A Gay Guy’s Guide to Cuba

bookGreg Shapiro is a millennial travel hacker. From backpacking South America to sailing around the world, he’s visited over 35 countries and counting. Greg is thrilled to share what he’s learned in his debut travel guide. Follow his travels on Facebook and Instagram @GuidedByGreg.

We met Greg aboard our Fathom cruise last year and were impressed by his wit and travel knowledge. We’re excited to welcome this articulate gay traveler, writer and artist to the MeetMeOnBoard family.

We were delighted to hear that your book 12 Hours in Havana is now available. We’ll delve into the book in a minute, but what ignited your love of cruising?

My first cruise was to Alaska in the 8th grade. I performed in the kids’ talent show and the lounge singer let me reprise my act in the Centrum. She made me fall in love with the idea that someone could just travel the world and perform. In my mind, there was nothing more fabulous than that.

Gay Guy's Guide to Cuba

Working on Royal Caribbean Brilliance of the Seas

Where did you work before Fathom and what were your duties?

I was at Royal Caribbean where my official job title was “Digital Signage and ITV Content Specialist.” I was in charge of the all of the TVs and touchscreens on the entire ship. On the Anthem of Seas, I deployed the emergency signage system, so my muster station was on the bridge. Sometimes it was exciting, like during a huge storm, when I had to trek to the broadcast room to make sure that all of the passenger cabins got free pay-per-view movies. Hero moment! When I wasn’t exploring the different ports, most of my time was spent wandering around the ship.

Gay Guy's Guide to Cuba

Fathom Adonia docked in Havana, Cuba

We met you abroad Adonia when you worked for Fathom teaching Spanish to cruisers. Our trip was to the Dominican Republic, and your very next voyage was to Havana. In fact, it was the first cruise ship from the USA to sail to Cuba in 50 years. How did it feel to be a part of that historical moment?

It was the most incredible sail in of my life. From the moment we saw Havana on the horizon, an electric energy swept across the ship. The Cuban people lined the ocean wall and cheered our arrival. When I stepped out of the port onto the street, we were crowded like celebrities. It felt like I was meeting long-lost cousins at a family reunion.

Havana, Cuba

Tell us some stories that you remember about cruisers on those first few voyages to Havana.

Escorting an older couple on their motor-scooters. Havana’s streets are very uneven so we had to crisscross the street and ended up stopping traffic. The wife almost rolled into the ocean, but we grabbed her just in time. The couple didn’t seem to notice any of the commotion around them. In fact, they had a great time!

The most touching thing I witnessed was when I helped reunite a woman with her neighbors she hadn’t seen in over 50 years. She’s an American who had to flee Cuba with her family when she was a little girl. When I saw them all together, I was crying my eyes out.

What are some common mistakes that visitors make in Cuba?

Asking “Are you a communist?” You can come across as confrontational and put Cubans on the defense. If you’re insistent on talking politics, ask “What was life like for your parents growing up?” It’s a softer approach that lets someone open up on their own terms.

The streets of Havana, Cuba

The streets of Havana, Cuba

What strikes you most about the Cuban people?

They are multi-talented. They speak different languages, probably play an instrument, and are well-versed in history and politics. A college professor could be your tour guide, a heart surgeon could be your taxi driver. Cubans are also very familiar with music and entertainment from the United States. They watch episodes of “Game of Thrones” and “Scandal” from a weekly hard-drive that comes from Miami and then gets passed around the country. And they love Obama.

What should LGBT visitors know about Cuba?

Cuba has that same machismo culture as the rest of Latin America, but add a massive Revolution that weakened the Catholic Church, gave women equal rights, and brought with it new sexual dynamics. Compared to other Latin American countries, Cubans are much less conservative in their views on casual sex, dating, and marriage.

Still, the government has a rocky history of persecuting LGBT people. Though Fidel Castro did try to make amends for it before he died. Even though gay marriage isn’t legal, Mariela Castro, President Raúl Castro’s daughter, is an outspoken advocate of it, so that may change soon.

In Havana, you can find gay social life all around you, as Internet dating has not yet replaced interacting on the street and in bars. Public flirtation and affection is part of the culture. If Cubans think you’re attractive, they’re not afraid to let you know. One-night stands are common. If you’re looking to get laid, know that because multiple generations share an apartment, so you should probably offer to host. Most importantly, use the same caution that you would in any foreign country.

Gay Guy's Guide to Cuba

Besides the novelty (especially for Americans), why visit Havana?

As a Caribbean port, it’s barely lost its virginity. You don’t see the crazy development around the cruise terminal like you would find elsewhere. It feels like a European port, where can get off the ship and just fold yourself into the hustle and bustle of a real city. And the art and culture is so unique. Live music everywhere, gorgeous architecture, white sand beaches, tasty food, fruity cocktails, and all for a low price. Clearly, I’m obsessed.

We loved the fact that your book was well-organized, very clear and made a lot of information digestible. Tell our members how it works with the interactive map.

I’m a big fan of the travel app Maps.Me. It downloads offline maps to your phone, and then when you don’t have wi-fi or cell signal, the map only needs your iPhone or Android’s GPS to work. An app like this is perfect for a city like Havana.

You can download the restaurants, stores, museums, and other points of interest covered in 12 Hours in Havana as a set bookmarks with just a few clicks. You’ll have turn-by-turn directions and never get lost.

Gay Guy's Guide to Cuba

Now that your book is launched, what is in the future for you, Greg?

I’m going to take a short break from writing to get back to my art. I do wood carving and printmaking that’s inspired by my world travels, both on and off the ship. Check out my store on Etsy, NJWoodCo.

For more travel tips and photos, follow me on Facebook.

OUR TAKE: We can’t wait to get to Havana and this book will definitely be on our iPhones. The book is well-written and perfectly organized with different options for the time you have available, and works beautifully with the interactive map. Particularly important is that the map function works even in the spotty internet of Cuba. Five Anchors!

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  • Rob Belles

    SWEET!!

  • silvia

    You did know that being Gay in Cuba was illegal during the Castro regime, until they got wind of catering to all people, including Gays would add to the revenue brought in. So now, it’s very much part of tourism.