The Caribbean is filled with incredible islands, beautiful hotels and gorgeous beaches. However, most people never get to see more than one island or maybe even more than one beach if you travel on land. Chartering luxury all-inclusive catamarans and sailboats has become significantly more accessible and available throughout the Caribbean and is a truly unique and private way to experience everything the Caribbean has to offer. If you’ve ever been curious about how chartering a boat works and what to expect, this guide is for you.

How does a charter work?

At the most basic level, chartering a yacht is chartering a private, bespoke, luxurious experience that is centered entirely around you and your guests. Unlike booking an all-inclusive hotel with 3,000 of your fellow humans, an all-inclusive charter is about as polar opposite as you get. The only set times are when you depart the dock and when you return. The food you eat, the times you rise, rest and dine are entirely set by you. 

While the experience itself is the opposite of a hotel, the actual process of picking and booking your charter is a lot like looking for a resort that suits your needs. First, you’ll want to consider how many guests will be aboard the boat in order to determine how many bedrooms you’ll need.

Next, you’ll want to consider where you want to be in the Caribbean. There are boats focused in different areas, like the BVIs, USVIs, Bahamas, etc. Charter websites will tell you the locations of the vessels and you can go from there. 

Budget will also play a big factor in your planning. More and more all-inclusive charter experiences are popping up around the Caribbean and may be a good option. Unlike traditional yacht chartering, all-inclusive charters will typically include everything from your diesel, food, alcohol and non-alcoholic beverages, water equipment and the crew. When looking at more traditional style, non-inclusive charters, you will typically need to budget higher than expected for gas, food and everything else. 

Once you select your charter experience, the company or owner will contact you with a preference sheet so they can personalize the entire experience for you. You’ll find common questions like dietary restrictions, types of beverages you enjoy versus ones to avoid, what type of activities you like on a holiday and more in order to plan where the boat will go and what is stocked on that boat. 

Where can I look for yachts and book my all-inclusive yacht experience?

There are a number of different brokers that offer seemingly endless options for travelers based on your interests and needs. Sail Play Dine, for example, focuses on the Caribbean and has very clear pricing and inclusions on their website. For example:

You can see on the pricing whether the yacht is all inclusive or an a la carte pricing model, allowing you to make the best choices for your needs. When you have found a few boats of interest, you can inquire with the broker and continue the discussion further to book. Booking via a broker is a lot like booking via a travel agent for any other vacation.

Are all charters all-inclusive?

The short answer is no. While all-inclusive charters are popping up more and more across the world, you’ll typically find these types of charters in popular areas, like the Caribbean. Traditional yacht charters, particularly on larger motor yachts, usually include a charter fee + 30% (more or less) for ancillary items like food budgets and motor oil. If you are looking specifically for an all-inclusive catamaran or sailboat, be sure to ask the broker if you are unsure. 

What is the cost of chartering?

The prices vary extensively depending on the type of vessel, quality of the service and the size of the boat. You can find stunning catamarans that accommodate 6 people on a 45-foot catamaran, like the one we had the chance to experience, for about 18,000 USD for one week:

Considering the inclusions and the experience, this is a great deal. As you will start to notice, the price increases as the vessels get larger, but there is really something for every price point.

What should I bring on a charter?

There are a few differences between a land vacation and a sea vacation, and part of that comes down to the packing. While you may be rocking some 5-inch espadrille wedges on land, boats are pretty much a shoe-free zone at all times. Similarly, there will always be a bit less storage on a boat than at a hotel, so with that in mind, here’s what I would recommend for 7 days at sea:

• Sunscreen and LOTS of it. Water is a reflective surface so the sun tends to burn you faster at sea.
• Sunglasses WITH croakies. I’ve lost a few pairs of sunglasses to the ocean, be sure to snag some croakies on amazon before heading to your vacation.
• 1 pair of sneakers and 1 pair of flip flops. If you do any land activities like hiking or shopping, you’ll want a pair of shoes, but otherwise, leave your 6 pairs of heels at home.
• Bathing suits and cover ups. You’ll find you’ll spend most of your days lounging out on the boat, soaking up the sun so no need for much else!
• A few lightweight dresses and long-armed shirts. After a day in the sun, I always like to cover up a bit in the evening for the breeze and also to get out of the sun a bit.
• Books, kindles & ipads! I love reading on vacation & listening to music from the (usually) built in speakers onboard.