Cuba has long been one of my most asked-about trips, and for good reason. With so many misconceptions surrounding travel, especially for Americans, I totally understand the curiosity. Yes, you can visit Cuba legally, and we did under one of the 12 approved travel categories. “Support for the Cuban People”. And that’s exactly what we did. What unfolded was one of the most eye-opening, heart-expanding experiences I’ve ever had. Find recap here & here

Entry & Accommodation

Visa: Costs $100 and is purchased at the airport before your flight. Please note give yourself time to fill out the forms at the airport.

You can’t stay in government-owned hotels, so you’ll need to book a casa particular (a private homestay). Honestly, this is the best way to experience the real Cuba, it’s more personal, more immersive, and supports locals directly.

Where to Eat

Santy Pescador A must. The swordfish was incredible. My favorite meal in Cuba. It’s tricky to find, but worth it.
El del Frente Get the mixed tacos.
ChaChaChá Bar-Restaurante The food was just okay, but the WiFi is strong (a rarity!).
El Floridita Bar Have a daiquiri here like Hemingway did. It's a classic.

Cigar

One of the items on my “30 Before 30” list was to smoke my first cigar in Cuba.. We booked a Cuban cigar master class that included rolling, tasting, and a full hands-on experience. It was one of the best activities of the trip. Our host was incredibly passionate and knowledgeable.

Tip: Book with IVAN – Here’s the Airbnb experience. Highly recommend! This experience made me really appreciate cigars and now I smoke them even back home!

Beyond Havana

While Havana is the heartbeat of Cuba, I strongly suggest exploring beyond it.

Miramar is full of stunning architecture and embassies (the Moroccan one is especially beautiful).
Varadero is known for its gorgeous beaches. It was chilly when we went, but I’d love to return and experience it properly.

Giving Back

I filled my luggage with basic necessities to donate. Items like women's care products, baby clothes, diapers, soap, toothpaste, medication, non-perishable food, and small toys are incredibly hard to come by in Cuba. And when you do it’s insanely expensive a Barbie around 100 USD.

I gave away everything I brought. I carried some Barbie's & Hot Wheels to give to kids & I’d highly recommend doing the same. It’s a small gesture that goes a long way.

The Reality

Cuba is beautiful, but it’s also a place filled with hardship. Visiting really put things into perspective for me. I left feeling more grateful than ever — especially for the simple things we often take for granted.

Things to Note

WiFi: Extremely limited and unreliable. Definitely not the place if you need wifi to work remotely.
Food: Don’t expect culinary excellence — ingredients are scarce. Embrace the experience for what it is.
Money: No foreign bank cards work in Cuba and there are no banks to take cash out. Bring plenty of cash and exchange some into Cuban pesos (We exchanged around $400 is a safe amount for 3 nights)
Snacks: Pack your own! I brought things like crackers and jerky, anything simple. Even if you don’t need them, you can donate them at the end of your trip.
SIM cards Although we didn’t end up using local SIM cards, in hindsight, we definitely should have. I have AT&T and my man had T-Mobile, and our international data wasn’t covered—so our phone bill ended up being very high. Something to keep in mind.

Cuba is rich in culture, history, and spirit. It’s a destination that will move you, not just for its beauty, but for the strength and warmth of its people. I hope to return one day, and I encourage you to experience it for yourself — mindfully, respectfully, and generously.