The author on a Sunsail charter in the Kingdom of Tonga.


The author on a Sunsail charter in the Kingdom of Tonga.

The process of planning an offseason charter can seem daunting to the uninitiated. The world is a big place, with seemingly countless options for a snowbound boater seeking some warm-weather relief. Yet if you keep a few simple questions in mind, you’ll be well on your way to organizing the charter trip of your dreams.

First, before you start Googling international charter fleets, decide who you would like to accompany you on the upcoming boating adventure. Do you want to share this with your spouse or partner, another couple, family members or a group of friends? Each will provide a very different experience, from an intimate cruise for two to a rollicking full boat.

If you’ve decided that a larger group suits you, which family members or friends will you include? Will you bring children along, or will this be an adults-only vacation? Remember that not everyone enjoys the same type of holiday. Crewmembers need to be compatible — and able to share close quarters.

This is very important. No matter what the brochures say, no cruising yacht is roomy enough to separate soon-to-be-ex-BFFs who can’t stand another minute in each other’s sight. Compatibility can make or break a charter trip.

Once you’ve chosen your crew, pull out your maps and guidebooks or research possible destinations online. Consider the experience level of everyone on board as you do this. If you’re new to chartering, you may want to focus on destinations like the British Virgin Islands; with its well-protected waters and numerous anchorages, the BVI are among the most user-friendly charter-cruising grounds in the world.

Also think about what types of activities you’d like to do. Are you interested in spending all your time boating? Or would you rather limit your time under way in favor of relaxing on the hook and on shore? Are you eager to sample as many ports of call as possible, or would you rather focus on specific spots? Are you or your crew excited about watersports such as scuba diving, snorkeling or windsurfing? Would you like to participate in land-based activities like hiking, horseback riding or sightseeing?

Have everyone make a list of what they hope to experience on the cruise, and then compare notes. One person might want more of a self-sufficient experience at sea with full provisions on board, while another might want to visit restaurants, pubs, shops and marina facilities. Some boaters are keen to log as many nautical miles as possible; others are content to live aboard while enjoying more traditional tourist activities. Making sure all your crewmembers are on the same page right away is key to a successful cruise, and your collective goals will point you in the right direction as far as destinations are concerned.

Budget and available time also point the way. If you have limited amounts of both, you might want to consider the Caribbean, Bahamas, Florida or perhaps Baja California. Travel costs will be less, you won’t have to sacrifice too many days in transit, and you won’t have to worry about jet lag. If you have more funds and vacation days available, you may wish to venture farther afield, perhaps to the Mediterranean or the South Pacific.

As you discuss destinations with your crew, you’ll also need to consider the timing of your trip. If you don’t mind crowded anchorages and waiting for tables at waterfront restaurants, the holidays and spring break won’t be a problem. If you want a more solitary — and more economical — experience, consider chartering in the fall or in the window between New Year’s Day and the onset of spring break.

Aboard "Never Say Never" in the Abacos... just before Hurricane Wilma.

That being said, be aware that the Atlantic and Pacific hurricane seasons run through November 30. You may want to consider purchasing travel insurance if you book a charter in October or November. You and your charter operator also should discuss your available options if a hurricane does bear down on your destination once you’re already there. My husband and I had to cut a charter cruise short and flee the Abacos in advance of Hurricane Wilma; we remain eternally grateful to the Moorings’ staff for working so hard behind the scenes to rebook all of our flights out of the Bahamas and Florida.

Some destinations have specific weather patterns of which you also need to be aware. For example, the Sea of Cortez is notorious for strong northerlies in February and March. If you hope to cruise here during those months, prepare to adjust your expectations. Sailboats may have to shorten sail or motor under bare poles, and whether you’re under sail or power, there’s a good chance the commercial port may close or you may have to hunker down in an anchorage for a day or two to ride out a gale.

Do your homework and research your chosen destination. Pick up a travel guide or, better yet, a cruising guide to see what an expert has to say, and then make a final decision on where and when.

Now, will you charter a powerboat or a sailboat? Do you want to go with the type of boat you know best, or would you like to try something different? Charter companies offer traditional sailboats, sailing catamarans, power catamarans, express yachts, motoryachts, trawlers — yachts of every imaginable flavor.

Once you’ve chosen the type of yacht you want to charter, you’ll need to decide on the yacht’s size. For example, will that 30-footer be big enough for six people? Or can two people handle that lovely 45-footer?

To start, you’ll want to make sure you have enough live-aboard space for everyone, and bear in mind that published comments about the number of people a boat “sleeps” is optimistic. Make sure that each person has his or her own bed — or that each couple has its own stateroom. No one should have to make do with the convertible dinette or a narrow settee. What might seem fun or charming for a night will be dreadful by week’s end.

As far as short-handed chartering is concerned, review the prospective charter yacht’s equipment list online or request it from the company. If you’re interested in chartering a 45-foot sailboat with your spouse, for example, it will be helpful if that yacht incorporates such features as a roller-furling jib, lazy jacks for the mainsail and sheets led aft to the cockpit.

In other words, if the yacht has the right gear, you won’t need to staff up.

On a bareboat charter in the Apostle Islands National Lakeshore.

Next, will you choose a bareboat charter or a skippered charter? For a bareboat charter, the charter company will ask you to fill out a skipper’s resume. Representatives want to see that you’ve either passed a charter-cruising course or that you have equivalent on-the-water experience as a skipper. If you don’t have that requisite experience, you can hire a skipper through the charter company; he or she will have full responsibility for the yacht, although you and your crew will also assist in the boat’s handling and day-to-day operations.

Even if you have plenty of experience, hiring a skipper is a wonderful option if you are going to be chartering in unfamiliar waters or would simply like a more laid-back cruise. My husband and I hired a native skipper on a charter in the Kingdom of Tonga and quickly realized it was the best decision we could have made. Not only did he know all the best anchorages and must-visit spots, he regaled us with island legends and stories.

And on a charter in Baja California Sur, our skipper gave us the insider’s tour of the Pichilingue Peninsula when a gale shut down the port at La Paz, and he ensured that we saw as much as possible on our unexpectedly shortened cruise.

Finally, make sure you have alternate itineraries in your back pocket in case something goes awry with the original plan. From unfavorable anchoring conditions and inclement weather to shifting crew needs, forgotten provisions and technical difficulties, unforeseen glitches can wreak havoc with the best-laid plans. Be flexible, and you just may find that the unexpected bits prove to be the best parts of the whole trip.