Featured, Travel, Travel Tips

How To Experience Cuba Part 2: Join a Group

December 12, 2016

So ya’ll know group trips are my favorite way to travel. My post about How to Plan a Girls Getaway is my most popular post of all time, so that must mean a lot of you like jet-setting with your girls too! When my crew isn’t heading to a place I want to visit, I usually look for groups trips with cool folks already going, throw it out there to a few ride-or-die travel homies, and #bookdatish immediately.

With a little help from Madame Google, I found an upscale travel group called Up in the Air Life  that visited Cuba in 2016, and plans to return next year. Over the holiday break I caught up with founder Claire Soares to see what it’s like traveling to Cuba with her company.

Claire. Girl. There are currently 14,790 people in the Up in the Air Life Facebook group. The sheer numbers can turn off introverts who can’t deal with all of those people. How do you take the 20 questions, 99 problems, and everything that goes down in the DM to create a smaller, cohesive experience for so many people?

Our trips that we curate typically host only 15-20 people. Only our “once in a lifetime” trips like Egypt and our Annual Meetup are larger trips with over 50 people. Our trips are unique in that the curators have gone to the specific destination, and 90% of the itinerary has been tested out and tweaked to meet our standards. We work with locals on the ground to ensure we have the latest and greatest across the board, and tweak as necessary to give customers the best bang for their buck.

What does “upscale travel” look like in Cuba? If I roll with ya’ll are we gonna be sipping Moët at daily cocktail parties on a yacht off the coast of Havana? Eating strawberries covered in edible gold, imported from a remote village in Heaven? Or did I take it too far there?

Ha! You have a great sense of humor and some great ideas! We may need to add strawberries covered in edible gold soon. All jokes aside, Traveling with Up in the Air Life, whether Cuba or any other destination, means “Just show up for a great time.” Last year for Cuba, our clients received an assortment of gifts including a custom made cigar box with their name on it, book bags, and much more. But shhhh! We can’t tell all our secrets!

Our upscale experience includes a fully curated itinerary focused on Afro-cuban history, dining at hip restaurants, and staying at a proper hotel versus a hostel. Last time we stayed at the Hotel Nacional, and this year we will stay at a hip boutique hotel with a rooftop pool. We have some tricks up our sleeves like drop top tours for the group, but let’s not spoil all the surprises.

Are the daily activities on your trips mandatory or optional? What about folks who want a little freedom to do their own thing?

All activities are optional on all our trips. Clients can always skip a day, although most don’t skip anything we plan. In our future trips, we are building more free time so people don’t suffer from FOMO and exhaust themselves.

Based on your experience in Havana last year, what are the top places you want to return to on next year’s trip?

Definitely La Guarida Restaurant. The rooftop absolutely blew me away! We will also will visit Collejón de Hamel, which is my favorite because of the music and dancing. You can feel the Afro-Cuban music in your soul – we are connected to them. We will also visit the Artisans Market in Havana for great local shopping and of course Casa de Africa, El Aljibe Restaurant (which received rave reviews from Anthony Bourdain), Plaza de Revolution, and much more

Here are a few highlights from our Cuba trip on Ebony.com

Well that all sounds awesome! Where can folks sign up? Do you need someone to hold your phone or clipboard something on your next trip? My schedule is currently open.

People can click here to sign up for the 2017 Cuba trip [May 2017]. We may have an opening for a clipboard holder in the future. We will keep your name on the top of the list! 🙂


If group travel isn’t your thing, no worries! You can save some money by planning your own, or enlist the help of a travel agent so you don’t have to lift a finger!  See below for more info on both, plus some of my own tips.

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