Tips for First-Timers on a Sailing Charter Vacation
Contemplating a vacation under sail? It’s easier than you think. Here are some pro tips on planning, executing, and enjoying a sailing charter whether in the British Virgin Islands, Mexico, Croatia, or beyond.

Bareboat or crewed?
First, decide how you want to sail. Will you be the skipper on a bareboat and have responsibility for navigating, anchoring, troubleshooting, and generally managing the charter, or do you prefer to let a captain handle the boat and maybe a chef do the cooking? Professionals aboard a crewed charter mitigate risk and stress, but they also make the charter less private and more expensive. No experience is necessary.
To bareboat charter, you must have some experience. It’s less expensive, but you’ll need basic sailing, anchoring, and docking skills. You’ll plan the itinerary, monitor weather, and tend to your crew. Some charter companies offer a midpoint solution by providing a “partial captain” who’ll stay aboard for one to three days until you learn the ropes.
Where to go, who to book with, and what kind of boat to choose?
There are many places to go and lots of charter companies to choose from, both regional and international. Both experiences can be good, but for the first outing you may want to stick with one of the “majors” because they offer booking advice, easy payments, loads of support onsite, and decent boats.
The Moorings, Sunsail, and Dream Yacht Charter may be a bit more expensive than local outfits, but they offer fewer surprises along the way. For example, vacation planners at Sunsail answer questions on the phone and handhold you through the process. Start with a company’s website for fleet information, destinations, packing tips, and sample itineraries
The British Virgin Islands in the Caribbean are the most popular destination for beginners due to line-of-sight navigation, steady trade winds, and lots of shoreside entertainment like restaurants and bars. With greater skill comes more adventure, so soon you’ll be able to explore the far-flung islands of Greece, the remoteness of the Sea of Cortez, or the beauty of Tahiti.
Choose between a monohull and a catamaran. Monohulls are usually smaller, easier to handle, and typically cheaper. They’re also more plentiful in the Med. Tropical destinations tend to offer more cats that have a shallower draft and more room, separation, and privacy aboard.

When to book, when to go, and whom to bring?
Like tour companies, charter organizations operate on high, low, and shoulder seasons. The Mediterranean is busy in the summer while the Caribbean perks up in the winter. The key is to avoid hurricane, typhoon, and meltemi seasons, which bring strong winds to different parts of the world. Shoulder season is less busy, offers lower prices, and sees smaller crowds in anchorages and restaurants. Shoulder season in the Caribbean is May and June and early November, while the Med is less crowded in May and October. Some charter companies offer pricing discounts or extra days (such as 10 days for the price of seven), so ask about specials.
Depending on the destination and time of year, plan to book six to 10 months in advance. If booking for peak season holidays such as Christmas or New Year’s or peak summer in the Med, make it 10 to 12 months ahead. For off-peak cruising, you may be able to book three to six months out, and if you have a flexible schedule, you may be able to take advantage of last-minute deals.
For your first time, target a few days or a week, and don’t over-plan your itinerary. Be flexible, stay in the present, and if you like a specific place, be spontaneous and take extra time. Rushing makes for a lousy vacation and a cranky crew. Speaking of which, choose your crew carefully. Bringing non-sailors, non-campers, young kids, and the seasick will definitely impact your vacation.
What about paperwork, briefings, and costs?
For bareboating, you’ll sign a contract, and you’ll need your sailing resume and crew list with the names and passport information of all guests. You’ll also complete insurance waivers and arrival information.
Technical and chart briefings are essential, so don’t plan to skip them. Some companies require you to watch online videos prior to arrival and attend onsite briefings as well. The chart briefing walks you through setting an itinerary and provides local knowledge. The tech briefing teaches you how to run the boat’s systems such as the generator, tank manifolds, electronics, and dinghy operation. Both briefings are invaluable.
Expect to add insurance fees and fuel and provisioning costs to the charter base price. For crewed charters, plan a tip of 10 to 20 percent of the base cost of the charter for the crew. Consider adding toys such as SUPs and kayaks, but remember these are priced per day or per the length of the charter, and they’re not cheap. For best results choose the “partial provisioning” option if there is one where you have some basic foodstuff brought aboard by the company, but you’ll also have the flexibility to dine out often.
Why not start now?
Chartering isn’t hard, and there are so many tools to help along the way. If you’re new to boating, consider a crewed charter. If not, take the plunge on your own. A bareboat sail in the BVI may open doors to a lifetime of adventure vacations around the world.
~By Zuzana Prochazka