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Old 12-22-2011, 06:45 PM   #1
Join Date: Dec 2011
Home Port: Sherman Oaks
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Exclamation A COUPLEíS SAILING CHARTER GONE WRONG Thirteen DOs and DONíTs of Chartering a Boat

A Couple’s Sailing Charter GONE WRONG
Thirteen DOs and DON’Ts of Chartering a Boat

We were so excited to start our honeymoon in the beautiful British Virgin Islands. My wife and I both had some sailing experience, but never sailed together, although we did take a Coast Guard 3-day navigation course together. We booked a 10-day sailing trip on a Beneteau 463 with a local chartering company in the BVI. The pictures of the boat on the website looked alluring, and the owner of the chartering company, led us to believe he was an honest, nice man. We were really looking forward to our first romantic time on the water.

We didn’t foresee the problems we were about to encounter. We made some bad choices that could have been avoided had we done a bit more homework, and had some good solid advice like what follows in this article. You MUST be careful with whom you do business with in regards to sailing charters or you’re setting yourself up for frustration and lies.
In order for you to avoid the bad experiences we had, we’ve put together some helpful DOs and Don’ts that all vacationers considering chartering a boat should know.

Honeymoons—or any vacation for that matter—can get expensive. The total cost for our honeymoon with flights, charter, food, hotel, and miscellaneous expenses was over $9,000. The last thing you want is to spend half of your time in a wet, moldy smelling boat, and in the company of someone you don’t know and don’t particularly what to be around.

Our Introduction to the Boat

Our journey started on a red-eye flight out of Los Angeles at 9pm to Charlotte, North Carolina. In the morning, we caught the final leg of our trip over to St. Thomas, U.S. Virgin Islands. From the airport, we grabbed a taxi over to the ferry that would take us to Road Town, Tortola, where our boat was waiting. By the time we arrived to spend our first night on the boat in dock, it was almost dark. We expected to be greeted by the owner of the chartering company, who we had established a relationship with. Instead his maintenance man who had no control in making decisions, and no personality as far a we could see greeted us.

The minute we saw the boat, we knew this was not the boat the owner has described. We were exhausted from the trip and didn’t have the energy to make a big deal about it then, so we grabbed a taxi and went into town to grab some food and light provisions. Then we headed to the boat for the night.

In the morning, I realized that this was not the newer 2005 Beneteau that the charter company had promised. It looked worn and tired. And, like the night before, the owner did not come to greet us to check in and ensure that we were set and satisfied. Again, he sent his maintenance man to do the boat orientation who told us the owner had left the island for a week and could not be reached.

I immediately told the maintenance man I was not pleased with the condition or age of the boat and may wish to charter for a shorter period of time. For instance, the GPS provided on this boat was about 20 years old and the screen looked like my first PC computer back in the eighties.
He replied there was nothing he could. I could either:

Complete the contract, pay the balance and sign the necessary papers; or
Be stuck on my honeymoon in Road Town without a boat, without reservations for alternate accommodation, and without knowledge of any other chartering companies.

I decided to give him the check and asked him to hold it until we could reach the owner and work out a suitable arrangement. (The owner had insisted we pay by cash) The maintenance man promised to hold the check. After all, the owner already had a $500 deposit on a credit card which covered almost two days of the Charter cost. And, I did not expect him to lie. I completed the contract under a bit of duress.

The Captain

Then we were introduced to our check out captain, who seemed like a nice chap with, as he made it clear, “a lifetime of experience.” He asked us to join him for breakfast so we could get acquainted. During breakfast, “getting acquainted” was pretty much listening to him talked about was himself and his stories. After I paid the bill for all of us, we jumped into his car, which looked like it was ready for the wrecking yard. And, there were open empty beer bottles all over the interior, which he later told us was a way of life in the islands. The captain explained that the police were far more interested in seatbelt laws then they were in drinking and driving. We really didn’t think about it, as we were interested to get on the water. We got back to the boat, hopped aboard and took her out for a sail.

We came back into port in the evening and the captain invited us to a party for one of his friends. We agreed and went along for the ride, ending up at a bar-restaurant which seemed like a nice stop. When I went to try to sit at a table with my new wife and have some alone time, the captain joined us. We ended up again paying for his dinner and the eight or so drinks that he had (it was $2 drink night, so that helped!).

My wife and I both had not sailed in a couple of years and never together, so she felt more comfortable if we keep the captain with us for a couple of more days to get familiar with the islands and the boat. He said that if we keep him on for a few days, we need to provide his meals.

With the exception of one lunch, the captain joined us for every meal over the next two days. He never once excused himself knowing that we were a honeymooning couple and perhaps may want some time to ourselves. He drank beer throughout the day from the provisions we supplied and at night always ordered mixed drinks and wine.

While we were happy to provide his meals as is expected, we didn’t realize this arrangement included his bar tab and expensive dinners while sitting with us. This was, of course, on top of his day rate, and the tip he guilted out of us…telling us that I must not have liked him as I didn’t tip him. Seemed to us he had eaten and drank very well for three days!

It Rained, and Rained, and Rained!

It rained heavily on day three and four of our trip. The dodger had been removed from the boat at some point (promised in the contract, however), so sitting out on deck during the rain was impossible if you wanted to stay dry at all. Down below, things were a bit soggy as well! The boat was leaked from four hatches and along the side of the salon, leaving only two places to sit that were dry. The beds in both aft cabins got soaked, resulting in a bad, musty smell in the cabin.

And the air conditioning, which was in the boat specifications, did not exist either. It would have helped the hot, humid conditions with all the hatches closed.

We decided to put the boat in for repair and air-dry the beds. The beds needed aired out, the leaks needed to be fixed, and the refrigerator switch wasn’t working properly by this time a well. As we pulled the boat back to dock, the captain’s exact words to the maintenance man over the phone where, “This boat is leaking like a sieve!”

The owner was still unreachable to us, but the maintenance man assured us he had been in touch with the owner who promised he would refund us for the two days we had to pay for other accommodations.
At this point, I checked my bank account online. The check that the maintenance man promised not to deposit was cashed. When I asked him why he lied, he replied that the owner told him to cash it and he had no choice because the owner’s the boss.

So, at this point, we had no alternative but to keep the boat and wait for the repairs or loose a substantial amount of money. We grabbed our backpacks and carry-on’s and headed to catch a ferry to Norman Island where a beautiful hotel awaited us— a much-needed relief from the rain and a captain who had unrelenting talk about nothing but himself for three days. I don’t believe he asked one question about us!

There was no doubt he knew his way around a boat, but we didn’t need a chaperone for our honeymoon and he didn’t seem to get it. We didn’t want to be rude and in any way ruin our honeymoon, so we just went with the flow.

Finally on Our Own!

Two days later, our boat was brought to the resort where we were staying (Cooper Island Beach Club—a completely delightful experience!) and moored up. Finally, five days after our arrival, we were alone and on the water. Unfortunately, but not surprising by this time, nothing was fixed appropriately. The refrigerator worked haphazardly and the boat leaked badly again when it rained a couple of days later. They left us a sailing guidebook, which the captain insisted we have to help us navigate. The only problem…the sailing guide they left us was so out of date, mooring fees were only $5. They are now either $25 or $30. We just laughed it off. We were not going to let anything else spoil our last five days of sailing. We bought ice for the refrigerator, got good directions from locals, and on the next rainy night we made the best of it by going to a local restaurant. Of course, the rum helped quite a bit!

All in all, there were three very rainy nights with which we had to contend. If the boat had a proper dodger, had not leaked excessively, and actually had the air conditioning promised as part of the boat’s specification on the website, we would have weathered the situation just fine. After all, the “hot” rain you get in the Caribbean generally just requires a quick change of shorts and shirt in the cabin and your dry and comfortable.

Remarkably, the day before our last we had a perfect three and half hour sail from the Bitter End to Norman Island with winds at about 18 mph. That one sail made the trip as it was what we finally came for—to sail together alone.

Even with the hardships we encountered with the charter company and our captain, we both looked at each other and smiled, knowing that this is what we came for—our first real sail together, now as husband and wife. We perfectly trimmed the sails into their optimum position to take advantage of this perfect breeze. Sailing together can be a growing experience for a couple and this trip fused our bond together even tighter.

The Final Chapter

The day we returned the boat, the owner was nowhere to be found. I called him a day before and left messages and sent emails but could not reach him. I wanted to settle the reimbursement and the account before we headed back to the States. I wanted our dealings with them done! No luck, however, in finding him while we were on the island. Upon our return home, I sent him several emails and finally contacted him by Skype. He said he was reviewing our claims, but also said that the captain and the maintenance man were not backing up our complaints about the boat. Somehow they “forgot” about the leaking boat, soaked beds, dripping hatches, the refrigerator not turning on, etc. I finally got an email from the owner a week later saying nothing about the reimbursement. He only mentioned that gas was not included. I forwarded him an email from him where he clearly said gas would be included. I haven’t heard back yet.

Moral of story, make sure you are dealing with a reputable chartering company and heed the points in the Do’s and Don’ts section and your on your way to a perfect sailing vacation. Most of all, have fun and may the wind be right so you can find the joy as “the canvas can do miracles.”


Make sure you know exactly the year and condition of the boat. Have it in writing and make sure it’s clear in your contract. Add a clause that allows you to decline the boat or switch to another comparable boat the meets your approval. In the case of our charter, there were no other boats that were ready or better.
Steer clear of small chartering companies with low inventory. Ask how many boats are available before agreeing to charter. As we noticed on the water, over 90% of the other chartered boats we came into contact with were newer, nicer, better equipped boats.
Get a list of equipment in writing and approve the list prior to chartering. We were promised air conditioning and a dodger that we ended up needing desperately, were promised, but didn’t get it.
Make sure you get a boat that’s easy to sail. Make sure the boat comes with electric winches, auto-pilot, GPS and Chart Plotter at the helm (not in the cabin). Our auto-pilot did not work! Sails were old and sticky and with no electric winches, difficult to hoist.
When you do a check out, make sure you go through each item and test it. If it does not work, make sure they fix it or give you another boat. Again, always make sure there are other boats, unless you completely trust the chartering company to deliver the boat you agreed upon. Be careful and thorough as it often takes a few days to notice the problems. We did not have steaming lights, anchor lights, deck lights, cockpit lights, stove was not lighting properly, GPS was useless, inverter worked haphazardly, refrigerator not working, get a sailing guide, one water tank cracked, water tank and gas tank gauges not working. The gauges alone could have saved us over $120 in gas and water we did not need.
Make sure your chartering contract covers you if the boat needs repairs. The company should either exchange the boat within 24 hours and, at their expense, put you up at an “equivalent to the boat rate” hotel. Most sailing charters can run $280 to $500 a day, so make sure you have a reimbursement agreement.
Try to pay by credit card so you have a least some leverage to dispute or partially dispute the charges. If your chartering company does not accept credit cards—and preferably American Express, as they are the best at disputes—you should steer clear of them and find another company.


When you hire a captain for a few days or your entire trip, make sure you provide ONLY onboard provisions for him or her or agree on a per diem. You are only required to make sure they have food onboard, otherwise they can go anywhere they wish to eat or drink. You DO NOT have to entertain or have them come with you when you leave the boat. Your captain is a service professional who is there to navigate and drive the boat. You are not responsible to take him or her to dinner if you do not wish to do so.
If you want to provide drinks, like beer, onboard for your captain, then be clear as to how much you are comfortable with them drinking.
Make sure your charter company provides a free check out with a captain or charter employee. All reputable chartering companies include a basic check out with your chartering package.
You should interview your captain by phone and ask him/her pertinent questions to qualify them as someone you want to spend time with. When you are on a boat, it’s close quarters and everyone need to get along. Take your time and interview the captain. Make sure the chartering company is finding the right person for you. The owner led us to believe it was a honeymoon gift when actually he wasn’t being charged at all by the captain.
Get your exact costs for your captain and usual tipping schedule (if any) in writing. Know with whom you are dealing and what it will cost you.
Make sure the chartering company provides a proper sailing guide. The captain should take time to go over the hazards as well as popular destinations. Make sure you understand the buoys, signage, mooring colors, dingy mooring, reefs, and so on. You should spend at least an hour with the captain and plot a course that you feel comfortable with. The captain should also review the beach flag colors in the area you will be sailing. For instance, a purple flag in the BVI’s means marine sea life —which in our case really meant jellyfish. We swam into the beach at The Baths in Virgin Gorda under a red flag not knowing that this is dangerous and swimming is not advised. It was a good hard swim back to the dingy.

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Old 12-23-2011, 02:17 AM   #2
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Home Port: Washington DC
Vessel Name: SV Mahdee
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Cruiser Log members typically aren't chartering boats--but often that is a great way to see an area or check out a boat that you may be interested in the purchase of. Thanks so much for sharing your experience here. I did edit your post to remove the "incriminating" names as well as personal contact information.

I am reminded of a couple things:

First--the "Captain Ron" DVD and believe that you have recounted much of the experiences that many, many people do have when chartering a boat or hiring a captain. It really helps to have a personal reference to the charter company and/or to a specific captain.

Second--each person has a unique set of requirements of what they consider absolutely must be onboard the boat (e.g. chart plotter at the helm? electric winches?) and the less experience one has the more one seems to want on the boat. Same with captain vs not.

Finally--if the vessel in question didn't have the safety systems required for use (e.g. flares, nav lights, e.g,) you might have been in deep trouble should you get boarded. Don't accept a boat that doesn't have these minimum safety systems in place as YOU are accepting responsibility for the problems that may arise.

Fair winds,

"Do or do not. There is no try." - Yoda

What we're doing - The sailing life aboard and the Schooner Chandlery.

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Old 12-23-2011, 02:47 PM   #3
Join Date: Oct 2005
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This is a story from the 80's and early 90's and in Greek waters !! As a charter captain living in BVI for the last 20 years I am shocked and embarassed by this episode. (Hastily adding that I only nowadays skipper for friends or friends of friends nowadays!)

We have "A" fleets and "B" fleets and, obviously, still one (at least) "C" fleet here. Even in A and B fleets, things go wrong occasionally - after all, we are dealing with the three most volatile elements: Boats, People and The Sea. However there are absolutely no excuses here.

The original Poster has done a great service to those, especially first-timers, who are thinking of chartering anywhere and the Moderator has, in my humble opinion, been far, far too kind to an undeserving operation and "captain (??)" - though probably there are rules against naming and shaming?

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Old 12-23-2011, 07:41 PM   #4
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Hi, Tony,

Thanks for your insights. I am glad the original post was made since it is a good story and does point out some of the things one should look for. We don't make a habit of bad-mouthing particular businesses here--no--and figure that someone putting out the money for a BVI charter can get some references before their trip so warnings of particular vendors aren't needed here. As noted, doing charters aren't really high on the priority list of most of our cruisers.

For many years now, a good sailing club I know in the Washington DC area does an annual BVI 10 day trip with charter of between 3 and 6 boats each time. I've heard some really "interesting" stories about boats and things with those charters--and they're using "A" tier fleets. Sometimes things happen.

That combination of Boats, People and the Sea is tricky enough but throw in unrealistic expectations and...things can go sour really fast. Unfortunately, when people haven't chartered (or sailed much) before, all they've seen are a lot of movies and heard a lot of stories about great experiences. Even the best-of-the-best experiences can be a terrible let down for someone with too-high expectations of the sailing experience they are about to have.

Fair winds,
"Do or do not. There is no try." - Yoda

What we're doing - The sailing life aboard and the Schooner Chandlery.

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Old 12-27-2011, 01:05 AM   #5
Join Date: Dec 2011
Home Port: Rochester, NH
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Default I did this charter.

I did take this charter in 2002 in mid-July with my teenage sons and my wife. We did not make any booking up front but walked to the charter office negotiated a discount for a late season rate and before paying anything we checked the boat. Besides rude/neutral attendants we did not have any complaints. Making reservations ahead especially with a money deposit puts a person in an inferior position when it comes to negotiations. Let’s not forget they are all pirates up there.
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Old 12-27-2011, 08:01 PM   #6
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As far as editing out the names of the guilty ones, we're held to a higher authority here. Rants have, in the past, brought many a forum to its knees, though I doubt that the "C fleet" operation here has the money or clout to cause much trouble. Still, if anybody needs to get names and places, I'm sure that pharrison475 would answer any of your emails.

As much as we loved our life aboard, there are still places in the world where Peter and I would charter a boat rather than miss going there.

We met a fellow waiting to go through the Panama Canal while we were doing the same thing. His new sailboat was a disaster after leaving it in charter in the Caribbean for two years (not the V.I.'s, though). He was so horrified by the condition of his boat that he immediately pulled it out of charter and made arrangements to bring the boat back to his home in California. It took him weeks to get to Panama just because EVERYTHING (or so it seemed) was failing or failed en route. Bad, incompetent, and sloppy maintenance. Lazy care.

Most charterers wouldn't know enough about maintenance to recognize the jury-spliced wires, the debris tossed into the bilge, all the bits and pieces of wire and insulation that the boat boys were too lazy to clean up (they weren't being paid to tidy up after themselves, they were pushed to get as much done as they could). A beautiful boat became a frightening wreck in just two short years. And this can happen to charterer, buyer, borrowing friend.

It's a tale worth telling. Be careful.
In 1986 we went cruising for a few years. After 20 years and 50+ countries and several oceans, we are STILL "cruising for a few years".

MV WATERMELON (New) | Cruiser's Dictionary, free ebook

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Old 03-14-2019, 07:26 PM   #7
Join Date: Mar 2019
Home Port: Paros
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Default Good charter companies

Most of the companies are trying to do their best for their guests especially if we are talking about skippered charters. Skipper's sometimes can be rude or tired from successive weeks sailing. The best advice is to find small local companies were things are under control better.
If you are searching for sailing tours in the Greek islands, a small company is Greek Water Yachts. They offer couples sailing trips and honeymoon sailing trips.

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