9 tips for beginners chartering a boat in the Caribbean

I like to tell people that I am a certified skipper. It looks impressive. But the truth is that I only have confidence being a skipper on my little Laser sailboat with my crewed dog, and I even capsize from time to time.

I have completed all the Royal Yachting Association Day Skipper certification requirements and have a card to prove it. But after a week-long course in the Mediterranean and a few near-disastrous Med Mooring situations, my instructor’s parting words were something like, “If you ever charter a bareboat, take someone with you.” It didn’t inspire much confidence in my ability to use my brand new RYA Skipper card to charter a bareboat, a boat you charter without crew or provisions, on my own.

I researched flotillas (group charter with escort) and considered signing up for an additional sailing lesson, but ultimately took my instructor’s advice and recruited my friend, who has a little more experience and confidence than me, to follow my first bareboat adventure. We chose the British Virgin Islands for their abundance of beautiful bays, sight sailing, easy anchorages and steady trade winds.

Are you 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. Acquire navigation skills

If you dream of being the captain of a sailboat in a tropical paradise, gaining the skills and confidence to do so is readily available. There are many courses offered by the American Sailing Association or the Royal Yachting Association that will equip you with the skills you need to confidently charter a bareboat in the British Virgin Islands. Consider signing up for a week-long intensive sailing course. This will give you the skills to pilot a boat on your own.

2. When choosing a charter company, ask lots of questions

Finding a company that has well-maintained boats, on-the-water support, and good customer service will take a lot of the stress out of chartering and bareboat sailing. 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; its age, manufacturer and model. Ask for photos of the exact boat you will be renting. Ask what type of on-water support they offer. A good charter company should have a protocol for someone to contact you to immediately resolve any mechanical or technical issues. Read reviews and ask to connect with past customers. There are many charter companies to choose from in the BVI.

Scrub Island off Tortola in the British Virgin Islands.
Scrub Island (Photo credit: Heather Earl)

3. Choose a boat wisely

Once you’ve found a charter company you feel comfortable with, it’s time to choose a boat. Choose a boat just big enough for your gang. Bigger, more spacious boats are tempting, but for an inexperienced skipper, smaller is better. Choosing a monohull or a multihull is the next choice. If you have people in your crew who get seasick or are new to sailing, a catamaran is a good choice as they are more stable, won’t tip over and have plenty of living space above the boat. water, making it an option for accommodating people. with low mobility. The two motors in a catamaran give you more control under power so you can maneuver 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 December to April, the period with the driest weather and moderate temperatures, but as a novice skipper, May to September is the weather will still be good with smaller crowds and fewer boats to navigate. Choose the destinations you want to visit with the help of a good cruise guide and plan your itinerary. Short sailing days that start early will allow you to arrive in port with enough time to find a mooring ball and you will have fewer boats to contend with.

It’s a good idea to reserve a mooring ball at some of the most popular locations 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 to refer to. If being on the road becomes stressful, feel free 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.

Charter boats available at Bight Marina in Key West.
Fotoluminate LLC / Shutterstock.com

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 tight-fitting masks. Most charter companies will have additional equipment available for scuba diving, fishing and water sports. You may consider bringing an inflatable paddle board. A portable VHF radio is inexpensive and very useful when stopping at a fuel dock. Sailing (or cycling) gloves for line handling are a must, especially if you want your teammates to be happy. Closed toe boat or water shoes will protect everyone’s feet 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 plenty of reef-safe sunscreen and leashes for hats and sunglasses.

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

6. Plan to eat well

As a professional chef, I don’t leave food to chance. Provisioning a boat is a big undertaking and requires planning to make feeding everyone on board an enjoyable experience. It pays to plan meals and make a shopping list. Your charter company will have options for provisioning your boat, ranging from full to bare necessities.

Make a menu for all the days you will be on board, keeping in mind the days you will be dining ashore. Having a few things prepared in advance is imperative on the days you will be sailing. I prepare large batches of hummus, tuna salad, pasta salad, chicken curry or chickpea salad to have on hand for quick lunches along the way. Pre-cut vegetables, cheese and ready made dips are great things to have on board. Try to avoid stockpiling random ingredients. It is expensive and wasteful. Have a detailed meal plan and a grocery or supply list to go with it.

I like to bring a few basics with me, like nuts, snack bars, dried fruit, tea bags (for large batches of iced tea), and spice blends. Trader Joe’s and Penzeys offer travel-friendly spice blends and make on-board cooking simple. Customized, lidded, insulated cups for everyone on board will keep people hydrated and reduce trash and dishwashing.

Crew sharing duties aboard a catamaran in the British Virgin Islands.
Crew duty sharing (Photo credit: Heather Earl)

7. Prepare your crew and yourself

For a first bareboat experience, prepare and know what it takes to competently manage a boat and its crew. The American Sailing Association has good resources to help you prepare. A knowledgeable crew is also imperative to making your first charter experience stress-free and enjoyable for everyone.

Know in advance who is ready to participate in crew duties and assign tasks to them. Arriving at a mooring ball or a fuel dock is not the time to decide who is going to help you. Familiarize yourself with your crew with some basic knotting and crewing tasks. As a skipper, you must assign tasks and maintain control of the boat in all situations. It’s a good idea to have a conversation beforehand to make sure everyone on board knows who to listen to and what their job is.

8. Get help

Once you have chosen a charter company, boat and crew, determine what outside support you need and capitalize on the resources available to you. I usually weigh my options with a convenience vs cost analysis. I don’t mind cooking and I like good food, but if food preparation and provisioning is overwhelming, you can hire a chef on board, but keep in mind that you will need a additional cabin. If planning your trip and transfer is stressful, your charter company can organize everything for you. Your charter company will do a thorough tour of the boat with you. Ask lots of questions and clarify anything you are not comfortable with. If you’re still uncomfortable, ask them to pitch with you. They’ll help you get out of the harbor, show you how to use all the equipment, and practice hooking up a mooring ball. When you return the boat, you can have someone come to you and drive your boat into the harbor and moor it. Don’t be afraid to ask for help and support. This is how you learn and avoid damaging your rental boat on your first trip.

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 available for peace of mind. Know what the cancellation, late and refund policies are.

You don’t need to be a certified skipper to 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 sailing experience in the Caribbean.

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