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Big Waters, Small Craft: The ABC's of Chartering Your Own Boat

If you've never considered a sailing vacation, give it a shot. It can cost less per day than a standard European vacation, and it can be refreshingly interactive.

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By Nick Trotter

  Published: Feb 24, 2004

  Updated: Oct 11, 2016

February 25, 2004 -- Ah, winter in New York...gray skies, slushy commutes. It's times like these when I thank my lucky stars for people like my friend Dave and his casual invitation last year to accompany him on his annual trip to the Caribbean. Not one for the crowds on cruise ships or throngs on beaches, Dave goes on a cruise of his own design and whim: he charters a yacht and picks a few lucky friends to sail along with him. This year's trip was to Antigua and Barbuda, two islands that are a bit off the beaten track, though popular with sailors. I had sailed small boats years ago at summer camp, but had little experience with anything that could properly be called a "yacht." As it turned out, it was truly smooth sailing; we had cloudless skies, great snorkeling, and miles of uninhabited beaches to explore at our leisure.

If you've never considered a sailing vacation, give it a shot. It can cost less per day than a standard European vacation, and it can be refreshingly interactive -- you'll gain skills in all sorts of technologies, from the latest in satellite navigation to the truly ancient workings of wind and sail. And it is unquestionably the most romantic way to explore the islands. Here a some tips for planning your trip.

How to Charter a Boat

Chartered yachts and sailboats are usually privately-owned boats on loan to a charter company to help the owner pay off the cost of the boat. A decent boat can easily cost the same as a decent house, so many owners purchase a boat, perhaps a few years before retiring, and lease it to a charter company that will rent it out (or "charter" it) until it's paid off and the owners are ready to take over. In the meantime, it's there for you to use.

When chartering a yacht, you can research the charter companies yourself, or you can hire a broker. The brokers' main selling point is their expertise: they know what boats are available in the area you want to sail. They can also act as your complete travel agent, arranging airfares and accommodations for before and after the cruise. Many offer travel insurance or will connect you with insurers. (Of course, Frommer's always recommends purchasing your trip insurance from a separate company -- not the outfit that's selling you travel.) Brokers can also trouble-shoot if problems arise along the way -- with, say, missed flight connections. If you want a worry-free experience, a broker may be the way to go. On the other hand, brokers won't always know about deals that you can get from the charter company itself. Dave got quite a good deal for us by negotiating directly with Sunsail and paying the deposit quickly, though he did it several months in advance. He did test the waters with a broker first; since we were going to Antigua, they also recommended Sunsail. You can read Frommer's review of several charter companies -- including rates and contact information -- at www.frommers.com/destinations/caribbeanandtheatlantic/0217020356.html.

The most important factor in choosing a charter company and boat is location: what territory do you want to explore? Think big: any coastal area has potential for great sailing, so go to parts of the globe you're interested in. Australia? The Mediterranean? British Columbia? Large charter companies like Sunsail have facilities all over the world and can help you narrow your search; smaller companies are more limited in geography and can be harder to find without a broker, but can make up for that with customized service and local expertise. You must consider other activities you're interested in, such as snorkeling and diving, land activities mountain climbing or casino gambling. Of course, we recommend that you consult travel guides before planning your trip -- they will undoubtedly help to orient you. Frommer's covers the entire Caribbean in a single book, and has individual guides for many of the islands, not to mention the rest of the world. As far as recommended sailing territory in the Caribbean goes, we had a great time sailing and snorkeling in Antigua and Barbuda, and Antigua can lay claim to the title of "Sailing Capitol of the Caribbean," particularly in April with its legendary Sailing Week. The British Virgin Islands also have a great reputation for both sailing and snorkeling, as do St. Vincent and the Grenadines.

The season is also critical to your planning. In the Caribbean, summers are extremely hot and humid. Winters (roughly mid-December through mid-April) are warm and sunny, making them the "high" season for travel here, and therefore much more expensive. Hurricane season runs from June through November, and is of particular concern in August, September and October. Many feel that the best season for sailing here is mid-April through early June -- it's still cool and prices are low. We decided to go over Thanksgiving week in order to beat the high-season prices and keep the incursion into our various work schedules at a minimum. I did miss Mom's turkey and stuffing, but the lobster was delicious! And obviously, if you're sailing in New Zealand or British Columbia, the season issues are all completely different. Again, guidebooks are essential for planning.

The ancient problem of seasonal wind direction -- will also affect your sailing itinerary, and this should be considered when planning. The "trade winds" that blow in the Eastern Caribbean are "easterlies," that is, they travel from east to west, with some variation from northeast to southeast. These variations can depend on the season, as well as whatever high- or low-pressure systems are lurking out in the Atlantic. It's much easier to travel with the wind (or across it) than to sail upwind, so a trip from Antigua to St. Kitts is quite easy, while the reverse is not much of a vacation. We sailed north and south between Antigua and Barbuda with no problems. If you do want to sail from island to island, particularly where this involves crossing international boundaries, consult carefully with your agent or chartering company to review the issue of clearing in and out of customs and immigration. If you've hired a skipper, he or she will obviously be knowledgeable in this area. A large company like Sunsail has facilities on many of the islands, so it's rarely a problem to pick up a boat on one island and leave it on another. However, this will complicate your airfares, and smaller companies may not give you this option.

Airfares can, of course, be the most complicated matter you deal with. Because of the workweek before Thanksgiving, we decided to book our charter starting on a Sunday. Flying in from New York, I saved two hundred dollars by flying on Thursday instead of the weekend, but this savings was offset by the fact that I had to pay for accommodations for two nights. My friends traveling from Denver, however, found that they could each save a thousand dollars (!) by flying down on Thursday instead of Saturday, so the hotel bill was a small price to pay, and we all had two extra days to explore Antigua on land. We all flew home on Wednesday two weeks later, and saved some money flying midweek then as well. Check all the online discount websites, and if you're hiring a travel agent or broker, be sure that they check them all as well.

You will also need to decide if you want to hire a crew with your boat, or to "bareboat" -- crew it yourself. Bareboating requires certification in the skills necessary to handle boats of the size you'll be chartering; Dave got his certification through the American Sailing Association (ASA; www.nyss.com/asa.html). Certification courses are generally week-long cruises of their own with a certified teaching skipper, and predictably cost as much as a cruise and a class put together; they should be considered only if you're a committed sailor, planning multiple charters over the next few years. Via the ASA, experienced sailors can skip the course by "challenging" the ASA exam and proving their skills to get certification.

Crewed charters usually have a skipper and a cook, or just a skipper. Naturally, they're more expensive than bareboating; Sunsail will add a skipper to your bareboat package for $150 per day, and a cook for $110 per day. No sailing skills are necessary for crewed charters, though they can help, and of course you'll learn a lot. Often, if you have the skills but not the certification, the skipper will be happy to sit back and let you sail the boat yourself. Of course, if an out-of-this-world, luxurious experience is what you're after, you can get a huge boat with polished wooden sundecks, drinks served promptly at happy hour, and a uniformed crew, including a highly trained chef in the galley. Just be prepared to pay for it.

When planning your crew or passenger list, go with friends, but make sure they're good friends. The boat will be quite confined, and you can't just go out for a walk. And much as you may like your cousin Bob when you see him at Christmas dinner, you may not want the kids to have to pull his finger after every meal for ten days! Crewing also brings up a cautionary note: while proper planning will eliminate most dangers, the sailing skills of the crew (or lack thereof) must be considered. As Skipper, Dave was responsible for the boat and everything on it. Though I am uncertified, I was officially designated the First Mate since I had more sailing experience than anyone else on the trip. This was not to be taken lightly; if anything had happened to Dave, I would have been responsible for getting the boat safely to a port. The ocean is a very large, dangerous place -- an extreme form of wilderness -- and ignorance can be fatal. A boat in danger is no place for decisions by committee, and a clear, knowledgeable chain of command is essential. Don't go unprepared.

The size of the boat is important, as it directly affects the comfort of the crew (not to mention the cost). We sailed on a 45-footer with a crew of six adults, though our boat supposedly slept ten, including two on the convertible dining table. We all agreed, though, that seven would have felt crowded and that ten would only have been appropriate for college students who find that sort of thing "fun." For the six of us, there was ample dining room below decks, and just enough room in the cockpit while we were underway. And no more than three people were necessary at any given time to hoist and lower sails, or otherwise actually sail the boat. It was quite easy and comfortable.

For families concerned about bringing children, consult with the charter company to see if they have age restrictions. The youngest child Dave said he'd want to take would be six or seven, though committed boating families have safely raised kids on yachts for decades. Any yacht can be fitted with netting around the lifelines to keep the small fry from slipping through. Certainly everyone on board must know how to swim; at the discretion of parents and skippers, kids can be ordered to wear life jackets whenever they're on deck. This won't prevent them from having a good time, and may save your hair from graying. The skipper should also be happy to run a "man overboard" drill -- it's fun, takes about five minutes, and is a good test of basic seamanship.

The bottom line when planning is: how much will it cost? For a one-week sail after April 18th (when prices go down), Sunsail's website quoted a price of $4,335 for six people bareboating on a 43-foot boat in the British Virgin Islands. That comes out to $723 per person, plus the cost of food (which is discussed in more detail below) and airfare. Adding a skipper for a week will increase the cost by $175 per person. If you've just got to get out of the winter weather before February ends, expect to pay $1,500-2,000 more per week for the whole package. You can adjust your pricing by choosing vessels of different lengths and/or adding more people to your crew, of course.

Packing

Packing involves a number of factors, and personal comfort is, well, very personal. Do bear in mind that unless you're going for a private luxury cruise, your berths will be small, closet space may be nonexistent, and you stand a good chance of having to sleep next to whatever you bring. Pack a duffel bag, not a suitcase, and limit yourself to a single piece of luggage if you can. In the Caribbean, you will sweat; it's usually cool and breezy on the water, but on land you'll feel the heat. Cotton is cool, but can be very difficult to wash and dry; linen dries well, but will wrinkle; and synthetic fabrics dry and stay good-looking, but aren't always very comfortable. Dave brought one cheap cotton t-shirt for every single day. His son Alan brought three synthetic shirts that he'd bought from travel or outdoor-equipment stores, and he laundered them regularly on board. I brought a mix of cotton and linen and did reasonably well, and we all bought souvenir t-shirts and wore them. Three or four light pairs of shorts will suffice for a week-to-ten-day cruise; if you plan on dining at the tonier yacht clubs and restaurants ashore, remember that many of them won't allow shorts, and may in fact require jackets and ties for men and dresses below the knee for women. Most bars and restaurants are quite casual, though nobody wears their swimsuits around town. I don't recommend jeans under any circumstance: they're heavy and a nightmare when wet. If you will be flying home to cold weather, take a light but warm sweater, or arrange for someone to pick you up at the airport with a coat. And since you'll be surrounded by water, you can expect anything and everything to get wet at some point.

You will need to be careful about footwear; the hiking on land can be among the great attractions of the Islands, but you won't be able to wear land shoes on the boat (to protect the deck from the grinding effects of sand, and to keep it from migrating into your berth) We went barefoot on board (with plenty of sunscreen between the toes) and most of our group had synthetic sandals (Tevas or Chacos) which were particularly nice -- and easy to rinse -- when beaching the dinghy and going into town.

Sun protection is a supreme consideration: the sun is brutal and relentless, and on a boat there's no escape from it. Remember that light reflects off of water, so you'll be getting it from below and above. It's easy to ruin your entire vacation by getting sunburned on the first day, so take lots of high-SPF, waterproof sunscreen and use it liberally and often. A hat is essential; a wide brim is best, but make sure you have a chinstrap in case it blows off. Baseball caps will protect the eyes but get you burned on your temples. I recommend taking a bandana or two which can be tied around the neck or worn Sheik-style under a cap to protect the ears and neck. Sunglasses are also a must. Make sure they have UVA and UVB protection (most do these days) and get polarized ones if you can: they reduce glare off the water and will help you navigate among the reefs. Bug spray will be a great comfort in the evenings and on land; one of our group brought a bottle of SPF-15 lotion combined with insect repellant which was quite handy on afternoons near shore.

Sadly, if you are prone to motion sickness you may have problems with this kind of trip, particularly on passages between islands where the waves of the open ocean will be unavoidable. Staying above decks and keeping an eye on the horizon can control mild queasiness, and ginger supplements -- even soft drinks or candy -- can also help. Eating regularly and staying well hydrated are essential. Various prescriptions are available, so consult your doctor: one of Dave's sons who'd had problems with motion sickness on a previous cruise was prescribed a patch which he wore at all times. He credited it with saving his vacation. Properly prepared, you shouldn't have any major troubles.

The boat can come with plenty of fresh linens and towels, as well as cookware. Our boat came with clothespins for drying things out on the lifelines, but take a few if you're nervous. Better yet, request a full inventory from the leasing agent before you leave home. The charter company will give you charts (as well as their recommendations and requirements as to where you should or should not sail) and a cruising guide with information on the territory you'll be in. The most popular guides for the Caribbean are by Chris Doyle and are well worth a look before you fly down. Donald Street wrote the original book on sailing the islands, and his books are informative and quite entertaining; however, they're more sail-techy and are frequently confusing owing to the way they've been updated over the years. Cruising guides for all parts of the world are easily available from sailing equipment suppliers such as www.landfallnavigation.com.

Underway

The first challenge you'll encounter is provisioning -- buying food for the cruise. Most charter companies will do the provisioning for you, for roughly ten percent over what you'd pay to do it yourself. Dave and his wife did the provisioning for our trip, but had to go all the way into St. John's, the capitol city, to get to a large supermarket and the cab fare back to English Harbour, where our boat was docked, was expensive. They reckoned that next time they'd let the charter company do it. As a group, we spent about $870 provisioning for a ten-day cruise, not counting two meals on land, which included the Thanksgiving lobster. We had to go ashore twice for more sandwich bread and fresh fruit and vegetables, which don't last long on a boat. The boat came equipped with a small grill that was great for steaks, burgers, and barbecue. All things considered, we ate well, and had very little left over at the end, which we traditionally left as a sort of tip for the crew cleaning the boat.

Sailing itineraries, as mentioned before, are heavily dependent on wind and are best left as day-to-day decisions. However, one of our group had to fly home three days before the rest of us did, so a safe place to get her a cab to the airport was built into the schedule.

We took command of the boat on a Sunday evening at about 6 p.m., well past dark and safe sailing. The winds were weak, due to a low-pressure system out in the ocean, so we motored out to our first anchorage the next morning and spent two days snorkeling the reefs. We then spent a day sailing to Barbuda and were there for three nights; then we sailed back to Antigua, dropped off our friend, and dinked-and-dunked down the west coast of Antigua for the last three days before spending the final night back in the dock in English Harbour. Coral reefs at the mouth of every bay make anchoring a big challenge; to navigate them safely, plan on being anchored by 3 p.m. so that there's plenty of sunlight overhead.

Water consumption, in general, is an important issue. We bought lots of bottled water for drinking. The boat came with two 150-gallon tanks, which we filled with fresh water at the start of the cruise. There were two freshwater showers on board, but we avoided depleting our supply by using salt water to wash dishes and ourselves, rinsing both dishes and bodies with fresh water afterward. Not all soaps will work in salt water: Joy is one dishwashing liquid that will, and Pert is one shampoo that works as a body-wash. We would jump off the back of the boat, then get back on and suds up, and jump off again to rinse. Of course, the freshwater showers are more comfortable, but you'll probably have to replenish your supply at a harbor along the way, which will affect the freedom of your itinerary. Not all harbors have a freshwater supply for boats! The restrooms, called "heads" in sailor-speak, cleverly use hand- or foot-pumps to irrigate, using salt water. They can pump the waste into holding tanks when you're at dock or anchored, and are pumped out when offshore. The tanks clog easily, though, so minimize your use of paper, and have a bag available for other waste.

On the boat, it's easy to fall into nature's rhythms: we were usually in bed by 9 p.m. and up by 7 a.m. The berths are small and can be cramped, particularly if you don't pack light. And though most of them have small fans, they can get hot and stuffy. If you're in dock or near shore, wear inspect repellant. Dehydration is dangerous and deceptively easy when you're surrounded by all that water: Drinking a gallon or more a day is a safe plan, and go easy on diuretics like caffeine and alcohol.

Antigua and Barbuda are still remote enough that there wasn't much reason to leave the boat at night, so we played lots of Scrabble and had plenty to read. In much of the Caribbean, though, the nightlife is plentiful and you can spend every night bar-hopping ashore. Just don't drink so much that you can't handle the dinghy ride back to your yacht, though, and remember that the bays will be dark and therefore dangerous.

If you are interested in augmenting your own sailing skills, check with your local sailing associations (they exist even in land-locked places like Colorado) for classes. Dave also took a course in basic navigation through the Coast Guard Auxiliary in Denver. On the boat, he mostly let the autopilot do the steering and the GPS receiver do the offshore navigating, but these machines can only help if you know what they're doing. I found some good books online (at www.landfallnavigation.com) to bolster my own knowledge of navigation and chart-reading, and we all pitched in and learned a lot about basic rigging and boat-handling. It was a fun and occasionally challenging way to connect with the elements and each other.

It was a brilliant vacation, one different from any I'd ever had, and far from the most expensive. We had a blast, and found a sure-fire way to deal with the mid-winter blues: starting to plan next year's charter.

Have you chartered a boat before? Who did you use? How was your trip? Tell us on our Cruise Message Boards.