9 Tips For First-Timers Chartering A Boat In The Caribbean, According To A Skipper

I like to tell people I am a certified skipper. It sounds impressive. But the truth is, I am only confident in being a skipper on my little Laser sailboat with my dog as crew, and even I capsize occasionally. 

I did complete the entire Royal Yachting Association Day Skipper certification requirements and have a card to prove it. But after a weeklong course in the Mediterranean and a few near-disastrous Med Mooring situations, my instructor’s parting words were something like, “If you ever rent a bareboat, take someone with you.” That didn’t instill a lot of confidence in my ability to use my shiny new RYA Skipper card to rent a bareboat, a boat you lease without a crew or provisions, on my own.

I researched flotillas (a group charter with support) and contemplated enrolling in an additional sailing course, but in the end, I took my instructor’s advice and recruited my friend, who has a bit more experience and confidence than me, to go along on my first bareboat adventure. We chose the British Virgin Islands for their abundance of beautiful bays, line-of-sight navigation, easy moorings, and steady trade winds. 

Chartering a boat in the Caribbean for the first time? Here are some tips from a certified skipper.

Virgin Gorda (Photo Credit: Heather Earl)

1. Get Some Sailing Skills

If you dream of captaining a sailboat in a tropical paradise, getting the skills and confidence to do it is easily accessible. There are numerous courses through the American Sailing Association or the Royal Yachting Association that will get you the skills you need to confidently rent a bareboat in the British Virgin Islands. Consider enrolling in an intensive, week-long sailing course. This will give you the skills you need to skipper a boat on your own. 

2. As You Choose A Charter Company, Ask Many Questions

Finding a company that has well maintained boats, on-water support, and good customer service will take a lot of the stress out of chartering and sailing a bareboat. Many charter companies have standards for the age of their fleet. Take your time and ask questions about the specific boat you will be on; how old it is, the manufacturer, and the model. Ask for pictures of the exact boat you will be leasing. Ask what kind of on-water support they offer. A good charter company should have a protocol to get someone to you to fix any mechanical or technical problems immediately. Read reviews and ask to connect with past clients. There are many charter companies to choose from in the BVI. 

Scrub Island (Photo Credit: Heather Earl)

3. Pick a Boat Wisely

Once you have found a charter company you feel comfortable with, it’s time to pick a boat. Choose a boat that is just big enough for your gang. Bigger and roomier boats are tempting, but for an inexperienced skipper, smaller is better. Choosing a monohull or multihull is the next choice. If you have people in your crew that get seasick or are new to sailing, a catamaran is a good choice as they are more stable, don’t keel over, and have abundant above-water living space, making them an option for accommodating people with limited mobility. The twin engines on a catamaran give you more control under power so you can maneuver up to a mooring ball or dock more easily. 

4. Make A Plan, But Be Flexible

The best time of year to sail in the British Virgin Islands is widely considered to be from December to April, the time with the driest weather and moderate temperatures, but as a newbie skipper, May through September will still be great weather with smaller crowds and fewer boats to navigate around. Pick the destinations you want to visit using a good cruising guide and plan your itinerary. Short sailing days that start early will get you into port with enough time to find a mooring ball, and you will have fewer boats to contend with.

It is a good idea to reserve a mooring ball at some of the most popular places with the BoatyBall online reservation system. Plan your last night close to where you need to drop off the boat. Your charter company should have a recommended itinerary for you to refer to. If being underway is getting stressful, don’t hesitate to change your plan and enjoy where you are. Spending your days swimming, snorkeling, and hanging out on deck with a good book is just as rewarding as filling the sails with wind. 

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5. Pack Your Bags

Charter boats are usually well stocked, but pay attention to what comes with your boat, and make sure you have all the items for the activities your gang will want to do. Most boats come with snorkeling equipment, but if snorkeling is your thing, bring your own well-fitting masks. Most charter companies will have add-on equipment available for scuba diving, fishing, and water sports. You may consider taking along an inflatable paddle board. A handheld VHF Radio is inexpensive and really helpful when pulling up to a fuel dock. Sailing (or cycling) gloves for handling lines are a must have, especially if you want to keep your crew people happy. Closed-toe boat or water shoes will keep everyone’s feet protected and prevent falls when working on deck. Refer to the packing list your charter company has compiled. Resist the temptation to overpack; space is limited, and you don’t need a lot of clothes. Bring copious amounts of reef-safe sunscreen and leashes for hats and sunglasses. 

Editor’s Note: You can find reef-safe sunscreen on our list of the year’s best suncreen products.

6. Plan To Eat Well

As a professional chef, I don’t leave the food to chance. Provisioning a boat is a big undertaking and takes planning to make feeding everyone onboard an enjoyable experience. It is worth the effort to plan meals and make a shopping list. Your charter company will have options for provisioning your boat, ranging from fully stocked to just the bare necessities. 

Make a menu for all the days you will be onboard, keeping in mind the days you will be eating meals ashore. Having a few things prepared ahead of time is imperative on the days you will be sailing. I make big batches of hummus, tuna salad, pasta salad, curry chicken, or chickpea salad to have on hand for quick lunches while underway. Precut vegetables, cheese, and ready-made dips are all great things to have on board. Try to avoid stocking random ingredients. This is expensive and wasteful. Have a detailed plan for meals and a shopping or provisioning list to go along with it. 

I like to bring some basics with me, like nuts, snack bars, dried fruit, tea bags (for big batches of iced tea), and spice mixes. Trader Joe’s and Penzeys have spice mixes that are great for travel and make cooking aboard more streamlined. Personalized, lidded, insulated tumblers for everyone onboard will keep people hydrated and cut down on garbage and dish washing. 

Sharing Crew Duties (Photo Credit: Heather Earl)

7. Ready Your Crew And Yourself

For a first-time bareboat experience, be prepared and know what is required to competently manage a boat and crew. The American Sailing Association has some good resources to get you ready. A competent crew is also imperative to making your first-time charter experience stress free and enjoyable for everyone. 

Know ahead of time who is willing to help with crew duties and assign them jobs. Pulling up to a mooring ball or fuel dock is not the time to be deciding who is going to help you. Have your crew become familiar with some basic knot tying and crew jobs. As the skipper, you need to assign tasks and keep control of the boat in all situations. It is a good idea to have a conversation ahead of time to make sure everyone on board knows who to listen to and what their jobs are. 

8. Get Some Help

Once you decide on a charter company, a boat, and a crew, determine how much outside support you need and capitalize on the resources available to you. I generally weigh my options with a convenience vs cost analysis. I don’t mind cooking and I like great food, but if preparing food and provisioning is overwhelming, you can hire an onboard chef, but keep in mind you will need an extra cabin. If planning your travel and transfer is stressful, your charter company can arrange all of it for you. Your charter company will do a thorough walkthrough of the boat with you. Ask a lot of questions and clarify anything you are not comfortable with. If you are still uneasy, ask them to launch with you. They will help you get out of the harbor, show you how to operate all the equipment, and practice hooking a mooring ball. When you are returning the boat, you can request someone to come out to you and drive your boat into the harbor and dock it. Don’t be afraid to ask for help and support. That is how you learn and how you avoid damaging your charter boat on your first voyage.

9. Read The Fine Print

Read your charter contract carefully to understand everything that is included and what extras (like fuel) you are responsible for. Get the highest amount of insurance offered for peace of mind. Know what the cancelation, delay, and refund policies are. 

You don’t have to be a certified skipper to take on a bareboat in the British Virgin Islands. If you are an experienced sailor and do a little research and a lot of pre-planning, you can have an amazing Caribbean sailing experience.

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