Cheapest Family Vacation Ever? A Caribbean Sailboat for $42 a Day

Sunrise in the British Virgin Islands. (Photo: JP Hellums)

My husband and I grew up sailing with our families. For our recent family vacation, we were daydreaming of sharing our love of the ocean with our teenage children. But with a vacation budget to stick to and the non-stop programming of a cruise ship not what we had in mind, we decided to charter a sailboat with another family to explore the British Virgin Islands.

The BVIs offer easy-to-navigate waters that are tailor-made for sailing, whether you’re a first-timer or a seasoned sailor. Prices vary according to the type of boat you choose and the level of service and amenities you require. With current seasonal discounts, a group of eight people can find amazing deals for as low as $42 per person per day for a mono-hull boat that you sail yourself.

The cost benefit of a boat-charter vacation is that the price covers your accommodations, a self-catering kitchen, transportation to inaccessible island locations, as well as unmatched scenery and adventure every day of your trip. (Food and water toys are extra.)

Tortola’s marina, where our charter originated. (Photo: JP Hellums)

Get started by checking out Moorings, Sunsail, and Horizon Yacht Charters — which are based in Tortola — or Fairwind Sailing School Charters, based in St. Thomas. These companies can help plan a trip to suit any level of sailing experience. They also offer the option of hiring a skipper or, if at least two people in your group have sailing experience, “bareboating,” meaning you play captain. A skipper can be hired for an additional $190-$250 per day.

Bareboating, obviously, saves you a ton of money. If you want to learn how to sail, check out the American Sailing Association for an accredited school.

Related: Paradise Awaits—11 Reasons to Visit the British Virgin Islands

Raising the sails with friends adds to the fun. (Photo: JP Hellums)

We booked a bareboat charter without a skipper through Sunsail. We splurged on a catamaran, which is about 20 to 30 percent more than a traditional mono-hull sailboat, but offers significantly more living space. (In June, rates for catamarans start at anywhere from $51 to $59 a night, depending on the size of the boat and the charter company.) Most catamarans have a similar layout: four separate cabins and four bathrooms, plus an additional bunk for a hired captain or spare passenger. This allows for a little more privacy for a group of two families traveling together.

Eight days on a boat can be a lot of togetherness, so we recruited friends with kids of similar ages to our own. Our crew was made up of five teens and four adults sharing a 44-foot catamaran. It was cozy but still felt comfortable enough to spend eight days without a mutiny. The added benefit of sharing a charter-boat vacation: we were able to share many of the costs.

The nature walk on Sandy Cay. (Photo: JP Hellums)

When we picked up our boat in Tortola, we were given charts and detailed advice on the ideal itinerary for our group. The best part of a chartered sailing vacation is how flexible you can be about where you go and when. On one leisurely day of our trip, we were greeted by a bale of sea turtles from our over-night anchorage at Great Harbour on Jost Van Dyke, took a midday nature hike on Sandy Cay, and ended the day with snorkeling along the shoreline of our secluded anchorage at Soldier Bay on Norman Island.

Even if you hire a crew, it’s important to make sure everyone understands the basics of how the boat operates before you leave the marina on the first day. Another good idea is to give everyone a job to make them feel like a member of the crew and not just a passenger. Every member of our “crew” had a responsibility — by the end of the week the group was a well-oiled boat-savvy machine.

Related: #RealTravel: They Met and Fell in Love While Sailing in the British Virgin Islands

Our gallery kitchen provided everything we needed. (Photo: JP Hellums)

Provisions — food, ice, and drinks for the boat — can be supplied by your chartering company. It costs between $26-$30 per person per day for packages that include groceries for breakfast, lunch, and a few dinners. And the company will stock your boat so that everything is there when you arrive.

In order to save a little money, we choose to do our own provisioning by ordering online from Riteway Market; we were able to get our cost closer to $18-20 per person per day, including water, drinks, and alcohol for the adults. Everything was delivered right to our boat the day we arrived. We did have some issues with missing items, however, so for some travelers, the cost savings might not be worth the potential hassle.

Conch Fritters at Ali Baba’s on Jost Van Dyke. (Photo: JP Hellums)

We also packed lots of snacks from home, like granola bars and mixed nuts from Costco, and had “happy hour” drinks on the boat on the nights when we went ashore for dinner. This saved us from overspending at restaurants, which can be expensive in the British Virgin Islands, even at the most casual of beach bars. (A hint: if a simple chalk-board menu does not show the prices, be sure to ask before ordering or you might get a shock when the bill is presented.)

Related: How to Sail Around the World by Yourself (This Woman Did It!)

Taking the dingy to shore to find dinner and explore the Virgin Gorda. (Photo: JP Hellums)

Packing light is the way to go on a boat. Be sure that luggage is soft-sided and collapsible, so that it can be easily stored. E-readers are usually the most efficient way to carry reading material, however, the damp atmosphere and bright sunlight of a sailboat makes old-school paperbacks the preferred choice. A deck of cards and an easy-to-pack game like our favorite bananagrams should also be on the packing list.

Charters usually come stocked with an assortment of snorkeling masks and flippers. But it is wise to bring your own mask, as those supplied can be ill-fitting. Reserve kayaks and paddle boards with the charter company before the vacation begins and they will be packed onto your boat when you arrive. We found that having these water toys allowed extra independence to members of our group who wanted to explore on their own when the boat was at an anchorage.

Snorkeling in crystal clear waters was a highlight of our trip. (Photo: JP Hellums)

Charter companies offer “technology packages” that include everything from onboard 4G Wi-Fi to gaming consoles. We decided to forgo this expense and these digital distractions. It turned out that Wi-Fi was not something we missed. The restaurants that we visited had Wi-Fi access that allowed everyone to check email. And we encouraged everyone to stay on airplane mode while onboard to prevent phones from picking up expensive roaming charges. (The threat of these charges also discouraged sneaking below deck to check messages!)

Related: Ahoy, Matey! Grab the Helm at These Caribbean Sailing Schools

Keeping a written journal of the trip is an old-school way to record trip memories in a meaningful way. (Photo: JP Hellums)

What we did rent was a 12V DC wireless adapter that allowed us to plug an iPod into the yacht’s speaker system. Everyone uploaded his or her favorite tunes to a communal playlist before we left home. We discouraged the wearing of ear buds (“tuning out”) while the boat was under sail for safety reasons and instead held a daily on-deck dance party.

The kids, enjoying the Bitter End Yacht Club amenities. (Photo: JP Hellums)

Another thing we decided to do was to include two nights anchored at a yachting-friendly resort, the Bitter End Yacht Club. This was a great way to give the group breathing room by spending time ashore around the halfway mark of our vacation. The Bitter End is extremely family-friendly and allows boats that rent the resort’s moorings access to restaurants, a swimming pool, scuba excursions, hiking trials, and more. While the kids enjoyed the water toys and sunfish rentals, the adults indulged in the spa at Biras Creek resort, just the over the hill.

Last day of the trip. (Photo: JP Hellums)

It took a couple of days to get used to the close quarters and simple amenities, but everyone in our group experienced magical moments onboard the boat. The adults relished the opportunity to eat breakfast watching the sun rise over the water and the teenagers discovered the enchantment of lying on deck in the dark, talking as the stars gradually blanketed the night sky.

The result was a vacation that allowed everyone to completely relax and to forge real connections, completely removed from the stress and responsibility of every-day life.

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