Chartering a sailboat,
without hiring a
captain and crew

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This page updated: November 2011

Research and Preparation
Setting Up The Trip
During The Trip

Research and Preparation

Terrific book: "Smarter Charters" by Christopher Caswell.
Covers alternatives, planning, how to select boats and companies, various chartering areas.

Good book: "Cruising Fundamentals" by Harry Munns.
Covers onboard systems (engine, stove, head, etc), planning, navigation, etc with some emphasis on how big boats differ from smaller ones.

Lots of great info on's "Charterers" page

Lisa Batchelor Frailey's "The secrets of smart bare boat chartering"
Several bareboat chartering articles, including ratings of charter companies, in Aug 2000 issue of Cruising World magazine.
"Choosing A Charter Company in the BVI" article in 4/1/2001 issue of Practical Sailor.
"Bareboat Chartering 101" by Lynda Childress in Aug 2001 issue of Cruising World magazine.

Ahead of time, get everyone to agree what type of trip they want. Will the emphasis be on sailing, snorkeling/diving, partying ashore, relaxing at anchor, or what ?

Types of charters (summarized from "Smarter Charters" by Christopher Caswell:
  • Bareboat: you plan it, one boat, no hired crew, go anywhere / do anything.

  • Crewed: you plan it, one boat, hired skipper and maybe cook/deckhand, go anywhere / do anything.

  • Flotilla: company planned, multiple boats, hired crew on mother boat only, planned route and anchor together each night.

  • School: company planned, one or multiple boats, instructor on each boat, planned route and anchor together each night.

  • Special-interest: company planned, one or multiple boats, crew on each boat or mother boat only, planned route and activities and anchor together each night.

  • Head boat: company planned, one or multiple boats, crew on each boat, planned route and activities and anchor together each night, you book an individual berth.

From Bob Diamond on Boating Review Message Board:
The most popular first time charter location in the world is probably the BVI's (British Virgin Islands). The sailing environment is safe and easy compared to most other locations and the people there are generally very helpful and easy to get along with. All the major chartering companies are there, too. There is lots for a family to do while bareboat cruising in BVI's including snorkeling, diving, water sports, and beach combing. There are restaurants at just about every anchorage. About the only thing you won't find there is solitude. ...

Requirements you must satisfy to bareboat charter:
Ed Hamilton and Co.'s "Trial resume form"

From Jere Lull on the newsgroup:
[Re: ASA certification ... is welcomed with open arms ... is also a lot cheaper out of the hole, as they will often discount and or waive damage deposits. ...:]

NOT! in our experience. They don't waive damage deposits, though sometimes you can choose another option, but that was always available by the charterer's option. The only discounts Catamaran Charters and the Moorings recognize are recent repeat business.


No, the primary certification is a check that doesn't bounce.

Luckily, the BVI are so easy that it doesn't really matter. You can see where you're going, the landmarks are fairly distinct, and the bottom is usually tough to find with the keel.

BUT if the charter company "comps" the checkout captain's cost for a future charter or offers the checkout as part of the charter, take the offer! Our pages and the various cruising guides will tell you what things were like a couple of years ago, but local knowledge will be far more topical: what parties are "hot" while you're down, what reefs are particularly spectacular, what anchorages or restaurants shouldn't be missed. You'll want to return, so future comps aren't likely to be lost. You'll simply have to make sure the captain is well-fed while he/she is onboard -- rarely a problem.


From Glenn Ashmore on the newsgroup:
I have an ASA certificate and I can tell you it don't mean beans at Moorings, BVIYC, TMM or N/S. You still have to put up the deposit or buy insurance.

The thing it does do for you is give you a degree of confidence so you can enjoy your vacation. When you first take the responsibility for a 30,000 pound, $250,000 boat, there is a certain pucker factor that is not conducive to adjusting to "island time". The ASA course helps you get over that by the time you clear the jetty.


From Vic DeMattia on CompuServe's Sailing Forum:
FWIW, I have a boat in a charter fleet and am an active charter broker. ... The charter companies have a pretty low regard for any "official" bareboat certification, as the quality of the experience varies widely from school to school and student to student. For example, if you had a "helm hog" in your class, you just plain didn't get much helm time.

If the charter company isn't comfortable letting you sail away in someone's $100-400k boat, they will request (actually demand) that you take a captain aboard. That costs $75/day in the BVI now [1996]. These guys are great company, great tour directors, and superb sailors. For $75 or at the most $150, you get the royal treatment and the best hands-on education you can probably find.

... skip school and get a captain for a day if you or the charter company want reassurance.

From Paul Martin on the alt.sailing newsgroup:
The charter companies will ask what experience you have and based on that info and what you can demonstrate when you arrive at the boat, may suggest you take a hired captain aboard for a day or two of your charter. These are usually pretty nice guys/gals who have experience in your particular charterboat and also in the area you plan to sail. They are always fun to have aboard as well as useful (like staying aboard while you go ashore for dinner if security is questionable) and in many cases can make all the difference between a 'good' charter and a 'great' charter. They generally know where the most fun places to go are and how to avoid the crowds and can get you involved with the local ambiance if that is what you want. Most of them are doing it as much for the fun of meeting new people as for the money. And sure, it seems like they are getting a free ride and paid good money, PLUS TIP, but like I said, they are usually worth the cost.

And yes, I've been one.

From Bob Diamond on Boating Review Message Board:
... Overseas charter companies do not require certification but you will have to complete a resume listing your experience before you can charter without also taking on one of their skippers. They would like to see years of experience with you in charge including sailing (preferably chartering) on boats similar to what you want to charter in cruising situations similar to what they have to offer. ...'s "Why Take a Captain on a Bareboat Charter?"

Setting Up The Trip

From Jeff Twiss on Cruising World message board:
[Re: When chartering for the first time is it better to use a Yacht Charter Broker or go directly to the charter company? ]

I've done it both ways and will only use a broker now. Doesn't cost you any more, they know the companies and boats better than you do and they can serve as a go-between if anything goes awry. Don't know about all brokers, but Ed Hamilton takes credit cards which is convenient and offers you a bit of added security.

Bluewater about Chartering in the Virgin Islands
Ed Hamilton and Co. (slide show and other info)

From Grandma Rosalie on the WorldCruising mailing list:
I looked into a charter a couple of years ago (1996), and found that the rates for a bareboat with a captain (which we would have needed because we couldn't have been certified to sail the boat without one) were just as much as chartering with a crew (in the winter of course).

I have heard several people who were very disappointed in their experience with hiring a bareboat with a crew.

If you are going to have a crewed charter, it is better IMHO and also probably as cheap to hire someone who owns their own boat and/or charters on a regular basis. They have more to gain from pleasing you than a hired gun would have. The people we sailed with then (they are off cruising now) did so well that we bought a boat just like theirs.

More from Grandma Rosalie on the Yacht-L mailing list:
If you are going to be doing a lot of snorkeling, you might want to consider ease of getting back in the boat.

Sometimes there are discounts available if you take a charter because someone else cancelled at the last minute. If you are flexible about dates, maybe you can take advantage. But last-minute airfares might wipe out the savings.

From article by Amy Ullrich in 11/2006 issue of Sail magazine:
If connecting from one flight to another (usually in San Juan) in the Caribbean:
  • Allow extra connecting time; flights often are delayed, and there may be very limited choices once you've missed a connection. A 2-hour connection time between flights is a good idea, and more if you have to clear Security and Customs.

  • If your first flight is delayed before it even takes off, call ahead right away and start rebooking the second flight.

  • Before buying tickets, ask if there is a "ticketing agreement" between your second airline and other, alternative airlines. If there is, you'll be able to get an alternative airline (if they have a seat available) to accept the ticket from your second airline (the one whose flight you missed).

  • Lost luggage can take a long time to catch up; consider keeping basic clothing and critical items in carry-on.

From Bob McMillan on the newsgroup:
... I would suggest letting the charter company stock your boat with food. I have done it both ways and I got better food at not much of an increase in price. It was a great time saver, because it was all loaded on the boat when we got there. ...
From Sam Schleman on the newsgroup:
Each to their own: When I charter in the BVI's, we like to try the different and very good restaurants on the various islands. On vacation, we'd rather let someone else do the cooking and spend our efforts in enjoying what they cook.

I've found the charter company's provisioning is not so great, and most people who do so, end up throwing away or giving away huge quantities of food. If you are chartering out of Tortola, suggest you use Ample Hamper and pick your own foods. They are on the web. Just pick what you want, fax them the order and it will be delivered to your boat the morning of your departure.

Ask if these are included in price / present on boat:
  • Air fare, hotels at ends of trip, shuttles between them and marina ?

  • Fishing licenses and equipment ?

  • What are check-in and check-out and briefing times, exactly ?
    What are the penalties for missing deadlines ?

  • How are breakdowns handled (VHF, collect phone call, etc) ?

  • Does the dinghy have an outboard motor ? What kind of dinghy is it ?

  • Does the boat have roller-furling, anchor windlass, holding tank, cockpit cushions, bimini, how much water tankage ?

  • Are a kayak, a windsurfer, snorkeling gear included ?

  • Fees for waste pump-out, and replenishing fuel, water, propane ?

  • Mooring and harbor fees ?

  • If company were to force you to take a captain for first day or two, what is the rate ?

  • Value-Added Tax (VAT) included in all quoted fees ?

  • Charts ? Local cruising guides ?

  • Are you limited to a certain cruising area, or certain anchorages ?

To do:
  • Good idea to bring your own bottled water for drinking; water system on board may not be clean or palatable.
    Make sure you have lots of drinking water.

  • Good idea to bring your own small toolkit, and maybe a GPS and handheld VHF.
    Corkscrew and can opener.

During The Trip

From Ed Darling:
Checking everything is very important before you leave the dock. On our charter, the captain we hired noticed a small rip in the main sail while we were still at the dock. He pointed it out to the charter company and they made a note of it. The first time we set the sails the main ripped in half, we radioed the charter company and headed back to the dock. They were waiting on the dock with a good sail when we arrived. Problem solved without much inconvenience on our part.

I also believe the trip needs to be planned well before you get there. We did a very nice mix of snorkeling, eating, sailing, and partying. I like to snorkel and swim but not all the time, we also left a lot of time to just rest and relax so that we could enjoy doing some of the night life without getting over-exerted. The captain we hired also cooked over half of the meals that we had. In my opinion he made better food than most of the restaurants we went to, and everything he cooked had a island flair to it. ...

To do/ask when picking up the boat:
  • Operate all appliances and instruments at dock to look for damage, make sure you understand them.

  • Raise sails at dock to look for damage, and to make sure you understand reefing/furling systems.

  • Slightly lower and raise anchor at dock to make sure you understand how to do it. Also find what line to use for moorings.

  • Put engine into forward and reverse while still tied to dock, to make sure they work, and to find out which way propeller-walk goes.

  • Anything special when shifting between motoring/sailing ? Propeller shaft lock, water intake seacock ? What gear should transmission be in when sailing ?

  • Does depth sounder read from waterline or bottom of keel ?

  • Operate the dinghy to look for damage, make sure you understand how to operate outboard, has anchor, etc.

  • Meticulously note down and report every bit of damage when taking possession of the boat; the charter company will do the same when you return it, and may claim that you caused the damage.

  • Some charter outfits dock the boat for you when you return (someone comes out to your boat in a dinghy when you get to harbor).

From Mark Denebeim in 5/2006 issue of Latitude 38 magazine:
  • Anchoring is the most important skill to learn.

  • Drinking is by far the biggest cause of injury and death on charters. There should be a "designated driver" each night on any boat, and only a sober person driving the dinghy.

  • When picking up the boat, run the dinghy around the harbor for several minutes to make sure the outboard is reliable.

  • Always carry oars and anchor in the dinghy.

  • See if you can go food-shopping the day before picking up the boat, to avoid lost boat-time. Ask the charter company or supermarket if they can store perishables overnight for you.

Typical mistakes by charterers:
  • Bad anchoring: too close to other boats, not enough scope, don't "set" it, don't check for dragging periodically, etc.

  • Bad dinghy beaching: not tied up well enough.

  • Hitting a reef or shoal while entering harbor or anchoring. Look at the chart or guidebook ! Even if the area has lots of boats in it and looks safe.

From Susan Lunn and Kurt Schurenberg:
Moving in or out of the dock was the hardest part of the bareboating course we took in St. Augustine, Fla., a few years ago. We actually spent the majority of the course just docking and casting off. All boats work a little differently and it takes a while to get used to how the boat moves when you have it under power. Add some wind, and it can make it pretty hairy ...


Whenever we bareboat, we request that the charter company give us a pilot just to get out of the immediate marina area. The pilot ties on an extra dinghy to the boat, and hops off after getting us out of the marina. This works well and avoids any accidents with the boat. By the time we return the boat, we are familiar enough with it to dock it ourselves.

Drive defensively:
From Bob Padlowski on CompuServe's Sailing Forum:
Recently back from a 2-week charter in the BVI ...

One big change to me was the massive influx of incompetent sailors. Some had the good sense to hire skippers, but many went on crashing about in their chartered boats. If only their owners could see! We watched one couple as they picked up a mooring - LITERALLY!!!! The wife actually muscled the entire mooring assembly, ball, pennant, chain and all, onto the deck. We spent an hour at Soper's Hole one Saturday afternoon watching one Sunsail yacht after another bounce off other moored yachts. One charterer, in a hurry to leave his slip, sped out of his Med moor, cut the wheel too soon and too close to other yachts in their slips, and snagged TWO other yachts' anchors with his lifelines. With everyone on the dock (and we at Pusser's bar) yelling for him to stop, this skipper blissfully continued on, until one of the dock guys jumped from a moored boat onto his and cut the engine. Another motored over a mooring ball, caught the mooring line with his rudder, then backed up to free himself, right over a SECOND mooring line! While we were at the Bitter End, we watched a big new Moorings boat sail hell-bent for Eustachia Reef. Just as we expected a crash, they executed the fastest 180-degree tack-and-jibe I have ever seen! Geez, even WE could see the breakers from the beach!

It was a lot like watching a Marx Bros. movie, only wetter. I heard from several people with charter companies in the BVI that there was indeed a real influx of very green (maybe careless is more accurate) charterers.
From Michael Kneafsey on CompuServe's Sailing Forum:
I wonder if we were standing on the dock at Pussers at the same time in August. I watched the flotilla putting to sea and the first boat lost its dink, boat #2 went right across and turned and fouled the mooring lines on the boats on the opposite dock. They had to tow him off sideways, then away he went.

August experiences:

I did have my first serious near-collision. A Mooring 463 on Port tack didn't yield. I was making eye contact with the skipper so it wasn't a blind spot error. I felt he was going to fall off and was afraid if I fell off we would certainly collide. At the last second I fell off hitting the stern of his dink and swamping it. Away they went cursing me. Had I gotten the boat name I would have called Moorings, but I was busy.

Another new Moorings 505 (one with no name, so unsold) motored through Sandy Cay with the anchor down on the bottom. Drug up an anchor at Sandy Cay and ended up in a tangled mess, fortunately they already had all the fenders out :). I cleared that one and wasn't even offered a drink or a bandage for my hand! The second boat was unattended and I reset their anchor.


From Dave Barry:
We wanted to have a relaxing family vacation, so we got together with two other families and rented a sailboat in the Virgin Islands. There is nothing as relaxing as being out on the open sea, listening to the waves and the wind and the sails and voices downstairs yelling "HOW DO YOU FLUSH THESE TOILETS ?"

It takes a minimum of six people, working in close harmony, to successfully flush a nautical toilet. That's why those old ships carried such large crews. The captain would shout the traditional command - "All hands belay the starboard commode!" - and dozens of men would scurry around pulling ropes, turning giant winches, etc, working desperately to avoid the dreaded Backup At Sea, which is exactly the problem that the captain of the Titanic was downstairs working on, which is why he didn't notice the iceberg.