Best Sailing Destinations in the Caribbean

by | Mar 7, 2023 | Americas, CARIBBEAN

Sailing the Caribbean is an experience like no other. With its crystal clear waters, lush green islands, and vibrant culture, it’s easy to see why so many people flock here for a luxury sailing adventure.

Whether you’re interested in a romantic getaway or an unforgettable family vacation, plenty of amazing destinations in the Caribbean offer incredible experiences on board your private yacht.

From the US Virgin Islands to the Grenadines and beyond, discover our picks for the best sailing destinations in the Caribbean. Be prepared to traverse some of the most picturesque locations on our planet, forming memories that will remain with you forever.

Caribbean Sailing Destinations

Sailing the Caribbean is a dream come true for many. With its crystal-clear waters, white sand beaches, and stunning coral reefs, it’s no wonder why so many people flock to this part of the world for their sailing adventures.

Here are our favorite and, in our opinion, the best sailing destinations in the Caribbean:

Caribbean Sailing – iSaw Company

US Virgin Islands

The US Virgin Islands are an attractive cluster of isles in the Caribbean Sea, boasting crystal-clear waters, pristine white beaches, and lush greenery, a perfect spot for those seeking a relaxed but luxurious holiday.

With its crystal-clear waters, white sand beaches, and lush tropical vegetation, it’s no wonder this destination is so popular among travelers looking for a mildly luxurious bespoke trip.

US Virgin Islands – Josh Duncan


The climate of the US Virgin Islands is generally warm and humid year-round, with temperatures ranging from 75 to 85 degrees Fahrenheit (24 to 29 degrees Celsius). The rainy season can fluctuate, yet generally runs from May to October, depending on the area.

Despite these conditions, visitors will find plenty of sunshine throughout their stay and cool breezes coming off the ocean that help keep things comfortable even during hot days.


From sailing and snorkeling to exploring historical sites or simply relaxing on one of the island’s many pristine beaches, there’s an activity for every type of traveler here.

For those looking for more adventurous activities like zip lining or hiking up Mount Sage National Park, they won’t be disappointed either.

Plenty of cultural experiences are available such as visiting local markets or attending festivals like Carnival, which take place each year in St Thomas.

St Thomas – Karl Callwood


If you are someone who likes sailing and the sea but would rather have a more comfortable place to unwind and sleep after a day of exploring, there are a variety of places to stay, from fancy resorts to cozy villas, so you can find something that fits your budget and meets all your needs for a pleasant stay.

Many hotels offer a variety of alternatives, from sumptuous feasts and drinks to indulgent spa treatments, enabling you to make your getaway truly remarkable without overspending.

If you want something more private, plenty of rental homes are available too, which provide great privacy.

Accomodations Virgin Islands – steviep187 via Creative Commons

British Virgin Islands

The BVI is an archipelago in the Caribbean Sea, situated east of Puerto Rico. This area is known for its stunning beaches, lush rainforests, and transparent waters. It’s a prime destination for those seeking an unparalleled sailing experience.

British Virgin Islands – Dietmar Lichota

Sailing Conditions

Sailing conditions in the British Virgin Islands are ideal for all levels of experience. The waters here are calm and protected from strong winds by surrounding islands.

For those seeking to acquire or hone their sailing skills, the tranquil waters of the British Virgin Islands provide an ideal setting with no need for apprehension about facing turbulent seas.

Plus, with many isles nearby, you can traverse various sites each day while remaining within reasonable proximity to not deplete resources during your expedition.

Sailing in BVI´s – Ernie A. Stephens

Things To Do

When not on board your boat exploring these beautiful islands, plenty more fun activities are also available on land. You can go snorkeling or scuba diving off any number of beaches around the BVI’s and see an array of sea life, such as turtles, dolphins, and colorful fish swimming among coral reefs.

If you feel adventurous, then try kiteboarding or windsurfing. There are plenty of places offering lessons if needed too.

And after a long day at sea, there’s nothing better than relaxing on one of the many white sand beaches scattered throughout this paradise before heading back out tomorrow morning refreshed and ready for another adventure-filled day ahead.

British Virgin Islands – Cory Bjork

Accommodation Options

The British Virgin Islands offer various accommodation options, from luxury resorts to private villas tucked away with tropical foliage.

Whatever type you choose will depend entirely upon your preferences, but rest assured that whichever option suits you best will provide an unforgettable stay amidst breathtaking scenery.

BVI´s Accomodation – Dietmar Lichota

The Grenadines

The Grenadines are a group of 32 islands located between the Caribbean Sea and the Atlantic Ocean.

St Vincent is the largest of the Grenadine islands, with luxurious resorts and stunning beaches surrounded by tropical forests and blue waters.

Vincentians offer a range of recreational pursuits, from snorkeling and scuba diving to sailing, kayaking, windsurfing, and more. There are also plenty of opportunities to explore nature on land with hikes through rainforests or up volcanoes like La Soufriere or Mount Wynne.

You can also participate in cultural experiences such as visiting botanical gardens or learning about local history at Fort Charlotte or Fort Duvernette National Park.

Bequia is another popular destination in The Grenadines that boasts stunning white sand beaches surrounded by turquoise waters perfect for swimming and snorkeling among colorful coral reefs teeming with marine life.

On Bequia, you can visit historic sites like Port Elizabeth Town Hall or take part in unique activities such as turtle watching during the nesting season from March to June each year.

Mustique Island is one of the most exclusive destinations within The Grenadines, offering luxurious villas set amidst lush vegetation overlooking secluded coves ideal for swimming and sunbathing away from prying eyes.

Cocktails are served by attentive staff members at private beach bars dotting its coastline, while fresh seafood dishes can be enjoyed in excellent restaurants with live music performances creating a captivating atmosphere each night beneath the stars above its tranquil shores.

The Grenadines – Christian Lendl

St Martin / St Maarten

Martin / St Maarten is a Caribbean island in the Lesser Antilles, divided between France and the Netherlands.

This unique dual-nation destination offers visitors an unforgettable experience of French and Dutch culture, cuisine, and language.

The French side of the island features stunning beaches with clear waters perfect for swimming or snorkeling.

Grand Case Beach is especially popular among tourists due to its white sand beach, with restaurants serving delicious local dishes such as creole-style fish stew and conch fritters.

The town of Marigot also has some excellent shopping opportunities, including duty-free shops selling luxury items like jewelry, perfume, and electronics at discounted prices.

On the Dutch side of St Maarten/St Martin, you will find plenty of activities for adventure seekers, such as parasailing over Simpson Bay Lagoon or taking a jeep tour around Philipsburg, where you can explore old fortifications from colonial times.

If you feel lucky, many casinos also offer gaming tables and slot machines.

Maho Beach is another popular spot on this side of the island known for its close proximity to Princess Juliana International Airport – it’s not uncommon to see planes flying low overhead while sunbathing here.

St Maarten – Ramon Kagie


The Bahamas are a sailing paradise with warm waters, a variety of landscapes, and lots of sea life. The calm winds and clear water make it a great place to sail.

Every sailor will find something they like, from the busy city of Nassau to the calm waters of the Exumas.

While sailing in the Bahamas, you can visit the many cays and islands, each with its own special features and things to do.

Snorkeling and diving are fun things to do because you can see fish, coral, and even shipwrecks. The beaches are clean, with white sand and turquoise water.

Nassau has a lot to do and see, including duty-free shopping, colonial architecture, and busy streets. With their calm waters, quiet coves, and lush vegetation, the Exumas are a peaceful place to be. And the Abaco Islands are a great place to sail or go boating because of their charming towns and natural harbors.

When it comes to places to stay, there are options for every budget, from expensive resorts to small cottages in the middle of nowhere. In Nassau, there are many high-end hotels and resorts. On the Exumas and Abaco Islands, you can rent villas and cottages for a more private stay.

Bahamas – Pritman Pebam

St Lucia

St. Lucia is a Caribbean paradise boasting luxuriant rainforests, picturesque beaches, and an intriguing culture. It’s an ideal destination for those seeking a mildly luxurious, bespoke trip with plenty of activities.

The first thing that comes to mind when thinking about Lucia is the landscape’s natural beauty. The rolling hills have beautiful views, and the white sand beaches are perfect for soaking up the sun or jumping into the clear water. You can also explore nature by hiking through rainforest trails or paddling a kayak along rivers and coves full of wildlife.

If you like to experience local culture, there’s no shortage of things to do in St. Lucia. From street markets with handmade crafts and souvenirs to traditional music festivals with steel drums and calypso rhythms, you can get involved in all parts of life in this lively island nation.

You can also take cooking classes to learn how to make traditional dishes like green fig salad or saltfish bull using fresh fruits and vegetables grown on-site at local farms and other local ingredients.

When it comes time for some rest and relaxation after exploring all that St. Lucia has to offer during your bespoke trip, plenty of options are available.

Whether you prefer luxurious resorts with spas offering massages & treatments, private villas nestled amongst tropical gardens, or even camping under starry skies – you’ll find something suitable here.

If adventure is your style, why not try out one (or several) of St. Lucia’s many water sports? Snorkeling around coral reefs teeming with colorful fish species, sailing across turquoise seas dotted with tiny islands, windsurfing over rolling waves, and deep sea fishing off remote coastlines—whatever type of aquatic activity tickles your fancy, you’ll find it here.

St Lucia – Corinne Kutz


Antigua boasts 365 pristine beaches, one for each day of the year, making it a sailor’s paradise. The island’s warm waters and gentle winds make for ideal sailing conditions.

While sailing in Antigua, you can visit Nelson’s Dockyard National Park, a restored 18th-century naval base, and English Harbour, a hub for yachting and sailing.

Half Moon Bay is a must-visit, with its picturesque bay and calm waters. The island is also famous for its green hills and beautiful beaches, such as Pigeon Point Beach and Turners Beach.

In addition to sailing, there are plenty of things to do and see in Antigua. From exploring the island’s history and culture to simply lounging on the beach, there is something for everyone. For those interested in adventure, there are opportunities for snorkeling, diving, and hiking.

When it comes to accommodation, there are options for all budgets, from luxury resorts to budget-friendly guesthouses. English Harbour has plenty of high-end hotels and resorts, while other parts of the island offer more secluded options, such as rental villas and cottages.

Antigua is a top sailing destination with warm waters, diverse beaches, and rich history. With plenty of things to do and see and accommodation options, it’s no wonder why so many sailors flock to this tropical paradise.

Antigua – Rick Jamison

Turks & Caicos

The Turks and Caicos Islands are a tropical paradise in the Caribbean Sea. These idyllic isles, boasting their pristine white sands, glimmering azure waters, and verdant hilltops, have become a premier sailing locale for vacationers seeking an unforgettable getaway.

Sailing around the Turks and Caicos Islands is an experience like no other. From snorkeling with sea turtles to exploring uninhabited cays and bays, there’s something for everyone here. Because the water is calm, it is a great place for people who have never been sailing. More experienced captains can try some more difficult routes that wind through mangrove-lined channels or past tall limestone cliffs.

When you visit Turks and Caicos, try some local foods and learn about the culture. Sample freshly caught seafood dishes such as conch fritters or grilled grouper served with rice and peas at one of the many beachside restaurants throughout Providenciales Island. Or, indulge in traditional island favorites like Johnny Cakes (fried cornmeal dough) paired with a cold Kalik beer from Nassau Brewery on Grand Turk Island for an unforgettable experience.

If you’re looking for a unique shopping experience, head to Salt Cay, where you’ll find handmade jewelry crafted by local artisans using natural materials found on nearby shores, such as shells, coral, and semi-precious stones.

You can also pick up locally made souvenirs, including straw hats woven from dried palm fronds or hand-painted wooden carvings depicting scenes from everyday life in this beautiful corner of the Caribbean Sea.

Turks and Caicos – Nicole Keller

Puerto Rico

Puerto Rico is a Caribbean island that offers an array of experiences for those looking to explore its many wonders.

Puerto Rico is a paradise of possibilities, from its stunning coastlines and verdant jungles to its unique culture and scrumptious food.

Whether looking for a relaxing getaway or an adventure-filled vacation, Puerto Rico will surely please you.

Puerto Rico – Wei Zeng

The Beaches

Puerto Rico’s coastline stretches over 500 miles, with numerous beaches offering something unique for every traveler.

Isla Verde Beach, a highly sought-after destination with its powdery white sand and sparkling waters, is ideal for swimming and snorkeling. Other popular spots include Flamenco Beach on Culebra Island, Boqueron Beach on Cabo Rojo, Jobos Beach near Isabela, Luquillo Beach in Fajardo, and Seven Seas Beach near Fajardo.

Puerto Rico Coastline – Jonathan Medina

Culture & History

A trip to Puerto Rico wouldn’t be complete without exploring its long rich history and vivacious culture.

Old San Juan is home to some of the oldest buildings in the Americas and cobblestone streets lined with colorful colonial homes dating back centuries ago. Embark on a journey through El Morro Fortress or delve into the cultural depths of Museo de Arte Contemporaneo de Puerto Rico and Museo de las Americas, showcasing artwork from Latin American countries like Mexico, Colombia, and Peru.

For the outdoor enthusiast, Puerto Rico offers a wealth of activities. From hiking trails that lead to El Yunque National Forest, where one can observe rare birds such as parrots and toucans; kayaking tours along rivers surrounded by mangroves; zip lining across canyons; horseback riding on secluded beaches; cave exploration at Rio Camuy Cave Park; surfing lessons at Rincon Bay Surf School or simply soaking up some sun on any number of pristine sandy shores – there is something for everyone.

Sample the traditional dishes of Puerto Rico, such as mofongo (mashed plantains) served with pork cracklings called chicharrones or classic seafood dishes like ceviche made with fresh fish marinated in lime juice accompanied by coconut rice known locally as “Arroz con Coco.”

Refresh yourself with tropical drinks such as piña coladas made from freshly squeezed pineapple juice blended with rum – no wonder they call it paradise.

El Morro Fortress – Stephanie Klepacki

FAQs about the Best Sailing Destinations in the Caribbean

Where is best to sail in the Caribbean?

The Caribbean is a stunningly beautiful region with an abundance of sailing opportunities. For those looking for a mild luxury bespoke trip, the best place to sail in the Caribbean is undoubtedly the British Virgin Islands. With its crystal clear waters and picturesque coves, it offers some of the most breathtaking views in all of the Caribbean. From snorkeling to deep-sea fishing, there are plenty of activities to keep you entertained while taking in this paradise’s beauty from your boat. Whether you’re looking for relaxation or adventure, sailing through these islands will be an unforgettable experience.

Caribbean Sailing – _dChris via Creative Commons

What is the sailing capital of the Caribbean?

The sailing capital of the Caribbean is undoubtedly Antigua. This stunning island offers an abundance of crystal-clear waters, perfect for sailing and exploring the many cays and bays that make up this beautiful destination. From its protected harbors to its spectacular beaches, it’s no wonder why Antigua has become a favorite among sailors from around the world. With plenty of marinas offering excellent services and numerous activities, such as snorkeling and diving, this tropical paradise has something for everyone. Whether you’re looking for a relaxing day out on the water or an adventurous journey across the sea, Antigua will surely provide an unforgettable experience.

Antigua – Phil Hauser

What is the best time of year for sailing in the Caribbean?

The best time of year for sailing in the Caribbean is typically between December and April. This period offers mild temperatures, light winds, and calm seas. It’s also when many islands host their annual regattas and festivals, making it a great time to explore the culture of the region while enjoying some sailing. From June to November, it’s essential to be mindful of weather conditions when scheduling a trip during this season, as the region is prone to hurricanes.

The Caribbean – Ishan

Where do yachts go in the Caribbean?

The Caribbean is a vast and diverse region with many different yachting destinations to choose from. From the Bahamas to Grenada, a plethora of opportunities exist for those seeking an extraordinary sailing venture. The Virgin Islands offer stunning scenery and sheltered anchorages, while the Leeward Islands provide excellent wind conditions for experienced sailors. In addition, Martinique offers beautiful beaches and secluded coves perfect for luxury yachts. No matter your fancy, you can find a fabulous place in the Caribbean to embark on an unforgettable voyage with your yacht.

Caribbean Yachts – iSaw Company


The Caribbean is an amazing place to explore by sailboat, with its magnificent scenery and diverse cultures.

From the US Virgin Islands to St Lucia, there are plenty of great destinations for sailors looking for a mild luxury bespoke trip.

Whether you’re looking for pristine beaches or vibrant nightlife, the best sailing destinations in the Caribbean have something to offer everyone.

But with so many options available, it can be hard to choose where to go – but you’ll be sure of an unforgettable experience whichever destination you pick.

Are you ready to explore the Caribbean in a unique and exciting way? Sailing is one of the best ways to take in all this region offers.

From white sand beaches, warm and clear waters, and stunning sunsets, sailing destinations are so popular.

Best Sailing Destinations in the Caribbean
Caribbean – Jono Hirst


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