Personal Finance

Cuba on your bucket list? Here are a few tips

One of the many antique cars passes as steam rises from a manhole in Old Havana.
One of the many antique cars passes as steam rises from a manhole in Old Havana. The Washington Post

Baby boomers are flocking to Cuba as travel restrictions on Americans loosen and U.S. airlines prepare to launch commercial flights there shortly.

Last year, more than 7,000 travelers booked trips to Cuba through Road Scholar, an educational tour company formerly known as Elder Hostel that caters to older travelers. That’s up from just a few hundred several years ago, before travel restrictions began to ease. Though the American embargo against Cuba is still in effect, Americans can now travel there on their own if they line up a schedule of educational activities that fulfills certain criteria.

The average age of travelers on Road Scholar’s Cuba trips is around 60, compared to 72 for all other excursions, said JoAnn Bell, the senior vice president of program development for Road Scholar.

Travelers say they are scrambling to cross off bucket-list items but also see the country in its current state before too much modernization occurs.

Paul Tamburello, 75, completed a seven-day trip organized by Road Scholar last fall. Fascinated by the region since the 1962 Cuban Missile Crisis, the retired teacher from Watertown, Mass., was struck by how little commercialization had influenced the landscape in the decades since.

Royce Menkus, 66, traveled there in 2013 with an alumni group from UCLA.

“My husband and I have been trying to go to the far-away and more physically challenging places while we have the health and stamina to do so,” she said.

Retirees thinking about taking the plunge should heed a few financial tips, experts said:

– Mind the budget. A recent seven-day Cuban educational trip through Road Scholar cost about $4,000, including airfare from Miami, while some trips through college alumni organizations were advertised at about $5,500. Ask any potential tour companies what, specifically, is included in the package and get details on the luxury level of the hotels and food service. If you’re booking a trip on your own, check out, which lists private apartments, houses and rooms for a wide range of prices.

– Look for flight deals. Experts say hotel prices have already shot up by about a third in anticipation of U.S. airlines beginning direct flights, so finding a bargain flight might be your best route to savings. JetBlue said it will launch $99 one-way flights to Cuba from Fort Lauderdale, Fla., beginning Aug. 31.

– Be ready to rough it. Particularly if you’re venturing beyond Havana, Menkus said, be sure to ask detailed questions about the accommodations. Adventurous travelers know they won’t be staying in luxury digs on this kind of trip, but make sure you’re aware of what you’re getting for your money.

– Get clear on tipping. If you’re booking an all-inclusive trip, be sure to inquire about whether the operator will be taking care of gratuities along the way. Tamburello said tipping was included in his package and he didn’t get hit with other unanticipated fees, but it’s another item to factor in if you’re going without a tour company.

Beyond the immediate financial issues, Tamburello said, consider what value a trip like Cuba will have as you work through the retirement bucket list. Just looking for a beach destination and consider the educational requirements perfunctory? Wait for more upscale hotel development to take hold, experts said.

“It’s like the art we looked at on the trip. There is knowing what the market value of the art is, but the second part is what it’s worth to you because it represents the trip,” he said. “The real value of the trip for me is in getting a deeper knowledge of the people and the place.”