Your Sailing Charter Questions- Answered!

In May 2019 and we had the best time chartering a sailboat in the British Virgin Islands as a family. We were on a 40′ catamaran through The Moorings and bareboated it for seven glorious days. We loved taking a sailing charter vacation with our kids so much that we went again in April of 2023.

I shared our experiences on Instagram (our trips are saved as a highlight if you want to view them). Through our sharing, I received numerous questions about our trip- from the cost, to the necessary skills needed to take such a trip, to the actual how to put the trip together.

Many of the questions overlapped so I wanted to answer them all in one spot to hopefully create a resource you could pin, bookmark, and reference when you’re ready to book your own epic sailing charter vacation adventure!

How much does a sailing charter vacation cost?

There is a boat for every budget, and the range is large. Pricing varies depending on the size and type of boat you choose (a 50’ catamaran will cost more than a 40’ monohull), and the time of year you choose to sail. Keep in mind that the ideal way to organize a trip like this is to invite multiple families or couples to join you, so that you split the cost evenly. The charters are not priced per-person; they are priced per-day. How you split the cost is entirely up to you. They also offer 4 different typed of charter: Bareboat Sailing, Power charters, Skippered charters, and all-inclusive Crewed charters, all of which carry different price points. Click here to price your specific trip.

Again, the cost varies depending on the type of yacht you charter, how many days you are on board, the time of year in which you charter, and whether you choose to Bareboat (sail it yourself), hire a Skipper, or opt for the All-Inclusive Crewed yacht with Captain & Chef.

By rule of thumb, monohulls (traditional-style sailboats) are the least expensive, and a 3-cabin monohull could cost roughly $6,000 for a week on the water in Springtime. Catamarans are much larger, more luxurious and spacious vessels, and the price reflects this. A 3-cabin catamaran for the same period as I just reference for the monohull would cost between $10,000-14,000. Then, we also have larger 4-cabin models which would run closer to $20,000 per week. In the offseason (hurricane season in the Caribbean), many of those costs are roughly halved, such is the varying degree of pricing depending on the time of year.
If you would like to hire a Skipper, you can do so and this will cost roughly $259 per day, plus gratuity.

The most important things to consider are:

The number of people in your group – are there enough cabins on board for everyone to be comfortable? Most yachts feature en-suite cabins, but some have bathrooms that must be shared, this is good to take into account.
What type of yacht are you interested in? Are you interested in a more traditional sailing vacation? Then consider a monohull. If you and your group need more space, and perhaps more stability and less rocking, then consider a catamaran. If sailing isn’t your thing, consider a power catamaran, which features the space and stability of its sailing counterparts, but is much faster and gets from A to B in half the time.
There are 3 main types of charter experiences: Bareboat, Skippered, and Crewed.
- On a bareboat charter, guests are expected to sail the yacht themselves. Believe it or not, this is the core of the business and the vast majority of our customers prefer to captain the yacht themselves. Many are sailors and even own their own boats back home. In some destinations, such as in Europe, official sailing certification is required, but in most of our destinations you simply need to complete our Resume of Sailing experience, which will qualify you to captain one of the yachts.
- On a Skippered Charter, you hire one of The Moorings’ Skippers to captain the yacht for you. The Skipper will take 100% responsibility for the handling of the vessel, and will stay aboard the yacht with you for the duration of your charter. In most cases, the skippers are locals who are well trained, and know the destination inside-and-out, offering a unique experience and in many cases allowing you to see hidden gems you may have otherwise missed. Many times the skippers become good friends with the guests, and they keep in touch long after their charters are finished.
- Aboard a Crewed yacht, guests enjoy the service of a professional Captain and Chef crew. The crew lives aboard their yacht full time, and charter guests are treated to all-inclusive service throughout their trip. Obviously, no experience is required here. Simply sit back, relax, and enjoy the ride. Your crew is there to take care of everything from sunup to sunset.

Do you have to have prior sailing experience?

If you plan to do a Bareboat charter and sail the boat yourself, yes, prior sailing experience is required. Depending on the destination in which you choose to sail, official sailing certification may be required, but in most of The Moorings locations, including in the British Virgin Island, you simply need to fill out a resume of sailing experience beforehand, and The Moorings will inform you whether you are qualified. Alternatively, if you do not have sailing experience, you can always hire a Moorings Captain to do all the work for you while you relax!

How complicated is it to plan a sailing charter vacation? How long did it take?

At its core, this vacation is relatively simple to organize: pick the destination you like, pick a date you want to travel, and pick the boat that fits your group best. However, these are completely customizable vacations, and the more time you spend sorting out the finer details of the trip, the better your experience will be.

Do you want The Moorings to pre-provision the boat for you? Do you want a kayak or paddleboard on the boat? Also, there are no set itineraries, so spend some time researching what locations you want to visit while you are on charter. This planning is half the fun!

Generally they recommend booking your charter 6 months in advance, giving you plenty of time to iron out the details in a stress-free manner. If you are looking to travel over a busy time, like the Christmas and New Year holidays, you’ll want to plan sooner.

You will turn in your crew list (who you are bringing with you) and your provisioning list (think online shopping grocery list) about a month beforehand. The Moorings is a full-service travel agency and can help guide you step-by-step through the entire process, complete with booking your flights for you and your group.

What are the things you are grateful you packed? What are the things you wish you would have left behind?

I’m glad we checked one bag because it was really nice to bring our own sunscreen. I am a big fan of Blue Lizard because it’s a physical sunblock that actually rubs in well- AND it’s safe for marine life.

I’m also glad we packed: Barbies, Tevas (they are the only shoe I wore), multiple bathing suits, hats, a cover up, one cute dress, and paperback books. Things we brought that we definitely did not need to bring: make up, cute sandals, more than 2 dresses for the girls, a hair straightener (lol!), and nori sheets. I had heard you could get fish and roll your own sushi. Good in theory, but we ended up just packing them and bringing them back home with us.

For a full packing list, please visit this post.

Did you have to reserve mooring balls at each island/anchorage?

It’s a new development to be able to reserve mooring balls at all. However, BoatyBall is making that possible. BoatyBall mooring ball rentals open up at 7:00 AM each day, and in our recent experience, they are completely booked by 7:02 AM, so be ready to hop on and make your selection.

While we used the service twice, we typically did things the usual way- first come first serve. We knew which mooring fields were popular and made sure we arrived early enough to be able to snag one.

Absolutely! There are many ways to do this as a novice, including hiring a captain for your whole trip. We did a charter several years back with both a captain and a cook and they let you help as much as you’d like, or just sit back and enjoy without lifting a finger. It’s such a unique and adventurous vacation that it will be one your family will talk about for a lifetime.

Where else is good to sail, besides the BVIs?

This is a tough question. The Moorings has locations all over the world, each with their own unique benefits and experiences. It all depends on what you want to get out of the trip. Do you want to get away from busy towns and marinas and anchor off a white sand beach in a harbor all to yourself? Then consider the Exumas, Bahamas. Want to go scuba diving and fishing? Consider Belize. Want to island-hop while sailing longer distances? The Windward islands from St. Lucia to Grenada offer fantastic open-water passages. Want something with a more exotic flair? Try Thailand or French Polynesia. Or if you want to explore ancient seaside towns steeped in history and culture, try a yacht charter in Greece or Croatia. The world is your playground with a vacation like this.

Did the kids feel cooped up on the boat? Were they bored ever?

Thank goodness for books, audiobooks, and Barbies because our girls never seemed to feel bored on the boat. Our longest sailing stretch was just shy of four hours and they spent it reading, then playing Barbies, then sitting on the front of the boat watching the waves while I told them stories and sipping ginger ale. Also, the vacation is an adventure in itself and the kids are enthralled with searching for dolphins, steering the ship, and other fun that naturally comes along with a trip like this.

How much does it cost to have a captain?

It varies slightly from destination to destination but budget about $250-300 per day. Also, you will have to allow one of your cabins to be used by the captain.

Were you worried about safety? What about the safety for kids?

We were not concerned about safety. We felt comfortable with the main moorings and anchorages we stayed in and know that the British Virgin Islands are a very safe place to be in general. As for water safety with the girls, this was a top concern/priority. We went over the ground rules sternly at the beginning of the trip and stayed vigilant. And although the girls wore life vests whenever they were outside the salon, we made sure they both were at a point that they could swim unassisted as well.

How much did you budget for food for the week? Were the grocery stores expensive?

Yes, the stores were expensive! That’s island life though, as everything has to be imported. We ended up spending about $700 on groceries for the week on our first trip, though that also included tequila, rum, beer, wine, bottled waters, and some household items. We only ate out a few times though, as I wanted to see what it was like to cook on a boat.

On our 2023 adventure, we used The Moorings provisioning service. I created a list of groceries I wanted and they were delivered to our boat when we boarded. The convenience was excellent, though they didn’t have everything I requested, so we grabbed a few items ourselves. The total was roughly $450 because we planned to eat most dinners out.

How far in advance do you need to plan a trip like this?

About 4-6 months is ideal to book a sailing charter vacation, but the earlier you book the better. This will ensure you get exactly the boat you want and gives you plenty of time to plan for your trip. They frequently have people book their yachts one year in advance or more.

Was anyone seasick? How did you handle that?

Hailey felt queasy on our long sail. The sea was rolling that day and inside the cabin you had to hold on to be careful not to fall over. We set sail while we were finishing up breakfast, so the girls and I were inside.

Hailey and Kaitlyn stayed down in the bedroom reading and about an hour into the trip Hailey said her tummy felt funny. I put her up front, in the breeze and looking at the horizon with a little ginger ale, and she was fine about 15 minutes later. Lesson learned: best to be up top or out front while underway. No one ever truly got sick though.

I think it really depends on your child’s personality and your comfort level. For me, Kaitlyn (newly 5 years old) at our first sailing charter vacation was the minimum age I would take on the trip. More importantly than age, we wanted to wait until both the girls could swim. Even though they always had of life jackets, it felt better knowing they both could swim as well.

Were you nervous not having a captain?

Yes! When David came back from orientation and told me we’d be fine on our own, my eyes almost popped out of my head. Our first mooring experience was nerve wracking, but after that first night, I agreed with David. We could totally do it on our own. It’s actually much less intimidating then it seems, especially if there are two people up for the adventure and challenge.

How did you find a boat to rent?

We have done sailing charters with two different companies, and I recommend going with The Moorings.

How did you choose which islands to sail to/spots to visit?

We had been the the BVIs on a charter before and had a good feel for the islands. We each picked out one or two spots that we knew we wanted to take the girls to (The Baths, Anegada, and Foxy’s on Jost Van Dyke) and then filled in the rest based on location and priority. We knew we wouldn’t be able to see it all, so we prioritized.

How does the bathroom situation work?

This was hilarious because I have been on a couple sailboats and know the drill- no toilet paper in the toilet. However, when we told the kids about this, their wide eyes had us rolling with laughter. In all seriousness, it’s quite simple. Use the toilet as you would anywhere else, wipe with toilet paper, place toilet paper in a small, hidden trashcan right next to the toilet, then use the switches right next to the toilet to flush everything down.

Most anchorages and mooring fields have trash pick up so it’s easy to get rid of as often as you want. For the week we were on the boat, we did not need to worry about emptying the holding tank.

Also, I have heard that they made toilet paper that can be flushed, but being it was a rental, we didn’t want to risk any issues so we stuck to the tried and true method!

What was your itinerary?

2019 – see the full details and pictures here

Day 1: We picked up our boat on Tortola in the afternoon, motored across to Peter Island and got a mooring ball for the night.
Day 2: We took a big leap from Peter Island to the north side of Virgin Gorda to see The Bitter End, and stayed the night at a mooring ball at Biras Creek.
Day 3: Virgin Gorda to Anegada.
Day 4: Anegada to The Baths (for the Day) and spent the night at a mooring ball at Marina Cay.
Day 5: Marina Cay to the Sandy Spit to Jost Van Dyke.
Day 6: Jost Van Dyke to Cooper Island.
Day 7: Cooper Island to Virgin Gorda, stayed at a mooring ball right next to CocoMaya.

2023

Day 1: We boarded the boat and went straight to Norman Island to snorkel in the Caves. We visited Willy T’; stayed the night at Norman Island.
Day 2: Visited the Indians for snorkeling then to anchor at Salt Island.
Day 3: Spent the day at The Baths and ended at Bitter End Yacht Club at Virgin Gorda; dinner at Saba Rock.
Day 4: Visited Oil Nut Bay by dinghy, and stayed a second night at Bitter End Yacht Club.
Day 5: Anegada
Day 6: Visited The Sandy Spit, then stayed the night at Cooper Island.
Day 7: Visited Peter Island and the Bubbly pool on Jost Van Dyke, then stayed the night near Foxy’s on Jost Van Dyke.

I can’t recommend this trip enough. It’s a once in a lifetime adventure… that I hope to do many more times.

If you have any other questions, please leave them in the comments and I’ll be sure to answer them!