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HomeCharterCaribbean Yacht Charter Vacation: 6 Tips for Choosing the Perfect Experience

Caribbean Yacht Charter Vacation: 6 Tips for Choosing the Perfect Experience

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Mocka Jumbies and Rum...

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Long gone are the days when chartering a yacht to sail the Caribbean is akin to the plot of the 1992 comedy movie, Captain Ron. Today, it’s luxury yachts rather than lemons, professional rather than rum-soaked crew, and a pleasure cruise rather than pursuit by pirates. It’s no wonder that the global yacht charter market size is expected to reach $10.2 billion by 2027, spurred by travelers’ interest in luxury marine tourism and personalized services, according to the Yacht Charter Market Size, Share & Trends Analysis Report, by Grand View Research. 

Here are six tips to help choose the perfect Caribbean yacht charter vacation:

1. When to Go?

Many people choose to enjoy a Caribbean charter vacation from November through April, according to Carol Hansen, digital marketing, content, and creative manager for Annapolis, MD-headquartered Dream Yacht Worldwide, with Caribbean bases in the U.S. and British Virgin Islands, St. Martin, Martinique, Guadeloupe, and Grenada, as well as Cuba and Belize. “These months are slightly cooler with less rainfall.” 

Keep in mind that everyone else wants a piece of this prime time in paradise too, so expect more crowds and busier waters. 

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“If you want to dodge the crowds, the quieter months of May and November could be your hidden treasure. Referred to as the shoulder season, this time of year often has more affordable rates and quieter anchorages since it’s the off-season,” says Susan Restauri, senior project manager for Waypoints Yacht Charters, in Annapolis, MD, with Caribbean bases in the U.S. and British Virgin Islands. 

Courtesy Waypoints Yacht Charters
Courtesy Waypoints Yacht Charters

2. Where to Go?

Roughly 80% percent of the Caribbean’s charter yachts are based in the U.S. and British Virgin Islands, says Carol Kent, president and owner of Carol Kent Yacht Charters International in Marblehead, MA. “This area is ideal for island hopping, snorkeling, and diving. Each island offers different vibes, cuisine, and entertainment along with good anchorages. First-time charterers are delighted with the short cruising distances. Also, both have the most charter yacht selections when planning your vacation.”

For more experienced sailors or charterers, discover another area such as St Martin/St Barth’s and Anguilla as this makes for a great week, recommends Sarah Sebastian, director and charter specialist with Nicholson Yacht Charters & Services, based in English Harbour, Antigua. “We also have the Southern Caribbean, which is my absolute favorite, from St Lucia south. St Vincent is an excellent place to board or Canouan in the heart of the Grenadines.”

St. Vincent and the Grenadines are a more challenging sail. However, says Lesley Hayes, crewed yacht specialist at Horizon Yacht Charter’s base in St. Vincent & the Grenadines. However, “the islands are less crowded and more unspoiled. I would definitely recommend the Grenadines once sailors have a couple of years of skippering experience under their belts.”

Courtesy Waypoints Yacht Charters
Courtesy Waypoints Yacht Charters

3. Bareboat or Crewed?

Bareboat versus a crewed charter is like comparing camping to a stay at the Ritz, describes Dick Schoonover, manager of the crewed yacht clearinghouse, CharterPort BVI, in Tortola. “Perhaps the ritual of getting up in the morning and making coffee yourself is something you relish. Or would you prefer to softly awaken to the aromas of freshly brewed java wafting through the air, the morning’s fresh grind already prepped by your top-notch charter chef? Meanwhile, your affable captain has already checked the anchor, hauled in, or stowed whatever water sports gear may have been in use, and is prepping your yacht for the next day!  Easy-peazy!  On a crewed yacht charter, all you have to do is determine how much milk or sweetener you want in that first cuppa joe.”

Crewed yacht charters are usually ‘all inclusive’ in pricing, meaning the crew, including everything from navigating to cooking and cleaning, and water toys on board, are included in the prize. Bareboaters need to provision, cook, and clean on their own. Water toys are often an extra charge.

Generally speaking, experienced skippers prefer to bareboat, says Horizon Yacht Charter’s Hayes. “We occasionally do get experienced skippers choosing crewed charters for special occasions, or skippered charters if chartering a larger yacht than they are used to sailing. If you have no sailing experience, then you have to have a skipper or crew onboard.”

Courtesy Dreamyacht Charters
Courtesy Dreamyacht Charters

4. Monohull or Multihull?

Monohulls offer a classic sailing experience with their traditional design and excellent upwind performance, says Waypoints Yacht Charters’ Restauri. “They can provide a more intimate connection with the sea and are often favored by experienced sailors. Multihulls, such as catamarans, offer stability, spaciousness, and shallow drafts that allow you to access shallower anchorages. They’re great for those who might be prone to seasickness and those who prefer more space and comfort. Your choice should depend on your sailing preferences and comfort priorities.”

Photo courtesy of Carol Kent Yacht Charters International
Photo courtesy of Carol Kent Yacht Charters International

5. Power or Sail?

Motor yachts offer a lot of freedom timewise, says Nicholson Yacht Charters’ Sebastian. “They are fast and stable and can get to the destination very fast, giving more time for watersports, shore excursions and just relaxing in a picturesque anchorage. Motor yachts are more expensive as fuel and food are always extras, they usually have more crew than a monohull or multihull, so the service is 5-star star.  They nearly always have motorized watersports equipment and trained crew to teach guests how to use it safely. Motor yachts do make a great option to charter for a group of friends or a family.”

On the other hand, “sailing offers a quieter and more eco-friendly experience, allowing you to savor the journey and the beauty of the surroundings. If you’re looking for a leisurely and immersive experience, sailing might be the way to go,” says Waypoints’ Restauri.

Photo courtesy of Carol Kent Yacht Charters International
Photo courtesy of Carol Kent Yacht Charters International

6. Bring the Kids?

The idea of yachting with youngsters and teens sometimes gives parents pause: What if they get bored? What if they need to be constantly supervised? What about the internet for entertainment? says Carol Kent Yacht Charters International’s Kent. “Yachting with babes to teens, each age group requires thoughtful packing and planning. Whether you hire a nanny for the babes or take your teens on a magical week of hiking, swimming off your boat, fishing, and using water toys, this vacation beats Disney!”

Essentially the yacht is a huge playground for kids with swimming and watersports every day, theme nights, and treasure hunts, adds Nicholson’s Yacht Charter’s Sebastian. “Crew love to have families with children onboard. Children also gain a whole new wealth of experience without even knowing it and a very healthy respect for the water.”

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Carol M. Bareuther, RD, is a St. Thomas, U.S. Virgin Islands based marine writer and registered dietitian.

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