When considering Caribbean boat charters, there are a couple of essential elements. These include the type of boat to charter as well as the Destination. In this article, we want to help point you in the right direction for the best charter for you.
The turquoise waters and vibrant culture of the Caribbean beckon, but how to explore them? Two popular options emerge: crewed charters and bareboat charters.
Indulge in excellent sailing conditions, then flock to the Caribbean during high season.
Read our guide before you charter a boat in the Caribbean.
Speak with a BVISAIL Charter Specialist for personalized recommendations based on your travel style, budget, and preferred destinations.
Get My RecommendationsA Caribbean boat charter is a private yacht vacation that allows travelers to explore multiple islands with a customized itinerary aboard a sailing yacht, catamaran, power catamaran, or motor yacht.
On a private yacht, it’s just your group and crew. Resorts mean shared pools, crowded beaches, and communal dining. A charter delivers true exclusivity.
Resorts keep you in one place. Yachts let you wake up somewhere new every day — Virgin Gorda, Norman Island, Jost Van Dyke — all in one trip.
Resorts serve hundreds. On a yacht, your captain, chef, and crew focus entirely on your preferences, tailoring every detail to your group.
Skip the crowded shorelines. Yachts access private beaches, hidden anchorages, and elite beach clubs that resorts simply can’t reach.
At a resort, families scatter across activities. On a yacht, everything travels with you — water toys, meals, and bonding moments in one floating home.
When finding a Caribbean boat charter, consider the different types of boats themselves. Often these charters are Yacht Charters, Catamaran Charters, Sailing Charters, Inclusive Charters, and All Inclusive Charters.
Here at CKIM Group, we may use different types of language except “All” Inclusive Charters. We don’t like to use the word “All” as we feel it can mislead. Primarily, the customary gratuity of 20% is not included and can consequently mislead one.
We will focus on Caribbean Sailing Catamarans, Motor Yachts, Traditional sailboats, “Monohulls,” and Power Catamarans. In addition, we’ll break each vessel type down into two factors: advantages and price differences.
Sailing Catamarans are probably the most popular and abundant type of Caribbean Yacht Charter. Several key elements play a role in this. One is that they are spacious and comfortable. If you are looking for a sailing experience, then a sailing catamaran is perfect for a yacht charter vacation.
Sailing catamarans share their distribution between two hulls with a wide stance. This not only gives much more stability than a traditional monohull, but it also provides a great space. Typically, the staterooms are disbursed within the two hulls, allowing for a large common area above the hulls. This area will have the galley and main salon area.
Other desirable features on sailing catamarans are easily accessible swim platforms at the aft and sunning trampolines at the front of the boat. Also, some sailing catamarans often have a flybridge lounge at the top of the vessel, providing a clear line of sight to the distant coastline.
Tell us your dates, guest count, and destination interests, and we’ll curate a shortlist of the best available yachts.
Curate My Yacht ShortlistFirst, please discuss with your CKIM Group charter broker what is and is not in the charter price.
Typically with Sailing Catamarans in the Caribbean, it will be “Inclusive.” Inclusive typically means that the essential items, such as provisions “food, beverage, and snacks,” as well as no additional fuel costs, are inclusive of the price.
Remember that it is exclusive of customary gratuity of 20% as a rule of thumb. We think “All Inclusive” sounds a bit bland.
Motor Yachts are, of course, a popular type of Caribbean boat charter. A significant factor in this is the motor yachts’ speed and a more direct way to each destination. With its traveling source being its engine, it can reach faster to the next port with possibly more destinations within the window of your charter timeframe.
Tell us your dates, guest count, and destination interests, and we’ll curate a shortlist of the best available yachts.
Curate My Yacht Shortlist
Ultimately a Caribbean Motor Yacht charter will probably end up with higher costs when compared to Sailing yachts. In addition to the charter rate, you may need to add the advanced provisioning allowance “APA.”
As mentioned, these additional costs would primarily include fuel and the provisioning you chose. The budgeted APA for a motor yacht charter in the Caribbean is approximately 30-40% of the charter rate if it is plus expenses.
Traditional Caribbean sailboat charters certainly have their appeal and demand. Many still speak about having their charter experience on a monohull sailboat as they feel it’s a more traditional sailing vacation. Discover the pros and cons of sailing yacht charter.
Tell us your dates, guest count, and destination interests, and we’ll curate a shortlist of the best available yachts.
Curate My Yacht Shortlist
To keep it simple, monohull sailboat charters in the Caribbean are typically the same as catamaran sailboat charters and are “Inclusive.”
However, the larger monohulls are usually plus expenses. Currently, the demand seems higher than the supply for traditional sailboat charters, so if interested, you will want to plan early.
A power catamaran is a bit of a hybrid between a sailing catamaran charter and a motor yacht charter, leading to a corresponding change in price. Power catamaran charters have the same travel ability while on charter as motor yachts. Therefore power catamaran charters in the Caribbean have their demand and are a popular choice among luxury yacht vacationers.
Tell us your dates, guest count, and destination interests, and we’ll curate a shortlist of the best available yachts.
Curate My Yacht ShortlistRegarding costs, power catamarans are a bit in between sailing catamaran charters and motor yacht charters. More times than not, they will have an additional APA. However, it should be lower than motor yachts due to the power catamarans’ more efficient fuel consumption.
Caribbean yacht charter costs typically range from $20,000 to over $100,000 per week, depending on yacht type, destination, season, and included services.
| Charter Type | Weekly Range |
|---|---|
| Sailing Catamaran | $25,000–$40,000 |
| Luxury Catamaran | $40,000–$100,000+ |
| Sailing Yacht | $20,000–$35,000 |
| Power Catamaran | $25,000–$80,000+ |
| Motor Yacht | $50,000–$100,000+ |
For a deeper dive into seasonal pricing, inclusions, and real charter examples, explore our Caribbean Yacht Charter Cost Guide.
Spacious catamarans, calm anchorages, and safe snorkeling make yacht charters ideal for family vacations with kids of all ages.
Romantic sunsets, private beaches, and luxury service create unforgettable honeymoons or intimate getaways.
Yachts provide private meeting spaces, team‑building activities, and upscale amenities for productive yet relaxing retreats.
Large yachts accommodate grandparents, parents, and kids together, offering shared experiences with personalized comfort.
Island‑hopping, diving, and water sports deliver adrenaline‑filled adventures across diverse Caribbean destinations.
So now, let’s dive into a somewhat broad breakdown of the popular destinations for boat charters in the Caribbean. In doing so, I’m going to divide the Caribbean islands into two areas you may have mentioned. The Leeward Islands are the Northern chain closer to Puerto Rico, and the Windward chain is a bit further south of the Leewards.
Here’s a map showing the Windward and Leeward Islands of the Caribbean.
We’ll start with the BVI, arguably the most popular boat charter destination in the Caribbean. This is for good reasons as follows. The BVI has a good sailing/cruising area since the islands form a necklace around the Sir Francis Drake channel.
Because of this, it’s pretty easy and accessible for boat charters to simply get to their exceptional tropical islands and hot spots. You’ll also enjoy many excellent diving and snorkeling areas with gorgeous marine life ready to explore.
These islands in the BVI include; Tortola, Jost Van Dyke, Virgin Gorda, Anegada, Norman Island, Peter Island, and more. Indeed, so much things to do and see when you charter a yacht in the BVI.
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The USVI is also a popular charter destination with its International airport making it a bit more convenient for Americans. In addition to this, no passport is needed for U.S. citizens. The main island of the USVI is St. Thomas. It has many beautiful sandy beaches canopied by palm trees, excellent shopping, and resorts.
Another lovely island in the USVI is St. John; with its unspoiled national park area and many exceptional beaches, St. John is undoubtedly worth spending some time on.
This unique island has dual personality, with French ambience and laid-back Caribbean vibes. Both seasoned and first time sailors may enjoy a diverse and exciting sailing adventure at St. Martin.
For more information visit: St. Martin/St. Maarten
Then, sail to the neighboring islands of Anguilla or St. Barths. St Martin is an ideal starting point for island hopping adventures.
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Include St. Kitts in your itinerary for a truly memorable Caribbean experience. Wander through the historical gems of the Caribbean at Brimstone Hill Fortress. Or drop anchor at secluded coves with powdery white sand and turquoise waters.
The Windward Islands lie between the Caribbean Sea and the Atlantic Ocean. They make up the southeastern edge of the Caribbean Sea and are a bit further south than the Leeward Islands.
They include Barbados, Martinique, St. Lucia, St. Vincent, and the Grenadines, Grenada with Carriacou and Petit Martinique, as well as Trinidad and Tobago, located northeast of Venezuela. These islands are called Windwards being more accustomed to trade winds on the Western side when traversing the Atlantic Ocean than those on the Eastern side – or Leewards.
There are some positive factors here, especially when considering one of the Caribbean boat charters during summer or winter. Many yachts move down to the Windwards island chain for the summer season because the islands are further south, making them considerably more out of the hurricane season of late summer.
One of the most common mistakes first-time charter guests make is choosing a destination before understanding which yacht experience best fits their travel style. The right yacht often determines the success of the entire vacation.
Charter Expert Insight
Our yacht charter specialists help clients compare destinations, yacht types, and pricing to find the best fit.
Talk to a Charter SpecialistCrewed catamarans start around $25,000 per week, luxury sailing yachts range $20,000–$35,000, and premium motor yachts exceed $70,000.
Charters typically include the yacht, accommodations, crew, meals, water toys, and itinerary planning. Taxes and gratuities are additional.
Popular destinations include the Bahamas, British Virgin Islands, St. Lucia, Grenada, and Antigua — each offering unique sailing appeal.
December to April is peak season with ideal weather. May–June and November offer quieter shoulder seasons and better availability.
Most crewed charters are all‑inclusive, covering meals, drinks, and activities. Some motor yachts use an APA (Advance Provisioning Allowance) system.
No. Professional captains and crews handle navigation, service, and safety, so guests can simply relax and enjoy the journey.
Catamarans fit 6–10 guests; larger motor yachts can host 12–14 with more luxury amenities.
Catamarans are more spacious and stable, while sailing yachts offer a traditional, performance‑focused experience.
Book 9–12 months ahead for peak season; shoulder season allows more flexibility.
December–April has the best weather, while May and November balance savings with good conditions.
Embark on a Caribbean adventure with a boat charter tailored to your dream vacation. Aboard a luxurious crewed yacht, soak in sunshine and azure waters as your chef caters to your every whim.
Whether you seek the serenity of the Grenadines, the cultural charm of St. Lucia, or thrilling watersports of Antigua, boat charters cater to every desire. Moreover, dive into the crystal-clear waters surrounding St. John, snorkel alongside vibrant fish in Tobago, or explore the rich history of St. Kitts.
From romantic getaways to family excursions, discover the perfect Caribbean escape with our comprehensive overview of boat charters and destinations.
For more information on this, please read about the Grenada Crewed Catamaran Charters.
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
