Take a quick trip to Cuba with Sunset Key Cottages’s turnkey, completely curated tour that brings travelers through the heart of Havana and has them home in time for dinner.


For generations, the logistics of visiting Cuba have made the island seem much farther away than the 50-minute flight from Key West to Havana. But now that the once-reclusive island has reintroduced itself to America, Sunset Key Cottages offers its guests a headache-free, single-day trip to experience the nation’s culture, including rum making at the Havana Club Museum and a trip through a sweet-scented cigar factory. Here’s what else to expect.

What’s Included

The all-inclusive trip for you and five others (note: you must all be guests at Sunset Key) includes a private flight, ground transportation, all activities, all meals, and a personal escort and trip facilitator (to secure the visas, file the necessary paperwork, and orchestrate all the excursion’s elements). This isn’t a getaway that requires hours of online research on your part – you’ll be able to relax knowing that someone else is handling the details.

Before the Trip

The night before the trip, a rum expert will host an in-cottage tasting of various types of rum for your group and discuss the rich history of this spirit that has fueled Cuba’s economy for decades. Then, at 8 a.m. the next day, you’ll be whisked to the Key West Airport to meet your personal escort and hop on a private 50-minute flight bound for Havana.

Itinerary Highlights

You’ll eat well in Cuba, with breakfast and lunch at notable Havana restaurants like Floridita, La Bodeguita del Medio, or La Guardia (depending on the day). After breakfast, your group will embark on a private architectural tour – walking or driving, depending on your preference – led by a Havana historian, who will point out the city’s architectural high points, like art deco gems Teatro América on Galiano Street and Hotel Nacional in the Vedado neighborhood.

Later, a local cigar sommelier will pull back the curtain for your group during a private tour of one of many cigar factories. Housed in old colonial-era buildings all over Havana, they look very much the same as they did in the mid-nineteenth century. You’ll get an inside look at the process, the people, and, of course, the tobacco. Finally, there’ll be a private, docent-led tour of the Havana Club Museum of Rum. Calling back to your tasting the night before, you’ll get to see the rum-making process in action, from the sugarcane to the distillery to the ageing cellars.

If time permits, the group’s escort will take you shopping, to additional art galleries, or out for drinks – whatever you prefer with what time is left over.

Where to Stay Sunset Key Cottages