What to Wear : CUBA

Photo by  Jules Appleby  on our trip, March 2018

Photo by Jules Appleby on our trip, March 2018

So you’ve already booked your trip and the countdown is on, but what outfits should you pack? You want to be comfy while looking good. We totally get it! We’ve been visiting since 2015 so we’ve nailed it down for you. We’ll guide you from head to toe.


Hats are super recommended. This will protect you from the warm, Cuban sun throughout our walks in the city and while we hang beachside. Bring your cutest sunhat, cap, etc.


Sunglasses are must so don’t forget ‘em! You’ll wanna protect yourself from that bright sun…especially if you’ve had one too many mojitos the night before. We’ve all been there!


Light breathable fabrics like cotton and linen are your bff here. Cuba is warm, typically in the 80s, so tees and tank tops are advisable. Everyone is usually dressed very casual so you won’t stand out. A light jacket or long sleeve is also advisable for evenings depending on the month you’ll be visiting.

Photo by  Andrea Posadas  on our trip, March 2018

Photo by Andrea Posadas on our trip, March 2018


Casual dresses made with a lightweight fabric are perfect, not only for photo ops, but they’re so comfy during a day spent exploring the city. Something a little flowy or loose will be comfortable to walk in under the warm sun.


Shorts for men and women are the way to go! Your favorite denim shorts or something in cotton are great choices. Skirts and light weight pants are other great options. If you’re doing a fancier dinner out, you’ll want to switch out from the shorts into pants, skirt or dress.


Think comfy! You’ll be doing a lot of walking. A lot of the roads and sidewalks are uneven or cobble stoned, which will do a number on your feet in heels. We know it sounds cute for that photo with a classic car and if you prefer fashion over function thats totally cool too, but don’t say we didn’t warn ya! We recommend you opt for stylish sandals, flats, or sneakers. You’ll thank us later!

Photo by  Jules Appleby  on our trip, March 2018

Photo by Jules Appleby on our trip, March 2018

Basically, Cuba is very warm so as long as you keep that in mind while packing you’ll be good. Overall, a more casual look will be perfect for your time in Cuba. Bring a nice, “smart casual” outfit or two for a night out or dinner, but other than that casual is the way to go. If you have any more specific questions, shoot us an email.


What You Really Need to Know About Visiting Cuba (Now)


A note to our fans, from Natalie and Andrew

Photo by Nicholas Roberts

Photo by Nicholas Roberts

Written by Tyler Anneliese Moselle

Last week, you may have heard the news about President Trump’s new travel restrictions in Cuba. We watched the press conference with anticipation and were brokenhearted to learn that travel to Cuba will be lessened.

 We want you to know, that our trips have always been aimed at supporting local families and businesses, and will continue to do so. We pledge that we will continue to bring groups of curious, like-minded travelers to Cuba in the hopes of creating more peace and understanding.

 Since we began bringing groups to Cuba over the last two and a half years, we have witnessed the positive changes that the influx of tourism has brought firsthand. We were fortunate to be in Havana the week that President Obama visited Cuba. What we witnessed was the hope and positivity of a new future for both Cubans and Americans.

 Good, hard working people were finally able to open their own businesses and begin to vastly improve their lives.

 In 2016 alone, non-Cuban American visitors to the island soared 74 percent thanks to return of commercial flights. Cuba’s 615,000 visitors from the US last year was a record, while still a fraction of the island's 4 million visitors.

 To us, the tightening of travel and commercial ties with Cuba feels like a step backwards.

We want to let travelers better understand how the new policy will change travel going forward.

 Take a closer look at exactly what POTUS’ newly-signed, six-page directive calls for:

  1. In the regulations, travel is now restricted to people traveling with groups with OFAC licenses.
    We are fortunate enough to be one of those companies.

  2. You’ll need to know what exactly constitutes legal forms of travel to Cuba going forward.
    Should Americans want to visit Cuba for “educational purposes”, they can only do so in tour groups, just like before 2016.

    While under President Obama, U.S. travelers could travel under a dozen various license categories—from educational, relgious, journalistic, family-related visits, or even simply under a “general” license—tourism was still prohibited.  

  3. President Trump is cutting out what are known as “people-to-people trips”.
    This is sub-category of “educational purposes” allowing U.S. citizens to tailor their own trips and travel to Cuba on their own—definitely one of the most popular methods with  U.S. travelers since President Obama and President Raúl Castro of Cuba announced they would begin begin normalizing relations between the two countries  back in 2014.

  4. Those visiting for educational reasons will now be required to apply with the Treasury Department and visit with a licensed tour group.
    (Like us.)

  5. Island visitors can continue to “self-certify” under a general license that they are traveling to Cuba for one of the reasons that are left.
    Also, Cuban-Americans should know they can continue to visit and send money to their family in Cuba.

  6. The new policy additionally prohibits financial transactions which benefit the Cuban military’s business arm—a.k.a. Grupo de Administración Empresarial (GAESA).
    This is POTUS’ effort to put more money in the pockets of free and private Cuban businesses and cut the influx of cash to Raúl Castro's regime.

    So, U.S. travelers will have less say about where they spend their money in Cuba, as the Cuban government has control over plenty of the travel and tourist economy. This includes state-run hotels—even one of the first hotels to open on the island in decases, the Four Points by Sheraton Havana among other big brands—restaurants, and more.

    (It’s estimated that 60 percent of the total Cuban economy is under GAESA’s authority. Perhaps up to 80 percent of the tourism economy is controlled by them, too.)

  7. Renting private properties, like Airbnb rentals, will be permitted.
    Diplomatic relations and Obama's revocation of the "wet foot, dry foot" policy that gave Cubans preferential immigration treatment will also stand.

  8. Americans can continue to return home with their Cuban cigars.
    (Thought you should know.)

  9. But not everyone agrees this is a smart move.
    Congressional Democrats and some Republicans seeking more engagement with Cuba and business-minded conservatives—the U.S. Chamber of Commerce, for example—argue this could hurt U.S. businesses and jobs.

  10. What about commercial flights, you ask?
    Last summer, air travel began between the U.S. and Cuba for the first time in over 50 years. These flights will continue uninterrupted under Trump’s Cuba policy, however with lower anticipated travel, a number of carriers will be scaling back their Cuba operations. So if that keeps up once people-to-people trips halt, tour groups may be forced to book more expensive, charter flights. Cruises will also be permitted to make stops

  11. Okay, but when does all of this go into effect?
    Since Friday June 16, the U.S. Treasury and Commerce departments have 30 days to kick off drafting all the new rules under POTUS’ new policy. We’ve also heard “the process takes as long as it takes”.

  12. Travelers who have already scheduled a trip to Cuba can still travel as planned.
    ...until the new regulations take effect.

  13. Not everything is clear yet.
    The Treasury Department must share exactly what this means for those who book trips before the new rules, but visit the island after they are release.

We will contintue to stand with the people of Cuba. None of this will stop us from sharing the “live like a local” experience with more eager travelers. If anything, it will spur us forward to continue to bring our two amazing cultures together!

 If you have any questions we didn’t answer here, please don’t hesitate to contact us or leave a comment below!