Five Questions To Ask About Your Next Sailing Charter

Must-Ask Q’s About Your Next Sailing Charter Vacation

If taking a sailing vacation in the New Year is a high priority, there are five critical questions to ask before you plunk down your credit card.

charter sailing vacation bahamas1. Who? Who will travel with you? If your crew members are active sailors and/or experienced charter sailors, your destination possibilities are wider. If you plan to travel with new or inexperienced sailors, you may want to choose a “user-friendly” destination such as the British Virgin Islands, where you have the option of more sheltered sailing waters.

One of our experienced charter writers once expressed that she no longer goes on charter vacations with newcomers, as taking charge of the boat and navigation felt stressful and too much like work. Hiring a captain could solve this problem, and most good charter companies will be happy to send a captain (and cook!) along on your weeklong charter.

2. What? What kind of sailing do you aim to do? Would you like to spend the bulk of the day under sail, or is getting to the destination to paddle, snorkel, dive, collect shells on palm-fringed beaches, or go to beach bars have more appeal? Or a mix? If sailing for most of the day is a high priority, you may want to charter a monohull. If small-boat activities or onshore exploration are high priorities, you may want a multihull (also offering ample room for storing said small boats on deck).

3. When? Most working sailors don’t have unlimited vacation time, and parents may have to work around school schedules. When are you free? Your free time restrictions may help you choose your sailing charter destination. If you’d like to charter in Croatia, yet are only free in February when it’s cold there (and the season does not open until the end of March), you need a new plan. Our editor (who should know better) was surprised to find out that at the beginning of March the water in the Bahamas is cold enough to need a wetsuit. These are just two examples of how your vacation window may determine the right charter destination for you. When in doubt, call a charter company and educate yourself about destinations and seasons.

4. Why? As with any other travel plan, fellow travelers should agree on the reasons and goals for the trip. Goals could include: exploring new places, relaxing and taking in the scenery, or jumping into all the activities of the region (hiking, paddling, diving, touring, dining). The best charter companions find a happy medium, where some go touring and the others relax on the boat. It’s important to discuss the possibilities in advance, however, as many may have a slightly different view of how “relaxation” is defined.

5. Where? Knowing that “everywhere!” is not a solid answer for planning purposes, you must choose one place per trip. When you visit a big charter company website, you may feel dizzied by the options: Bahamas, Virgin Islands, Mediterranean, Pacific Northwest, Asia, New England, or right here on the Chesapeake. Gather your family or prospective charter crew together in one room and ask the four questions already noted. You may find their responses enlightening, and the right charter destination for you will come into focus.

** When you take your 2024 charter, send a note to [email protected] so that we can share your trip tips with SpinSheet readers. Happy charter sailing!

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