Visit 12 Islands for $19,999 With the ‘ClassPass’ of Caribbean Travel

Nov 16, 2017

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Welcome to Caribbean Comeback, in which TPG shines a post-hurricane, pre-season spotlight on the region. Stay tuned for more stories throughout the week, and be sure to share tips in the comments if you’re planning an upcoming trip. 

For most of us, New Year’s resolutions take the obvious form: eat healthier, be nicer to strangers, start volunteering more. But, a website that offers travel deals to the Caribbean, thinks people should aim higher in 2018.

The site’s new Beach of the Month Club works as follows: You can join anytime from now through Dec. 31 by paying a one-time fee of $19,999 per person. Starting the second weekend of February — and continuing every second weekend of every month thereafter, for a total of 12 months — you’re sent to a different Caribbean island. Each trip lasts three to four days and is covered by that initial $19,999 outlay — including flights. And anyone can sign up, just as long as they can fly to and from a U.S. destination.

The Pitons on St. Lucia. Image by Paul Baggaley / Getty Images.
The Pitons on St. Lucia. Image by Paul Baggaley / Getty Images.


CheapCaribbean plans to withhold destinations from club members until two to four weeks before departure — a travel roulette, of sorts. (And for some, maybe part of the fun?) Throughout the year, though, members will touch down in Antigua, Aruba, Grenada, Grand Cayman, Curacao, St. Croix, St. John, St. Lucia, Turks & Caicos, St. Kitts, Barbados and Bermuda (which is often grouped with Caribbean travel even though it’s not technically in the Caribbean Sea). Save for St. John and St. Croix, most of these islands were spared the worst during the hurricanes this fall. CheapCaribbean had this list planned before the storms, and a rep explains that the company will continue to monitor recovery efforts on the two U.S. Virgin Islands before firming up exact travel dates. The company will also monitor the weather — one can imagine the brouhaha that would ensue if Beach of the Month Club members were sent to a scorching-hot destination in the middle of August or, worse, an island in the path of a hurricane.

Although you can’t choose hotels, all of them will be four- or five-star, and half of them will be all-inclusive. CheapCaribbean hasn’t confirmed specifics yet, but they’re looking at properties like Bucuti & Tara Beach Resort, a 104-room, eco-friendly boutique hotel in Aruba, and the Santa Barbara Beach & Golf Resort in Curacao.

How does the math work out? At the Santa Barbara Beach & Golf Resort, advance-booking rates for the second long weekend in February (Feb. 8 to 11) range from $230.30 (for a resort-view double) to $258.30 (for a water-view king) — about $691 to $775 for a three-day trip, and $921 to $1,033 for a four-day trip. (The highest-end suite goes for $1,126.30 a night, but it’s doubtful that’d be on offer for Beach of the Month Club members.) And sure, February is still high season. In May, a search for the second weekend (May 10 to 13) yielded advance rates of $161.85 (for a resort-view double) to $200.85 (for a water-view king) — or about $485 to $602 for three days and $647 to $803 for four. Subtract that from each trip’s total expenditure — 12 trips for $19,999 computes to $1,666 per trip, per person — and you’ve got a good sense of where airfare factors in.

By comparison, if you tried to independently book those February and May dates at the Bucuti & Tara Beach Resort, you’d encounter a five-night minimum. (Other availability searches indicate that the property is considerably more expensive than the Santa Barbara Beach & Golf Resort.) 

Image of Barbados by Tristan Ashurst / Getty Images.
Image of Barbados by Tristan Ashurst / Getty Images.


With so many good points flights and points hotels in the Caribbean these days, it’s clear this initiative — the latest in a long line of monthly subscription services, from ClassPass to BarkBox — will draw its share of skeptics. But Dana Studebaker, CheapCaribbean’s senior director of marketing, stands by its upsides. First, members don’t have to do any heavy-lifting; signing up for the service requires clicking a button and filling out an online payment form. And once you’re part of the club, you don’t have to plan any part of any trip. “A whole vacation is booked for them, and all they have to do is wait for the next getaway’s details to be sent through,” she said. “That’s it.” Customers don’t even have to think about the dates of their trips — they just need to be free every second weekend of every month, for a year. That in itself is an interesting proposition; you’re not allowed to change the itinerary, even if you’re faced with a scheduling conflict or have a personal preference about visiting some islands over the others. And, with the exception of the food and drink at non-inclusive resorts, all of the trips are fully paid for ahead of time, allowing members to fully submit to vacation mode. “The club members won’t have PTO (paid time off) days stockpiled with nowhere to go at the end of the year,” Studebaker added.

So far, no has signed up for the Beach of the Month Club yet (it launched Nov. 1). Being sent to a secret Caribbean island every month may sound swell — if a little stunt-y — but it’s hard to compare this program with, say, a new case of wine waiting on your doorstep every month. The right customers will have a lot of free time, some considerable spare cash and, as Studebaker points out, a certain type of spirit. “It’s really for those wanting to do something daring in 2018,” she said.

Featured image by Ian Rogers Photography / Getty Images.

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