Bareboat Charters in the Caribbean: Freedom to Explore

The 47-foot catamaran the author chartered from Sunsail.
The 41-foot catamaran the author and her husband chartered from Sunsail.

By Susan Fogwell

Whether you’re an experienced sailor or a novice, a chartered or bareboat sailing vacation is the ultimate, carefree adventure. Time is measured by the sun’s altitude and declination, not the timepiece on your wrist. You’re on island time -- with no worries!

With no set schedule, you have the freedom to island hop, raise and lower the anchor at your discretion, explore as many islands as you wish, or just sit back and relax with a Pina Colada. Moreover, you can accessorize your sailboat with toys: windsurfers, kayaks, scuba, and snorkeling gear.

Bareboating is chartering without a captain; you’re in command of your own vessel. With a regular charter, a hired captain –- for an additional fee -- comes with the boat. Depending on your qualifications, each has its advantages.

In order to bareboat, you must prove your sailing competence to the charter company. This usually involves a series of questions testing your knowledge along with personal sailing references.

Recently, my husband and I with two other couples bare boated out of Bas-de-Fort, Guadeloupe. The boat was luxurious and brand-spanking-new. From Guadeloupe, we sailed to Antigua for the world renowned Antigua Race Week.

We stayed on the south coast of Antigua at Falmouth Harbour along with multi-million dollar mega-yachts. Each day we positioned our catamaran at the windward mark in order to watch the boats in the race raise their spinnakers. On the last day, we sailed to the practically uninhabited island of Barbuda – 30 nautical miles away.

Antigua Race Week
Antigua Race Week

With the exception of a rustic seasonal resort, which was boarded up, nothing else exists on the island. It’s meant for pure escapism and is only accessible by a boat.

We returned to Antigua for the final races and then headed south to Guadeloupe’s outer islands, Les Saintes. The main town, Terre Haute, is a mini St. Barts. Other than the French families and sailors who visit, it’s unknown to most. Among all of us, this was our favorite spot.

There are several charter companies to choose from. After fully investigating the top three, we decided on Sunsail, based in Annapolis, Maryland. They had the best price for the same size catamaran as the other companies.

With more than 1,000 boats in their fleet and 36 bases in 23 countries, you can customize your charter according to your likes and dislikes. For independent travelers seeking an adventurous vacation on the water, this is your ticket. Not only is it a unique vacation, but it can be cost effective as well.

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Sunsail offers discounts during the off-season and during specific weeks called “Reef Weeks.” Moreover, after you have completed your first charter, you will be offered a 20% repeat charter discount. Sunsail has an alliance with American Airlines offering discounted airline tickets to the Caribbean as well.

Catamarans have become a popular choice in the chartering world due to the spaciousness, stability, and privacy that a monohull doesn’t offer. They offer bountiful creature comforts with a deck-level saloon and a roomy cockpit.

Catamarans at Sunsail
Catamarans at Sunsail

We chose a 41-foot Lagoon catamaran for the seven-day excursion. Each of the two hulls has two full staterooms, and private heads (bathrooms). The boat easily sleeps eight people. Bareboating with three or four couples at approximately $6000.00 during Reef Week makes it an affordable trip. Other than owning your own boat, how else can you flit from one island to the next, on your own time?

Depending on your needs, there’s a cat for every wallet. Or, if you prefer a monohull for its natural sailing abilities, this is a good option as well.

In addition, there are other expenditures: customs fees on each island, dockage, water, electricity, fuel and, of course, provisioning the boat. However, anchoring in a snug harbor is free. Most importantly, for a modest fee, optional insurance is offered for each individual; pay it and you’ll have peace of mind.

Sunsail provides snorkeling gear and kayaks at no extra charge. We discovered that the snorkeling gear was well-used; the masks leaked and it was difficult to find a pair of fins that fit well. I would recommend bringing your own snorkeling gear.

The author above Les Saintes
The author above Les Saintes

The sit-down kayaks provided are basic; unless you’re a die-hard kayaker, they serve their purpose. Windsurfers can be rented by the week through Sunsail’s affiliation with local rental shops; and can be stored on the bow of the boat. Our one-week windsurfer rental in Guadeloupe cost $230 euros ($294US).

Our charter began at 6 p.m. on a Sunday. In order for the trip to get off to a good start, it’s judicious for the entire crew to arrive at their given destination at least a day in advance. Arriving on the first official day of the charter is not realistic; it’s asking for problems that are avoidable.

If the slightest thing during your traveling day doesn’t go as planned –- such as a flight cancellation -- you will have the other crew members and boat waiting while the clock is ticking. You don’t want to show up a day late and have the whole week’s itinerary disrupted, let alone a crew that will be more than slightly peeved.

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On the same note, it’s prudent to book your departing flight for the day after the end of the charter. Our charter officially ended at 11 a.m. the following Sunday. Don’t push it and think that you’ll be able to make it to the airport for a 2 p.m. departure to San Juan. It’s unrealistic and unfair to the rest of the crew. Book a hotel for the night and depart the following day. This is not a time to skimp on a couple of nights at a hotel or resort.

Windsurfing in Barbuda
Windsurfing in Barbuda

Provisioning the Boat

Also, keep in mind that someone has to provision the boat. Sunsail offers to provision the boat, but it’s much more expensive than if you did it yourself. They will send a checklist of grocery items with marked-up prices. Unless money is of no concern, make the check marks and send it back to them.

However, by arriving a day early, you will have plenty of time to grocery shop at your leisure for exactly what you want. In our case, we rented a car, or Sunsail will call for a taxi. This is a group effort and it’s important that everyone is on the same page. If there are disagreements before getting on the boat, accept it as a red flag, because, believe me, it will all come to a head on the boat.

Last, but not least, the most important aspect of the trip is choosing people very carefully for the charter. I can’t stress this enough; it is paramount in order to have a fun and relaxing trip. For a solid week, you’ll be in close quarters with no escape. No pun intended, but if you’re not all on the same wavelength, your week in paradise will become stormy rather quickly.

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Susan Fogwell

  Susan Fogwell is a flight attendant for a major airline and a seasoned traveler. With the exception of Antarctica, she has traveled to every continent.


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