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Chartering a Yacht in the Caribbean

Chartering a Yacht in the Caribbean
Read Carefully

charter a yacht in the caribbean


Always wanted to sail around the British Virgin Islands in your own private yacht but have no clue how to do it? Chartering a yacht in the Caribbean can be confusing, who to book with, where to go, what to pack. That’s why I’m here.


Chartering a Yacht in the Caribbean


The most important choice you’ll make is whether to book bareboat (just what it sounds like, you get the boat and only the boat) or crewed (depending on the size of the boat, this is at least a Captain and chef, possibly also a steward). I cannot recommend paying for a captain and chef enough. Even if you know how to sail, provisioning your own boat, charting your own course and cooking all your own meals is no vacation. The inside knowledge of your crew will cover the cost and then some.


We work with Derek from iYachtClub. Their website will guide you on what type of boat to charter and answers every question you might ask. We booked our Christmas to New Year’s vacation through iYachtClub, we were so impressed that we came back for spring break.


sailing the British Virgin Islands


Reasons I love iYachtClub:


  • They sail out of St. Thomas which is the easiest airport to fly into from the US, lots of flight choices.
  • They have high touch hands on service, Derek or his staff will walk you through choosing a boat and crew, the crew is as or more important than the boat, and he will make sure you’re with someone that is just right for you.
  • Personal transfer, someone from iYacht will pick you up at the airport so you don’t need to navigate your way to the marina
  • Because they provision the boat in St. Thomas, food prices are better and there is a wider selection of food (i.e. Veuve and gluten free products).


sailing the British Virgin Islands


What Type of Boat to Charter


Look at the website and think about what really matters to you. Is price most important? Double up in rooms, we did 3 bedrooms, two kids in each bed. Want to water ski? Make sure the tender is big enough to water ski behind. Kids like to play in the water? Look at the toys, our boat had an aqua mat, paddle boards, water guns and bean bag chairs. It was heaven for kids, and me.


Review the crew. Want to fish? Book the Makai, Bill is a world class fisherman and has all the gear you need. Want to party? Pick a young crew. Serious about your food? Check out the chef’s credentials.


They have 38 different yachts to choose from, that can be overwhelming, what I love about this company is that they are happy to hop on the phone as many times as you might need to walk you through the decision process. Side note, yacht does not always mean huge boat with uniformed staff, it’s a large catamaran usually 38 feet or longer.


To get all your meals included, choose all-inclusive. You can still stop for a drink or a meal somewhere if you choose, but trust me, it’s cheaper and more enjoyable to have your meals onboard and just grab drinks at various ports of call.



sailing the British Virgin Islands

Where to Sail


You absolutely do not need to know this ahead of time, the Captain will be happy to help you chart your course. On our first trip I arrived with a scrap of paper where a fellow passenger from our flight had scribbled her recommendations. I’m assuming since you are reading my blog, you’re more of a planner than I am, it’s a goal I have.



chartering a yacht in the caribbean

family sailing vacation

Jost Van Dyke and the Soggy Dollar Bar


Ever since I heard there was a bar where they hang the dollars to dry, I was on a mission to drink there. You swim in from the boat and you can spend the day or just a few hours relaxing at the beach and enjoying a world famous Painkiller cocktail. True confession, they are not my favorite, I know everyone loves them, I prefer rum punches. It’s the Caribbean, you can get rum any old way you want it. They deliver to your beach chair, which is the kind of service I am all about.


Pro tips: Bring extra cash, the gift shop has a million things you’ll want. Take it easy on the rum, you still have to swim back to the boat.


chartering a yacht in the caribbean

sailing the British Virgin Islands


The Soggy Dollar Bar is so chill, they even let me behind the bar in my bikini and taught me how to make Painkillers. Ignore the teenage commentary on the video, I really need to hire a professional crew:




The Indians and The Caves


These are two snorkel spots right near each other. Your Captain will get a mooring ball and all of the boats come with snorkel gear. One morning I took the boys on my paddle board and we explored the caves, this is where they shot Pirates of the Caribbean. The caves aren’t deep or scary and the paddling is easy. We then spent a few hours just exploring the beach and making rock sculptures.


This is the best part of these types of trips, the agenda is unstructured and you and the kids can spend hours doing anything, or nothing. Keaton rode on the front and we took my camera gear in the waterproof bag, a must have when you book one of these trips.


sailing the British Virgin Islands bvicollage


Virgin Gorda, Bitter End Yacht Club and Saba Rock


Bitter End Yacht Club is one of the most famous resorts in the British Virgin Islands, though it’s where the super swank vacation, it also has a laid back barefoot vibe. The Captains of the iYachtClub boats all have a membership that allows them an hour of time on the little catamarans at Bitter End. Our Captain, Bill, took the boys out for the afternoon and taught them how to sail. They’re not ready to go out on their own, but they now have a few fundamentals, and a love of the sport.




Saba Rock is just a little 2 minute jetty boat ride from BEYC. The open air bar is the perfect spot for lunch, the wi-fi is free and the gift shop has some great finds. We learned that everyone in the Caribbean seems to have necklaces made from pirate ship coins. Keaton has read all about the Atocha, a shipwreck found by Mel Fisher with over 40 tons of gold and silver, and keeps asking for a pirate coin for Christmas. Since they are all over $1,000, that’s not happening. We did find a shop in St. John that makes replicas made from “some” of the silver found on the Atocha. They were $100 and impressed his friends. (This is the real deal, not the recreated coin)





Willy Ts


If you’ve explored sailing the British Virgin Islands at all, you’ve heard of the infamous, and debaucherous Willy T’s. This is a floating restaurant and bar that has earned it’s sketchy reputation. We took the kids for an early drink, they ate the food, it was as dodgy as we had suspected. There’s a shot ski over the bar and if you stay too late, they start running videos of previous parties. Unless you want to answer some uncomfortable questions about nudity and whipped cream, get off the boat early. That being said, I had a lot of fun and wear my t-shirt proudly.




Coopers Island and Coopers Island Beach Club


This is a great spot to overnight, stop for a drink, go scuba diving and shop. Not all at once. Of all our stops, this was the best shopping, great cover ups, t-shirts, etc. It’s a tiny little spot but has gelato, coffee and a great bar. It’s also one of the most reliable spots for turtle spotting. The boys spent hours snorkeling with the turtles, Macie and I spent hours shopping. It was really the perfect day.


The kids didn’t have a GoPro on them (for shame) but Wilson snapped this turtle pic from the boat:






My daughter brought a Polaroid with her and the kids had the best time doing their own mini photo shoots, I actually love these snaps from Cooper more than any other photos we took.




The Baths at Virgin Gorda


This is the only “must see” stop in the BVI’s, it’s miracle of nature the way these massive granite boulders are all just tumbled on top of each other. You’ll swim in from your boat and spend part of the day exploring the hidden grottoes and secret beaches. This is where a GoPro is a must. Go in the early morning when the crowds are lighter, it’s a cruise ship favorite so you want to get there before the hordes do. I wished we had brought a waterproof bag with some cash for a snack or drink.





Trellis Bay


This is a hidden gem that not many Captains will suggest, we love this spot. There is a water trampoline for the kids, a bar for mom and one of the most unique art studios I’ve come across anywhre, let alone on a beach. Aragorn Studios hosts full moon parties when they fill these amazing sculptures with fire and float them on the water, hundreds of boats arrive for the party, it’s apparently quite a scene.



sailing the British Virgin Islands


Christmas Cove in St. Thomas


This little cove is a great spot to overnight and paddle board around, but the real highlight (in my boys’ opinion) is the pizza delivery. There is a boat with a hellagood pizza oven, the Captain calls in the order and the pizza arrives by dinghy. The novelty alone was superlative, and the pizza was actually very tasty.




What to Pack


Read this carefully, pack almost nothing.

Now read it again. You only want a small soft sided duffel, there is rarely space to store luggage on a boat and you need almost nothing. I’m serious. Pack this, nothing more:


  • Two swimsuits
  • One pair water shorts, one pair cotton shorts
  • One tank top, one short sleeved t-shirt, one long sleeved t-shirt
  • Pajama bottoms
  • Light sweater or sweatshirt
  • Sundress if you really must – I promise you’ll never wear it
  • Sunscreen
  • Hat and sunglasses


This is what you will be doing every day, and if you stop somewhere for lunch or a drink, this is perfectly acceptable attire:




I wear my Birkenstocks on the plane and then slide them off when I got on the boat, I never put them on again until I’m headed to the airport. I wear leggings, the tank and the light sweatshirt when I fly, I could almost pack for this trip in a backpack. You don’t need a hairdryer, make up or jewelry. They will have soap and basic shampoo on the boat, I bring good shampoo and a razor. That’s my beauty routine for the week. The boys try to claim swimming in the sea as their beauty routine, I allow it until they start to smell.


family sailing trips

What to Do on the Boat


The question I’m most often asked is “What do you do all day?” Bring playing cards and books, you won’t need or want anything else. When you wake up the chef will have coffee on, I like to paddle board first thing as the sun is coming up. After breakfast (which the chef will prepare at whatever time you choose) the kids like to swim or snorkel then you plan your sail for the day. We never sailed for more than a few hours at a time, I usually took that time to nap.


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how to charter a




On the last two nights of our most recent cruise Keaton and I slept outside on the bean bag chairs. I won’t say that this was super comfortable or great for my back, but falling asleep under the stars and waking up to nothing but the sound of rocking water and the still ocean air was pure magic.




What You Need to Know


Ensure everyone has passport that is not expired. You won’t need it when you fly into St.Thomas is it’s a US Virgin Island. When you enter BVI territory the crew will clear customs for you, how easy is that? And yes, labeling passports is a brilliant idea.


family sailing vacation
family sailing vacation

Prepare for medical emergencies. I don’t travel without my own first aid kit, Benadryl and medical travel insurance. While on our Christmas sail my husband became ill and needed immediate medical care. this is when I learned that my Med Jet membership was useless. We were on the boat and his heart rate was through the roof and he felt like he was going to pass out. I called the number on my card only to find out that they are only helpful AFTER you’ve been admitted to a hospital. I needed advice RIGHT THEN. One fabulous part of sailing the BVI’s is VISAR, Virgin Island Search and Rescue, they are like 911 on the water. Call 767 from your marine radio or 284-499-0911 from your cell phone. They arrived by speed boat wearing crash gear, it was pretty awesome looking, if I wasn’t so worried about my husband I would have taken a photo. They got him on oxygen and determined he was severely dehydrated. They are a volunteer organization and the service is free, we donated.


The boat will have wi-fi when you are near an island, your kids do not need to know this. I have a global data and voice package with Verizon, my cell phone seemed to work pretty much everywhere.


Most charters leave at noon on Saturday, we flew in in the morning and got straight on the boat. If you decide to stay overnight on St.Thomas, whatever you do DO NOT stay at Bolongo Bay, it’s a dump.


Pre-Trip Shopping List:

GoPro – these are still the easiest to work with when snorkeling and the photo quality is good, the shot of the boat from inside the cave was taken on a Hero4. Get the buoy attachment, trust me on this one, I’ve fished my GoPro from the bottom of the ocean more than once.



Polaroid Camera – My daughter brought her mini-Polaroid camera with us and as I said, these have been some of our favorite pics. Buy extra film, the concept of real vs digital photos takes a little while to sink in.


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Dry Bag – Many boats will have dry bags for you to borrow, but you can’t count on it. Many of the sights are swim in destinations, The Baths, The Soggy Dollar, etc. You’ll want your cell phone, some cash and sunscreen, the easiest way to have what you need is to pack up in a light and easy to use dry bag


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Toys and Games – Our boat had a few board games on it, not all will. We played a lot of Monopoly and Poker. There are many travel sized games, and a good deck of cards is always necessary. We never leave home without a deck and colored pencils, it’s amazing how busy you can keep kids with just those two items. Add a rum cocktail and it’s a good night.



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Good Sunscreen – The sun is so powerful here you’ll burn quickly, trust me on this one. Flying carry on with sunscreen is always tricky, remember not to pack aerosol and have every person pack their own tube, I brought clear zinc for the boys and they still got a little burned. My favorite brand is Coola, it’s organic, smells good, and works.


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Good Books– You will never see your children do this much reading for pleasure. I recommend checking out my friend Jesse Kornbluth’s site Head Butler for some great recommendations. I swear to you these photos were not staged.


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Why You Should Book Your Yacht Charter Today


These boats sell out fast, hoping to go for Christmas? Call today, you might get lucky. Also, what could be better than Thanksgiving on a yacht?


This type of family time is golden, there is no cooking, no driving, no TV, no Xbox, just time to be together and read, play games, swim and nap.  Yes, I said nap. I napped so much on our last trip I’m pretty sure the crew thought I had a sleeping disorder.




Chartering a Yacht in the Caribbean

You can book online with iYachtClub on their website HERE. Or you can call Derek directly, he’s fabulous and would love to walk you through the various options. His cell, for LTM readers only, is 919-730-4569, or you can call their toll free number, 1-855-924-8252. I’m also happy to answer any questions, just shoot me an e-mail at


We paid full board for our first cruise and returned a few months later at our own expense but were hosted for four days for the purposes of creating a video. This was one of our family’s all time favorite vacations, and that is saying a lot. Our Christmas cruise cost about $2,000 per night.




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