My Epic Itinerary in Havana, Cuba: Where to Eat, Drink and Relax

For my birthday this year, I decided to take my third trip to Cuba, especially since some of my friends were already going to be heading there. I'm lucky enough to have met a few people on the island — Celia Mendoza of Concierge Habana — who helped put together an epic itinerary that turned this last-minute weekend trip into the vacation of a lifetime.

Setting the Stage

We stayed in villas in Vedado, arguably the most "posh" neighborhood in the city, bordering central Havana and Miramar, a historic district filled with embassies. Be warned: booking luxury villas in Havana is tricker than it is in most other places. While we went through a frustrating array of changes in villas and less than transparent pricing, at the end of the day, we ended up paying €6,200 (~$6,648) ‎for three days in two huge villas with a total of 12 bedrooms — seven in the main villa and five in the other — complete with our own security, cooks, staff, a fully-stocked kitchen and a nice private pool and cabana area at the main house. All in all, it worked out to about $185 per night per room.

Paying for our stay in euros allowed us to save a TON of money (about 10-15%), so it may make sense to change your dollars to euros in the US before your trip so you won't get hit with the 10% tax + 3% fee for exchanging dollars in Cuba — the euro is pretty close to parity with the US dollar at this point anyway (~$1.06 at the time of booking). On top of that, we noticed most places that wanted to charge us in US dollars weren't even calculating anything close to the current exchange rates, so across the board, it was cheaper for us to pay with euros instead.

Concierge Habana's itinerary also provided lots of opportunities to interact with the Cuban people so it would satisfy the US government's "People-to-People" visa requirements. I don't use travel agents often, but for trips to Cuba I absolutely recommend it, especially since they can work out all the payments in advance so you don't have to carry a ton of cash around — since there aren't any ATMs in the country — and they're familiar with all the top places to go.

On this trip, our group even had security built into the price, which wasn't really necessary to have from a safety perspective — Havana is safer than most international cities — but proved to be amazing because they were able to get us into the very best clubs and restaurants and we never had to wait in a single line or worry about dealing with the language barrier (even though many of us do speak Spanish). It's always great to have a local show you around, especially in Cuba where you can't Google everything the way you can here in the US — the internet access is very limited!

There are plenty of other things to do in Havana, so by no means is this a definitive guide to the city, but here's a look at what we did and the places we visited. We all had an amazing time and I hope you will, too!

Day 1: Havana's Art Scene and Dinner at La Guarida

My friends and I arrived throughout the day in Havana and I managed to get through customs and immigration within 15 minutes after landing. My secret: don't bring along checked luggage, as it can take forever to come off the plane and it's not uncommon for items to get lost. The group and I spent a nice, relaxing day by the pool and went for pre-dinner cocktails at the The Candy Factory, a 10,000-square-foot art studio and exhibition founded by Damian Aquiles that's carved out of the old Estrella candy factory in Cerro, just behind Estadio Latinoamericano, the baseball stadium President Obama visited on his historic trip to Cuba.

Damian Aquiles is the husband of Pamela Ruiz, an American living in Havana and a really fascinating person I had met on my first trip to Cuba. They'd set up The Candy Factory as a place to see Damian's art and host events, so it was a really cool space to kick off our weekend and talk with the artist about his work.

I'm a huge fan of his "Running Men" piece, which is made from the hoods of vintage cars that are on their way to the scrap yard. After my first visit to Cuba, I purchased 50 for around $6,000 and installed them in my kitchen at home — they get shipped individually so you can buy as many as your heart desires. If you're interested in his art, his wife Pamela (who is from New York) was great to work with and shipping artwork to the US was very easy.

For dinner, we headed to La Guarida, arguably the hottest spot to eat at in Havana. It's located inside a gorgeous early-twentieth century palace and is where everyone from European monarchs to movie stars dines when they're in town. Madonna had her birthday party there, so clearly, I had to as well!

After a fabulous dinner, we headed over to La Fábrica de Arte Cubano, or, the Cuban Art Factory — known for being a place where locals come together to enjoy jazz, contemporary dance, concerts and other exhibitions — where we received a guided tour of the space and had drinks upstairs in the VIP area.

Day 2: Vintage Cars, Gay Beach and Havana Nightlife

Day two began with us being picked up in classic American cars, which is something everybody should experience at least once on a trip to Havana. Because there were a lot of Cuba newbies in the group, we decided to take a tour by car around the city through Siboney, Miramar and Central Havana, stopping to visit art galleries like Arte Continua, and to get a better look at Havana Vieja, the 500-year-old colonial part of the city that's now a UNESCO World Heritage Site.

I had never realized that there was such a vibrant gay scene on the island — Raul Castro's daughter, Mariela, is a very ardent supporter of the LGBT community. Cuba also happens to be one of the only countries in the world where transgender individuals can receive free gender reassignment surgery. As far as the Caribbean goes, many countries are anti-LGBT rights, especially in Jamaica, where transgender and LGBT people have been killed.

Although I know Cuba has a dark history in terms of human rights — like jailing dissidents — I found the atmosphere to be surprisingly welcoming to the LGBT community. We had many gay people in our group and at no point did we feel discriminated against. Our hosts (Celia and Pamela) also introduced us to a lot of other gay people while we were there.

We went to "Mi Cayito," Cuba's first gay beach, located about an hour outside the city center. I recommend renting chairs and eating a delicious lobster and fish lunch out on the beach. The waves were great, the water was warm and the locals were very friendly, so it was a fun day for all.

We couldn't visit Havana without seeing a show at Tropicana Cabaret, which also offers a pre-show dinner — I tried it on my first visit, though, and the food was sub-par even by Cuban standards, so instead, I highly recommend going out to dinner elsewhere before seeing the show. We had a great meal at La Cocina de Lilliam, one of Cuba’s oldest traditional paladars (private restaurants) and the winner of the International Arch of Europe (IAE) award in 2013.

This was my second time at the Tropicana and it was just as spectacular as I remembered. A dance extravaganza under the stars, I highly recommend sitting as close to the stage as possible. Celia was able to get us the very best table in the house and we also went up on stage after the show and shook it Cuban style, thanks to the free bottles of Havana Club rum that come with your admission!

After the Tropicana show, we headed over to popular gay club Karabali for an epic drag show, where we had a table at the stage (thanks again to Celia). The drag queens were amazing and lots of laughs and dancing ensued.

Day 3: Sightseeing, Pamela's Dinner Party and Dancing All Night

We had a nice lunch in Old Havana at El del Frente, which has a great open air roof deck and amazing cocktails. This place is known for its muddled fresh fruit and rum drinks, so needless to say, our meal dragged on for several hours. The food was okay, but the best part was that no one had their cell phones with them, so our meals were so much more enjoyable because we actually paid attention to each other — and not our phone screens!

Our last night in Havana had to be special, so we went all out. Pamela Ruiz (who we'd visited on Day 1) is known for hosting these epic dinner parties where you can see anyone from diplomats, politicians, big names — like Katy Perry and Nancy Pelosi — and now, The Points Guy! It's always a cool mix of people at her house and I even got a chance to meet fashion designer Nanette Lepore. If you're even in Cuba and Pamela's having a party, know that she does keep it pretty exclusive. That being said, if you book your trip through Pamela and Celia with Concierge Habana, they can usually make it happen for you.

After dinner, we ventured over to Café Cantante Mi Habana, which had a really long line to get in. With a great mix of locals and singers, it was a great spot for us to dance the night away. Remember to dress to impress though, as shorts and flip flops aren't allowed.

Day 4: Flying Home on Spirit

Many say you need to get to the airport three hours early for international flights, and while you probably don't want to risk it, three hours seems a little extreme, especially since I managed to get through security at José Martí International Airport (HAV) in 20 minutes on this trip.

HAV isn't very nice, although there is Wi-Fi you can purchase, but it's pretty slow. There aren't a whole lot of food options either, although there is a solid VIP area (just kidding). Instead, I'd recommend getting to the airport about 1.5–2 hours before your flight so you don't have to kill so much time there.

I actually flew Spirt back to Fort Lauderdale (FLL), which was a surprisingly decent experience and didn't cost me much, although the carrier did just announce it'll be ending service to the island on June 1.

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Global Entry isn't even a question when you're flying back from Cuba, as it cuts down on time spent in customs when you get back to the States. I told the customs officer at FLL that our trip's purpose was "People-to-People" since we'd met lots of Cuban folks and artists throughout our stay. Note that the customs agents seemed pretty flexible when it comes to that and no one in our group had any issues — you can purchase your visa through the airline before you go, no questions asked. We had no issues with visas on the Cuban side either.

Bottom Line

Overall, it was a zero-stress, super-fun weekend that was less than an hour flight from Miami. Flights are pretty cheap right now and you can stay at an Airbnb or at Casa Particualres if you want to save even more money and get to know the locals. As for hotels, Hotel Saratoga is really nice, but pretty expensive. And remember, it's cash, cash, cash in Cuba — you won't be able to access any ATMs in the country so make sure you bring enough to last for your entire trip, plus a little extra for emergencies.

Booking it all through our travel agents Cilia and Pamela from Concierge Habana made planning the trip so easy — they know everything that's going on in Cuba so they can tailor a great trip for you. And just for full disclosure: I have no business relationship with them, I'm only speaking so highly of them because they planned such an amazing visit for me — if they can get 18 high-maintenance New Yorkers to have a flawless vacation, that's saying something. It was an amazing 34th birthday in Havana and who knows where I'll go next year.