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The most beautiful islands to explore by sailboat

Best Destination Guide

Whether one is in the Mediterranean Sea, Caribbean, or the colder seas of the North, there are many fascinating, often little-known islands all waiting to be discovered, and the best way to do this is aboard a sailboat!

Some locations are more famous and well-known not so much because they are more beautiful than others, but because they are more convenient and easier for mass tourism to reach. While some islands are well connected to the mainland by planes or ferries, there are other islands that are more difficult to reach and certainly less touristy. 

Some are inhabited only during the high season and are so wild that they have just a few restaurants and a few houses, or not even that. Others are larger and structured for tourist accommodation, but the fact that they have no airport and have to be reached by one or more ferries leaves them sheltered from mass tourism.

If you are looking for tranquility, nature and authentic places, this is where you need to head for, and there is no better way to do so than on board a sailboat

A sailing vacation ensures a number of advantages: first and foremost, the ability to move freely as the wind blows, move from one cove to another in no time, reach bays and caves that would otherwise be unreachable, and go ashore by tender to explore the most unspoiled places. 

If you don't know which one to choose, in this article we recommend some well-known and lesser-known islands to include in your itinerary-you'll be spoiled for choice!

The most beautiful islands to see in the Mediterranean...

Lavezzi Islands - Corsica, France

Lavezzi Islands - Corsica, France

Located in the azure Mediterranean between Corsica e il Northern Sardinia, the paradisiacal Lavezzi Islands dominated by nature invite sailors to explore. Also called the "Seychelles of the Mediterranean," the islands can be reached from Bonifacio or the Maddalena Archipelago. Of all of them only the island of Cavallo is inhabited, the others have remained almost completely wild; only Lavezzi, Cavallo and Piana can be reached by boat. Bays with white and golden sand beaches, granite rocks, and fauna and flora rich in different species make this small archipelago something rare and unique. Landing on one of these islands you will be greeted by the scent of laurel, wild herbs and sounds of sea birds. Sailing through these waters you will also have the opportunity to spot some dolphins.

Vis - Split Archipelago, Croatia

Vis - Split Archipelago, Croatia

The island offers just the right combination of unspoiled nature and life on land. It is definitely one of the most interesting Croatian islands to explore by sailboat thanks to its rugged coastline that forms more than 50 bays. Whether you decide to stop at a roadstead to enjoy the silence and admire the starry sky, or dock in port for an evening out in one of the many typical towns, you'll be spoiled for choice. There is certainly no shortage of caves on the island to explore by swimming or dinghy. The most famous is the Blue Cave of Bisevo where the light colors the walls a deep blue, a mesmerizing sight not to be missed. But there are more than just natural caves: Vis has long been a military base and still retains the scars of that period. In fact, the island is home to several now-abandoned submarine moorings: the long, narrow cavities that were created to house them are a very special type of "cave" to see, or an alternative mooring for your sailboat.

Giglio Island - Tuscan Archipelago, Italy

Giglio Island - Tuscan Archipelago, Italy

Giglio Island is one of the most beautiful islands in the Tuscan archipelago. Inhabited by a few residents who are mostly involved in fishing, the island offers scenery of great beauty both above and underwater. Not surprisingly, it is a favorite destination for divers and nature lovers. The hinterland is dotted with numerous trails suitable for everyone. Visiting it by sailboat you can see striking coves such as Cannelle, Caldane and Campese with clear water and a beach covered with quartz crystals. Perfect destination for a weekend getaway even during the low season months.

Sifnos - Cyclades Islands, Greece

Sifnos - Cyclades Islands, Greece

Located in the western Cyclades, this island is little known compared to neighboring Milos and Paros, but it has something to offer for everyone, both on land and from the sea. The island surprises with the lush nature it hosts among olive and almond trees, oleander-covered valleys, hills of junipers and herbs. Those who love to walk will get lost in the narrow streets of Apollonia, the main town, and picturesque villages such as Kastro characterized by typical white houses with blue domes. The island has the distinction of housing as many as 365 churches, one for each day of the year, all to be discovered. The coastline is rugged, creating many bays and coves to explore by sailboat.

Ustica - Sicily, Italy

Ustica - Sicily, Italy

If you are spending a boating vacation along the Zingaro Nature Reserve, you cannot fail to make a detour to Ustica, which is less than 40 nautical miles from Palermo. Its characteristic is the presence of numerous caves rich in marine fauna, which open along the high and steep coastline, natural pools, numerous rocks and shoals present all around. Legend has it that in the past the island was the home of the sorceress Circe, narrated in the Odyssey; today it is one of the most intact Marine Protected Areas in the Mediterranean. The best way to explore this beautiful island is by sailboat: it will allow you to tour the whole area without too much difficulty and reach the most hidden coves.

Alonissos - Sporades Islands, Greece

Alonissos - Sporades Islands, Greece

Among the most remote of the Sporades islands, but undoubtedly the closest to nature. The island is entirely protected by a marine park and preserves its ecosystem, so much so that it is still one of the few in the Mediterranean inhabited by monk seals. The park includes not only Alonissos but also nearby islets such as Peristera, Gioura, Piperi,... all uninhabited but easily accessible by sailboat. Here, more than anywhere else, you are surrounded by the blue sea; everywhere you turn, you will see nothing but deep blue waters. The island is the ideal destination for nature lovers, you will not find sandy beaches or settlements to party in, only peace and tranquility surrounded by unique landscapes. Little curiosity: the island was the set of the famous movie "Mamma Mia" starring Meryl Streep.

Sa Dragonera - Majorca, Spain

Sa Dragonera - Majorca, Spain

If you are spending your vacation sailing the waters of Mallorca, you cannot miss Sa Dragonera, the dragon-shaped island and nature reserve. The island is easily accessible from Port d'Andratx, Camp de Mar, Paguera or Sant Elm. It is home to numerous diving areas, hiking trails, and the Far Vell lighthouse, which offers breathtaking views of the Mallorcan coastline. Almost no other place in the entire Balearic archipelago offers such an opportunity to avoid the city chaos. Immerse yourself in nature and be enchanted by the flight of seabirds, lizards, and beautiful views!

Galesno, the island of lovers - Croatia

Galesno, the island of lovers - Croatia

Famous for its unique shape depicting a heart, the island lies between the Dalmatian coast and the island of Pasman and is a true work of natural art. By looking it up on satellite maps you can admire its perfect shape. It is an ideal destination for couples in love and can be reached only by boat. More than an island, it is an islet, measuring only 132 square kilometers, surrounded by crystal clear waters that vary in shades of blue and emerald. Completely uninhabited, it is home only to lots of vegetation and rocks. Be careful because being a private island it is not possible to dock without permits.

La Graciosa - Canary Islands, Spain

La Graciosa - Canary Islands, Spain

This island is an unspoiled paradise; located north of Lanzarote, it can obviously only be reached by sea. Arriving by private boat you will need a permit to reach the harbor or anchor in one of the beautiful bays. The island has no paved roads and by exploring it you will feel catapulted into the Wild West. You can also rent bicycles and reach the more secluded beaches. The island is said to have been a source of inspiration for Robert Louis Stevenson in writing his novel Treasure Island.

Linosa - Pelagie Islands, Italy

Linosa - Pelagie Islands, Italy

Together with Lampedusa and the islet of Lampione it forms the Pelagie archipelago. The volcanic origin has given the island an extraordinary, almost lunar landscape that bewitches those who approach. There is only one port on the island where you can dock and refuel, otherwise you will have to stop at the roadstead and reach land by tender. A simple island, with little to offer by land, but so much by sea; in fact, the best way to appreciate it is on a sailboat. A stop at the Faraglioni, one of Linosa's most striking coves where black rocks frame a sea of incredible turquoise and emerald hues, is a must. The island is famous for its seabeds, among the most beautiful and richest in the Mediterranean. They are suitable for divers looking for adventure, but once the boat is moored in one of the many coves even children can snorkel and be enchanted by the parrotfish and all the life forms that inhabit these waters. There are also two beaches, Pozzolana di Levante and Pozzolana di Ponente, where sea turtles lay their eggs.

The most beautiful islands to discover by sailing

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... and in the rest of the World

  • Antigua - Caribbean

    The flower-shaped Caribbean island known for its wildlife and beaches. Remaining isolated for a long time, it is home to some of the world's rarest animals, such as the runner snake. It is a popular sailing destination thanks in part to the famous Antigua Sailing Week regatta that attracts sailors from around the world each year.

  • St. Vincent - Grenada, Caribbean

    An island of volcanic origin that is completely green and known for its natural beauty. It is home to numerous tropical plants and animals, as well as colorful and rare species of birds. It offers entertainment opportunities for evenings ashore thanks to numerous seaside towns all to explore.

  • Big Major Cay or "Pig Island" - Exuma, Bahamas

    Bizarre island in the Bahamas famous for being inhabited only by pigs and a few other animal species. How pigs arrived on the island to this day is unknown, everyone tells their own version, what is certain is that you cannot fail to stop on this island during your Bahamas vacation and be greeted by these friendly animals.

  • Curieuse Island - Seychelles

    After the pigs of the Bahamas, you cannot miss the giant tortoises of the Seychelles! Curieuse Island, in addition to being home to the rare Coco de Mer, is home to a hundred giant tortoises that live free grazing on grass and leaves. You can spend the day petting them and relaxing on the beautiful Anse San Jose beach.

  • Skellig Michael - Ireland

    This is a rocky island that became famous thanks to the movie "Star Wars Episode VII: The Force Awakens." Since the release of the movie, the crowding on the island has grown by leaps and bounds. However, it is not possible to get there alone, because even when the sea is calm, it is not entirely safe to dock here. The more adventurous who take this trip will be rewarded by the island's wild beauty and its unique romantic nature.

  • Stockholm Archipelago-Sweden

    Some 30,000 islands, some reachable by car or bicycle, but most are a sailor's paradise and explorable only by boat. Sailing through a breathtaking "garden" consisting of small, pristine rocky skerries and larger islands promises an unforgettable, adventure-filled experience!

Guides & tips

Balearic Islands by sailboat

Balearic Islands by sailboat

Corsica by sailboat and catamaran

Corsica by sailboat and catamaran

Croatia by sailboat

Croatia by sailboat

Greece by sailboat

Greece by sailboat

Cyclades islands by sailboat

Cyclades islands by sailboat

Grenadines, Martinique, Guadeloupe and St. Martin by sailboat 

Grenadines, Martinique, Guadeloupe and St. Martin by sailboat 

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