Our experience chartering sailboats in the Caribbean over the years brings us a lot of joy and fond memories. Let’s explore a bit about each experience and place. We will conclude with a few recommendations for chartering your own sailboat in the Caribbean.
The Grenadines
We are not sailors, although my husband has tried on several occasions, so we always opt for a crewed boat. Our first sailing experience was many years ago on our honeymoon. We booked a stateroom on a very large (>100 feet), monohull yacht leaving from the harbor in Saint Vincent, Grenada. We sailed the lower Grenadine islands of Bequia, Mystique, Mayreau, and Palm Island, to name a few. It was a wonderful experience, although I was quite seasick on the first night. We already had the Caribbean islands in our blood, but this experience cemented our love for the beauty and diversity of the islands. The company we booked through is no longer in service.
St. Martin/Saint Maarten
Marigot in Saint Martin, the French side of the Caribbean Island
Our next sailing adventure was years later aboard a catamaran. We were invited to join two other couples on a birthday celebration for a seven-night adventure that left out of St. Martin. The catamaran was spacious, with queen beds, dry baths, air-conditioned cabins, and a lovely captain and first mate who took care of every need. We had somewhat of an itinerary, but each morning the captain held a meeting to give us options for the day. It was relaxing, peaceful, and just a marvelous experience overall.
The company we booked through was Moorings. They offer chartered services from multiple locations throughout the world. Options include bareboat, skippered, crude, and cabin charters. This is a highly reputable company and one we certainly recommend.
British Virgin Islands
Our next sailing adventure was out of Saint Thomas on a 50-foot monohull. We were the only guests aboard besides the captain and his first mate. On this vacation we were celebrating a new stage in our lives, so we booked the boat. For 10 nights.
Our cabin was air-conditioned, and we kept cool enough. The wet bath was adequate, but not ideal. The captain was a part-time physician from Wisconsin and the first mate was his significant other. Captain Dave knew the USVI and the BVI like the back of his hand. He was an excellent sailor and cook! Since we were the only guests, we had plenty of options each day, and we sailed and explored nearly every island in the area. Water toys on the boat included a kayak and snorkel gear.
Beautiful sunset scene on the island of Virgin Gorda in BVI
Believe it or not, we found Captain Dave through the VRBO website. Until then, I didn’t know VRBO offered these unique vacation options. The charter fee was all-inclusive, which included the captain, the first mate, and all food and drinks on the boat. When we went ashore for lunch or dinner, we paid.
One of my favorite parts of this trip was the sailing we did at night. Beautiful and magical all at the same time! Unfortunately, Captain Dave is sailing in other parts of the world and is no longer chartering his boat.
U.S. Virgin Islands
Our most recent experience in April 2023 was only for two nights, but still thrilling. We used VRBO again to locate Captain Alex. His monohull was about 40 feet with three cabins, one of which he used to sleep in. Another couple whom we had invited along, joined us on their first overnight sailing experience, and they loved it! This charter only included the captain, no first mate.
We stayed several days in advance at the Ritz Carlton Club on St. Thomas, then took the ferry from St. Thomas to Cruz Bay, St. John. It’s about a 20-minute ferry ride. Captain Alex picked us up in his dinghy and ferried us and all our luggage out to his sailboat. He provided breakfast and lunch as part of his chartering fee. On our first night on the boat, we purchased deli meat, bread, and cheese to eat for dinner while watching the sunset over the Caribbean. The second evening, we all went ashore for dinner and Captain Alex joined us.
This cruise was considered half board and the daily rate was $980 a night for the entire boat, with the skipper. We split the cost with the other couple, thus making the experience about $500 per night, per couple. There were no additional costs, except the gratuity we gave the captain, which was $100 per couple. This was an amount of our own choosing.
Our Recommendations
If you are new to sailing, we recommend an all-inclusive crewed charter, as it allows you to fully enjoy the experience without having to worry about navigation, safety, cooking, or cleanup! For two to four guests, either a monohull or catamaran will work fine. We do feel that catamarans have a little more room and are easier to walk around, but they are also likely to be a little more expensive. If there are more than four guests, a catamaran or a motor yacht is the best choice. The catamaran will be less expensive.
Overall, our experience chartering sailboats in the Caribbean has been fabulous. It is a wonderful way to fully immerse yourself in the natural beauty and unique culture of this part of the world. With so many options available, you’re sure to find the perfect sailboat, destination, and itinerary to suit your interests and preferences. It’s a good idea to research each type of boat and the various options available before making a final decision. You want to ensure that you choose the right boat for your needs and preferences.
Please read our other post for information on the different types of sailboats, the best locations, and what it costs to charter a boat in the Caribbean. If you want general information on visiting the U.S. Virgin Islands, take a look here.
If you have additional questions or need some advice, please send us an email. We are here to help.
Have you ever wanted to sail your way across the Caribbean? We have chartered several sailboats over the years and can tell you this is a wonderful way to experience the beauty and diversity of the Caribbean islands. There are several options available, depending on your preferences and budget. If this type of travel is intriguing to you, let’s walk through the ins and outs of sailboat charters in the Caribbean.
Types of Sailboats
Monohulls
The most traditional type of sailboat is the monohull. Monohulls are typically designed with a deep keel, giving them the ability to sail upwind more efficiently. Monohulls vary in size, from 10 to 100 feet, with an average length of 30 to 35 feet. This length sailboat can easily accommodate a couple or small family. Longer sailboats will of course accommodate a larger group.
Sailboats in the bay, Rodney Bay, St. Lucia.
Monohulls are generally faster and more responsive. This makes them a popular choice for experienced sailors who enjoy the challenge of sailing. A small engine helps sail or putter around the islands when sailing is not an option.
In terms of amenities, monohulls typically have one or more staterooms with a dry or wet bath, and hot water. A wet bath includes a marine toilet, a shower, and a sink, all within the same enclosed space. This means the entire space can become wet during use. A dry bath means the shower is separate from the toilet and sink.
Bed sizes can range from twin to full to queen and maybe a king on the larger monohulls. There may or may not be air conditioning. Small fans may be attached to the walls to keep the sleeping area cooler. You can also keep the portholes open so that air will blow through to keep you cool. There are storage cabinets and cubby holes on these boats but generally, there is not much space for storing a lot of luggage.
The kitchen area below the deck will have everything you need to cook. There is a small refrigerator, a stove, a sink, and cabinets to store dishes, food, and so forth. The size of the boat will determine the amount of available deck space. And, getting around the sailboat up top can be challenging given the limited amount of space.
Catamarans
Catamarans are another popular choice for sailing in the Caribbean. Two equal-sized hulls parallel each other and are connected by a deck. The hulls of a catamaran are wider than those of a monohull, which provides greater stability and makes them more comfortable to sail on. Those who want a more stable and comfortable sailing experience will want to opt for a catamaran.
Catamaran is sailing through the Bahamas
Typically, catamarans are more spacious than monohulls. The wider hulls of a catamaran also provide more living space both inside and outside, making them a popular choice for families or groups. They can also be faster than monohulls, which makes them a great choice for those who want to cover more distance in a shorter period. Like the monohulls, catamarans will also have an engine to assist with sailing or navigating tight places that make it difficult to put the sails up.
The amenities available on a catamaran are not too different from those of a monohull. The beds may be larger, and you may be more likely to have an air conditioner in your room. You are also likely to have a dry bath.
The kitchen is fully equipped with everything someone needs to prepare meals. There may also be freezer space beneath the floor to hold more food. Lastly, there is generally room up top for a dining area (as well as below deck) and sitting space.
Motor Yachts
If high-end luxury is your thing, you may want to consider chartering a motor yacht. These powerboats typically have larger and more powerful engines than other types of sailboats. They are great if you want to cover a lot of distance in a short amount of time and prefer the convenience of a powerboat over the slower pace of a sailboat. There are no sails on a motor yacht.
Two luxury yachts anchored in the Caribbean
Motor yachts vary in size, from smaller boats that accommodate a couple or small family, to larger boats that can accommodate groups. They offer many of the same amenities as a luxury hotel. There will be air conditioning, larger beds, and beautifully appointed bathrooms. People who charter these boats prioritize speed and comfort over anything else.
All three types are excellent sailboats to charter in the Caribbean. Again, it really comes down to preferences and budget.
Locations to Charter Sailboats
There are many destinations from which you can arrange sailboat charters in the Caribbean. We have sailed from 3 of the 6 locations below. We promise each location has its unique charm and offers different activities and sights to explore.
U.S. & British Virgin Islands
The U.S. Virgin Islands (USVI) and British Virgin Islands (BVI) are among the most popular sailing destinations in the Caribbean. With calm waters, steady winds, and over 60 islands to explore, it is an ideal location for sailing novices and experienced sailors. The islands are home to many marinas, charter companies, and yacht clubs that offer sailboat rentals, as well as a variety of anchorages and moorings for boaters to explore.
Marigot in Saint Martin, the French side of the Caribbean Island.
St. Martin
St. Martin is a popular sailing destination located in the northeastern Caribbean. The island is divided into two parts. The French side offers a relaxed, European atmosphere. The Dutch side offers more lively nightlife and entertainment options. St. Martin is a popular starting point for sailing charters. Many companies offer sailboat rentals and access to nearby islands such as St. Barts, Anguilla, and Saba.
Antigua
Antigua is a beautiful island located in the eastern Caribbean, known for its stunning beaches and turquoise waters. The island has many marinas and anchorages, making it a popular destination for sailboat rentals and charters. Antigua hosts the annual Antigua Sailing Week. This event attracts sailors from around the world and is a must-attend event for sailing enthusiasts.
Pigeon Point Beach and Falmouth Harbor, Antigua.
Grenada
Grenada is a small island nation located in the southern Caribbean. It is known for its beautiful beaches, friendly locals, and vibrant culture. The island has several marinas and sailing clubs that offer sailboat rentals and charters. There are also many nearby islands to explore such as Carriacou and the Grenadines.
St. Lucia
St. Lucia is a stunning island located in the eastern Caribbean. It is known for its lush rainforests, stunning beaches, and scenic coastline. The island has several marinas and sailing clubs that offer sailboat rentals, as well as many anchorages and moorings for boaters to explore. St. Lucia is an ideal destination for sailing enthusiasts who enjoy a mix of scenic beauty, culture, and adventure.
Bahamas
The Bahamas are located off the coast of Florida and offer a unique sailing experience in the Caribbean. The waters here are shallow and clear. This makes it easy to spot marine life, and there are plenty of deserted beaches and cays to explore. The sailing conditions are generally calm, making it an ideal destination for families and beginners.
In deciding where to charter a sailboat in the Caribbean, consider the options you have to get to the island. For example, if you are coming from the U.S., it may be easier to fly into St. Thomas, USVI. If you are traveling from France, St. Martin may be easier. Your charter location decision should not completely depend on how long it takes to get to where you want to go, but it should be a consideration.
What it Costs to Charter a Sailboat
The cost of sailboat charters in the Caribbean varies widely depending on the type of boat option you choose. In general, there are two main options: bareboat charters and crewed charters. Bareboat charters are ideal for experienced sailors who want to sail on their own and explore the Caribbean at their own pace. Crewed charters, on the other hand, come with a captain and maybe another crew member or two who will take care of everything for you, including sailing the boat, cooking, and cleaning. This option is perfect for those who want to sit back, relax, and enjoy the scenery without having to worry about the technicalities of sailing.
When it comes to cost, bareboat charters are less expensive; while the cost for crewed charters will vary depending on the size of the boat, the number of crew members, the number of sailing days, and so forth. Below are some costs you can typically expect with bareboat charters and charters where you are responsible for hiring a crew.
Base Charter Fee
The base charter fee is the most significant cost associated with chartering a sailboat or motor yacht. This fee covers the use of the sailboat. The base charter fee varies depending on the size of the boat, its age, and the destination.
Crew
If you choose to hire a crew, the cost will be added to the base charter fee. The crew usually consists of a captain, a chef, and additional crew members. The crew is responsible for navigating the boat, preparing meals, and providing customer service during the charter period.
Super yachts in the harbour of Antigua
Fuel
Fuel costs are typically not included in the base bareboat charter fee and are the responsibility of the charterer. The amount of fuel required depends on the size of the boat, the distance traveled, and the time spent on the water.
Provisioning
Provisioning is the process of stocking the boat with food, beverages, and other supplies for the charter period. The cost of provisioning is typically not included in the base charter fee and is the responsibility of the charterer.
Insurance
Most charter companies require the charter to purchase insurance for the boat and crew during the charter period. The cost of insurance varies depending on the size of the boat, the destination, and the length of the charter.
Taxes
Depending on the location, there may be additional taxes or fees associated with sailboat charters or motor yachts in the Caribbean. These costs are typically added to the base charter fee and can vary depending on the destination.
Additional Costs
Depending on the charter company, there may be additional costs associated with chartering a sailboat or motor yacht, such as docking fees, cleaning fees, and gratuities for the crew.
Another Option
If all this seems a little overwhelming to figure out on your own, you may want to consider a private crewed charter company where many of these fees are incorporated into the weekly charter price. With this option, there are fewer surprises at the end of your vacation! And an even less expensive option is to choose a crewed sailboat vacation where you simply reserve a stateroom along with other guests. If you don’t like being in close quarters with people you don’t know, this option may not be for you. However, you may also find a group of people that become friends forever.
What’s the Bottom Line for Cost?
So, how much money are we talking about here? For example, a 3-bedroom catamaran sailing out of Tortola in the BVI for seven nights will cost between $15,000 and $25,000 at the all-inclusive rate. If three couples are traveling together you would divide the total cost by three. To lower the cost, you might ask the boat owners if they will offer you a half-board rate, which includes two meals a day, usually breakfast, then lunch or dinner. The least expensive option is to see if you can just hire the skipper. You would then be responsible for your own meals, drinks, bedroom cleanup, etc.
The key message is that the cost of sailboat charters in the Caribbean will vary depending on several factors, including the size and age of the boat, the destination, and the length of the charter. It is essential to carefully review the charter agreement and all associated costs before booking. Chartering an all-inclusive sailboat is not inexpensive, but we promise it will be a trip worth remembering. Check out Moorings, a leader in sailboat charters to learn more.
Our Recommendations
If you are new to sailing, we recommend an all-inclusive crewed charter, as it allows you to fully enjoy the experience without having to worry about navigation, safety, cooking, or cleanup! For two to four guests, either a monohull or catamaran will work fine. We do feel that catamarans have a little more room and are easier to walk around, but they are also likely to be a little more expensive. If there are more than four guests, a catamaran or a motor yacht is the best choice. The catamaran will be less expensive.
Caribbean island of Grenada
Overall, our experience of sailboat charters in the Caribbean has been fabulous. It is a wonderful way to fully immerse yourself in the natural beauty and unique culture of this part of the world. With so many options available, you’re sure to find the perfect sailboat, destination, and itinerary to suit your interests and preferences. It’s a good idea to research each type of boat and the various options available before making a final decision. You want to ensure that you choose the right boat for your needs and preferences.
Conclusion
If you want to know about our personal experiences of sailboat charters in the Caribbean, you can read about them here. For general information about traveling in and around the U.S. Virgin Islands, be sure to explore our travel guide to St. Thomas as well as our blog post on how to pick the perfect getaway in the U.S. Virgin Islands.
