How to Charter a Yacht in the Caribbean

Here’s how to hire a captain to sail your family through the tropical islands of your choice—all chef-prepared meals and drinks included.

By Maryann Jones Thompson

Did you know you could charter a private yacht in the Caribbean for not that much more money than a good cruise would cost? You’d be swapping this…

for this:

A private yacht charter gives you an experienced captain to sail your family and friends through the tropical islands of your choice—all chef-prepared meals and drinks included. Spend your days snorkeling sky blue water and combing deserted beaches, and your nights in secluded coves stargazing or at beachfront reggae parties. No wonder the pirates loved the Caribbean.

We talked to Nancy Van Winter of eNVy Yacht Charters, a free yacht brokerage service with extensive experience matching families with boats in the Caribbean—and around the world—to present ROAM’s family travel edition of “Yacht Chartering 101.”

ROAM: What are the top destinations for family yacht charters?

Nancy: The Caribbean is by far the most popular because you can often visit multiple islands in one day. In the course of a week in the BVIs—British Virgin Islands—you might see a dozen islands. Or you could do St. Martin, St. Bart’s, Anguilla in one week. Or if you preferred something different, you could go down to St. Vincent in the Grenadines.

Mexico and Hawaii do have some places to charter yachts. And Central America – for example, Belize and Panama – is picking up. Other destinations are Bahamas, Maldives, Croatia. And Cuba will become more popular in the next two years— it’s not that easy right now, but there’s a lot of interest. Also there are megayachts—over 150 feet— cruising Indonesia and Thailand.

From a family standpoint, older children might also be interested in Europe. But most of my clients are water people—they want to get in the water or be on the beach. In Europe, destinations are less about snorkeling and more about culture so many people stick to the Caribbean.

ROAM: Why do you recommend the BVIs in particular as a first place for families to go on a boat charter?

Nancy: As I mentioned, the BVIs have many islands and they are all very close together. It’s only 45 minutes between islands and land is always in sight. I don’t often send clients to St. Vincent and the Grenadines for a first trip because it’s three to five hours of boating between the stops. You can’t necessarily see the island you’re heading for.

The BVIs have a diversity of sights and sounds you can’t get anywhere else in the world. The water is so calm and protected; and there are a lot of nice little coves to tuck into at night—not every destination has that. A cove might have a secluded beach or a wild party onshore, but on the water it’s still calm and quiet. Oh, and the BVIs happen to be classically Caribbean gorgeous.

In the Caribbean, each set of islands has a different personality. The BVIs are laidback and casual. It’s a “2 pair of shoes” island—you just need flip-flops and one other. St. Martin and St. Bart’s are more fancy and European, where people go out at night. There are also topless beaches, which bother some families, and there aren’t as many beaches that you can pull up to that aren’t public. St. Vincent and the Grenadines are more remote, so you’ll spend more time on the boat to get between islands; this is similar to Greece, which is also great, but there’s a lot of time spent on open water.

The other element to consider is support. For example, Belize and Panama still need more land-based support for the charter industry. No great boat is going to go there and risk losing a part and have to wait for a replacement to be delivered. The Caribbean has the facilities and land support.

The Caribbean is the cheapest destination too—there is no tax on yacht charters in the Caribbean. Even Florida charges 4 percent to 13 percent, and European taxes are in the teens.

ROAM: Who decides where to go when you book a charter?

Nancy: Prior to going, you will get an itinerary. The crew will review the itinerary with you, asking for example, Have you been to Virgin Gorda? Yes? OK, we won’t go again. It’s all figured out prior to arriving at the boat. But because a charter is so personalized, if at breakfast Mom says, “Please stay here, we love this cove,” it’s possible; it’s your boat.

ROAM: What’s a typical day like?

Nancy: Every morning starts with breakfast prepared by the chef. The captain uses that opportunity to discuss activities—a water activity, hiking, a beach day, reading books, going ashore. Usually the boat moves and lunch is in another place. Then, there are more water sports, or beach time or hiking, followed by a nice cocktail for Mom and Dad, playing games on board and then dinner. Then maybe you hear a band on shore, so you get the dingy and go ashore to hear music. We have boats with movie screens on deck, or you can stargaze from the top deck.

ROAM: Tell us more about the activities.

Nancy: There’s always swimming, fishing, snorkeling and the beach. Some boats offer scuba, sailing, windsurfing, kayaking, rafting, water-skiing, stand-up paddle boarding – even yoga! During the days, you can do or learn an activity—or you can read a book and nap. On shore there are quiet beaches, villages, shopping and hard-partying bars.

ROAM: How does the cost of a yacht charter compare with that of a cruise ship?

Nancy: The cost of a nice cruise ship is about $1,000 to $1,300 per person for a week; a low-end boat might be $500 to $800 per person. But that doesn’t include any shore excursions, activities or drinks—which all add up on a cruise. When on a chartered yacht in the Caribbean, we have a wide range of costs, but typically it’s about $2,400 per person on a catamaran with six to eight guests. That includes all meals, all drinks, all snacks and all excursions—sometimes scuba diving is extra, it depends on the boat. What’s not included is the chance to hang out with thousands of new friends as you would on a cruise!

ROAM: How can yachts cater to family interests better than a cruise ships?

Nancy: Yachts give more personal attention than large ships. As I mentioned before, the itinerary is completely customized to your family’s interests and can change at any time if you desire.

Activities are also tailored to each client. I had a family who said that their daughter was into turtles. So the crew spent the week finding spots to snorkel and swim with turtles. Another time, a mom asked the crew to help get her son out of the cabin and off his iPad. The captain told her son, “If you don’t play your iPad and you go snorkeling with me for four days, you can put a pie in my face.” He snorkeled and the captain got pied.

In my opinion, a yacht crew works harder for clients with kids versus those without. In fact, that’s why some of my crews don’t discount for kids, because they work a lot harder to keep them entertained and busy versus a boat of couples relaxing, talking and drinking. (Though I do have a few boats that do charge less for children.)

On my yachts, for example, I can match the right crews to the right families. I have crews that specialize in dealing with kids who are picky eaters or have food allergies. One chef might make osso bucco for the adults and chicken tenders for kids.

Charters are also great for multigenerational trips. If grandparents take their kids and grandkids on a large cruise ship, everyone scatters to do their own thing. Maybe they see each other at dinner—if that. On a yacht, everyone has breakfast together and spends most of every day together sharing experiences.

ROAM: What about the pirates of the Caribbean? Is it safe?

Nancy: The Pirates of the Caribbean is just a movie. I’ve never had any crime on my charters or had any situation that felt unsafe in 10 years. There are always rumors of people going aboard boats and stealing items, but the crews are very aware, and will be careful to lock up when everyone goes ashore.

ROAM: What are the benefits of going through a broker? What does a broker do?

Nancy: You can book a boat on the Internet, but most reputable boats will point you to a broker if you want to book. The captains like working with brokers because they know we can matchmake and work through any discrepancy that might arise. In a dispute with the boat, we serve as an intermediary.

When you pay for the boat, I put your payment in an escrow account run by the Charter Yacht Brokers Association. If you send money to a boat captain directly and he disappears, you’re out of luck.

If a mast breaks, or there’s engine trouble or a storm, and you book directly, you have no recourse if you don’t have the protection and service of a broker. For example, I had clients booked on the first voyage of a yacht that was relocating from Tonga to the Caribbean. A storm delayed the boat’s arrival at the Panama Canal and they missed their appointment to cross—small boats lose their place in line. So a month out, I got a call from the captain saying they might not be back in the Caribbean in time to take my clients. I was able to go to my resources and get them a boat for the same price, a actually bigger and better one. So having the service of a broker saved my client’s vacation.

Brokers also have firsthand knowledge of the boats and crews we represent. Over the next two months, I will be in the Caribbean visiting more than 100 yachts and meeting their crews. That’s why brokers like myself can match clients to the right boats. Not every boat is for every group. For example, do all cabins share a bath? Some clients are fine with that, some aren’t. I will give you the all the pros and cons of each boat. Some boats are lovely, but they would be terrible for a 13-year-old boy and a 6-year-old girl. Some crews can’t deal with high-energy kids and prefer couples. But I have a lot of clients with kids, so I get to know each crew and ask them what kinds of activities they do to keep them happy. One boat I had organized treasure hunts for the kids.

Another benefit of a broker is that the client doesn’t pay my fee—the boat does. So there’s no additional fee for travelers to have the expertise and protection of a broker.

ROAM: What’s the best way to get to the BVIs?

Nancy: To get to the British Virgin Islands, ideally, fly to Beef Island on Tortola. You can also fly to St. Thomas and fly on to Beef Island, or take a $60 round trip ferry from there. To get a better airfare, you can always fly midweek and charter a boat starting midweek – you don’t have to go Saturday to Saturday.

ROAM: What’s the best season for the Caribbean?

Nancy: It’s best from November to July; more boats are in the water. At other times, there aren’t as many to choose from, because they make repairs to the boat or head to the Mediterranean.

Officially hurricane season is August through the end of October, but lots of clients want to go year-round; they go in July and August and the weather is still fine. In fact, so many boats have gotten fully booked for that time that some captains are not taking their boats off the market until the fall so that they can serve August vacationers. You can get hurricane insurance, but there has not been a hurricane that has cancelled a weeklong vacation yet for my clients—knock wood. One captain told me there has only been one day in 22 years where he had to take guests off the boat in August and put them in a hotel. More typically, a bad storm means your boat hunkers down in a marina.

ROAM: How far in advance do you need to book?

Nancy: Book as far out as possible, more than a year in advance for a holiday period. Eight months out, I’ll start matchmaking with clients: finding out about the family, what they like to do, dietary issues, and find the boat that is the perfect fit. The only way to guarantee that is to do it in advance.

Book spring break now, in autumn. It isn’t more expensive, and it’s easier to get because everyone’s breaks are different. For the Christmas holidays, the cost is 10 to 15 percent more expensive. For Thanksgiving, there’s no premium, but it’s a popularity contest and the most organized family wins. Bottom line: it’s never too early to book for what you might find is one of the best family trips on the planet. Like many of my family clients, you’ll want to charter again and again.

Maryann Jones Thompson – November 2015

ROAM Founder & Editor

After a thousand years in publishing as a business journalist, ghostwriter, content strategist and market researcher, Maryann brings her experience traveling as a backpacker, businessperson, expat and mom to writing and editing for ROAM.