on Anse Source d'Argent beach. Catamarans anchor off quiet bays with clear water and few boats.
Each year the Sydney to Hobart race starts on Boxing Day in the harbour. Boats race about 628 nautical miles south to Tasmania across Bass Strait. Visitors can watch the start from the shore or by ferry. The harbour also has quiet coves and beaches such as Store Beach.
A chain of islands and rocks called the skjaergard shelters the sea route north. Sailors can follow calm inner channels from here to Alesund. Sognefjord, the longest fjord in Norway, reaches inland about 200 kilometres. Colourful wooden warehouses at Bryggen line the harbour where Hanseatic ships once docked.
Li Galli, three small islets near Positano, are named for the Sirens of Greek myth. Sailors anchor beside them to swim in clear green water. Skippers can sail from Amalfi to Capri in about half a day. Steep cliffs, lemon terraces and colourful villages slide past the deck.
Trollfjord is a narrow inlet only about 100 metres wide and 2 kilometres long. Steep mountain walls tower over the water on both sides. Boats visit red painted fishing villages such as Henningsvaer and Reine. In summer the midnight sun keeps the sky bright all night.
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