Sailing the Caribbean: the most exciting boat cruise you can enjoy this year!

Bequeathed by inclining palm trees, silky white sands and azure blue waters, stands the exquisite conglomerate of the Caribbean Islands. The North Eastern gales and slanting sun rays add to its demeanor making this place a sailor’s paradise. Bounded on all sides by the Caribbean Sea, it flutters its wings over 700 small to big landmasses comprising the Greater as well as the Lesser Antilles of the West Indian topography.


Exploring this Lucayan Archipelago calls for a Caribbean sailing charter as an inevitable option to meander around this picturesque coastline. Get onboard, stretch your sails and harness the trade winds to instigate your vessel against the lashing waves.

While the Caribbean attracts tourists year-round, plan your trip between March and June when temperatures dwell between 25 and 30°C, and the northern gales hit shores at around 40 knots. Clear skies and balmy winds create an ambiance to bask in the temperate glory and give you that ultimate tan!

There is a reason this equatorial paradise draws in search of some sailing charters. Nowhere else will you find that unique blend of lip-smacking Caribbean delicious food, postcard-worthy beaches, colonial history diving and sultry Latin culture. And what better way to explore archipelagos that are little and the island chains in the own catamaran? Reserve a sun-soaked Caribbean sailing cruise today thank us when your friends go green.


What our Caribbean sailing vacations all have in common are warm and steady trade winds in picture perfect landscapes, plus plenty of great bars to chill out with three or a killer rum punch!

Related: What to Expect When Hiring Yacht Charters in Caribbean?

Top 10 islands to discover in the Caribbean –

Having noted all circumstantial intricacies, it is time to lay your eyes on the 10 major islands which lay the foundations for your West Indian voyage:

  1. BVI (British Virgin Islands):

caribbean-sailing-cruise-bviThe British Virgin Islands or BVI is considered as the yachting ecstasy of this geography. Sun-soaked beaches, sheltered harbours, and private bars provide ample reasons for chartering sailboats in Caribbean; while the shores await your presence with rich olive bushes in the backdrop.

BVI itinerary is never complete without paying a visit to Tortola or Jost Van Dyke. As dusk falls, BVI’s 30,000 inhabitants come to life on its brightly lit beaches. Amidst this languidness, Tortola emerges to be the hub of the cacophony housing close to 24,000 residents on its blessed landmass.

Virgin Gorda, on the other hand, will welcome you with a kaleidoscope of thatched cafes serving mouth lacquering Caribbean-French cuisines on fresh banana leaves. Complete your BVI yacht charter experience by encompassing Greater Camanoe, Guana Island, Beef Island and Scrub Island in your itinerary as well.

The British Virgin Islands are ranked as one of the world’s top cruising destinations. Together with some excellent sailing and idyllic protected anchorages a yacht charter, flotilla vacation or sailing schools class from the BVI guarantees as much fun as you can handle — it is the destination of choice for people who like a party as much as they like to sail.

  1. Puerto Rico:


To the immediate west of the British Virgin Islands lies the promising isle of Puerto Rico. It comprises the islets of Culebra, Mona and Vieques under its jurisdiction. With San Juan as the capital port city, it houses close to 3.4 million inhabitants.

What stands as the highlight of Puerto Rico is taking your Caribbean sailing charter through the Spanish Virgin Islands (Passage Islands). A multitude of water sports is prevalent on these coastlines which include snorkelling, scuba diving and associated activities.

  1. Antigua & Barbuda: 


Your sailing rentals in Caribbean must incorporate the twin islands of Antigua & Barbuda as must-visit destinations. Nested between St. Kitts in the north and Guadeloupe in the south, this group of islands is a sovereign state in the Caribbean.

A total of 365 coasts conjoin themselves to form Antigua which personifies nightlife through its thrumming beaches and exclusive private bars. Shake a foot or two to the Caribbean beats while you gently sip on a glass of locally made red wine.

Going around the place on a sailboat charter Caribbean will require you to set the base at Nelson’s Dockyard and hovering around the sister islands of Antigua and Barbuda. Dominate the trade winds with a bareboat or enjoy complete luxury with a crewed vessel.

  1. Grenada


Your Caribbean sailing holidays must drop anchors at Grenada. Lying at the extreme south of the Caribbean, Grenada redefines tranquility in the most awe-inspiring manner. Known as the “Spice Isle of the Caribbean,” it is embellished with numerous crater lakes and black sandy beaches that house some rare species of flora and fauna.

  1. Vincent & Grenadines with Barbados

sailboat-charter-caribbeanWhen in St. Vincent & Grenadines, you ought to embark on the white sandy beaches of Barbados. Both of these islands lie on the same plain and adorn similar climatic conditions throughout the year.

  1. St Barts


Those coming from the BVI consider St. Barthelemy or St. Barts as their immediate eastward docking point. While the likes of Colombier Beach, Shell Beach and St. Jean Beach are impeccably beautiful here, your Caribbean sailing vacations must not terminate without opting for snorkelling or scuba diving.

  1. St Marteen


St Marteen, on the other hand, can be considered as the elder sibling of St Barts. It is adorned by cobble-stoned paths that line whitewashed houses with crimson roofs on either side. This island is precisely known for its heritage white wine and numerous breweries.

  1. Cuba


If you desire to stretch the extreme western limits of the Caribbean, then Cuba should be your destination. However, when in Havana, the capital of Cuba, your Caribbean sailing charter must not leave shores without paying tribute to the historic Plaza de la Cathedral dating almost 1000 years in time.

  1. Martinique


Sandwiched between Dominica to the north and St. Lucia to the south, Martinique stands as another unspoiled Caribbean sailing destination. While white sandy beaches make their presence felt in the northern shores, the southern edge embarks on an indented coastline.

  1. Dominica


This island stands as a hotspot for tourists around the world owing to its ultra-clear skies and obstruction free horizontal views. Every skipper prefers to sail around Dominica due to the absence of rough waves and consistently steady trade winds.

Dominica will treat your Caribbean sailing charter with a multitude of activities including an active nightlife, quality pubs and tongue-twisting local cuisines.

Wherever you go, you will find a warm welcome and terrific setting. You’re certain to return home relaxed, refreshed and ready to begin planning your sailing trips Caribbean.

Excursion in Caribbean’s top 10 –

Since now you have got a hold of the top 10 places in the Caribbean to lay your feet on, it is time to take a sneak peek at the best excursions, these hotspots have to offer.

When talking of excursion, it shall be wise to begin with the largest island of the group – Cuba. Amongst other Caribbean sailing destinations, Cuba perhaps offers the best Scuba diving opportunities.

Treat your visuals to the exquisite coral reef in the Las Antillas or hire a glass bottom boat and witness the bewildering marine life with your naked eyes. While Cuba will mesmerize you with its aquatic flora and fauna, an eastern shift to Puerto Rico will guide you to the historic San Juan. Time dating back its existence to the 16th century A.D., and the San Juan ruins at Caparra that lie in proximity to the ocean are worth experiencing.

Once done with Puerto Rico, it is time to drop the anchor of your sailboat rental in Caribbean on the British Virgin Islands. With a cluster of 30, these Virgin Islands are every cruiser’s paradise. With steady northern gales, it houses a series of sailboats procrastinating on the turquoise Caribbean Sea.

Sail down the St. Barthelemy channel hitting shores of St.Barts to the south and St. Martins to the north. Considered as sister islands, hiring a motorboat is the ideal option for meandering around these shores.

Next, your sailing trips Caribbean will include the islands of Dominica as prime coral reef attraction. Couple it up with the mud baths at St Barts and your Caribbean boat charter holiday will transpire into a priceless memoir.

Sailing further south, St. Vincent and Grenadines are known for their sailboat catamarans, ricking these indented coastlines. Another crucial point of interest is the kite cruising facilities along with ample snorkelling possibilities.

Last but not the least, Grenada marks the southern limit of the Caribbean islands. This island is known for its numerous day cruising possibilities to the Grenadines as well as to Barbados. One can even drop one’s anchor on Trinidad & Tobago or the mainland of Latin America.

Private sailboat charters – Your ultimate cruising vessel:

While the West Indian islet group offers a multitude of Caribbean sailing charter possibilities over its crystal blue waters, experts recommend choosing a sailboat over their motorised counterparts. The reasons justifying such a recommendation go as follows:

  • With consistent northern trade winds haloing the islands year long, sailboats never run out of throttle juice.
  • A sailboat will allow its inhabitants to enjoy the tranquility of the ocean away from the metropolitan humdrum.
  • Be it double-hulled or mono hulled; these vessels suffice within one’s Caribbean sailing budget.
  • Their extensive availability over other vessels in the region gives another good reason to charter those.

In addition to this, sailboats offer wide decks with varnished maple wood floorings. So, you along with your companions can simply lounge in the temperate glory while sipping a glass of red wine in one hand and relishing on a mutton steak in the other.

However, after choosing a sailboat over other voyaging possibilities, people are often confused between a bareboat and crewed boat chartering options. So, let’s take a look at each one in details.

  1. Crewed vessels:

Whether you choose a motor yacht, cruise, sailboat or catamaran, we recommend you for our crewed options. A crew will comprise of an able skipper, his cabin associates, a chef and other assistants on board.

In simple terms, you will be able to relax cross-legged as your skipper takes you around the Caribbean islands one after the other. To make your sailing trips Caribbean more special, your chef will prepare numerous exquisite delicacies that will enchant you utterly.

A skippered bareboat is less expensive than a yacht, but the strain of knowing the inside information about the area, determining your course and navigating through coral is eliminated. If this sounds you need, just let us know and we’ll arrange for you to have an experienced skipper on your bareboat charter and sailing the Caribbean.

  1. Bareboat vessels:

Quite often, we come across adventurous souls who are experienced sailors and wish to dictate the ocean on their own terms. If you belong to the same herd, then bareboat charters will suit you the best.

Simply, set your path, fix a compass and instigate your Caribbean vacation over the turquoise waters and clear blue skies.

A “Bareboat” charter is a yacht hire in which you take full responsibility for all aspects of the boat and travel: navigation, sailing, mooring, motoring, cooking, cleaning etc.. Bareboat charters offer enormous freedom to go where you need (within the limits of your contract and navigable waters!), when you need, providing you with a unique vacation experience.

With freedom comes responsibility and you have to consider it in order to enjoy a relaxed and fun Caribbean sailing cruise – among the members must be an experienced sailor or motor boat captain. Bareboat leases also require that everyone on board pitches in, so that the charter experience is one of teamwork. The skipper should not just understand how to manage the ship, but also how to organise and manage the “team” as well, especially on a sail boat.

You do have the option of adding a qualified skipper that will take the responsibility but still give the impression of having your own boat to you during your Caribbean sailing charters. They will often want you to help them raise the sails, trim the jib, drop anchor, etc., and you may take the helm whenever you like (just put a beer in the skipper’s hand, that normally works!) .

Caribbean sailing vacations cater all tastes

  • Parents appreciate a secure place for their children’s security (Caribbean sailing charters with family and kids).
  • Young kids love the beaches and all of the action.
  • Teenagers enjoy the waters ports, the night life and the opportunity to experience another world.
  • Couples enjoy all of the above, in addition to the chance to sail a larger ship than they would ordinarily own.
  • Honeymooners prefer their privacy.
  • Everyone enjoys the freedom to do as they wish.


Types of bareboat charters for your Caribbean sailing cruise

Typically bareboating refers to catamarans or sailboats while bareboat refers to any vessel that can be chartered without a skipper or crew. We have, while the majority of our bareboats are sailboats. If you’re looking for a motorboat you will need to have a powerboat license that is valid.

Recommended: Here’s Your Direction for Hiring the Best Yacht Rentals in Caribbean!

Bareboat Monohull Sailboats for sailing the Caribbean

The timeless bareboat charter give you performance, freedom and the feeling of sailing. There are thousands of sailboats worldwide, ranging from 30 to 50 ft and from 1-5 cabins. If you would like the enjoyment of pure sailing, and have experienced sailors aboard, we’d generally recommend a monohull sailboat.

Important Tips: Caribbean travel guide

Bareboat Catamarans for Caribbean sailing vacations

Catamarans are one of the fastest growing areas of the charter business as they deliver great comfort and privacy, for relaxing with family and friends whilst providing communal areas that are grand. Catamarans don’t tip providing for a feeling on the ship. Their draft also makes them better adapted for getting closer to shore when exploring inlets and islands. Usually the minimum duration of Caribbean sailing charters aboard catamaran is 5 days, but contact us if you wish to rent a boat for less days and we will assist you customising your perfect yacht rental Caribbean.

If you’re a party of several couples or a family, with sailors, we recommend a catamaran. Since the boat is bigger note, catamarans are generally more expensive than a monohull. But you get the payback in space for everybody.

Bareboat Motor Yachts for your next Caribbean sailing cruise

If you just need to get somewhere, or have a good deal of places to see and desire speed want out, there is a bareboat motor yacht right for you. It is possible to charter bareboat power boats for multiple days, but typically they’re chartered for a day, requiring certification and a deposit and are over 40 feet.


Crewed charters for sailing the Caribbean

Paradise can be found. The lush, green canopies of islands that are various stand in stark contrast to the deep blue hues of the ocean waters, making island hopping a experience. For those who like variety and tranquility, the Caribbean has beaches that range in colour from white to pink to black. Caribbean islands are certain to have a harbour and sailing the Caribbean is the next destination on your bucket list!

All kinds of yachts are available for your Caribbean crewed charter yacht holiday. We can work with your budget to find you a selection of charter choices that are amazing. This is your unique vacation and it’s our goal to make certain that it’s tailored just for you, which means you choose the islands you would like to explore, you decide the pace, and you opt for the sort of Caribbean yacht charters which is appropriate for your requirements. Start thinking about what things you want to see and do! We’ll help you plan the vacation of a lifetime!

Types of motor yacht charters for your Caribbean sailing vacations

Crewed motor yachts for sailing the Caribbean


Crewed motor yacht chartering combines the service and friendliness of an elegant resort with complete freedom to explore amazing destinations without ever worrying about the crowds. If you want the exhilaration of being on the water with the wind in your hair, freedom to explore, privacy, support, pampering food and drinks that are well-mixed, then we suggest a crewed motor yacht charter for Caribbean sailing vacations!

Crews on luxury yachts are hired, extensively trained and dedicated to one yacht. It’s their job, livelihood and enthusiasm to manage your yacht charter and the well-being of the clients aboard. The boat runs and are focused on your pleasure and well-being. The crew takes care of the upkeep, sailing, cooking, cleaning and navigation, and are specialists in the region where you are cruising. Yacht crew members are typically educated and experienced in the specific areas of responsibility they hold. And needless to say, they must be people and service oriented. Because the crew is dedicated to the yacht and lovingly care for it, crewed yachts are generally in excellent condition. A good crew is a genuine team that works together effortlessly. The best crews know give you the privacy you need on your vacation as well as how to offer service.

Crewed catamarans for sailing trips Caribbean


A luxury crewed catamaran charter offers the ideal setting for the ultimate family getaway- space, privacy, luxury and comfort at reasonable prices which are somewhat unique in the world of yachting. For those who want to combine sailing, relaxation and comfort in some of the most exotic destinations on earth such as the BVI, Antigua, Grenadines, Cuba, Bahamas, Martinica, we would highly recommend chartering a luxury crewed catamaran.

Related: Hire luxury yachts for your charter in Bahamas

Catamarans, because they float on two pontoons – do not “heel” (roll back and forth with the waves and wind), and allow for large interior areas for living and socialising, while providing the ultimate sailing experience and still ensuring privacy, for your Caribbean sailing charters.


Pondering over the requirements:

Before you begin your Caribbean sailing trips on a bareboat charter, it is crucial to take a look at some of the requirements you need to fulfill. It will include –

  1. A sailing resume depicting your previous cruising experiences as well as the types of boats cruised by you.
  2. The mooring as well as anchoring capabilities you have which will let service providers decide whether you require any onboard assistance or not.
  3. Your updates and renewed sailing license which permits you to sail vessels larger than 70m in length.
  4. Your navigational abilities and mechanical skills. You can choose to opt for technical assistance as per your requirements.
  5. Time period after which you go out on a voyage.

To get hold of a bareboat, you need to fullfill the above criteria to ensure a safe and sound Caribbean sailing charter.

Setting up the itinerary:

Sailing in the Caribbean requires you to set up a precise itinerary that will cover all the major ports as well as avoid the unnecessary rush of speeding through every island. The following section presents three distinct 5-Day, 7-Day and 14-Day trips around the Caribbean Islands.

Itinerary 1 (5 Days Plan):

Your 5 day sailing plan to the Caribbean Islands will include Dominica, Martinique, St Lucia, St. Vincent & Grenadines and St. Lucia to say the least.


Day 1:

The first morning of your Caribbean sailing itinerary will begin by setting sail from the coast of Dominica. Nested below Guadeloupe, it is embellished with clear skies and warm weather all-round the year.

Allow your chef to prepare some exquisite delicacies for you on board while you cruise past the scintillating coastlines of Marie – Galante and bend south towards Martinique. End your day by anchoring on one of the isolated shores of Martinique and doze off with a star-laden sky above.

Day 2:

As the sun appears from beyond the horizon, hop over to Mount Pelée standing as the ecological hotspot of this area. A brief trek will take you to the summit which offers astounding views of the setting sun against the sapphire blue backdrop.

Once done, resign back to your Caribbean sailing charter and treat yourself to some coastal breakfast. Leave the Martinique shores behind you, and look ahead to the historical magnificence of St. Lucia which stands at 4 hours sailing distance.

Day 3:

St. Lucia is a small and happening island where your primary activities will include snorkeling and a load of water sports. Once evening settles, take a brief stroll on its beaches but return to your vessel by the evening.

Day 4:

Opt for a day charter and sail around St. Vincent and Grenadines and back to St. Lucia by the evening (In the way, halt at Clifton Island for lunch)

Day 5:

Conclude your 5 day sailing in Caribbean by heading back to Dominica and setting the last anchor.

Itinerary 2 (7 Days Plan):

When planning for 7 days, Puerto Rico and the BVI come as necessary annexations to the context.


The First Day:

Morning of Day 1 will see you initiate your Caribbean sailing charter from Jost Van Dyke of the BVI. Meander around the coastline preferably on a catamaran and hit the shores of Tortola. Have your meal and set sail towards Virgin Gorda as you sail through Scrub Island, Guana Island and Beef Island.

The Second Day:

Wake up in the morning to find yourself amidst cerulean blue waters on all sides as you gradually head towards Anguilla. Halt at Anguilla and take a motorboat to Prickly Island offering awe-inspiring visual retreats. Once done, pick up your anchor and sail towards St. Kitts and Nevis.

The Third Day:

The island conglomerate of St. Kitts & Nevis known for their Turtle beach awaits your presence. Set your barefoot on this sandy layover and witness numerous small and large tortoises lying around you.

The Fourth Day:

Day 4 of this Caribbean yacht trip will bring forth the likes of Guadeloupe. Soak in the languidness as you sail past Guadeloupe and on to Dominica. The absence of flashy resorts and concrete jungles escalates Dominica’s virgin ambiance.

Post-dusk, take a brief stroll on its beaches and return to your vessel to experience the saliva lacquering delicacies prepared by your onboard chef.

The Fifth Day:

Martinique and St. Lucia will comprise the fifth day of your Caribbean sailing charter. After passing through the tranquility of Guadeloupe, embrace the coastal humdrum of Martinique with grace.

St. Lucia does not lag behind with ample trekking possibilities around its indented coastline.

The Sixth Day:

The penultimate day of your sailboat charter Caribbean will take you to the southernmost tip of Grenada. Bask in the temperate glory as your vessel cruises along the white sandy beaches contemplated by rich olive mangroves.

The Seventh Day:

Your Caribbean vacation will come to an end with the final drop off at Trinidad and Tobago from where tourists will be able to board their returning international flights.

Set the tone for a 14 Days yachting itinerary –

When looking to invest a couple of weeks in your Caribbean sailing charter, then you must not leave shores without visiting Cuba and the Dominican Republic.


  • Day 1:

The mightiest of all the Caribbean Islands, Cuba will welcome your Caribbean sailing holidays with its ultimate grandeur. Drop your anchor on the capital port city of Havana – the mystic cosmopolis of this Caribbean archipelago. Take a stroll around the city and do not leave shores without visiting the El Capitolio and La Cabana.

  • Day 2:

The second day of your sailboat rental Caribbean will take you eastwards to the island republic of Dominica. Known to be a busy port city, it is lined by tarmac streets and state of the art amenities. The same evening, sail to the all-famous British Virgin Islands.

  • Day 3:

Welcome to Puerto Rico! The place where beef steaks meet grape vines. Indulge your senses in delectable delicacies of this small coast town while watching dolphins hopping against the set backdrop.

  • Day 4:

Spend the whole of day 4 in exploring the intricacies of the BVI which include Jost Van Dyke, Tortola, Scrub Island, and Virgin Gorda as the leading tourism destinations. Drop the anchor of your Caribbean sailing charter anywhere you like and go snorkeling. You can even take a raft and start fishing if you wish to.

  • Day 5:

Sail past the indented coastline of Virgin Gorda towards Anguilla and the southeastern waters. Experience the white sandy beaches on both sides as your yacht passes through the Anguilla channel.

  • Day 6:

The sixth day your Caribbean sailboat rental or motorboat rental will transpire into a whole day voyage to St. Barths and St. Marteen. Drop anchor at St Baths for a break and continue your maritime cruise parking at St. Marteen by dusk.

  • Day 7:

Your next stop is Antigua & Barbuda. Witness how 365 small islands have skirted themselves to become one port town. You can choose to halt here for a day or simply travel south-west to Dominica.

  • Day 8:

By the afternoon of Day 8, your Caribbean sailing charter will reach Dominica. On the way, pass by Guadeloupe! This port city will offer a place for your yacht to rest and allow you a lazy walk along the shores and the marine drive. Get onboard and reach the not-so-bustling island of Dominica.

  • Day 9:

Spend a day at Dominica sailing along its coastline, indulging in scuba diving as well as getting the perfect tan. The following morning, sail to Martinique on your Caribbean sailboat charter.

  • Day 10:

The tenth dawn will welcome you to Martinique where you will spend some time and cruise to St. Vincent & Grenadines by dusk (the penultimate location of your charter).

  • Day 11:

St. Vincent is home to 110,000 inhabitants covering an area of 389 square km. Feel the temperate breeze brush against locks of your mane and balm your soul with its chilly gales here on day 11.

  • Day 12:

Hit Grenada, the final spot of your private sailboat charters Caribbean. Spend a day here and head back to your drop location that is Antigua and Barbuda, the next morning.

  • Day 13:

Sail northwards while leaving St. Vincent, Martinique and Dominica on your way back. Have your meals on board prepared by your chef as you sail back gradually.

  • Day 14:

On this day, the final drop of your Caribbean sailing charter will take place at the seaport of Antigua and Barbuda from where you can board your return flights to your country.

Factors affecting a yacht charter in the Caribbean:

Before you set on your Caribbean voyage, there is a multitude of factors that you need to ponder upon. These include:

Factor 1 (Best time to sail):

Experts recommend that the ideal time frame to rent a sailboat in Caribbean is between March and June. During this period, consistent light breezes embellish the clear blue skies aiding in maritime voyages.

Moreover, with temperatures being a notch above the average, you will find less crowd and hence, more docking space on its beaches.

Factor 2 (Peak seasons):

If you are looking to experience the population goliath band the outrageous nightlife of the Caribbean, then Christmas is your time. The island conglomerate bustles with a horde of tourists flowing with the “New Year” mood.

Related: Plan your New year’s Eve in the BVI

However, due to increased demand, prices are high. So, it is advisable to go for advanced bookings as renowned yachting companies provide discounts. Private sailboat charters Caribbean on a long-term basis will also be gifted with extended cuts in the price bracket.

Factor 3 (Package Booking):

If you are looking to bring your family and kids, then a package booking will be ideal for you. From a complete sailing itinerary to the intricacies of water sports, each and every amenity will be included in the package.

One additional info you must take note of – the minimum days to hire a sailboat is 5.

Understanding the difference between cabin charters and solo yachts –

Cabin charters are effectively meant for people who wish to experience a yachting vacation without renting the entire vessel. These come as an affordable option for tourists looking to venture around the Caribbean without investing a hefty amount.

Solo Caribbean sailing vacations, on the other hand, refer to booking an entire vessel. This comes in a package and tourists can book the vessel as a bareboat or a crewed boat. While bareboat charters will allow the sailor to cruise as they wish, crewed vessels include a chef, a skipper and a full crew onboard.

Sailing trips Caribbean all year around

It’s apparent that many people remain wedded to the misconception that Summer, (or even Spring), is a lousy time to sail the Caribbean. Not only are the Spring and Summer months over sailing in the wintertime not a bad time to go, in many instances there can be advantages.

The other common concern about sailing in the Caribbean is that it’s hot in the summertime. Being islands without a significant land mass to capture and radiate heat, the Caribbean islands’ temperature remains well moderated by the sea. The average temperatures for example, fluctuate a 5 levels from January to July – the average high and low in January is 72 and 83, respectively, as compared to July when it’s 88 and 77. Most crewed yachts have air conditioning, if this is a concern for you and a number of bareboat are equipped as well.

The advantages are equally overlooked while the reality to sailing the Caribbean in Summer of this downside stays esoteric to many. The primary benefit, in my opinion, is how the sailing is, and just how much more of this Caribbean is opened up for exploration. The Winter months can be very windy – . This in turn makes the sea state comfortable if bringing along guests relatively new to sailing. In combination with the high wind speeds, North Atlantic storm activity periodically creates ground swell, which closes off many otherwise gorgeous anchorages which are open to the north.

The sun shines all year round in the Caribbean that is glorious. Daily temperatures remain separating the coolest and warmest months of the year. The Caribbean enjoys its season between May and December, with rain showers coming between November and June. The trade winds that affect this paradise ensure sailing conditions.

One way Caribbean yacht rentals –

If voyagers want to start and end their cruising vacation at distinct locations, they should go for one-way maritime cruises on the Caribbean Sea. Amongst the entire Caribbean archipelago, these are some of the popular one-way cruising itineraries that sailors can opt for.

  1. Jost Van Dyke to Virgin Gorda
  2. Antigua to St.Lucia
  3. Martinique to Grenada
  4. Dominica to Grenada
  5. Cuba to BVI

In addition to this, a person can create his custom one-way route before deciding to rent a sailboat in Caribbean.

Types of available charters –

The Caribbean offers a horde of chartering possibilities. While options for solo charters are present, your group or family vacation will receive numerous other options to choose from.

  1. Crewed charters:

Opt for a crewed Caribbean sailing charter service when sailing with your near and dear ones. Your vacation is sure to transpire into one of the finest memories of your lifetime, courtesy the impeccable crew of these vessels.

An experienced skipper, alternatively, will guide your yacht gently against the trade winds while your on-board chef prepares some exquisite delicacies for you.

  1. Bareboat charters:

When a sailor has enough familiarity and wants to experience cruising based on his own terms and routes, then a bareboat catamaran in Caribbean comes as the apt choice. By depositing your sailing license, you will be able to hop over and sail offshore.

     2.   Cabin/family:

Cabins are meant for solo travelers while family travels include a full yacht on rent. The crew will attend to your personal needs as you wander along the Caribbean shoreline with ease.

     3. Luxury vessels:

Exclusive or luxury vessels generally transpire into cruise ships. These yachts represent the epitome of indulgence with their grandeur. These mostly stand the highest on the price list.

     4. Motorboats:

If you are looking to plan a day charter with your friends, then motor boats can be the ideal option. These can travel up to 40 or 50 knots and owing to their ample living space, suit perfectly to one’s needs.

A look at the chartering tariffs in the Caribbean –

Yacht charters in the Caribbean vary from small vessels to exquisite superyachts. So, if you are renting a vessel for 5 day or 7 day itineraries around the Caribbean, then your expenses will range somewhere from $20,000 to $50,000.

However, a 14 day Caribbean sailing charter will cost you between $60,000 and $120,000. While all these prices depict completely crewed reservations, bareboat vessels come at a cheaper rate.

Note: Bareboat yacht rental prices in the Caribbean come down to 75% of its crewed counterpart.

In this respect, one needs to consider peak seasons as well. Hikes of as much as 25% are witnessed on prices during rush; so, it is always advisable to finalize all bookings well in advance.

What are the best marinas and ports in the Caribbean?

Sailing in the best Caribbean yacht charter is not the only luxury on offer. This island conglomerate includes numerous breathtaking marinas each of which is nothing less than awe-inspiring.

  1. Rodney Bay Marina

The island of St. Lucia houses the Rodney Bay Marina on its eastern shores. Situated on the white sandy beaches, it has the capacity to accommodate more than 250 ships in its harbor. What stands out about Rodney Bay is its lush green overview and thatched roofs that line this Marina.

  1. Isle de Sol

Your Caribbean sailing itinerary must include Isle de Sol as a must-visit docking point. Located in the St. Marteen Island, it offers a perfect stop between British Virgin Islands and St. Kitts. Superyachts as long as 360 ft can make their way into this docking port.

  1. Christophe Harbor

Situated on the northern shores of St. Kitts, Christophe Harbor adorns a beautiful golf course associated with this marina. Simply hop off and swing a few sticks before heading towards your next destination.

  1. YCCS Marina

When in the British Virgin Islands, docking in YCCS Marina is an unavoidable option. All catamarans and sailboat rentals in the Caribbean pass through Virgin Gorda before hitting St. Barths. So, make sure to dock at this port.

  1. Port de Gustavia

Travelling from the Virgin Gorda, St. Barthelemy will greet your Caribbean sailing charter at the Port de Gustavia. With clear skies and fluffy white clouds hovering over this dock, the port of St. Barths welcomes tourists with an array of mud paths lining its coastline.

  1. Falmouth Harbor Marina

Yachts making their way to the island group of Antigua and Barbuda need to dock at the Falmouth Harbor Marina at Antigua. This place is particularly popular for its extravagant nightlife and includes a selection of bars and pubs which are a welcome retreat for any traveler.

  1. Jolly Harbor Marina

Last but not the least; you come to the Jolly Harbor Marina situated on the leeward side of the Greater Antilles. In addition to docking yachts, it is home to a variety of aquatic flora and fauna. The place also offers snorkeling and scuba diving facilities within reasonable price brackets.

Additional notable factors:

One must keep in mind that yacht rental in Caribbean will incur additional docking as well as fuel costs. Docking costs will include the amount of time one needs to dock at the port as well as tariffs as charged by the Marina.

Fuel costs are dependent on the cruising route and any detours taken by the vessel. This depends on,

  • Any unfavorable climatic conditions.
  • Unprecedented changes by clients while on board.
  • Excessive docking sessions extending beyond the allocated limit.

In addition to the above conditions, fuel costs may also be affected by peak seasons. For instance, the period between October and February is considered as a yachting phase in the Caribbean; hence, prices are expected to be high if yachts are rented during this time frame.

Amenities receivable on a Caribbean yacht charter –

By hiring a sailboat in the Caribbean, you are facilitated to receive a horde of luxurious amenities which include:

  1. An able skipper:

Skippers of any Caribbean sailing charter are impeccably experienced about the sailing paths. Whether you follow a conventional route or a customized route, the captain will always be at your service explaining the perks and flaws of your choice.

  1. The crew:

Onboard crew members including hostesses gain their position only after proficient training in their fields. They will strive to ensure that your sailing experience is cherished for your entire lifetime.

  1. Cleaning and maintenance:

A sailboat rental Caribbean will be available to its customers in top notch condition. The expert maintenance teams at each of these Marinas ensure that guests receive the best quality service on board.

  1. Pricing and Others:

Before you book your slot, it may be worthwhile to know that yacht rental prices in the Caribbean do not burn a hole in your pocket. Moreover, any security deposit taken from you at the beginning of the voyage will be completely refunded by the end of the trip.

So, with all the information at your disposal, it is time that you book your slot at the earliest. Especially with an assortment of festivals knocking at the door, early bookings will help you avoid unwanted price surges due to the oncoming peak season in the Caribbean Islands.

About chartering in the Caribbean Islands

No other destination in the world offers such a selection of crystal clear waters, islands and sailing conditions. If you are on a motor yacht you may spend your charter island hopping, though we would suggest taking a leisurely pace so that you may find and absorb the Caribbean‘s different islands anchorages, marine life and nice white beaches.
It is recommended that you book at least 6 months in advance for the High Season Period that is from Christmas to Spring, obviously include the New Year’s Eve.
For further informations about sailing the Caribbean, to receive our professional assistance with your charter arrangements, customise your itinerary for boat rental in the Caribbean and organise your unforgettable journey, fill the form below or contact us directly:
Send us an email at
Call us or text us (also on WhatsApp): +393343600997
[sc_fs_multi_faq headline-0=”h2″ question-0=”Is it safe to sail in the Caribbean?” answer-0=”Yes, sailing in the Caribbean is safe and safer than most of the people can think. Few months of the year, only August and September, could have hurricanes and the major hotspots of piracy remain in Africa and Asia. ” image-0=”” headline-1=”h2″ question-1=”When can you sail in the Caribbean?” answer-1=”In the Caribbean Islands, you can sail practically all year round. The only months that must be monitored for sailing in the Caribbean are September and October, both subject to hurricanes. In most of the Caribbean, the best period to sail is from December to April. ” image-1=”” headline-2=”h2″ question-2=”How much does it cost to charter a sailboat in the Caribbean?” answer-2=”The cost to charter a sailboat in the Caribbean can start from 1.500,00 Euro per week for 6 guests in a sailboat with 3 cabins and up. The cost to charter a sailboat in the Caribbean depends on the charter period, year of built of the boat, dimension, and equipment. ” image-2=”” count=”3″ html=”true” css_class=””]



Share this Post