SailChecker · The Art of Charter™

Sailing Itineraries


47 curated yacht-charter routes across the world's most beautiful sailing grounds — day-by-day, anchorage by anchorage, by the team that's been booking them since 2011.

A note from our crew

"From the limestone walls of Dubrovnik to the lagoons of Bora Bora, these are the routes we have sailed, refined, and recommended for over a decade. Each is its own kind of week — choose the one that feels right, and we'll handle the rest."


Pick a region below to see day-by-day itineraries, vital sailing stats, and the practical detail you need to plan your charter.

The Caribbean
11 Itineraries

The Caribbean

Region

The Caribbean


Haunt of buccaneers, squabbled over by the French, Dutch, English and Spanish, the islands in the Caribbean Sea hold a special allure to those who count Robert Louis Stevenson's Treasure Island among their favourite books. Steady trade winds, warm seas, and more variations of rum punch than there are beachside bar tenders to mix them. For some time the Caribbean has been the charter destination — yet there is more than enough adventure for those seeking to get away from the crowd.

British Virgin Islands sailing itinerary
BVI 7-Day Route

British Virgin Islands

Our British Virgin Islands Sailing Itinerary discovers and explores the best the British Virgin Islands has to offer.

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Bahamas — Bimini to the Exumas sailing itinerary
Bahamas 7-Day Route

Bahamas — Bimini to the Exumas

Located between the North Atlantic and Florida's Eastern Seaboard, the Bahamas are composed of more than 2,400 cays and 700 islands. Most of them are uninhabited and surrounded by colorful coral and fathomless ocean trenches.

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Antigua sailing itinerary
Antigua 7-Day Route

Antigua

While Antigua is famous for its gorgeous beaches, there’s so much more to this Caribbean island.

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St Martin sailing itinerary
St Martin 7-Day Route

St Martin

The northern French half evokes a more distinctly European feel with its cafes and French-speaking populace. Here you can enjoy a more secluded atmosphere and remote sandy beaches.

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St Vincent & the Grenadines sailing itinerary
St Vincent 7-Day Route

St Vincent & the Grenadines

With St. Vincent's lush tropical rainforest and idyllic beaches, our St. Vincent Sailing Itinerary is perfect for eco-adventurers, looking to explore picturesque scenery.

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Grenada sailing itinerary
Grenada 7-Day Route

Grenada

Our Grenada Sailing Itinerary takes you through these magnificent Caribbean gems, stopping along the way to see the 18th-century spice plantations, superb flora and fauna, and spectacular underwater scenery.

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Martinique sailing itinerary
Martinique

Martinique

Discover Martinique and the surrounding islands with our Martinique sailing itineraries south and north routes.

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Cuba sailing itinerary
Cuba

Cuba

Previously closed off from the world, Cuba has remained frozen in time, giving it a one-of-a-kind culture filled with life, music, and color.

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St Lucia sailing itinerary
St Lucia

St Lucia

Culture abounds in the beautiful Caribbean Island of St. Lucia. Music, language, cuisine, and intellect come together to create a truly unique kind of magic.

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Puerto Rico sailing itinerary
Puerto Rico

Puerto Rico

Puerto Rico Sailing is a once in a lifetime opportunity with luscious forests, beaches, natural wonders, heritage, delicious flavors, a dynamic culture, colonial architecture, cultural events and adventure.

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Guadeloupe sailing itinerary
Guadeloupe

Guadeloupe

Find out more about Guadeloupe with our Guadeloupe Sailing Itinerary, and discover the beautiful beaches, mountains and green surrounding areas with our one of a kind itinerary.

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Croatia
8 Itineraries

Croatia

Region

Croatia


Over 1,200 islands stitched along the Adriatic coast, with calm seas, light afternoon breezes, and ancient Venetian harbour towns at every anchorage. The most popular bareboat sailing ground in Europe, and the bestselling region of the SailChecker fleet.

Greece
8 Itineraries

Greece

Region

Greece


More than 2,000 islands, the meltemi summer wind, whitewashed villages clinging to cliffs, and tavernas where the catch arrives at the table within an hour of the line being pulled. Three distinct sailing grounds — Ionian, Cyclades, and Sporades — each its own kind of week.

Ionian sailing itinerary
Greece 7-Day Route

Ionian

Steady winds, sheltered waters, and the gentlest introduction to Greek sailing — Corfu, Lefkas, Kefalonia.

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Saronic sailing itinerary
Greece 7-Day Route

Saronic

With a plethora of history and culture, our Saronic Sailing Itinerary is a great holiday for every type of traveller. You are sure to be charmed by the cute coastal towns and awed by the natural beauty!

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Sporades sailing itinerary
Greece 7-Day Route

Sporades

Use our Sporades Sailing Itinerary to get away from it all and have a bit of rest and relaxation on your holiday! The Sporades are uninhabited and will be the perfect place to disconnect.

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Cyclades sailing itinerary
Greece 7-Day Route

Cyclades

Archaeological ruins, rugged landscapes, and the Aegean Sea make the Cyclades the ideal sailing destination, with plenty of islands and sights to explore.

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North Ionian sailing itinerary
Greece

North Ionian

Find out more about sailing in Greece, with our North Ionian Sailing Itinerary. With turquoise waters, pretty towns, and some cool cities, there's plenty to do in the North Ionian Islands.

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South Ionian sailing itinerary
Greece

South Ionian

Let the South Ionian Sailing Itinerary capture your heart! We've curated a perfect trip consisting of twinkling waters, charming villages, and stunning vistas.

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Dodecanese - Kos Route sailing itinerary
Greece

Dodecanese - Kos Route

Our Dodecanese Sailing Itinerary is ideal for families and friends to enjoy together, while also discovering what the Dodecanese islands have to offer, with an itinerary to/from Kos and to/from Rhodes.

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Cyclades - Paros Route sailing itinerary
Greece

Cyclades - Paros Route

Archaeological ruins, rugged landscapes, and the Aegean Sea make the Cyclades the ideal sailing destination, with plenty of islands and sights to explore.

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Turkey
7 Itineraries

Turkey

Region

Turkey


Turquoise Coast — Bodrum, Göcek, Marmaris — where Lycian tombs sit above the bay and gulets motor between forgotten Greek ruins. The Mediterranean's best value for charter, and arguably its richest cultural sailing.

Far East & Pacific
5 Itineraries

Far East & Pacific

Region

Far East & Pacific


Beyond the Mediterranean and Caribbean lie the great cruising frontiers — limestone karsts of Thailand, the Whitsunday's Whitehaven Beach, and the volcanic atolls of French Polynesia. Longer flights, but the rewards justify the journey.

Indian Ocean
1 Itinerary

Indian Ocean

Region

Indian Ocean


Remote, warm, and underexplored — the granite islands of the Seychelles, where giant tortoises wander the beaches and the snorkelling is as good as anywhere on earth.

Beyond our published routes

Don't see your destination?


We charter to over 60 destinations worldwide — these are just the routes with detailed itineraries published. Tell us where you'd like to sail and we'll build something tailored.

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