top of page

Leeward and Windward Islands

While our personal favorite is the USVI & British Virgin Islands, we have direct experience with yachts based in the St. Martin (see our favorite places to visit), St Barts, Anguilla, Antigua, Grenadines, and further down island. There are many beautiful locations to charter a yacht.  What is considered ideal are areas where there are island chains without long open ocean passages that are comfortable to sail in within 8 days/ 7nights with plenty to see and enjoy the tropical paradise.  With temperatures averaging around a balmy 70-85 degrees, day and night, the Caribbean Sea offers warmth year-round and lovely trade winds and perfect sailing conditions. 

While the Virgin Islands are the prime sailing destination, the next in the chain of islands is called the Leeward Islands of St. Maarten, St. Barths and Anguilla, and Antigua and Barbuda.  A bit off the beaten track, but wonderful islands to explore are Saba, St. Eustatius and St. Kitts & Nevis.

Further into the Eastern Caribbean are other French, Dutch and independent islands that are lesser-known for chartering, but those that have sailed the main cruising areas might want the added adventure of sailing around French islands of Guadeloupe and Martinique or the eco-tourists dream island of Dominica.

5 Reasons Why we love the Leeward & Windward Islands:

  • Various itinerary options: With various starting and ending ports as well as island destinations to choose from, a crewed charter in the Leeward or Windward Islands presents a multitude of itinerary options. We can provide expert and first-hand guidance in selecting the right itinerary option for you and your group. Learn more about your itinerary options in the Leeward Islands and the Windward Islands

  • Perfect for repeat groups: If you've already "been there, done that" in the USVI & BVI, the Leeward & Windward Islands offer an exciting alternative. A charter in this area will provide experienced charterer's with a slightly more adventurous experience with more dramatic sailing experiences as well as cultural comparisons

  • Uncrowded Islands: The Leeward & Windward Islands offer more remote destinations than the popular during the season USVI & BVI yacht charters to the north. 

  • Mingling with the cruising community: Here you'll find a colorful, fun-loving group of people who live aboard their yachts. Pull up a chair next to one of them and they'll regale you with tales of their years working & sailing in this part of the Caribbean.

  • The Flora, Fauna & Food: Once you sail South of St. Martin, the meaning of the word "the Tropics" truly reveals itself with an abundance of green tropical plants & flowers as well as fruits and vegetables. We can honestly say that we ate our way through the Southern Islands of the Caribbean...and enjoyed every bite! 

Leeward and Windward Islands
The Grenadine Islands




The Leeward Islands, extending from Anguilla in the north to Dominica in the south are some of the world's most beautiful islands and sought after summer vacation destinations.


At the top of this chain of islands is Anguilla, sporting one beautiful beach after another. It is one of the smallest islands although not overly populated. The white-sand beaches here are pristine and the local people are excited to have you visit their island. 

Like Anguilla, the island of St. Martin (St. Maarten) is small in size. It is, in fact, one of the smallest islands to be divided by two nations, the French and the Dutch. Although the island falls under these two governments, the great influence of European style mixed with Caribbean traditions makes St. Martin a truly unique destination. It is also the perfect place to be based for yachting trips to neighboring Anguilla, St. Barth’s, Saba, St. Eustatius, St. Kitts, Nevis and Montserrat islands.

The tiny island of St. Barts (St. Barths or Saint Barthélemy) is also a fantastic spot for sailing charters. The island is distinctly influenced by the French, which is evident in the exotic culture, cosmopolitan atmosphere, local language, and French-influenced cuisine. St. Barts is a favorite destination for the rich and famous, who frequent the island on luxury yacht charters to enjoy the excellent restaurants, luxury resorts, and amazing scenery. Come here and it is clear to see why it is sometimes referred to as the Caribbean's French Riviera.


Next is the island of Saba, an extinct volcano which makes up part of the Dutch Antilles, along with St. Martin and St. Eustatius. Approaching Saba by boat and the landscape appears rather rugged with no sandy beaches on offer. However, this island boasts some of the best diving spots in the Caribbean and is definitely worth visiting if you can organize a local dive guide. The waters are, in fact, part of the Saba Marine Park, which is protected, so it is advisable to check in advance where you can drop anchor. Anchorages are plentiful around other parts of Saba where diving and fishing are also permitted.

St. Eustatius, or just Statia, is another tiny island with a terrain dominated by a dormant volcano known as, The Quill. We have a great story about climbing The Quill on our sailing adventures! Statia is a fantastic place for scuba diving excursions, especially on the leeward coast of the island, which is rife with marine life and numerous ancient wrecks waiting to be discovered.

South of Saba and Anguilla lies the beautiful island of St. Kitts, a tropical haven, and increasingly popular cruising area. Slightly southward is Nevis, the sister island to St. Kitts and an equally popular destination for yachting and water sports activities. The islands of St. Kitts and Nevis are full of historical sites and many interesting trials that are best explored with a knowledgeable local guide.


Another fascinating place to sail to is Montserrat. Although some of the island is off-limits due to its ever-present volcanic activity, the north-west side of the island welcomes charter boats in Little Bay port. If you are chartering this area, it is advisable to plan ahead and contact the port authority for updates on sailing conditions.


If you are sailing north-east of the Montserrat or south of Anguilla, you will find one of the best-kept secrets in the Eastern Caribbean, the island of Barbuda. It offers an extensive coastline with some of the most glorious deserted beaches, stunning coral reefs, and unspoiled landscapes. Barbuda is the picture-perfect tropical island escape. You can spend days without seeing anyone else in sight, lazing on a beach all to yourself.


If you are looking for a bit more activity and opportunities for socializing, visit the island of Antigua. The island has much to see and do. You can get involved in many sailing and water-sports activities and on-land adventures, making it an exciting place to visit throughout the extensive summer season. The island has always been a popular destination for boats thanks to its many safe anchorages and large marinas such as Falmouth Harbour and Jolly Harbour in the south and Nonsuch Bay on the west side of the island.


South of Antigua is the large and mountainous island of Guadeloupe. Guadeloupe is renowned for its delectable gastronomy, offering excellent dining options and several major food festivals that are held annually. If you are stopping here on charter, be sure to do your provisioning on the island to get a taste of the local delicacies, wines, and rum.

Sailing south from Guadeloupe and you will arrive at Dominica, one of the most unique islands in the eastern Caribbean. Unlike its neighbors, Dominica is less frequented by the hoards of summer vacationers and so the island remains relatively unspoiled. You are more likely to find eco-tourists, explorers, and adventurers visiting Dominica's attractive shoreline.

The Leeward islands are, without question, a fantastic place for a sailing holiday. If you are chartering a yacht in this region, you could easily spend a full week just exploring the northern Leeward Islands. After all, leisurely sailing in this part of the Caribbean is what it's all about. If you do want to get a few nautical miles under your belt, you could lengthen your itinerary to include longer passages by cruising farther south to the picturesque islands of St. Kitts, Nevis or Antigua. Here's a suggested itinerary

Beautiful Island Beach


The Windward Islands are located at the southern end of the Caribbean, inclusive of Martinique at the top of the island of Grenada down below. The charm and natural beauty of these islands attract thousands of visitors each year with many looking to charter a yacht in the Caribbean.


Martinique is one of the largest in Windward islands of the Lesser Antilles. Although a province of France, Martinique has a diverse mix of cultures and ethnicities which contribute greatly to the charm of the island. It is the perfect place to start a holiday in the Caribbean with picturesque fishing villages hugging the coastline and well-facilitated marinas, such as in the capital city of Fort de France, which is an excellent location to embark on your sailing vacation. As well as being the most cosmopolitan city in the West Indies, Fort de France is also a popular port for seafarers visiting the Caribbean. The beautiful bay is worth a visit even if you are not chartering a yacht in Martinique. As expected, the food here is delicious - a fantastic fusion of French, Caribbean, and Creole styles. If you have the time, stop and sample the exotic delicacies at street-side market stalls or any of the local restaurants and cafés. To walk it all off you can enjoy a stroll down the Parisian-like streets and onwards to the sprawling waterfront park.


The great thing about Martinique is its close proximity to the neighboring islands, which means that sailing options in this region are endless. You can easily just spend a whole week just cruising the coast of Martinique. For longer yacht charters, you can sail towards Dominica in the north or cruise southward to St. Lucia, the Grenadines, and Tobago Cays.


If you are heading south, spend some time in St. Lucia. It is quite possibly one of the most alluring islands of the world. This tropical paradise lies directly under Martinique and is a top sailing destination in the Caribbean. Rodney Bay, the main harbor situated on the north-west of the island, has become a mecca for yachting tourists and has all the amenities one would expect from a first-class marina. There are shops, luxury hotels, restaurants and plenty of places to rent yachts and boats for private charter or deep-sea fishing excursions. There is so much to explore in Saint Lucia including breathtaking waterfalls and thermal pools, beautiful botanical gardens, dormant volcanoes and the island's most renowned landmarks the mystical volcanic Piton Peaks. St. Lucia is truly a unique place with infinite possibilities for those who venture ashore.


Another gem of the Caribbean is the lush green island of St. Vincent just south of St Lucia. Arrive by boat and Saint Vincent appears to be glistening like an emerald jewel in the sea. The island's impressive, La Soufrière, volcano dominates the landscape - a phenomenal cavern still bubbling with activity. Sailing around the coast and one can definitely see evidence of volcanic origin. The jet-black beaches are quite spectacular as are the ivory white shorelines, making St Vincent one of the very few places in the world to have different colored sands.


Start your Caribbean yacht charter from the capital, Kingstown, which is the major port and commercial center for Saint Vincent and the Grenadines chain of islands. It is a city worth exploring with a stunning waterfront, old buildings, and churches, a famous flea market on Saturdays and a historic Botanical Garden.


The Grenadines are a group of small inhabited as well as uninhabited islands lying between St. Vincent in the north and Grenada down south. The weather here is near perfect for much of the year with sailing conditions at their best from November to April. Charter a yacht in the Grenadines and you will find a group of islands unsurpassed in their beauty. It is no wonder these islands were chosen as the set for the box office smash the “Pirates of the Caribbean”. There are numerous anchorages here, marvelous lagoons, spectacular reefs and long stretches of pristine white beaches found at all of the islands. We recommend taking some time to explore Bequia, Mustique, Canouan, Union Island, Carriacou, and the stunning Tobago Cays, which are less frequented by charter boats.

At the southernmost point of the Windward islands is Grenada, the island of spices and tropical fruit. The picturesque capital of St George is best seen by foot. Plan ahead to organize a mooring or anchorage so that you can jump ashore. Your time on land can be spent visiting the bustling farmer's market, spice plantations or a leisurely drive down the scenic garden route.

bottom of page