Wondering what destinations you can sail? No matter what your sailing experience is, Yacht4Less will help find the perfect sailing yacht charter for you!
In this guide, find the TOP 10 sailing routes around the world based on sailing experience level:
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The best part about sailing is that the whole world is your oyster! However certain destinations will be a better fit, depending on your sailing experience. Learn about the best sailing routes around the world for beginners to advanced levels.
Located in the East Mediterranean, the Greek Isles are a fan-favorite and are great for sailors of all levels! Here you can enjoy exploring golden sandy beaches, delicious greek food, and stunning panoramas of blue and white-washed houses built on the hillside.
With ideal sailing weather and an abundance of coves and bays for safe anchorage, Greece is the perfect sailing experience for beginners.
We specifically like the Southern Ionian Islands for novice sailors, as the sailing conditions are reliable and consistent. You’ll find constant and stable winds to propel you forward. You’ll never have to worry about surprise changes in the tides or the breeze - so you can relax and sail on!
For more advanced sailors we recommend a sailing yacht charter in the Cyclades. Here you’ll find stronger winds, usually Force 4 or above, from late June to mid-September. Morning and evening winds during high season are usually more manageable, but it definitely take an experienced sailor to navigate!
Destination Highlights: rock climbing on Itháki, Vasiliki and Myli Beach on Lefkada, hiking Mount Énos on Lefkada, sample local wines in Robola.
As the main sailing hub of the Adriatic Sea, Croatia is a can't-miss sailing experience. Enjoy the rich history of the region by wandering around the walled Medieval cities. Explore the abundant natural beauty with vineyards, local farms, forests and ocean.
Croatia has nice moderate winds that are much calmer than some other sailing routes around the world. All the islands are situated in close proximity to one another, so there are much shorter crossings when island hopping. With a variety of mooring options, you can choose from large marinas, small ports, to natural anchorages. But, rest assured - you’ll have no problems finding a place to park it for the night.
Destination Highlights: Sail through the Kornati Islands National Park, explore the UNESCO World Heritage Site of Dubrovnik City, wander the gardens at Lokrum Island, swim and bathe in the Krka Waterfalls of Skardin.
With over 50 islands, islets, and cays, the British Virgin Islands offer plenty to explore. As one of the best places to sail in the Caribbean, you’ll find beautiful warm weather, amazing snorkelling, and lots of beaches.
The BVIs enjoy nice calm waters, and due to the magnificent trade winds, you can count on a constant breeze. You’ll also enjoy easy line-of-sight navigation, where all you need to do is use visible reference points on land, or major landmarks to guide the boat.
Destination Highlights: Visit the Soggy Dollar Bar or Foxy’s on Jost Van Dyke, Swim in the baths at Virgin Gorda, Hike Norman Island.
Another one of the best places to sail in the Caribbean is the Bahamas. As home to one of the largest protected marine parks in the world, you’ll be able to spend your holiday snorkeling and swimming all day long!
For a Beginner sailor this is paradise! A tropical dreamland with perfect sailing conditions? Doesn’t get much better than that! The Bahamas enjoys steady trade winds of around 15 knots, and slightly more open water sailing, making them ideal for a beginner sailor, or an experienced sailor who wants to chill and relax.
Destination Highlights: Taste the delicious lobster in Green Turtle Cay, snorkel amidst the remains of the USS Adirondack at Man-O-War Cay, Sunbathe on Winding Bay’s bright white sand.
With 500km of coastline Mallorca is a top sailing yacht charter experience! In addition to Mallorca, the largest Balearic island, you have Ibiza and Menorca to explore as well. With nature, nightlife, and great culture, the Balearics have it all.
Because of the wonderful climate and excellent sailing conditions, the Balearics are a top yacht charter Mediterranean destination. It is good for a range of experience levels. More novice sailors will want to stick to the summer season to avoid the Mediterranean’s winter storms.
However, an experienced sailor could go at any point of the year. Also note that in the West coast of Mallorca it is tough to find moorings other than the Port de Sóller, and that in Alcudia, sudden strong swells can catch you by surprise.
Destination Highlights: Enjoy the island’s lovely little coves like Caló des Moro, Take a detour to the National Park on the island of Cabrera.
With an abundance of itinerary options, Italy has something to offer all sailors, regardless of experience. Enjoy sumptuous food and drink, rich cultural history, and stunning beauty around every turn.
For intermediate sailors, Italy offers Sicily. Here you’ll find more challenging navigation for an exhilarating sailing experience. You’ll also enjoy consistent winds, a narrow tidal range, and shorter sailing distances for island hopping.
Destination Highlights: Island hop through the UNESCO-protected Aeolian Islands, explore the quaint towns dotted along the Amalfi Coast, visit the wine country of Tuscany for a tasting or two.
Now, with 365 beaches on one island, Antigua is the beach lover’s dream. Here on Antigua you’ll find flora and fauna in abundance. Immerse yourself in the island culture at historical English Harbor. Swim with the turtles at Green Island.
With the lovely trade winds and an abundance of safe anchorages, Antigua is a great sailing destination.
Destination Highlights: Learn all about Antigua’s maritime history at Nelson’s Boat Yard UNESCO World Heritage Site, stop by Low Bay, Coco Point, English Harbour and Carlisle Bay, disconnect from civilization and go to Green Island, an uninhabited paradise.
Corsica is one of our favorite yacht charter Mediterranean locations! A French island, Corsica is a natural beauty and rich with culture. Swim with the whales and the dolphins in the deep blue waters of the Med. Enjoy the local Cosican cuisine and the friendly and welcoming people of the island too.
For those with a sailing license, or a skippers license, Corsica can be a great bareboat charter destination as it requires more advanced sailing experience. Here you’ll find stiffer Mistral winds due to the isolated thermal patterns. When navigating Corsica, it is best to wait for the wind to subside.
Winds are extra strong on the north cape of the island where the winds gather in the Bonifacio Strait, between Corsica and Sardinia. Since you’ll find brisk westerlies on the west coast of the island, a counterclockwise itinerary makes for easier sailing. The east coast is home to more protected anchorages.
Destination Highlights: Anchor in the Cove of Roccapina where there is a natural sculpture of a Lion, visit the Scandola Nature Reserve UNESCO World Heritage Site, explore the quaint town Cargèse.
Unspoilt by massive waves of tourists, Thailand is a sailing paradise for those with advanced sailing experience. Island hop in South East Asia, as you discover beautiful coastlines, mountainous terrain and magnificent beaches and coral reefs.
While a sailing license is not mandatory to charter here, you will need to demonstrate your sailing abilities with a resume. Thailand has a mix of long and short island hops, and plenty of line-of-sight navigation. However, a sailing yacht charter here can get quite windy due to the south westerly winds during the rainy season, which can get up to 27 knots. The tidal range in Thailand is also much larger than, say the Mediterranean. At 2 meters, you will need to plan in advance.
Destination Highlights: Scale the cliffs at Tonsai Bay, Hike through the rainforest at Ko Lanta, do some fishing for sailfish, mahi-mahi and giant trevally at Ko Racha Yai.
Relax in remote French Polynesia on a sailing experience of a lifetime. On your sailing yacht charter in French Polynesia you can explore Tahiti, Bora Bora, as well as Raiatea - known as the Windward and Leeward Islands. Coral reefs, and waterfalls seem to be more plentiful than people in this secluded, unspoilt destination.
For a French Polynesian sailing experience you can expect light southeast winds between 10-15 knots. Sometimes in the late summer (July & August) you may get strong winds of 20-30 knots and swells of 3-4ft, which is why French Polynesia may be best suited for those with sailing experience.
Also, there are larger open-water crossings between islands (6hrs or shorter), so for advanced sailors you can choose longer sailing distances.However, you will also enjoy easy line-of-sight navigation
Destination Highlights: Discover the volcano that formed Bora-Bora on the island of Topua, enjoy a drink with fellow seafarers at the Bora-Bora Yacht Club bar, explore the archaeological site of Taputapuatea Marae in Opoa.
If no one in your group has sailing experience, the most important step is choosing a destination that matches beginner level conditions. Some sailing areas are naturally more suitable for first time sailors, offering predictable winds, short distances between ports, well marked channels and good marina infrastructure.
Understanding these differences is essential, especially when considering a bareboat charter, where responsibility for the yacht and route planning lies with the crew.
This is where careful preparation becomes crucial. Selecting calm cruising grounds, limiting daily sailing hours and avoiding regions with strong winds or challenging navigation can make a significant difference to the overall experience.
Yacht4Less helps first time charter guests assess whether a destination is suitable for their skill level and explains when a bareboat charter may be realistic and when additional support should be considered. By matching experience level with the right sailing area, even newcomers can enjoy a safe and rewarding introduction to sailing holidays.
For real-time availability and pricing on sailing yacht, catamaran, gulet, power catamaran, and motorboat deals, visit our real-time search engine. This tool allows you to explore the best charter options instantly and secure your dream yacht charter with ease.
The yachting community's most-asked questions, answered by our experts.
Greece (Ionian), Croatia, the Bahamas, and the British Virgin Islands offer calm waters, short passages, and predictable winds - perfect for novice sailors.
The Ionian Islands are beginner-friendly with calm conditions, while the Cyclades challenge advanced sailors with strong Meltemi winds.
Yes. With short distances between islands, calm winds, and well-equipped marinas, Croatia is one of the easiest and most scenic sailing regions in Europe.
The BVI features line-of-sight navigation, sheltered waters, and steady trade winds - ideal for easy island-hopping and stress-free charters.
Yes. With steady 15-knot trade winds, warm waters, and safe anchorages, the Bahamas offer tropical sailing that suits both novices and relaxed cruisers.
The Balearic Islands (Spain), Italy (Sicily, Amalfi, Aeolian), and Antigua provide slightly more challenging winds and navigation while remaining manageable.
The Balearics mix calm coves with sudden swells and limited moorings on Mallorca’s west coast - requiring more confidence and planning.
Corsica, Thailand, and French Polynesia offer strong winds, tidal challenges, and remote island sailing - ideal for experienced skippers.
Yes, due to long distances, strong trade winds, and remote anchorages, French Polynesia is best suited for advanced sailors with offshore experience.
Beginners should choose calm, sheltered seas (Greece, Croatia, BVI). Intermediate sailors can explore the Balearics or Antigua, while experts tackle Corsica, Thailand, or French Polynesia.
Yes, you can easily enjoy a yachting holiday by opting for a skippered or fully-crewed charter. A professional skipper takes full responsibility for the navigation, safety, and mooring of the vessel. This allows you to relax and enjoy the scenery without needing any technical knowledge, making it an ideal choice for first-time sailors or families.
