When I was presented with the opportunity to host a delegation of IYBA members to Cuba, my first thought was: “Wow! I get to see it before it’s over-developed – before it gets the Disney treatment”, as so many have put it. Because travel to Cuba by most U.S. residents was forbidden for so long, it was hard for me not to create a mental picture of a paradise undiscovered. Going there in person, however, showed me that while Cuba is indeed lush, tropical and cultural, it is by no means Shangri-la. And that is why it’s important that we as yachting ambassadors help to manage expectations about Cuba for our clients who wish to go.

Maria Romeu of Cuba VIP Yachts was our very excellent travel concierge, who attended to every detail of our journey. Since our purpose was to preview the marinas and accommodations ahead of the clients, the customized itinerary was specific to things that are important to charter professionals. She arranged marina tours; organized presentations by the marina personnel, and coordinated ground transportation, hotel accommodations, special private tours of hotels and retailers, and other unique requests that invariably pop up from such a large group. Our trip included a tour of two areas of Cuba: Havana and Varadero. These were two completely different experiences; both equally fascinating.

Day 1: Arrive in Havana

• Stroll the area

• Dinner at San Cristobal – This restaurant hosted

President Obama on his visit to Cuba.

Day 2: Old Havana Four Plazas walking tour

• Lunch at La Guarida

• Tour of Hemingway’s Havana Home

• Tour of Hotel National – Mafia Bar

• Salsa Dancing lessons (optional)

• Dinner on our own

Day 3: Day trip to Veradero

• Lunch at Waco’s Club

• Marina Veradero Visit

• Tour Hotel Xanadu Mansion – formerly the beach house of

the Dupont’s.

Day 4: Classic Car Parade to Marina Hemingway

• Lunch at Rio Mar

• Afternoon on our own

Day 5: Depart for the airport


The capital of Cuba, Havana enjoyed its heyday back in the 1930s and ’40s when the rich and famous came to take part in its famous nightclub scene. Today, this formerly vibrant city is haunted by poverty, and while many of its buildings display beautiful European architectural influences, they look abandoned, unsafe, and in desperate need of a pressure wash.

The Cuban government currently is undertaking a large-scale renovation of Havana, starting first in the historic old city, which dates back to Spanish colonial days. (So far, this massive project has only reached a few peripheral neighborhoods.) The Cuban capitol building, El Capitolio Nacional, is in the midst of renovation with scaffolding covering its dome. The building itself is nearly a twin to our U.S. Capitol Building, except, I was told, the footprint of the Cuban version is one foot wider and one foot longer. Kind of a “one-up” competition by the Cubans.

Directly next door to the capitol is arguably the most beautiful building in Havana, if not in this hemisphere: El Gran Teatro Alica Alonso. Our guide explained that the Cuban government spent many millions renovating its structure, and it now rivals anything you would expect to see in any great European city. This beautiful building now houses the Cuban Ballet and Opera, and is said produce some of the leading ballet dancers around the globe.

Havana has a very active arts scene, as is evidenced by the numerous art displays we saw in museums, hotels and restaurants, as well as outdoor murals. At the Hotel Park Central, we saw one exhibit so moving that our group had to do another lap around the display to take it in for a second time. The craft market has thousands of prints (some original, some made in China) for sale, for tourists who want to take home some Cuban artwork.

Salsa dancing lessons by the local Cubans is a must do for anyone visiting Havana. For $10 per person, local dancers hosted us through mastering the basics steps. After about 15 minutes of instruction, they whistled to their friends and a whole gang of local salsa dancers appeared, complete with authentic Cuban music and spicy Cuban attitude. It turned in to a totally awesome pop-up salsa dance party. Truly something for the bucket list!

The vintage car parade we took out to Marina Hemingway is also a must do while in Havana. Our guide ordered six classic convertibles to pick us up from the hotel, taking the route along Embassy Row, where most of the foreign embassies are located. These houses originally belonged to wealthy Cubans prior to the Revolution, and the neighborhood resembles the Art Deco district in Miami’s South Beach. The cars ranged from a 1928 Ford to a 1956 Thunderbird and all with varying levels original equipment. Everyone in our delegation rode out to the marina in a quintessential Cuban classic car. You couldn’t wipe the smiles off our faces.

Our lunch at La Guarida was equally memorable. Our tour bus took us deep into one of the most deteriorating parts of the city and parked right outside of a hollowed-out three-story building. The first two floors were abandoned, with an ancient, grand staircase leading up to the top floor. The restaurant had no sign and no street numbers. Locals didn’t even know the restaurant existed. The walls were riddled with pockmarks and holes that looked more like something you’d see in a building in Aleppo than in Havana. The second floor was strung with clotheslines where the staff were drying dozens of tablecloths and napkins used in the restaurant. We all thought we had been taken to the wrong place. But when we arrived at the third floor, the space came alive with typical Cuban restaurant décor, a fascinating mixture of antique china & garage sale style furniture, lively Cuban art on the walls and fine dining table service. The food was authentic upscale Cuban food in a hip restaurant scene.

Havana has its share of problems. The WiFi is iffy, if it exists at all. The hotels will change money to the local currency, called a CUC, but they regularly run out of money to exchange. There are no ATMs and I doubt you would have much of a chance to use a credit card, even if you have one that works in Cuba. The sanitation is spotty, and we found we often had to hold our breath and step carefully when walking through the city.

The hotels charge an exorbitant price for what some might consider less than optimal housing. Our hotel was clean and safe, but had basic rooms, very spotty WiFi, and not a very good breakfast buffet. Overall it was acceptable for non-discriminating guests like me, but your clients may have higher expectations. Havana does have more upscale hotel options., however. One person in our delegation had the opportunity to tour the Hotel Saratoga and said it was exquisite with a price point of around $550/night.


Our trip to Varadero was quite different. We loaded up the tour bus at 8 am for a three-hour ride out to see this mid-century resort town east of Havana. Along the way, we were stopped three times by the Cuban police, who informed us the roads were closed ahead for bridge repairs. Three separate routes, all closed for the same reason. But once we finally arrived, we were pleasantly surprised by the upscale amenities, clean and well-manicured landscape and relatively vacant, 1,200-slip modern marina. While not yet complete, a megayacht facility is being built here that will accommodate the increased electrical demands and requirements of larger yachts.

The resort town itself is similar to Port Lucaya or any other well-developed location in the Bahamas. In addition to hotels along the beach, Varadero has a straw market, a large waterfront restaurant, and even multiple catamarans available for day-long booze cruises. Our stop at the Hotel Xanadu Mansion was a high light, with everyone meeting on the third floor for a panoramic view of the beach and golf course, live music and mojitos.

Back in Havana, we found that the Hemingway Marina personnel are working very hard to provide the level of service we take for granted in our U.S. marinas. What we have to remember is that the Cuban people have only recently been exposed to yachts and the yachting lifestyle. Many things that we take for granted, like checking in at Customs, refilling water tanks or arranging for land excursions are not automatically/easily available to guests. The Cubans are trying to climb the learning curve quickly, but educating all of the parties involved to provide a high level of service takes time and patience. 

What is most important is to gently dissuade your clients from the idea that they can show up, waltz off their boat and discover a new-found, “forbidden” paradise full of capitalist pleasures. Cuba is still a communist country and the communist government is still very much in control. If you have clients who wish to go, please make sure to find a verified Cuba travel professional to help them navigate the uncharted situations that invariably arise on an adventure such as this. Our guide Maria was great, and there are many companies now specializing in yacht services on the island.

If I had to take one concept away from this trip, it’s that the Cuban people and their passion show through in every aspect of the country. If your clients want a cultural experience and don’t have 5-star service expectations, they will enjoy the Cuban people and their pride in their country. The art scene is fresh and enriching, the food is fantastic, and the contrast of pre- vs. post-revolution Cuba is fascinating. But, if your clients are accustomed to the finer things in life, and don’t like to be delayed or inconvenienced during their exploration of an island gem, then Cuba may not be ready for them.

See full photo gallery on IYBA website.

Article Author: Cindy Sailor