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17 tips for choosing a charter

Our expert has answers to chartering questions

From cat vs. monohull to the best time to fly to the islands,

our expert has the answers to all of your chartering questions

1. What advice would you give first-time charterers as to whether they should choose a bareboat or crewed charter?

First of all, it is a matter of budget, as a crewed yacht can cost significantly more than a bareboat. For example, the crew gratuity alone is 15 percent of the charter fee. But for the sake of argument, let’s assume money is no object. Here are the main aspects of each configuration.

Preparing and departing

Read the other stories in this package: An alternative to ownership   Charter contacts   Roomy cats are making waves

On a bareboat, you are completely on your own for everything: boat preparation and check out, handling, sailing, provisioning, etc. Just provisioning, inspecting the boat, and attending the chart and boat briefings can take the better part of a full day. On a crewed boat, you simply show up and, literally 30 minutes later, the boat can cast off. No worries.


On a bareboat, you must take care of everything as far as sailing and handling the boat are concerned. This means you also must make correct decisions about weather, prepare itineraries, make sure you arrive early enough at anchorages, anchor properly and keep anchor watches if the night weather is rough, among many other things. On a crewed boat, you can choose to do as much or as little sailing as you like. You can ask the skipper to teach you sailing, sail the boat yourself, or relax all day and do nothing at all. At all times the worries and hard work are for the skipper, as is the liability if something goes wrong.

Provisioning, cooking and cleaning

On a bareboat you must provision, cook, do the dishes, clean the boat, etc. This implies a decision on how to equitably share the numerous chores between crewmembers. On a crewed boat, you send your personal food and beverage lists in detail. When you arrive at the boat it will be stocked, and the chef will prepare meals according to your preferences, diet and the like. There is no cooking, no dishes to do, no cleaning … nothing.

Simply put, a fully crewed charter allows guests to do nothing but relax and enjoy, or do some or all the sailing work (the fun part only) on a whim. If you don’t have the budget for a full crew, a midrange solution could be a skippered bareboat.

2. What is a skippered bareboat?

A skippered bareboat is a bareboat charter with a freelance skipper on board — provided by the charter company — for all or part of the cruise. Some charter companies might insist that a skipper be on board, either for a day or two to refresh the head charterer’s sailing skills or for the entire charter if it feels the sailing skills of the head charterer and crew aren’t up to par. Of course, this costs extra — from $125 to $150 per day depending on the area.

This is a good option if you want to ultimately bareboat but aren’t comfortable enough with your boating skills yet, or if you are discovering a new or challenging sailing area and want a guide for a couple of days or the entire charter. Whatever the reason, a good skipper should teach sailing, which can be an excellent experience.

Keep in mind that the skipper isn’t a housekeeper or mechanic. And the charter party is responsible for feeding him or her. (Most, however, do cook their own meals, though they are not obligated to do so.) This can add up almost to the same price as some fully crewed yachts. However, the charter company or charter broker will not match your party’s interests with the skipper’s.

3. How much sailing or cruising experience should you have before taking your family on a bareboat charter in the Caribbean?

You should be comfortable sailing the type of boat, in terms of size and rigging, you are going to charter. If you are dinghy sailor on a lake, you likely won’t be able to handle a 40-plus-foot boat on the ocean. But if you’ve sailed a 28- or 30-footer on a lake or in coastal waters, whether cruising or daysailing, you’ll probably get by safely and successfully in the Caribbean if you respect the sea environment and comply with obvious seamanship guidelines. However, you will need different skill levels depending on where you plan to charter.

If you aren’t sure of your abilities, here are some suggestions.

• Take a bareboat chartering course near home. Several reputable companies provide them. Understand, though, that the courses will not make a sailor out of you if you have no previous experience, but they can be a valuable complement to what you already know.

• Do a weeklong sailing school charter.

• Ask your charter company to provide a “friendly skipper” for two days to help acquaint you with your boat and the area. It isn’t free, but it is worth the price.

• For your first charter, try to cruise with at least one other experienced sailor on board. Yes, the Caribbean is beautiful, but the trade winds can blow hard. Two pairs of experienced hands are, in my opinion, a minimum to safely handle a 32- to 45-foot boat in a new environment.

It may seem obvious, but I should mention that it is a bad idea to lie about your sailing abilities. Serious charter companies will make sure you are capable before they let you leave the dock with a $200,000 boat. And it can put you in a situation that could endanger you and your crew. Don’t do it.

4. How strong should your navigation skills be?

It depends on the charter area. There are basically two levels of sailing in the Caribbean: the Virgin Islands and the rest.

USVI (St. Thomas, St. John) and BVI

These are phenomenal sailing grounds. Island-hopping is line of sight, and the layout is such that most “crossings” are short (two- to three-hour sail on average) and well-protected. Winds are mostly ideal and sustained 10- to 15-knot easterlies. This doesn’t mean conditions cannot get rough. But if you apply good seamanship skills and listen carefully to weather forecasts, as any prudent skipper should, you will be fine. And the BVI have a lot of overnight mooring balls, so you can do an entire cruise without anchoring.

Here’s the sailing experience you’ll need for the Virgin Islands.

Navigation skills

• mostly line of sight navigation with no tricky passages (most are protected)

• basic knowledge of charts

• position-plotting

• basic understanding of weather forecasts

Weather and winds

• 12- to 18-knot easterlies (20 to 22 knots some days), seas 2 to 5 feet

• tropical waves from July to September that can be pretty brutal


• comfortable handling mooring buoys (day and overnight) with bridle setup

• good holding grounds for easy anchoring when needed

• protected anchorages with few, well-marked hazards

• must be able to quickly and correctly assess when reefing is necessary

The rest (St. Martin, St. Bart, Martinique and Guadeloupe, St. Vincent, Grenadines)

The sailing gets much more challenging as you move south. Waters are open, and the winds are generally stronger than in the Virgin Islands. Crossings and passages are much longer, and line-of-sight navigation, while still sometimes possible, must be complemented by good knowledge of chart plotting and current observation.

Here’s the sailing experience you’ll need for the rest of the Caribbean:

Navigation skills

• long crossings and passages on generally open, unprotected waters

• chart navigation (frequent plotting and use of GPS)

• understanding of tides and currents

• good understanding and interpretation of weather forecasts

Weather and winds

• 18 to 25 knots, seas 3 to 8 feet


• frequent anchoring in variable conditions, must be very comfortable anchoring and using a snubber

• relatively protected anchorages but not always

• occasional Med-moor and/or marina slips

• must be able to quickly and correctly assess when reefing is necessary

Keep in mind that these are only guidelines. Weather and navigation conditions may vary dramatically from usual patterns, which is why the ability to understand weather forecasts is essential.

5. What are some of the more common mistakes new charterers make?

First-timers can be too ambitious with their itineraries and sometimes overestimate their skills. The itinerary should be very conservative. Allow ample time for the segments that you’ll be sailing to weather — it always takes longer than anticipated — and schedule a one-day break by midcharter in a nice anchorage for sightseeing ashore, snorkeling, etc.

Never overestimate your skills. Being on vacation doesn’t mean being casual about safety. Seen from a protected anchorage, the sea never looks as rough as it is in reality. When in doubt I leave the anchorage with one reef in the mainsail. It is always easier to shake out a reef that isn’t needed than to take one in rough weather.

I cannot count the number of times I have told my charter guests not bring suitcases on board. There is simply no room for them, unless you are one couple in a three-cabin boat. Yet they show up with a big smile and … a suitcase. Guess what? The suitcase gets emptied and stays in a locker ashore, if there is one available. Everyone must pack their belongings into a collapsible duffel bag.

Inevitably most people pack too much stuff. I did this for a long time, then started to thin my bag to what I really use. I was tired of hauling it back home with half the contents unused.

6. What advice do you have regarding choosing a crew?

Understand that spending a week or 10 days with six people on a 30- or 40-foot boat is not like vacationing in a home. Carefully choose sailing mates with whom you know you will get along. Ideally they should be easygoing, happy people. A charter with a tense atmosphere is a nightmare and a guaranteed recipe for a ruined vacation — and ruined friendships.

A good way to test your friends is to organize a couple informal “meetings” before the charter to discuss ideas about the itinerary and the program. You probably will see right away how tolerant they are about others’ suggestions, and how they react when others disagree with their ideas.

Fair and equitable participation and sharing of the chores on board are absolutely essential. When friends go sailing together they become a crew, and a crew must have rules and roles. The skipper must brief first-time sailors thoroughly and define everyone’s roles according to desires and physical capabilities. Some people just want to read and sunbathe, and there’s nothing wrong with that as long as you know ahead of time.

7. What information should charter companies tell you but typically don’t?

Anything that’s negative, like (depending on the charter company) challenging sailing conditions, difficult anchoring areas, age of the boat, safety of the region in terms of crime, local taxes, what is included. (This is more common in the Med, where a few years ago some charter companies were providing a dinghy without an outboard, for which you had to pay extra.)

8. What is the difference between “first-tier” and “second-tier” charter companies?

A first-tier company has only new boats in its fleet and keeps them in service from 3-1/2 to five years before retiring them. A second-tier company has used boats in its fleet, most of which are retired from first-tier companies. Good second-tier companies offer older, well-maintained boats, not necessarily with the latest gadgetry but at considerable savings compared to first-tier companies. Some may have a few new yachts too, but the bulk of the second-tier fleets will offer used boats. Does this mean the boats have been trashed, or that you could end up in a nightmarish cruise on one of them? Absolutely not, in most cases.

9. What are the pros and cons regarding monohulls vs. catamarans?

I am a monohull fanatic, and when the going gets tough offshore I would much rather be on one than on a catamaran. For chartering, however, cats offer a number of advantages.


On deck: A catamaran feels about twice the size of a similar-size monohull, both on deck and below. The cockpit — the highlight of catamarans — is usually huge and on the same level as the saloon, which, along with the typical panoramic windows, enhances the feeling of spaciousness. And the foredeck has a big net between the hulls, which makes a great sun-bathing area. As a result, a catamaran rarely feels crowded. Most are equipped with dinghy davits at the transom, which means no towing the dinghy and, thus, no drag on boat speed.

Down below: Catamarans provide considerably more room below deck than a monohull. A typical 42- to 45-foot cat will have four large staterooms with rectangular queen-size berths — no more pointy berths — each with an en-suite head. A 38- to 42-footer will have three or four staterooms and two or three heads. Because of the catamaran layout, there is full privacy in every cabin, and you’ll hear nothing from one cabin to another.


Stability: The key fact to remember is that catamarans don’t heel under way or roll at anchor. This usually makes seasickness a non-event. The stability factor also is good for older and/or first-time sailors.

Speed and maneuverability: Catamarans are faster than monohulls under power or sail, unless going to weather. They are shallow-draft boats that can get into places monohulls often cannot, and can anchor closer to shore. Lastly, cats enjoy a phenomenal maneuverability. And with two engines spread apart, a cat of any size literally pivots around its central axis.


A hard-core monohull sailor once said: “When I sail a cat, I feel like I am driving my living room.” He meant that a cat doesn’t convey the “real” feeling of sailing, with the rail in the water. That is precisely because a cat does not heel, whereas a monohull does, sometimes a lot. So if you are in for hard, pure sailing, you won’t get that feeling on a cat.

Cats typically don’t sail well upwind and require different techniques for tacking and anchoring. They have more windage than monohulls, and without the keel and ballast have a tendency to bob at anchor when a gust hits. Catamarans take up twice as much docking space as monohulls, which can be a problem in areas where spending nights in marinas is a necessity.

For pure charter enjoyment, there is no question that a catamaran wins hands down. However, for the pure enjoyment of sailing, and beating hard to windward, nothing beats a monohull.

10. When is the best time to book a charter?

Booking patterns have changed considerably over the last five to seven years. Vacationers used to book cruises as far as a year in advance. Today, a significant percentage of charters are booked within three months of the departure date. As a result — with the exception of the year-end period, which still remains a special time — charterers look for deals until close to when they want to depart. This is due to the availability of Internet discounts, either from the charter companies or from outside sources, including buying unused charter weeks directly from charter boat owners. I recommend you start shopping about four to six months ahead of time, with good discounts starting to appear within two or three months before departure time.

11. When is the best time to fly to the islands and why?

By flying midweek to the Caribbean you’ll avoid the cruise ship weekend switch, which can be a nightmare at the Puerto Rico airport, the main hub for most Caribbean connections. And you’ll start your charter when base personnel aren’t busy and have more time to handle your requests.

12. How early before the charter begins should you arrive at the base?

I don’t recommend casting off in an unfamiliar boat in unfamiliar waters after a 10-hour trip. Most charters typically start at noon, so arrive at the base around 2 or 3 p.m. the day before. This will afford time to provision without rushing and unwind before leaving to get in the “groove.” Also, charter companies schedule chart and boat briefings that you must attend, so that day ahead of schedule fills up pretty quickly.

In addition, I recommend a “sleep aboard” start, which allows you to spend the night on the boat before the charter commences. It’s much cheaper than a hotel room when shared by two or three couples and gives an opportunity to get familiar with the boat and stock provisions.

13. What are various ways to provision for a charter?

You can either order provisions from the charter company or provision the boat yourself. The former costs more, around $20 to $25 a day per person, but is easier, with provisions usually delivered to the boat. The latter typically is less expensive but requires a little more effort on your part.

Charter companies offer many types of provisioning packages, from minimal to all-meals and everything in between, including “à la carte” provisioning. Whichever you choose, make sure your entire party gets involved in this process. If you are a first-timer, going to an area for the first time, or going to a very remote location, my advice is to take advantage of the charter company provisioning. If you are more experienced or going to an area like the Mediterranean or the French Antilles, you will find plenty of stores for provisions.

In busy charter areas, like the BVI, some supermarkets will take your provisioning sheet by fax and deliver goods to the boat upon your arrival. Others will send a car, free of charge, that will drive you back to the boat with your provisions. When available, this is, in my opinion, a better solution than buying from the charter company.

Some experienced charterers bring part of or all their food from home in coolers. I have done this many times. You can shop at your favorite store — certainly cheaper than in the islands — and you get your favorite foods. Most Customs officers let you travel with food, unless it is raw fruits or vegetables, for example.

14. As a bareboat charterer, what should I pay particular attention to during the boat inspection or walkthrough. What questions should I ask? What should I make sure is in place and working?


Make absolutely sure the refrigerator and freezer are in working order. A good charter company will run the systems before you arrive so that both will be cold when you step aboard and need to store your provisions.


Before leaving the dock check that the outboard starts easily, runs smoothly and spits water. If it is an inflatable make sure it is properly inflated and that you have an air pump on the boat. Check the gasoline level. Items that definitely must be on board include paddles or oars, a long painter (not chafed) and a dinghy anchor.

Ground tackle

Go to the bow, grab the windlass remote control — or whatever controls it — and raise and lower the anchor a few times. You certainly don’t want to discover that the anchor doesn’t come up when you have to move in a hurry.

Pay attention, ask any questions you have, and have as many crewmembers as possible attend. Make sure the briefing covers the following:

• location and operation of all seacocks

• bilge pump procedures

• location of flares and fire extinguishers

• windlass operation (both electric and manual in case of power failure) and location of reset button

• testing the stove and propane safety system

• operation of refrigeration systems and fridge drain

• marine heads and holding tank procedures

• reefing procedure

• hoisting the main a few feet to be sure it goes up and down freely

• unfurling the headsail a couple of turns to be sure it furls smoothly

• location of emergency tiller, tool box and first-aid kit (should be fully stocked)

• testing the VHF and other electronics (with the briefer present)

• location of engine oil dipstick and cooling water tank

• starting the main engine and testing the transmission in forward and reverse (with the briefer present)

15. What should the first day of the charter consist of?

You shouldn’t sail a lot on the first day. You likely will cast off by the end of the morning, after taking care of any last-minute odds and ends, so start with a short sail toward an anchorage not more than two hours away. What you want to do is leave the marina and go anchor or moor, settle down and take your marks before doing more serious sailing. This is especially true if you’re coming from cold weather. On the second day, you’ll be ready to leave early and attack your first real segment. Also, try to build your itinerary so that you’ll be sailing to weather for the first part of the trip and downwind for the second part.

16. What is your favorite area to charter in and why?

The U.S. and British Virgin Islands offer good, predictable winds, easy navigation, great anchorages and beaches, and an endless variety of places to go — secluded or not. A magical place.

17. If you could offer only one piece of advice to ensure a successful charter, what would it be?

Do it with the right people.

Michel Benarrosh’s Web site,, provides independent chartering information, including discounted unsold weeks from charter companies and how to charter directly from charter-boat owners, as well as in-depth guidance for charterers, and charter-boat buyers and owners. Benarrosh has been a charter-boat owner for many years and was president of the Moorings Owners Group, an independent association of 250 Moorings charter-yacht owners, for 10 years. Benarrosh also is a yacht broker licensed in Florida.