sailboat cruising the caribbean

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If you’re looking for a sailing vacation ruled by the sun, moon, and tides, you’ve found it!

Island Windjammers offers six, ten, and twelve-night sailings aboard our classic clipper ship Vela, schooner Diamant, and sailing yacht Lyra! Vela hosts twenty-six guests, Diamant accommodates ten guests, while our new addition Lyra has room for eight. This is small ship cruising at its finest.

Our Island Girls are fully-crewed and feature air-conditioned cabins, private bathrooms, portholes, and all modern comforts.

Your Captain sets the course. Each day is a new adventure. Free your mind from schedules, and savor each moment as the crew hoists the sails, the trade winds fill the canvas, and you set off to your next secret island destination.

There’s no rush. You’ll have plenty of time ashore to explore vibrant villages, sip rum at quirky beach bars, or laze the days away on pristine beaches.

Even the nights are magical. Shipmates gather on deck to dance, share a joke or tell tales of the day’s adventures. Lean on the rail, and steal a kiss under a canopy of stars.

Live in the now, and breathe it all in. This is island life--and you’re living it!

ALWAYS ON ISLAND TIME

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Caribbean sailing: Top tips from two years exploring this cruising paradise

• March 12, 2020

The Caribbean is a veritable cruising paradise. Terysa Vanderloo shares her tips from two seasons exploring the islands

Cayo Diablo is an idyllic diving spot off Puerto Rico

Rodney Bay in St Lucia was our first taste of the Caribbean and turned out to be the perfect introduction to cruising this area. There was an abundance of restaurants and bars, as well as the local village of Gros Islet a mile away. Someone from the marina told us to head over on a Friday night for the weekly Jump Up, so when the time came we duly walked down the rickety jetty towards the lights and thumping music.

The streets were thronged with people, locals and tourists alike. There were food stalls lining the street selling all manner of barbecued meat and fish, interspersed with makeshift bars groaning under the weight of jars and bottles bearing hand-written labels. We learned the hard way that purchasing one of these rum punches would ensure a headache the next morning: they were far more potent than the sweet, fruity taste let on.

Soufriere and the unforgettable Pitons of St Lucia make a spectacular welcome for cruisers. Photo: Alamy / Robert Harding World Imagery

We were thrilled with our introduction to the region, thinking that we had quickly identified the ‘real’ Caribbean. However, over the following season we came to learn that this broad term doesn’t encompass the many nuanced differences between cultures in this part of the world.

Despite their similarities, there are no two islands that are truly alike in the Caribbean. Even the French islands that we visited – Martinique, Guadeloupe, St Barth and St Martin – shared only a common language and the same supermarkets; in many other respects they were very different.

The Windward Isles

Nick was desperate to return to the Tobago Cays, which he recalled being utterly idyllic when he’d visited them during his Yachtmaster course several years previously. That had been in the low season. It transpired that the Tobago Cays are a very different place in the middle of January.

Article continues below…

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I did see my very first turtle there (it lazily swam around the boat, then promptly darted away as I clumsily jumped in the water for a closer look) but the anchorage was otherwise so overcrowded it was fairly unappealing. We left after just one night. Grenada, a little further south, gave us our first insight into ‘liveaboard’ culture.

There is a permanent liveaboard community in Grenada and we quickly fell into a pleasant routine of listening to the radio net in the morning, joining in with themed happy hours each evening, and I was even persuaded to go along to a group yoga class. There was always something to do and it was clear that many people made it to Grenada and then saw little point in moving on. We, however, had the rest of the Caribbean to explore.

Photo: Alamy / Chris A Crumley

Martinique proved to be a favourite. There are a variety of anchorages along its leeward coast, the most spectacular of which is surely at the foot of Mount Pelée, a volcano that towers above the tiny village on the seafront, and early last century wiped out all but two of its inhabitants when it spectacularly erupted.

The island’s French culture is evident as soon as you step off your dinghy ashore. Baguettes, pastries, wine and cheese are plentiful and there are several hypermarkets out of town for provisioning .

Nick and I spent a long and memorable morning negotiating our way by public transport to the HyperU. Giddy with the range of products at our fingertips, we bought a pressure cooker, a bread machine and filled a trolley with groceries, wine and beer, only to realise that we had no way of transporting all our goodies to the boat. One expensive cab journey and an over owing dinghy ride later, we had finally stocked Ruby Rose .

Photo: Richard Langdon / Ocean Images

Dominica was another highlight. It is easily the most spectacular island in the Lesser Antilles that we visited: a jumble of forest-covered volcanoes jut into the sky, their peaks often obscured by cloud. One Sunday evening at sunset the local families all converged on the beach where we were anchored.

Swimming in the sea with them, chatting about their lives and watching the kids take turns leaping from the pier, a background of golden-tinted jungle rising behind them, was an experience that will stay with me for a long time. It’s these low-key, everyday experiences that make this cruising life so special.

We continued north to the Leeward Islands, stopping at Les Saintes, a small archipelago of the French Antilles, north of Dominica. It has a strong resemblance to the Atlantic coast of Brittany, not least due to its architecture and excellent restaurants.

From Les Saintes we made our way to Guadeloupe and Deshaies, where it rained and the wind howled for days on end. We were going stir-crazy being stuck on board and eventually made a break for Antigua. Our punishment was enduring eight hours of being tossed around and feeling seasick before gratefully arriving in Falmouth Harbour.

Here we found many bars and restaurants of unusually high quality (the standard of food in restaurants in the Caribbean is generally not nearly as good as we’re used to in Europe, even on the French islands). We stuck around for the Antigua Classic Yacht Regatta, determined to get our hands on the famous ‘red hats’, given out only at the closing event.

Tickets for the final event were a challenge to get hold of, but we dutifully spent several evenings bar-hopping and ingesting large quantities of rum in order to secure our entry to the party.

After bypassing Nevis and St Kitts due to a rapidly-closing weather window, we spent several very rolly nights in St Barth’s notoriously uncomfortable Gustavia anchorage. I don’t normally ‘do’ rolly anchorages, but for St Barth I was willing to put up with a lot.

The town was extremely picturesque, and as quintessentially French as it’s possible to find in the Caribbean. We had fresh baguettes, cheap wine and fois gras daily, and enjoyed looking in all the upmarket shops.

St Maarten was a necessary stop for us as we had decided to upgrade our tender and do some other boat maintenance. We had planned on a week there, but ended up staying for three; something we were warned about the very first morning on the daily radio net. “This place has a way of sucking you in!” Mike, the net controller, cheerfully informed us.

The Caribbean is also famed for its sailing regattas. Photo: Paul Wyeth

There was a large and friendly community of liveaboards and cruisers on the island, many of whom were stopping for repairs and maintenance just like us. This meant that every evening at the local hangout Lagoonies there were always familiar faces and we used this opportunity to connect with old friends and make new ones.

The longer we spent in the Caribbean, the more the community became a part of our lives. One weekend we headed to the St John, in the US Virgin Islands, anticipating a quiet few days alone. However, it was not to be. As we picked up a mooring buoy (no anchoring allowed) we were hailed on the radio; friends of ours had seen us on the AIS and were coming on over.

They invited several couples we had never met before but followed on social media, who happened to be in the area. So five couples of a similar age converged and our plans for solitude and recovery were abruptly postponed.

Photo: Tor Johnson

What followed was a weekend that couldn’t have been better if we’d planned it: by day we went diving for lobster, hiking, and, on one particularly memorable afternoon swam with a dolphin and her calf who seemed just as excited to play with us as we were with them!

It was truly the most magical experience I’ve had while cruising. By night we’d descend on somebody’s boat, eat lobster, drink rum cocktails and be serenaded by the two guitar players and singers of the group.

These few days epitomised what we loved about cruising the Caribbean and it couldn’t have been a better end to our time there. The islands of the Lesser Antilles were varied and each had its own culture, character and distinctive beauty.

Every time we had to move on we felt the pull to stay; only our sense of curiosity and adventure kept us sailing. We were ultimately rewarded with all the friends we’ve met and the beautiful islands we’ve been privileged enough to visit.

• 1. Introduction
• 2. Best places for...

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• The Blue Hole of Belize: Nestled in the Lighthouse Reef, the Great Blue Hole is a massive underwater sinkhole. This natural wonder, over 300 meters in diameter and 125 meters deep, showcases stunning marine life and geological formations, making it a world-renowned dive site.
• Piton Mountains in Saint Lucia: The iconic Pitons, two volcanic spires rising dramatically from the Caribbean Sea, are a UNESCO World Heritage Site. Gros Piton and Petit Piton offer breathtaking views and hiking opportunities, showcasing the unique geological features of the region.
• Pristine Tobago Cays Marine Park: This protected marine reserve in the Grenadines is a haven for marine life. Snorkelers and divers can explore vibrant coral reefs, swim with sea turtles, and enjoy the crystal-clear waters of this idyllic Caribbean destination.
• Historic Sites of San Juan, Puerto Rico : San Juan's Old Town, a UNESCO World Heritage Site, boasts colorful Spanish colonial architecture. El Castillo San Felipe del Morro and Castillo San Cristóbal, historic fortresses, reflect the city's strategic importance in the region's history.
• Dominican Republic 's Pico Duarte: As the highest peak in the Caribbean, Pico Duarte stands at 3,087 meters above sea level. Hikers can embark on an adventure through dense forests to reach the summit, where panoramic views of the island await.
• The Baths, Virgin Gorda : This geological wonder in the British Virgin Islands features colossal granite boulders creating stunning grottoes and pools along the beach. It's a natural playground for exploration, swimming, and photography.
• Morne Trois Pitons National Park, Dominica : Dominica's UNESCO-listed national park is a treasure trove of natural wonders. Boiling Lake, the second-largest hot spring in the world, and Trafalgar Falls, with its twin cascades, highlight the island's geothermal activity.
• Cuba's Viñales Valley : Known for its picturesque tobacco fields and limestone karst formations, Viñales Valley is a UNESCO site. The vibrant landscapes and traditional agricultural practices offer a glimpse into rural Cuban life.

Our Favorite Caribbean Cruise Ports for Small Ships

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• Diverse Currency: Be aware that the Caribbean is a region with diverse currencies. While some islands use the Eastern Caribbean Dollar (XCD), others, like Jamaica, use the Jamaican Dollar (JMD), and some, including Puerto Rico, use the United States Dollar (USD).
• Hurricane Preparedness: During the hurricane season (June to November), stay informed about weather conditions and consider travel insurance that covers unforeseen disruptions. Check local advisories and be flexible with your plans. Prices tend to be lower during this season.
• Island Time: Embrace the laid-back lifestyle known as "island time." Things may move at a slower pace, so plan accordingly and savor the relaxed atmosphere.
• Water Safety: Exercise caution with water activities. While the Caribbean boasts stunning beaches, currents and tides can be strong. Pay attention to warning flags, and only swim in designated safe areas.
• Local Cuisine Exploration: Dive into the local cuisine. Each island offers unique flavors, so try traditional dishes and street food. Don't miss specialties like jerk chicken in Jamaica or conch fritters in The Bahamas.
• Bargaining Skills: Brush up on your bargaining skills, especially in local markets. Haggling is common, and you may score better deals on souvenirs or goods by negotiating with local vendors.
• Transportation Options: Explore various transportation options. Some islands have well-developed public transportation, while others may require renting a car. Consider your destination's infrastructure for the best travel experience.
• Language Variation: English is widely spoken, but many islands have their own dialects or languages. Familiarize yourself with local phrases, especially if English is not the primary language spoken.
• Health Precautions: Be cautious about food and water hygiene. Stick to bottled water, avoid consuming raw or undercooked seafood, and use insect repellent to guard against mosquito-borne illnesses.
• Sun Protection: The Caribbean sun can be intense. Pack sunscreen, a hat, and lightweight clothing to protect yourself from sunburn. Stay hydrated, especially in warmer months.
• Cash vs. Cards: While larger establishments accept credit cards, it's advisable to carry some cash for smaller businesses or markets. ATMs are available, but check for fees and notify your bank of your travel plans.

Video: Sailing the Caribbean on a Small Ship Cruise

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Sail the Caribbean incl. The Bahamas

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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean including the Bahamas, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean region. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A one-way cruise: martinique to grenada, there are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

British Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Martinique, St Lucia & The Grenadines

Latest Blog Posts

Sailing charter versus resort stay: comparing the costs

A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

Charter catamarans for modest sailing holiday budgets

Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

The popular Bali Catamaran in all its variations

The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

The value of after-charter destination and boat reviews

At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

Chartering in Turkiye: feedback we just have to share

Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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