Abstract: I spent seven years sailing in the Caribbean and the South Pacific, chartering boats through Moorings on no fewer than ten occasions.This post won’t cover the standard information found in official manuals; instead, it’s purely about the many challenges I’ve actually faced, the money I’ve wasted, and the various lessons I’ve learned.It covers everything from how to choose a boat type, what kind of insurance to purchase, and what items you’ll need to bring on board yourself before setting sail, all the way to the specific situations that can easily result in a deduction from your security deposit when returning the boat—all explained in one comprehensive guide. This is ideal for those renting a boat through Moorings for the first time, or for those who have used the service before but have always felt that something wasn’t quite right.
Author’s Note: Based in Fort Lauderdale, Florida, I have worked as a boat rental broker for the past seven years. At the same time, I have regularly chartered boats from Moorings to sail routes to the Bahamas and the British Virgin Islands, accumulating over 20,000 nautical miles.This content is based entirely on real-life experiences and client feedback; it does not involve any brand sponsorship, and the prices and terms mentioned in the article are based on actual inquiries made in 2025.
Let me start with the conclusion: Moorings isn’t the cheapest option, but in terms of fleet maintenance and customer service responsiveness, it is indeed the most reliable in the Caribbean. The issue is that reliability doesn’t mean there aren’t potential pitfalls.
In 2019, I chartered a Moorings 4000 for the first time, setting sail from Tortola. At the time, I had no idea what to expect and assumed that, as a large company, their service would be thorough and reliable. But what was the result? The boat was missing three dock lines, the bottoms of the pots in the kitchen were covered in burn marks, and the air conditioner kept tripping the circuit breaker for no apparent reason. I called the base and waited forty minutes before someone finally picked up the phone.
It wasn’t until later that I realized most of these issues could have been avoided in advance.
When choosing a boat model, don’t just look at how many people it sleeps
Moorings’ fleet ranges from 32 feet to 58 feet in length; however, determining which boat truly suits your needs isn’t about simply counting the total number of cabins—it depends on the specifics of your itinerary.
If you’re planning a short island-hopping trip in the British Virgin Islands with daily sailing times of no more than two hours, then the Moorings 4000 or 433 will suffice. These boats have a shallow draft, making anchoring convenient and handling straightforward.The first time I sailed the BVI, I was on a 4000 with four people for seven days, and it was just right.
If you’re heading to Saint Vincent and the Grenadines, take my advice: you’ll need at least a 4,500 or a 5,000. That route includes open waters with high winds and rough seas, so a larger boat will be much more stable.In 2022, I took a group of friends on that route; we chartered a Moorings 4800 with six people aboard, and the trip took twelve days.We unfortunately ran into a stretch of extremely strong gales along the way. With six people on board, if we’d been sailing a boat one size smaller, I doubt anyone would have been able to sleep soundly that night.
A common mistake beginners make: when looking at boat models, they focus solely on the number of cabins, assuming that six people absolutely require six separate cabins. In reality, you’ll spend most of your time on deck, and the cabins are really just for sleeping.What you should really focus on is the deck layout, the size of the awning, and the capacity of the refrigerator.
For mooring vessels, even within the same size class, different models can have significantly different deck designs. For example, both the 4000 and 433 models fall into the 40-foot class, but the 433 has a more spacious bow deck, making anchor winch operations much smoother.If you frequently handle anchoring operations yourself, this difference will be quite noticeable.
Insurance: Don’t Skimp on That Little Bit of Money
Moorings offers several tiers of insurance coverage. I’ve seen many people choose the lowest tier to save money, only to have several hundred dollars deducted from their refund when returning the boat.
It’s important to clarify that with Moorings’ standard insurance, the deductible generally ranges from $1,500 to $5,000, depending on the package you choose. By paying extra, you can lower the deductible—down to as low as $500.
That time, on my first boat rental, I chose the plan with the highest deductible, thinking to myself that since I’m always extremely careful and cautious when sailing, an accident was absolutely out of the question. But what actually happened? As the boat approached the Norman Island anchorage, a sudden, completely unexpected gale blew up, instantly turning the boat sideways, and immediately afterward, the stern struck the anchor chain of a catamaran moored next to us.A scratch was left on the boat’s paintwork—roughly ten centimeters long. When it came time to return the boat, Moorings deducted $800 outright.
$800—that’s enough for me to enjoy several lobster meals.
In your situation, if this is your first time renting from Moorings or you’re unfamiliar with these waters, go ahead and purchase the package with the lowest deductible.The extra cost is generally in the range of $50 to $80 per day; for a seven-day trip, that’s less than $600, but it can make a world of difference to your peace of mind throughout your entire vacation. You won’t have to worry every time you dock.
One more thing to keep in mind: Moorings’ insurance does not cover sails.That’s right—you read that correctly. Damage to sails is not covered under the standard insurance policy. Gusts in the Caribbean can come on extremely quickly, especially during thunderstorms in July and August, when wind speeds can surge from 10 knots to 30 knots in the blink of an eye.If you don’t have time to furl the sails and the mainsail gets torn as a result, the cost of replacing it ranges from roughly $3,000 to $5,000.
When I first heard about this clause, I was instantly stunned.After that, I became more cautious: every day at dusk, no matter how calm and pleasant the weather appeared, I would immediately reef the mainsail down to the second reef. Although this was quite a cumbersome process, it ensured safety.
If something is missing on board, you have to bring it yourself
The boats owned by “Moorings” come with basic amenities: tableware, cookware, bedding, towels, and life jackets. However, when it comes to the finer details, you really shouldn’t expect too much.
Here’s a list of items I’ve actually used and found essential to bring yourself:
Kitchen items:
The so-called “sharp” kitchen knife provided on board is so dull that it takes a tremendous amount of effort just to slice a tomato. Eventually, I brought my own Chinese-style slicing knife specifically for chopping vegetables.
Coffee filters: While the ship might have a French press, filters aren’t always provided. If you plan to make pour-over coffee, you’ll need to bring your own.
Plastic bags and aluminum foil. Space in the ship’s refrigerator is limited, so portioning out ingredients can save a lot of room.
Sailing Essentials:
When it comes to sunscreen, be sure to choose a reef-safe formula. The British Virgin Islands has restrictions on regular sunscreen, and many bays have explicit bans. I use the brand “Reef Safe,” which works pretty well.
Sun protection gloves. The helm and winch are exposed to the blazing sun all day and get hot enough to cook food on.During my time in St. Maarten from 2020 to 2022, I didn’t have gloves, and the blisters that formed on my palms took a week to heal and return to normal.
Headlamp. It’s so much more useful than a flashlight for dropping anchor, going ashore, and checking the anchor position at night.
Personal Notes:
Earplugs are a must. The air conditioning compressor on the boat is ridiculously loud—so much so that I couldn’t sleep during my first three charter trips. It wasn’t until I brought earplugs that the world finally became peaceful.
Mosquito repellent. Mosquitoes in the Caribbean at dusk—especially during the rainy season—are far more ferocious than you can imagine.
Navigation and Electronic Devices: Don’t Rely on Them Entirely
All Moorings boats are equipped with GPS and electronic charts; however, to be honest, the frequency with which those electronic chart data are updated doesn’t always keep pace with changes in these waters.
I once ran into trouble while sailing through the Anegada Channel. The chart indicated a depth of twelve feet, but when I actually sailed through, the hull clearly scraped the sandy bottom. Fortunately, I was moving relatively slowly, so it didn’t lead to any serious problems.Later, a local captain told me that the sandbars in that area shift every year, and the update cycle for official charts simply cannot keep up.
Before every trip, I make it a point to not only use the electronic charts on board but also download Navionics’ offline maps onto my phone, then cross-reference the two. Additionally, it’s essential to purchase local paper charts—or at the very least, print out a copy.There’s a nautical supply store next to the Moorings base on Tortola; they sell them for $7 each, which is much more convenient than viewing them on a phone.
There’s one more thing that beginners tend to overlook: anchorage depths.
Much of the water depth data for anchorages in electronic charts was measured decades ago. Back in 2023, when I was at the anchorage on Salt Island, the chart indicated a depth of eight feet, but at low tide, the actual water depth was only five and a half feet.My boat has a draft of five feet, so I came within a hair’s breadth of running aground.
As a rule of thumb, once you arrive at an anchorage, don’t rush to drop anchor. Slow down the boat, circle the area once, gauge the water depth visually, and carefully observe where other boats are moored.If all the boats are moored farther from the shore, the water near the shore is likely to be shallower.
Boat Return Inspection: Areas Where You’re Likely to Be Charged
The inspection upon returning the boat can be strict or lenient, depending on the circumstances. It largely depends on which inspector you encounter and the condition of the boat at the time.
Based on my own experiences and those of others over the years, here’s a summary of situations where fines were imposed:
The most common reasons for fines:
Fishing line or seaweed tangled around the propeller—this is extremely common, especially after several days of sailing. When returning the boat, staff are assigned to go into the water to inspect it; if something is tangled, the cleaning fee ranges from $50 to $150.
The anchor chain has markings that serve as wear indicators; red marks are placed at regular intervals along the chain. If the wear is so severe that the marks are no longer visible, they will require you to replace the anchor chain, which can result in a very high fee.
If the refrigerator has an unpleasant odor—caused by food scraps not being cleaned out properly—and the door has been closed for several days, the inspector will smell it as soon as they open the door. The cleaning fee is $50.
I’ve made it a habit to spend two hours on a thorough cleaning the afternoon before returning the boat. I go over everything one by one: the kitchen countertops, the inside of the refrigerator, the bathroom, and the deck.I pay special attention to the refrigerator, wiping it down with a solution of vinegar and water, which is highly effective at eliminating odors. On the morning of the return, I also do a quick final check to make sure I haven’t left any personal items behind.
Additionally, the fuel and water levels must be the same as when you picked up the boat. Moorings requires that the fuel level and water level in the tank be exactly the same upon return as they were when you picked up the boat.They take a record when you pick up the boat and cross-check it again when you return it. If there’s a significant discrepancy, you’ll be charged for the difference—it’s not the most expensive penalty, but it’s a hassle.
As for Moorings’ customer service, to be honest,
Moorings’ customer service is decent when handling major issues, but when it comes to minor problems, it all comes down to luck. I have to mention this.
In 2023, I was based in Saint Lucia. At the time, the toilet pump in my cabin broke down, I called the front desk, and they told me the repairman wouldn’t be able to come until the next day. That night, five of us had to share a single bathroom. So I went directly to the marina manager and was a bit firm with him. Two hours later, the repairman arrived.
Lesson learned: When encountering issues at the base, don’t just rely on phone calls—go directly to the front desk to speak with staff. Face-to-face communication is much more efficient. Additionally, on your first day aboard, spend half an hour testing all equipment—including the air conditioner, water pump, stove, refrigerator,anchor winch, and windlass—and report any issues immediately so they can be resolved before departure. Don’t wait until you’re out at sea to discover them—by then, it’ll be too late.
Q: It’s my first time renting from Moorings—should I choose a monohull or a catamaran?
It depends on the number of people and the route. For groups of four or fewer, a monohull offers better handling and is more affordable. For groups of six or more, the space advantages of a catamaran become evident. However, catamarans sway more vigorously at anchor, so those prone to seasickness should consider this carefully. I’ve met several people who don’t usually get seasick but ended up throwing up all over the place on a catamaran.
Q: Can Moorings boats be rented for one-way trips?
Yes, but the cost is significantly higher. For example, if you depart from Tortola and return the boat to St. Maarten, the one-way fee generally ranges from $1,000 to $2,000, depending on the season and boat type.I suggest that beginners avoid one-way rentals, as you’ll have to fly back to your departure point to pick up your rental car after returning the boat, which is quite a hassle.
Q: What is the best time of year to visit the Caribbean?
The peak season runs from mid-December through the end of April. During this period, the winds and waves are relatively calm, but prices are quite high and the marinas are extremely crowded. May, June, and November are considered the shoulder season, when prices are lower and weather conditions are generally decent.July through October is hurricane season. Although Moorings offers a hurricane protection policy, I do not recommend that beginners undertake long-distance cruises during this time.
Q: Is a skipper’s license required?
Moorings requires charterers to have basic sailing experience and be able to provide a sailing resume. While ASA or RYA certifications are not mandatory, they will verify your experience. If you have never sailed independently, you may be required to hire a local captain, at a cost of $150 to $250 per day.
Q: How is Moorings more expensive compared to other companies?
Their fleet is brand-new, well-maintained, and has extensive base coverage. For the same boat model, Moorings may be 20 to 30 percent more expensive than local small companies. However, many of the boats from small companies have been in use for seven or eight years—or even longer—and suffer from numerous issues related to aging equipment.I’ve witnessed a friend on a boat rented from another company whose engine stalled mid-voyage, leaving them waiting for rescue for a full six hours. At the very least, Moorings has never left me stranded at sea.
That said, Moorings isn’t flawless, but if you’re looking for a worry-free Caribbean sailing trip, it’s definitely the most reliable and dependable option, provided that you do your homework beforehand—and whatever you do, don’t make the same mistake I did on my first trip by boarding the boat completely unprepared and clueless.
The boat may be rented, but the vacation is yours. Put a little more thought into your preparations, and you’ll save yourself a lot of hassle down the road.
Wishing you fair winds.