Don’t Miss These Places When Sailing in Leeward Islands!

Have you conjured up a Caribbean yacht charter dream in your mind? Sailing on a bareboat sailboat, you too can encompass these islands which spread over a range of 700 miles, starting from east of Puerto Rico and ending with Dominica in the south. Encircling multiple geographical regions of French to the Danish – their diverse physicality ranges from coral islands to lush rainforests ending with volcanic craters. This mid-winters, you cannot afford to miss taking a sailing in Leeward Islands.

Related: Caribbean yacht charter prices

Known as a yacht man’s paradise, the ride ranges from the French quaint domain of Les Saintes, to the Danish influenced St. Maarten right up to Antigua and Barbuda. If you have a little more time to spare – add a couple more nautical miles to your itinerary to see the sister islands of Nevis and St. Kitts. The dormant Mt. Liamuiga is not a sight to miss!!


All set with your bareboat sailboat? Hail on – The Caribbean is ready to be explored!

Planning the perfect itinerary to explore the Leeward

From November through July, the trade winds south the tropical heat and make for the perfect time for a visit. Now, how would you plan a sailing itinerary in Leeward Islands? Well, the tropical landscapes, white beaches, and sparkling waters do call in for a plan. Take a look!

  • Start off with nightlife of Anguilla

Anguilla should be the first destination to moor your yacht. Northernmost in the range of islands – this boasts of turquoise waters, palms, and sandy beaches. From Shoal Bay East to Scilly Cay, after a long day of sailing, you have the beaches to party! 

  • Head straight to Barbuda

It is a must-visit in your sailing itinerary in Leeward Islands. With its coconut fringed beaches integrated with soft pink hues, you have a 10-mile-long beach walk to enjoy. Its share of coves and sheltered bays will provide you a chance to anchor your sailboat.

In the middle, don’t miss out on Antigua – known for its coral reefs and snorkeling escapades.

  • Let the southern winds take you to Dominica

After you leave those bays, follow the westerlies and land in the group – Marie Galante, Iles Des Saintes, and Dominica. From spectacular scenery to lip-smacking delicacies, this island is the combination of cosmopolitan with French traditions.

  • Give your taste buds a spice rush at Guadeloupe

The ‘cuisine island’ of the group, from sea-food to queen conch fricassee, just get back these dishes to your yacht and it will make your stay!


For the fashion lovers looking for some casino like lifestyle, moor your charter at St. Barths followed by St. Maarten. Your yacht charter in the Leeward Islands will have no issues as these atolls offer ideal anchors!

Why a bareboat for sailing in Leeward Islands?

If you have sailing experience and are in a small group of people looking to explore these Leeward Islands – it is best to choose a bareboat sailboat. You can add on an advisor to your team and a couple of water toys, as you move from one island to another.

  • With no strict diet, you can get back some local delicacies (Guadeloupe sea-food) to your boat and gulp it down with a glass of wine.
  • For those ‘not so happening’ nights on the beach – you can very well have a party aboard your yacht charter in the Leeward Islands.

This range of Leeward Islands is one of the most famous yacht charter grounds in the world, offering multiple options and breath-taking views. Don’t forget to book a bareboat sailboat in advance to avoid the annual rush! (P.S. Do submit your sailor’s license to get a bareboat vessel).  



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