“It’s a Rental” A First Timer’s Guide to Bareboat Chartering in the Caribbean

Story by Chrystal Young / January 29, 2018

Dreaming of chartering a boat in the Caribbean? Can you Imagine palmtree lined, white sand beaches kissed by azure blue waters and the sound of the surf lapping at the shore? There you are, standing on the bow, watching the anchor set in seven feet of crystal-clear water as a warm breeze caresses your cheek. Sailing in 15 knots of steady Trade Winds on a beam reach with the next island in sight. Now, that’s a happy place! Make your Caribbean island dreams come true for you, your family or friends. Book a boat, book the flights, and set sail! But where should I sail in the Caribbean, what can I expect when I get there, what should I pack, when should I go, I’m scared!? Here’s some help:

Where to sail in the Caribbean?

The chain of Caribbean Islands stretch from Puerto Rico in the north, south to Trinidad. THAT is a lot of sailing! All these islands have beautiful beaches, amazing blue water and yummy tropical drinks. There are so many awesome places to visit, but let’s narrow it down to a few favorites.

BVI: This is the most common answer when people decide to sail in the Caribbean. It has more charter boats available, light breezes for easy sailing and a routine route to follow. What is attractive about the BVI can also be what is unattractive. More boats means more traffic, light breezes can mean no breeze, and routine routes can be, well, so routine. It’s got all the cool guy attractions you have heard about at the yacht club – you just have to share it with so many other boats!

Antigua/Barbuda: If you would like something a bit further off the beaten track, try the hidden gem of Antigua and Barbuda. This area has a variety of beautiful anchorages and sometimes more interesting sailing conditions. The sail up to Barbuda is a 25nm open ocean passage and Barbuda is such a low lying island that you can’t see it until you get there. Interesting – and worth it!

St. Martin / Sint Maarten is a popular yachting destination in the middle of the Caribbean chain. There is a French side and a Dutch side so you will enjoy the best of both cultures.

Duty-free shopping is a popular past time with top fashion designs at bargain prices. Experience some of the best and most variety of culinary delights in the Caribbean!

St. Vincent, Grenada & the Grenadines: 72 miles of sailing paradise, untouched by mega-tourism. There are no 10-story-high casinos, no gimmicky bars, or lines of floating cities littering the harbor. You will find unobtrusive shore accommodations, beach bars made out of lean-tos and maybe a cruise ship anchored far away from the shore. This is the REAL CARIBBEAN!

What to expect?

When you land on the island, you will go through customs and immigration. Most of these officials take their job seriously – all the “i’s” dotted, “t’s” crossed. Best advice? Keep it simple and keep the conversation to a minimum. Have your passport ready, copy of your return ticket and address of the charter company. Now, “address” is a relative term since so many places in the islands don’t have an “address” as you know it. You might get the name of a marina or village – perfectly acceptable. Be respectful and in the end, let them know how happy you are to visit their island!

Packing: It is wise to pack a change of clothing in your carry-on. Or, at the very least, a bathing suit. Not only will it be 80 degrees when you step off the plane but you may or may not get your luggage right away. It happens! No problem – go sit on the beach with a rum punch until it arrives. (Hint: “No problem” usually means no problem for that person. YOU might have a problem, it’s just not THEIR problem. Hence the term – “No problem!”) Other things to pack are the typical summer items: shorts, t-shirts, nice summer dress for the ladies, a cover-up for sun protection and a light rain jacket for the occasional squall. Serious sailors should consider sailing gloves, a hat clip and strap for your sunglasses.

In your checked luggage: Your favorite sunscreen (hopefully one that doesn’t run into your eyes as you sweat), bug spray (look for 25% DEET), pocket knife, headlamp, a printed copy of your passport, mask & snorkel (You can get the fins from the charter base but you probably don’t want to put a used snorkel in your mouth.) Oh, and a 1⁄4” patch cord (headphone size) and 12v adapter for playing all your island music over the speakers!

When is the best time to charter

 The BEST time to charter, of course, is when you can actually go! Experienced charter guests often schedule a boat a year ahead of time – especially in high season. The most expensive time of year to go is usually 20 December to 3 January. The prices almost double during this time. But, if that is the only time you can go, GO! In general, the seasons are:

Prime Season (Dec. 14 – Jan. 3 & Feb. 8 – April 25) is the time of year when boats are in the highest demand and the weather is most desirable and cooperative for great sailing. During winter holidays and spring break, prices are high. Charter companies know this, of course, and the prices reflect it. Plan EARLY for prime season, not only for the boat but for flights as well. Last minute deals are rare.

Shoulder Season (Jan. 4 – Feb. 7 & April 26 – May 9) is a transition period for most people’s availability, and for demand. Double check your dates andtry to be flexible. You could save a lot of money just by adjusting your vacation by a day or two.

During Low Season (May 10 – Dec. 13), boats are in less demand which can mean fewer people to compete with on your vacation. But, it can also mean fewer services available, like stores, restaurants, and transportation. You can get great deals, and make last minute plans. Hurricane season is June 1 – November 30 (besides, who takes a vacation to the Caribbean during the summer?).

How does it work?

Gone are the days that all you have to do is pull out a credit card and they will hand over the keys to the boat. Charter companies are realizing that inexperienced skippers are not just destroying boats but doing harm to the environment as well. The skipper will be asked to send in a sailing resume. You can hire a skipper for a few days or your entire trip if you are not comfortable on your own. Or maybe you just want to sit back and enjoy a refreshing beverage or two without having to worry about being the skipper. When you get to the base, you will receive local charts, a cruising guide and boat briefing. Make sure you get familiar with the systems, know how to reef sails and check the gas in the dingy. Each briefing takes about an hour. Most charter companies don’t allow you to get on the boat until later in the day – 4 or 5 PM. You are prohibited from sailing after dusk, so often, you won’t be sailing that first day. Check out time is usually 11 AM.


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