News & Advice

Sailo Is the Latest (and Most Luxurious) Way to Travel to Cuba

The Airbnb of boats has launched a two-week chartered yacht trip that will cost you a pretty peso.
Image may contain Transportation Vehicle Boat Yacht Human and Person
Courtesy Sailo

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

Ever since the relationship between the U.S. and Cuba was restored in December 2014, the travel industry has jumped at the opportunity to get Americans to the once forbidden land. The first commercial flight between the two countries in 55 years took place in August and Carnival launched the first cruise in May. So, it was only a matter of time before a luxurious travel option would be available to tourists.

Sailo, the Airbnb of boats and yachts, just launched a bespoke two-week private yacht trip from the Florida Keys to Cuba. Travelers can customize the experience to their liking, but generally the trip includes island- and national park-hopping; private curated tours of Old Havana; sailing to the private island of Varadero; and partaking in water activities like scuba diving and lobster fishing.

All of this takes place on a 103-foot yacht that can hold up to eight guests and includes over-the-top amenities like an on-deck pool, barbecue, sun lounges, full bar, waterslides, two inflatable trampolines, two turbo jet-skis, snorkeling gear, paddle boards, and the optional add-on of a 37-foot Yellowfin tender fully stocked with fishing gear. Oh, and four cabins that could rival any five-star hotel.

This image may contain Human, Person, Vehicle, Transportation, Ship, Cruise Ship, and Boat

What It Was Like on the First U.S. Cruise to Cuba in 50 Years

“We have been captivated by Cuba, a land with a fascinating culture, history, and immense natural beauty—and, until recently, just beyond the reach of the average traveler,” Adrian Gradinaru, CEO and founder of Sailo, told Condé Nast Traveler. “And of course it’s surrounded by water, so we have created the Sailo Cuba boating trips as a perfect way to rediscover this land of wonder that’s just hours away from the coast of Florida.”

Although traveling to Cuba no longer requires the process of going through a travel agency, obtaining a visa, boarding a chartered aircraft, and keeping to a structured schedule, travelers still have to fall under one of the 12 categories of 'Purposeful Travel,' as outlined by the U.S. Office of Foreign Assets Control (OFAC). But, as part of the luxury experience, Sailo also takes care of all the complicated logistical details like legal formalities, local expertise and support, and trip planning.

So, you're undoubtedly wondering, what's the price tag for this lavish Cuban getaway? A cool $140,000. That's a lot of cash to travel just 90 miles, but for some, extravagance is worth any price.