Top 10 Places to Sail in The Caribbean

Island-Hop Your Way Through a Cultural Wonderland That’s More Than Just Palm-Fringed Beaches

Top 10 Places to Sail in The Caribbean

A sail in the Caribbean is the stuff dreams are made of and an experience not many get to experience. If you’re thinking of clocking onto island time, you’ll find there are over 7000 islands, islets, cays and reefs waiting to be explored. From the diving-paradise of the Cayman Islands in the north to the picturesque desert landscapes of Aruba in the south, it can be hard to decide which of these bite-sized destinations to choose from.

Sail Caribbean

Don’t let the size fool you, though, there’s a whole lot of culture, cuisine and cocktails to discover on each island. Whether you’re into lounging on picture-perfect beaches, hiking through jungle trails or snorkelling amongst colourful coral and tropical fish, there’s a Caribbean island out there for you.

1. British Virgin Islands

Natures Little Secrets

With well-developed marina facilities, white sandy beaches and delectable cuisine, the British Virgin Islands (BVI) are an easy choice for your next sailing trip. Mild winds and line-of-sight navigation between the islands are in store for you here making this a great bareboat charter option for all abilities.

Activities include snorkeling, diving, windsurfing, beach bar hopping and hiking but the one thing not to miss is the Baths on Virgin Gorda. Massive granite boulders sitting right on the beach that create a maze-like series of caves and pools just made for exploring.

British Virgin Islands Highlights
  • Go snorkeling at Brewers Bay
  • Grab a ‘Painkiller’ at the Soggy Dollar Bar
  • Visit the ‘Baths’ at Virgin Gorda
  • Explore the shipwreck at Rhone National Marine Park
  • Visit Jost Van Dyke’s White Bay
  • Spend the evening dancing to live music at Cane Garden Bay
Best Time To Sail BVI

There really is no bad time to sail. Like a bit more action? December through April is the high season and features a bunch of fun events including BVI Kite Jam and BVI Spring Regatta. 

May and June see the islands slowing down with a more peaceful atmosphere. The water is a touch warmer, the wind is a little gentler and rates are a bit lower.

During September and October you can expect a very slight chance of hurricanes. Take the low risk and you’ll find yourself alone in an anchorage with a pristine beach all to yourself.

Get Started
  • Read our full guide to a British Virgin Islands Catamaran Charter here.
  • Find out about last-minute bareboat offers in the British Virgin Islands here.
  • Check our British Virgin Islands Cabin Charter here.
  • Looking for something specific? Send us your special request here.

2. St Martin/St Maarten

St Martin is an Island in the Northeast Caribbean Sea Shared by France and the Netherlands

Known as ‘The Friendly Island’, our next pick delivers the perfect mix of European flair with easy-breezy Caribbean cool. You’ll find secluded beaches and coves, fresh-baked baguettes and French pastries, a fascinating colonial history and a fun boating culture with many social and competitive events throughout the year.

Even better, you get two countries for the price of one as the north side is governed by France and the south is owned by the Netherlands. Dutch St Maarten is where you’ll head for boating events, bustling nightlife, diving and shopping. Quieter St Martin is less-developed and has off-the-beaten-track, secluded beaches for days. Family sailers should take note that many of St Martin’s beautiful beaches are clothing-optional.

St Martin Highlights
  • Hike through Pic du Paradis
  • Get close enough to smell the jet fuel at famous Maho Beach
  • Find the latest French fashions at Marigot’s boutiques
  • Relax at the serene nature sanctuary of Loterie Farm
  • Sample tropical treats at an open-air market
  • Get spruced up for dinner along Grand Case
Best Time To Sail St Martin

St Martin doesn’t really have a distinct wet season like the neighboring islands but for the lowest chance of having rain disturb your day, plan to visit between January and June. Aim for the months between February and April for great weather combined with fun festivals like Heineken Regatta and Carnival.

The Trade Winds generally blow from December until March and then from June to August while hurricane season is from July to November.

Get Started
  • Need some inspiration? Check out our St Martin Sailing Itinerary here.
  • Learn more about booking a Yacht Charter here.
  • Find out about last-minute bareboat offers in St Martin here.
  • Ready for the next step? Let us know what you’d like here.

3. Bahamas

Made for Sailing with 700 Islands, Cays and Islets to Explore

Sailors tend to go crazy for the sheltered harbors, deserted islands and easy-to-challenging sailing areas around the Bahamas. And we surely agree with all the fanfare. Add in the gentle light winds, an easy line-of-sight navigation and the option of scuba-diving in some of the finest spots in the world and you’ve found yourself a bonafide sailors paradise.

Spread across 700 islands, the Bahamas is a place where many either make their living from a boat or sail to work in a boat, where three-foot iguanas greet you on the pristine beaches while colorful fish and friendly sea turtles are waiting just below the surface. Essentially, it’s a place where you’ll get the most out of visiting on a sailing holiday versus a traditional one on-land.

Highlights
  • Rent a golf cart and explore charming Harbour Island
  • Up your Instagram game with a photoshoot at Pink Sands Beach or quieter Greenwood Beach
  • Dive off Walker’s Cay and see how many sharks you can spot
  • Grab a mask and snorkel just about anywhere
  • Test your patience and head out bonefishing
  • Indulge in a local fish fry and wash it down with a sky juice
Best Time To Sail The Bahamas

September to May is a great time to sail the Bahamas when you can expect average temperatures between 18-27°C (65-82°F) while the weather can get up to 31°C (89°F) in the summer months.

The Bahamas knows how to throw a festival and you can usually find at least one big one each month but summer, in particular, is stuffed with lively events including the colorful Junkanoo in July.

Get Started
  • Plan your ideal Bahamas Sailing Itinerary here.
  • Check our Bahamas Bareboat Charter Guide here or the Bahamas Yacht Charter Guide here.
  • Ready for a sail in the Caribbean? Send us your special request here.

4. Grenada

"The Spice Island" Is a Laid-back Caribbean Beauty

You could easily spend an entire week sailing around Grenada and its 45 black and white-sand beaches, tropical rainforests, colorful corals and natural parks. If you’re up for an adventure, Grenada has a lot to offer.

Nature lovers, in particular, will adore the island’s abundance of hiking trails, waterfalls and coral reefs along with the local wildlife such as the armadillo, Mona monkeys, whales, dolphins and manta rays.

Highlights
  • Spend the day relaxing at stunning Grand Anse Beach
  • Stretch your legs at Grand Etang National Park
  • Cool down in Annandale Falls
  • Learn all about spices at Gouyave Nutmeg Processing Station
  • See how rum is made at a local distillery
  • Escape the tourists at nearby Carriacou or Petit Martinique
Best Time To Sail Grenada

It’s tough to beat the weather in Grenada. You’ll find average temperatures hover between 24ºC and 30ºC (75ºF-85ºF) with a hot, tropical climate year-round. January to May is the driest period whereas June to December has rain that falls in brief, heavy showers.

Get Started
  • Need some inspiration? Check out our Grenada Sailing Itinerary here.
  • Find out more with our Caribbean Yacht Charter With Skipper Guide here.
  • Or get in touch here for help planning your sail in the Caribbean.

5. St Vincent and the Grenadines

From Early-morning Volcano Hikes to Dozing the Afternoon Away in a Hammock and Everything in Between

If you’re looking for more of a balance between sailing and inland activities, St Vincent and the Grenadines seems to have a perfect mix. Your days can be spent beach-hopping through the 36 separate islands, exploring coral reefs and even hiking to the crater of an ancient volcano.

You can do as much or as little as you like and wherever you choose to spend the day, you can almost be guaranteed stunning views. Sunny strips of white-sand beaches, lush foliage at the centuries-old Botanic Gardens or the lofty views from Fort Charlotte are all on the agenda for the willing sailor.

Highlights
  • Snorkel in the Tobago Cays Marine Park
  • Spend the day at Salt Whistle Bay  — one of the prettiest in the Caribbean
  • Hike to the crater of La Soufrière volcano
  • Explore the churches, fort and nature trails of Kingstown
  • Take a stroll through the Botanical Gardens
  • Have a dinner or drink at the Sugar Reef Cafe
Best Time To Sail St Vincent and the Grenadines

The months of May and June are the sweet spots between the busy high season in winter and the hurricane season in the summer. Temperatures are pleasant and you might be lucky to catch the 12-day Vincy Mas Carnival, the island’s biggest festival.

Get Started
  • Find out about last-minute sailing offers in St Vincent and the Grenadines here.
  • Check our Cabin Charter in the Grenadines here
  • Looking for something specific? Send us your special request here.

6. Guadeloupe

Let the French-Caribbean Seduce You with It's Creole Touch

Secluded sunny shores, awe-inspiring scenery and Creole cuisine are all part of the package on a sail in Guadeloupe. This postcard-perfect island is governed by France and your senses will be on high alert as you smell fresh croissants baking right next to stands selling fragrant coconut sorbets. A delightful mix of European and Caribbean cultures.

Highlights
  • Hike amongst the mountain landscape of Parc National de la Guadeloupe
  • Island hop around the eight islands of Les Saintes
  • Make like Columbus get marooned on La Desirade
  • Sample some rum, chocolate and coffee on a plantation tour
  • Pick up some local delights at the vibrant Marche Couvert market
  • Snorkel in the calm waters of Plage Caravelle
Best Time To Sail Guadeloupe

Guadeloupe’s average temperatures vary based on the seasons, with an average winter temperature of 23ºC (73ºF) and a summer temperature of 30ºC (86ºF). The best time to visit is during the dry season between December and May when you can expect warm sunny days.

Get Started
  • Plan your ideal Guadeloupe Sailing Itinerary here.
  • Or, let us plan your ideal Caribbean sailing trip here.

7. Martinique

A Mountainous Stunner with Plenty of Local Charm

Another French-Caribbean island whose biggest drawcard is the stunning natural beauty. From the rugged and lush landscape in the north to the romantic white-sand beaches in the south, topped off with the commanding views of the majestic Mont Pelee volcano; it’s a lot to take in.

The capital of Fort-de-France is also bursting with cultural sites and spectacular history and it’s a lively city to get lost in. You’ll find a variety of museums, architectural wonders, narrow streets and markets just begging to be explored.

Highlights
  • Take a dip in the clear waters of Les Salines
  • Soak in the history (and some rum) at the Habitation Clement
  • Hike to the summit of Mont Pelee (or cheat with a drive up there)
  • Brush up on your French by bargaining with the vendors at La Savane Park
  • Take in the dramatic white stone effigies of the Anse Memorial
  • Visit the charming village of Sainte-Anne and its Notre-Dame church
Best Time To Sail Martinique

Martinique offers a subtropical climate with daytime temperatures averaging between 19ºC to 30ºC (66ºF to 86ºF). You can realistically visit any time of the year but December to June sees the least rain while winds tend to reach between 10-15mph and come from an easterly direction.

Get Started
  • Need some inspiration? Check out our Martinique Sailing Itinerary here.
  • Or get in touch here for help planning your sailing trip.

8. St Barts

Feel like a Celebrity in This Exclusive Tropical Paradise

Everything you’ve heard about this Caribbean hideaway is completely true. Chic shops, beachside bistros and glamorous beach bars are most of what you’ll find here as this former playground of the rich and famous is all about scenery, serenity and shoreside relaxation.

It’s a bit difficult to get to which means you won’t be exploring with the masses but once you make it, you might not want to leave again and we won’t blame you.

Highlights
  • Bask in the aquamarine waters of Baie de St-Jean
  • Stroll through the streets and sights of Gustavia
  • Escape the crowds at Colombier Beach
  • Try your hand at a new water sport at Anse de Grand Cul de Sac
  • Don’t miss Shell Beach’s all-day beach party
  • Catch the sunset from a hillside cafe in Lurin
Best Time To Sail St Barts

April to June is the best time to visit St Barts just after the expensive winter months and before the storms of fall. Temperatures are mostly constant year-round but you can expect more rain between September and November.

Get Started
  • Send us your special request here and we can help you plan your sail in the Caribbean.

9. St Lucia

Blessed by Nature with Tons of Breathtaking Beauty to Explore

Many of St Lucia’s top activities are based around nature and on an island packed with cascading waterfalls, lush rainforests, soaring peaks and hidden beaches, it isn’t hard to see why. The authentic Creole culture and laid-back attitude give you that Caribbean feel on land while the year-round trade winds are ideal for exploring the coastline.

In fact, Saint Lucia might have been made for sailors because one of the best views on the island is from the surrounding waters. Taking in all the splendor of The Pitons is only really possible from the sea.

Highlights
  • Take a mud bath at Sulphur Springs
  • Go chasing waterfalls – there are a lot of them!
  • Spend a day relaxing at Marigot Bay
  • Hike The Pitons and take in the panoramic views
  • Sip on sundowners at Rodney Bay
  • Party the night away at the weekly Gros Islet street party
Best Time To Sail St Lucia

May and June are the best months to visit St Lucia for both weather and cultural events. Temperatures stay around 30ºc (86ºF) most days and if you time it right, you could be there for the St. Lucia Jazz and Arts Festival.

Get Started
  • Plan your ideal St Lucia Sailing Itinerary here.
  • Looking for something specific? Send us your special request here.

10. US Virgin Islands

Three Separate Islands, All with Something New to Offer

The US Virgin Islands is made up of three main islands (St John, St Croix and St Thomas) and is a great destination for both beginner and seasoned sailors. Consistent year-round conditions, trade winds and line-of-sight sailing sprinkled with excellent diving sites and deep-sea fishing opportunities all make up the recipe for a sailor’s paradise if we ever saw one.

This quintessential Caribbean sailing experience is also very accessible, especially for US visitors and has a lively sailing culture.

Highlights
  • Wander around the streets of historic Charlotte Amalie
  • Snorkel and sunbathe at Buck Island
  • Dive the RMS Rhone shipwreck
  • Hike the Reef Bay Trail on St John
  • Escape the crowds at Brewer’s Bay
  • Enjoy a night out at Redhook
Best Time To Sail US Virgin Islands

You’ll find consistent temperatures with highs between 29ºC and 32ºC (84ºF and 90ºF)  throughout the year. Most rain occurs during the hurricane season with the greatest possibility between August and October while the driest (and best) months are from December to April.

Get Started
  • Send us your special request here and we can help you plan your trip.

Amazing Sailing Experiences

Our Amazing Customers


  • Great family vacation.

    I didn't think sailing with my family would be so much fun...

    Sailing for the first time.

    Alex
    Alex USA

  • I recommendate them !

    Everything went smooth, the paper processing, special requests and the specs of tht check-in procedure. Boat was also in good shape, so no complaints and a worry free holiday...

    We had a great experience with booking through sailchecker.

    <read more>
    Dick USA

  • Great service from Kate.

    Informative and looked for the best value for our family. Very good customer service on this side and in Greece. Great boat and skipper...

    Fantastic holiday from start to finish.

    <read more>
    Angela United Kingdom

  • Very professional outfit!

    They were very responsive and very quick to answer questions via email and instant chat. They had extensive knowledge of the area...

    We will most definitely use their services for our next bareboat sailing vacation.

    <read more>
    Kirsten W.
    Kirsten W. USA

  • Sail checker were professional from start to finish - we wouldn’t book through anyone else!

    Sailchecker were professional from start to finish - and were awesome dealing with a problem! Our first Yacht had serious issues and sail checker helped us to resolve it...

    They are easy to deal with, straightforward and honest and I would recommend them to anyone planning a charter holiday.

    <read more>
    Kat, H.
    Kat, H. UK

  • Coronavirus pandemic support has been brilliant!

    During the Coronavirus pandemic, Kate and her colleagues at Sailchecker have performed brilliantly. They have been considerate and highly efficient in re-organising our Turkey charter and also provided lots of assistance in getting our Yacht Security Deposit insurance policy transferred to match our revised charter dates.

    Truly worthy of a 5 star rating!

    <read more>
    Alan, R.
    Alan, R. UK

  • Sailing is the perfect family holiday.

    Would I go sailing again? OMG yes! Sailing is the perfect family holiday. Boys loved the activities, I enjoy relaxing as well...

    Sailchecker.com arranged a sailing cruise her family of 2 sons, daughter & hubby in the BVI with their own.

    Anne
    Anne USA

  •  Thank you sooo much!

    It was sail in the day… party at night. We couldn't have wanted a better skipper or a Spring Break!  Good times...

    Arranged for 6 friends to sail Spring Break in the British Virgin Islands for under $500 each.

    Tim
    Tim USA

  • We had an absolute blast !!

    All bookings and confirmations was always accurate with no delays. Our boat was also fabulously maintained and the Skipper new the area extremely well...

    Everything was down to the tee.

    <read more>
    Pieter Van R.
    Pieter Van R. Netherlands
SailChecker Yacht Charter and Sailing Worldwide Logo TrustPilot 4.9/5 Stars

Rated 4.9 out of 5 based on 160 reviews on Trustpilot

Got a Burning Question?

We’re Happy to Answer Any Yacht Charter & Sailing Question

Leave us a quick question here, or call your local office, the numbers are located in the footer below. When not arrange a call back?

girl at desk at yacht charter show
Recent Posts
Contact Us

We're can't wait to hear your sailing or yacht charter plans.

Not readable? Change text. captcha txt
0

Start typing and press Enter to search

view of the palm trees and ocean on a Belize yacht charter