Boat holidays in Lesser Antilles

The Lesser Antilles are one of the most interesting destinations in the Caribbean for sailing. From the Windward Islands in the south to the Leeward Islands in the north, there are hundreds of miles of coastline, small islands, sheltered anchorages, fishing villages, and ports with a rich nautical tradition.

At Sailwiz you can find different ways to discover them: sailing trips, boat holidays, sailing on large sailboats, learning experiences and multi-day island-hopping routes .

And you don't have to just look at a route and book it. At Sailwiz you can meet the skipper who organizes the experience, ask them about the sailing, what places they usually visit, what level you need, or if it's possible to adapt part of the route .

You can book a place if you're traveling alone, share the boat with other travelers, travel with your partner or friends, and, in experiences that allow it, book the entire boat .

Not everyone is looking for the same thing when they think about a boat trip in the Caribbean.

Some people want to spend a week sailing between islands and swimming in turquoise waters. Others are looking for a longer voyage, want to learn to sail, or use the trip to log miles. There are also those who want to embark on a historic tall ship and live for a few days as part of the crew. That's why at Sailwiz you won't find just one type of trip.

The platform brings together experiences shared by skippers and sailing professionals who know the routes and offer different ways to explore the Lesser Antilles. You can find, for example:

• Crossings between different Caribbean islands.
• Multi-day sailing vacation.
• Boat routes between Martinique, Antigua, Tobago, Grenada or the Windward Islands.
• Navigations through the northern Lesser Antilles, including Saint-Martin, Antigua and the British Virgin Islands.
• High-altitude crossings and experiences to rack up miles.
• Sailing on Tall Ships and large historic sailing ships.

The offerings change depending on the dates and experiences posted by the hosts, so it's worth checking the available activities to find the one that best suits your trip.

The best time to sail the Lesser Antilles is usually from December to May , when the trade winds blow more regularly, the sea is generally calmer, and temperatures hover around 25–30°C. This is the preferred time for many sailors to explore the eastern Caribbean, linking islands such as Martinique, Dominica, Guadeloupe, Antigua, and the Grenadines.

Sailing trips are also available between June and November , although planning depends heavily on the weather and the Caribbean hurricane season. For this reason, Sailwiz routes are not rigid itineraries. The skipper adapts the sailing, always seeking the best safety conditions and taking advantage of the wind to enjoy a more authentic experience.

If you're looking to sail with good winds, calm anchorages, and long days among the islands, the winter and spring months usually offer the most favorable conditions.

The price of a sailing experience in the Lesser Antilles depends primarily on the trip's duration, the type of vessel, and whether you book a single berth, a cabin, or the entire boat. At Sailwiz, you'll find options for a wide range of budgets, from shared cruises to premium catamarans. Currently, you can find experiences in approximately these price ranges:

• From €990 per person: shared multi-day crossings between the Lesser Antilles.
• Between €1,200 and €1,600 per person: one-week routes sailing between Martinique, Guadeloupe, Dominica or Antigua.
• Around €1,980 per person: 14-day voyages such as sailing between Grenada and Martinique, touring the Windward Islands.

In addition to these experiences per person, some skippers offer the possibility of booking a whole cabin on a catamaran or even renting the entire boat for groups and families , with prices that vary depending on the vessel and the season.

In each activity listing you can see with complete transparency what the price includes, the common cash expenses and speak directly with the owner before booking.

One of the advantages of booking an experience on Sailwiz is that you can find very different routes within the same destination. Sailing around the Windward Islands is not the same as sailing around the Leeward Islands.

Tobago – Grenada – Saint Vincent – Saint Lucia – Martinique
On Sailwiz you can find voyages like the one connecting Tobago to Martinique in about 10 days, sailing north through some of the main Windward Islands. The route may include stops in Grenada, St. Vincent and the Grenadines, and St. Lucia before reaching Martinique. It's a particularly interesting experience if you want a true sailing adventure through the Lesser Antilles, and not just a holiday where the ship stays in the same area.

Saint-Martin – Antigua
You can also find cruises sailing from Saint Martin to Antigua, visiting the Leeward Islands. Depending on sailing conditions, the route may include destinations such as Saint Kitts and Nevis or Anguilla.

Antigua – Tortola
Another Sailwiz experience connects Antigua with Tortola in the British Virgin Islands for approximately 10 days. On this type of voyage, the itinerary shouldn't be seen as a fixed tourist route: the skipper adapts the sailing to the weather and sea conditions. This allows for better wind utilization, finding suitable anchorages, and deciding how to use the available time.

BVI – Martinique
For those seeking a more nautical experience, Sailwiz offers voyages between the British Virgin Islands and Martinique focused on offshore sailing, mileage accumulation, and active participation on board. This is a good example of how Sailwiz offers both sailing holidays and experiences specifically designed for sailors.

Sailwiz experiences allow you to discover different areas of the Lesser Antilles.

Along the Barlovento routes, you can find destinations such as Tobago, Grenada, St. Vincent and the Grenadines, St. Lucia, and Martinique . Further north are Dominica, Guadeloupe, Antigua and Barbuda, St. Kitts and Nevis, Anguilla, and Saint Martin .

And some voyages continue to the British Virgin Islands , where you can sail between Tortola, Virgin Gorda, Jost Van Dyke , and numerous small cays. The beauty of doing it aboard a ship is that you don't necessarily have to choose just one island. You can make the journey between them part of the trip.

Additionally, the skipper can recommend where it's most worthwhile to stop depending on the time available.

The experience varies greatly depending on the vessel. At Sailwiz you can find sailboats, catamarans, schooners, and large sailing ships , depending on the activity. Let's take a look at the differences between them and see which one might best suit your needs:

• Sailing: Sail between Martinique, Dominica, Guadeloupe, Antigua or the Grenadines combining sailing, snorkeling, beaches and life on board.
• Mileage-gathering voyages: Linear routes of 10–14 days where you will participate in navigation, watches and planning alongside the skipper.
• Large historic sailing ships (tall ships): Experience sailing on a classic brig between Saint-Martin and Antigua as part of the crew.
• Catamarans: Some activities allow you to book individual places and others allow you to rent the entire boat for your group.

On each activity's page you can check the boat's features and talk to the skipper to find out what life is really like on board.

A Sailwiz experience can be much more than just sailing from one port to another. Depending on the route, you can spend a day sailing between islands and end up anchored off a beach. Another day you can go ashore to explore English Harbour and Nelson's Dockyard in Antigua , go snorkeling, or simply enjoy a relaxing afternoon on board.

At other stages you can sail between small cays, as happens in the British Virgin Islands, where the distances allow you to combine several islands and anchorages in the same day.

If you're interested in marine life, the Caribbean waters also offer opportunities to spot turtles, dolphins, seabirds, and, depending on the season and area, whales. And if you're interested in learning, many experiences allow you to participate in shipboard tasks: raising sails, steering, or assisting the crew.

Yes, in many of the experiences available on Sailwiz. You don't need a skipper's license to enjoy a sailing holiday or participate in a skippered voyage.

If you want to learn, you can use the trip to learn the maneuvers and participate in sailing. And if you simply want to enjoy the Caribbean, you can leave the sailing to the skipper and focus on exploring the islands.

Before booking, you can speak to the skipper and explain your experience. This way you'll know if the activity is right for you.

At Sailwiz you can find experiences designed for different ways of traveling through the Lesser Antilles .

If you're traveling alone, you can book a berth and share the boat with other travelers. If you're traveling as a couple or with friends, you can book several berths and enjoy the journey together. And when experience allows, you can also book and charter the entire boat , a particularly attractive option for groups who want to organize their own sailing trip.

You don't need to know other travelers beforehand or find a skipper on your own: Sailwiz connects those who want to sail with the skippers who offer the experiences.

Explore the available experiences and discover the Lesser Antilles from the sea. As always, you can contact us with any questions or speak directly with the skipper. We'll answer all your queries. With Sailwiz, you can book a single berth, travel with a companion, or, for certain experiences, charter the entire boat.