Best Sailing Holidays For Solo Travellers

You don’t have to be a sailor to enjoy the freedom of sailing. Even if you don’t have good sea legs there are calm bays across the globe so you can still enjoy the solitude of the sea. Sailing takes you from one port to another, giving you the chance to disembark every time and spend some time in a new city or village, or on a different beach.

Sailing is for everyone whether you want to be the skipper or just lay on the deck and catch some rays whilst watching the world sail past – literally! If you're looking for solo sailing holidays, for this article, I've included the best sailing holidays for solo travellers based on all the gorgeous destinations that I've visited and the most popular for solos. 

If you don't have time to read the whole article and want to know my recommended company, I recommend these Tru Travels Sail Ventures for the under 40 solo. They are budget, sociable and fun! For over 40s, G Adventures offer sailing trips.  

Sailing Holidays For Solo Travellers

1. Croatia

Sailing Holidays For Solo Travellers

When you sail in Croatia you get to try wine tasting and partying!

Croatia has fast become a hot spot for sailing and with calm bays, pretty towns and a great party scene, we can see why it has gained popularity. Most visitors don’t get as far as the five islands that surround Dubrovnik and Split so the best way to see what Croatia has to offer is on a sailing trip.

There are a thousand or so islands along the Dalmatian coast and you can moor at charming fishing villages, swim in an inland lagoon or visit the island of Vis, which only opened to foreigners in 1989 and remains surprisingly unspoilt. The island of Hvar is the best place to watch the sunset in Croatia and also has the best party scene.

Croatia has calmer sailing and is perfect for those who just want to experience sailing without having to actually take part. * Check rates and availability for Croatia sailing trip

2. Greece

Sailing Holidays For Solo Travellers

Greece has some beautiful islands to island hop

Sailing in Greece offers more than just beautiful coves, Greek salads and the traditional Ouzu. The Aegean is the birthplace of the Greek seamanship and gives an insight into the Greek way of life, both old and new. Begin your sailing adventure from Epidavros in the Saronic Gulf for historical cities and ancient ruins, all whilst sailing past ancient landscape and rugged coastlines.

You’ll be spoilt for choice from the Ionian Sea to the Sporades; visit heaven-sent islands, traditional fishing villages and olive groves. Take a catamaran cruise around the breathtaking volcanic island of Santorini all whilst sampling fresh local Greek cuisine.

With a choice of bareboat skippered, sailboats, flotillas or yacht charter, sailing here caters for every level from novice to the more challenging. Sailing trips in Croatia and Greece are from May to September. * Check rates and availability for Greece sailing trip

3. Turkey

Sailing Holidays For Solo Travellers

You many not have considered Turkey but its coastline is a great place to sail

Turkey has so many interesting and fascinating places that sailing around them is one of the best ways to explore the Turkish sites and coastline. You can choose a sailing trip for a few days or even a week to explore Turkey’s most beautiful islands such as St Nicholas Island, a beautiful place with great cultural value because of the ruins from ancient times.

Others are Tersane Island and Yessica Islands, where you can visit the largest naval port and the island on which, according to tradition, the devil lives.

If the boat starts from Fethiye, you’ll see places such as Bodrum, Marmaris, Kemer, Rodhos, Kos or Demre and also get a chance to swim along the way. There are plenty of ruins to see too. You can choose a luxury week self-catering holiday or if you are short on time, experience the Turkish coastline from just four days. 

Croatia, Greece and Turkey all offer some of the best sailing holidays for solo travellers. Sailing in Turkey starts in April and finishes in November making it an ideal destination for the beginning of the winter. * Check rates and availability for Turkey sailing trip

4. Caribbean

Sailing Holidays For Solo Travellers

Can you beat the Caribbean for stunning beaches?

Is there any better way to see the Caribbean than by sailing around it? Sailing around the Caribbean allows you to see more than one island, explore the gorgeous beaches and jump into the crystal clear Caribbean sea whenever you want. The Caribbean is grouped into clusters of islands. Although the islands are synonymous with families and couples, you can still explore them as a solo especially on a sailing holiday. 

Divided into the Lesser Antilles and the Greater Antilles you sail around the Cayman Islands, Dominican Republic, Jamaica, Cuba and Puerto Rico and stop off in Havana to experience a taste of Cuban life and Cuban salsa; see the Seven-Mile Beach in Jamaica and listen to some Caribbean reggae; or go diving at one of the three Cayman Islands.

Puerto Rico is a great destination to stop at and watch live, cultural performances at Plaza de Aromas after meandering past the colourful buildings in Old San Juan.

The Leeward Islands are another group of islands to visit. Experience the French islands of Saint Barts or Guadeloupe, or the English-speaking islands of Anguilla and the British Virgin Islands – an archipelago of sixty islands with National Parks and shipwrecks to explore.

Antigua is one of the main sailing hubs and has hundreds of beautiful white beaches. You can even go zip lining here. As some of the most exclusive in the Caribbean sailing to these islands will give you a different type of holiday than Cuba or Jamaica for example. * Check rates and availability for Caribbean sailing trips

5. The Maldives

Sailing Holidays For Solo Travellers

You don't need to be part of a couple to visit the Maldives

If you’ve ever imagined yourself sailing through a tropical paradise made up of 26 atolls and over 1,000 coral islands, you have to go to the Maldives.

The waters are a crystal-clear turquoise, and the sandy beaches are like something out of a postcard. It’s honestly one of the most beautiful places that I have been to.

The best part about sailing in the Maldives is that the winds are just right for sailing, and the lagoons are so calm that it's like sailing on glass. Plus, there are these amazing coral reefs that are perfect for snorkeling and diving. You'll get up close and personal with all sorts of marine life, from colourful fish to graceful manta rays on a traditional dhoni (or you can choose a more modern dhoni to hop aboard.

Sailing in the Maldives is like stepping into a dreamy aquatic adventure. It's nature at its most breathtaking, and an experience you definitely won’t forget. * Check rates and availability for Maldives sailing

6. Whitsundays

Sailing Holidays For Solo Travellers

If you're ‘Down Under' you have to visit the Windsundays

Where better to sail than at one of the Seven Natural Wonders of the World? The 74 Whitsunday Islands off the tropical coast of Queensland are Australia’s sailing paradise and are surprisingly lush. Secluded bays and inhabited islands offer relaxation and solitude and you don’t even have to leave the vessel. If you do want to explore, take an island or reef tour or just moor up and indulge in an island spa treatment.

The pearl of the reef has to be Whitehaven Beach – its pure white beach dazzles you as you approach by sea. Here you can see manta rays swimming along the shoreline and the only way to experience this white sand haven is by boat or a helicopter ride.

It has been named Queensland’s Most Beautiful Beach and also the friendliest! Take a swim in its warm bay or walk along its white shoreline, you can even polish your silver jewellery in its crystal clear waters.

The Whitsundays are perfect for relaxation and offer a choice of catamaran, bareboat or traditional sailing. You don’t need to pre-book either as you’ll find sailing companies in Australia. Book and board your sailing trip from Airlie Beach (and party here beforehand). * Check rates and availability for Whitsundays sailing trips

7. Thailand

Sailing Holidays For Solo Travellers

Known for its limestone karsts, Thailand is beautiful to sail around

Thailand is not only perfect for island hopping, but it’s also a dream destination to sail too. Picture yourself cruising on crystal-clear waters, surrounded by lush green islands and warm, welcoming locals (it’s not called The Land of Smiles for no reason),

Whether you're a seasoned sailor or just starting, Thailand's got it all. On the west coast, Phuket, known as the “Pearl of the Andaman,” is a renowned sailing hub with its picturesque anchorages and world-class marinas. 

And then there's the Andaman Sea's magical Phi Phi Islands and Krabi's towering limestone cliffs. If you head east to the Gulf of Thailand, you'll discover the Koh Samui archipelago with its calm, charming bays.

You can sail from Phuket to Ko Phi Phi on a 4 day trip or spend a week sailing from Phuket to Phuket past the beautiful Railay Beach, Phang Nag, Ko Yao Yai, and Ko Racha Noi. * Check rates and availability for Thailand sailing trips

8. Canary Islands

Sailing Holidays For Solo Travellers

The Canary Islands are a great option for sailing

If you’ve explored the Caribbean and Europe, then how about the coast of Africa? Located off Africa’s northwest coast, the Spanish archipelago of the Canary Islands boasts year-round sunshine, making it a sailor's paradise. Each island offers a unique experience, from the lively nightlife of Tenerife to the tranquil beaches of La Palma.

The trade winds provide excellent conditions for sailing, and the diverse coastline promises everything from serene coves to rugged cliffs. I love these islands that are just stunning with their volcanic landscapes and black sand beaches.

From Tenerife you’ll sail to Colon, then to the island of La Palma (which is popular for hiking) before heading to La Gomera, known as the magical island, before returning back to the popular island of Tenerife. * Check rates and availability: Canary Island sailing

Final thoughts…

These are just some of the best places to go sailing around the world. Sailing holidays allow you to have a holiday island hopping with like-minded others. Some sailing companies pair you with another solo traveller but you can upgrade so that you don't have to share a cabin with someone. Boat Outfitters are a good resource for sailing too. 

One thing's for sure, wherever you end up sailing, there is no better way to see the world than by exploring it from the sea. 

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Best Sailing Holidays For Solo Travellers

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