Our latest charter news
The Caribbean and Bahamas sailing season is upon us with top-rate boats for charter at competitive prices Learn More

Sail Martinique, St Lucia & The Grenadines

The Caribbean's Windward Islands: a Journey of Discovery

A collection of the Windward Islands subject to years of dispute between France and Britain, and now places of peace and tranquility. Between Martinique and Union Island are a series of easy day sails, a fascinating mix of French flair and British tradition amid the unequally Caribbean way of life.

Martinique is an important Caribbean charter hub, where the region's second-largest selection of boats are on offer (after BVI). This area is also served by a base in nearby St. Lucia. Let us sort though the boats available with all the quality operators in this part of the Caribbean, find the best deals and present the charter solution for you. It costs no extra to use our service and we will work hard to give you a boating holiday that's second to none.

Experience the Diverse Caribbean in Microcosm

Martinique

This rugged island is volcanic in origin, its interior mountainous and well-forested. Martinique is often referred to as the "Isle of Flowers" and it doesn't take much exploring of the natural landscape to see why. There's a lot going on in Martinique, and it all happens on Caribbean time. There is plenty to do ashore by day, and later the active nightlife brings the place alive.

Some of the Caribbean's most stunningly beautiful and safest anchorages are found on the western side of Martinique. In the south of the island, swimming and diving offshore the long, luscious beaches provide main attractions for visitors both land and sea-based. Northern Martinique is dominated by the active Mont Pelée, which erupted spectacularly in 1902.

Martinique is the most northerly of the Windward Islands of the Lesser Antilles chain, making it the ideal starting point for a one-way sailing holiday either north or south. The southerly passage passage to Grenada via St Lucia and the Grenadines is particularly popular.

St Lucia

St Lucia is a small tropical gem that is still relatively unknown. It is the sort of island that travelers to the Caribbean dream about, a place of natural wonders where you are greeted with warm hospitality. It's a volcanic island best known for the twin peaks of The Pitons, which rise over 2000 feet at the water's edge. Inland hikes take you where the rain forests shelter wild orchids, giant ferns and birds of paradise.

Visit Soufriere, the world's only drive-in volcano, or relax in the earth's rejuvenating heat in the pools at Diamond Baths. Spend an evening in Marigot Bay, one of the most beautiful spots in the Caribbean. If you tire of palm-fringed beaches, secluded anchorages and dive sites in every direction, St Lucia also offers a full range of recreational facilities. Enjoy the leisurely pleasure of touring by horse, or relax with a round of golf amid St. Lucia's entrancing natural beauty. There are also activities closely related to the traditional life of St. Lucia, including deep-sea fishing, "jump-ups" at Gros Islet, and the weekly market at Castries.

If you visit in May, take time out to experience the world-renowned St Lucia Jazz & Arts Festival.

St Vincent and the Grenadines 

Sail through gorgeous scenery to secluded beaches, calm anchorages and picturesque villages. Flying fish and dolphins help navigate your course across the waves. These lovely islands offer it all, from the bustling waterfront of Port Elizabeth on Bequia to the stunning natural beauty of the Tobago Cays - a group of isolated islets with incredible snorkeling on vividly colored coral reefs that give bareboat and crewed yacht charterers a little piece of paradise all to themselves. 

Like all the Caribbean's Windward Islands, St Vincent and the Grenadines present dramatic landscapes of lush tropical forests framed by sheer volcanic backdrops. For a beautiful combination of great sailing, gorgeous scenery and impeccable diving, these islands are just perfect for a yacht charter vacation. The pure white beaches, gorgeous bays and stunning diving will provided you with some unforgettable memories of your yacht charter vacation.

Planning a Windward Islands Charter

A sailing itinerary taking in St Vincent & the Grenadines from north overlaps easily with a charter out of Grenada. So if the Tobago Cays and Union Island are a primary destination, you may want to consider the alternative of chartering a yacht in Grenada.

There are a number of charter bases scattered throughout this region, and air access makes it possible to frame an itinerary from several places. While Martinique's place as the main hub for the region makes return or one-way charters from there the most practical and cost-effective options, whatever your objectives for the sailboat charter ahead, we will work with you to meet them.

Browse our yachts for charter in Martinique, St Lucia, & The Grenadines

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

Get in Touch

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.