Destinations, Trips from Orlando

What to do in Cuba: Cuba Itinerary for 4 Day Trip to Havana

I just got back from an AMAZING four day weekend in Cuba — primarily in Havana. Let me tell you, it pays to do your research.

We explored Havana and surrounding areas. Havana is amazing, but you want to know what you’re walking into. If I can say one thing: do your research. In our day an age, we are so “internet reliant” — we just don’t plan like we used to in times past. This don’t fly in Cuba. With limited internet, you want to know your game plan before you go. Even if you vary it, you’ll want a strong starting point.

Weekend itinerary for what to in Cuba – 4 days in Havana Cuba with this Orlando native.

Since I’m insane about research and planning, enjoy the fruit of my neurosis! Or, if you’d like to read Yelp and Trip Advisor for 100 hours, go for it.  🙂  I spent a year reading about Cuba (with increasing compulsion) before we went. And yes, we’re going to go again!

Weekend in Cuba: 4 Day Itinerary for Havana

Day #1 – Friday: Airport Arrival

Arrive in Havana. Get picked up from the airport by your Air B&B host. (They pretty much all offer this now.) It’s about $25-$35, depending on your host. It’s worth it, since that initial moment when you walk out from the terminal you just want to see a sign with your name on it. After you leave the airport, you need to change your money.

You’ll be immediately impressed with the outfits on the airport staff too.

Airport in Havana Cuba – Weekend in Cuba Itinerary

**TIP: Bring British Pounds or Euro, or any currency other than American dollars. You’ll get more from your exchange.

You will notice that pretty much all the cars in Cuba really smell like exhaust and are definitely “vintage”—but isn’t hat part of the charm? Your Air B&B host will be a great resource for you, so make sure to shower them with questions.

It’s nice to get an airport pickup when you first arrive for your weekend in Cuba.

Our Air B&B house in Havana was a really beautiful old mansion. We chose to stay a little bit outside of Havana Vieja (in Miramar) since it was cheaper and quieter. We paid about $30 a night for 2 people. You do have to budget in a $10 cab ride to get into other parts of the city though. (Get a $40 Air B&B coupon from here.)

I really loved how each room had a private second floor balcony. Great for sitting there in the morning with coffee or just writing in the evenings.

Our Air B and B in Havana had beautiful old world charm.

Our Air B and B in Miramar near Havana — about a 1 hour walk or a 10 minute cab drive. Quiet and with beautiful gardens.

We stayed in Mirama, about 10 minutes outside of Central Havana Cuba.

 **Tip: When you get to your Air B&B, immediately ask them to help you call the restaurants you want to eat at. You’ll need reservations to get in anywhere good.

Day #1 – Friday Lunch: El Chanchullero de Tapas

After you get to your Air B&B, you can head into Havana Vieja to start your afternoon. I recommend heading to El Chanchullero de Tapas. This amazing restaurant has some of the best (and best priced) food in Havana. If you don’t have a reservation, which you probably won’t have since you just got to Cuba, just ask to go to the rooftop terrace. You can sit on the 3rd floor terrace and get cocktails and tapas. The tapas are amazing: fresh ceviche, black beans and rice, little toast with chicken salad, tuna fresh.  The mojitos and piña coladas are about $2 each and they will make non-piña-colada-lovers LOVE piña coladas. (“You must try life to experience it,” said a Frenchman on the roof as he offered us his.)


Read about El Chanchullero de Tapas on Yelp here. Sure, it feels a little like a roof top spot in Brooklyn. But is that really bad? We loved it.

Bar of Tapas, is located in Lieutenant King 457A low, and / Bernaza and the Christ, (Place of the Christ), Habana Vieja, Havana, Cuba. A few minutes from places of reference such as: The Capitol, Hotel Telegrafo, Hotel Parque Central, Hotel Inglaterra, among many others.

Photos of El Chanchullero de Tapas:

Delicious tapas which really are more of a lunch. Drinks here are also INCREDIBLE!

Amazing tapas on the rooftop in Havana Vieja

Amazing mojitos and tapas on the rooftop of El Chanchullero de Tapas — if you don’t have a reservation, ask to go upstairs.

Want to eat INCREDIBLE food in Cuba? Head to this hipster feeling restaurant.

Amazing ambiance in this Havana Cuba restaurant.

Delicious food at this place in Havana – definitely on your Cuba itinerary!

El chanchullero menu, wonderful prices & food!

Day #1 – Friday: El Dandy People Watching

After lunch wraps, you might want to head 1 block down the street to El Dandy for a post-lunch drink or just to sit and people watch.


Read Yelp review on El Dandy here.

Street Brasil 401 | Plaza de Cristo in Old Havana

Pictures of El Dandy:

El Dandy is a delightful old world Hemingway style bar with no tourists, just genuine vibes. Enjoy some people watching there after lunch.

What to do in Cuba? Visit El Dandy, a great little place to chill.

El Dandy in Havana Vieja – great spot for your weekend in Cuba itinerary. People watching here is perfect!

What to do in Cuba? People watch in Old Havana.

Day #1 – Friday: Walking Tour

A great way to really get a feel for old Havana is to do a walking tour. Get in touch with me for a recommendation on a great 100% fluent English speaking tour guide. We used a 22-year-old named Gabriel who was super fun, fair, and very knowledgable.

Pictures of a walking tour:

Walking tour of Old Havana.

Watching the Cuban people – a favorite pastime for Americans in Cuba.

A walking tour is a great way to see old Havana – a must for your weekend in Cuba itinerary!

Walking tour sights of old Havana – weekend in Cuba.

See the amazing architecture and history of old Havana in a walking tour – great idea during your weekend in Cuba!

What to do in Cuba? Take a walking tour! See Plaza de Arms.

Havana Cuba is a photographer dreamland. What to do in Cuba? Take pictures!

Enjoy walking around old Havana Cuba.

What to do in Havana Cuba? Enjoy the architecture!

What to do in Cuba? Enjoy art in Havana’s hidden corners on a walking tour.

Day #1 – Friday: Dinner at Dona Eutimia

If you’re looking for a cute little old world Italian feeling place, this is just so quaint and lovely. It’s not uber-modern posh like El Cocinero (where the NYT review will immediately send you), but we liked it. And the lamb shredded is just insanely good. And the grilled meat on the stick takes about 25 minutes to cook, but it’s also amazing. You can’t go wrong with Dona Eutimia, but make sure you make your reservations! (You don’t get ranked #14 on Trip Advisor without being good.)

Weekend in Cuba – try eating at this delicious restaurant (as long as you make reservations!) Dona Eutimia is delicious.


Read Yelp review Dona Eutimia here.

Callejon del Chorro # 60-C | Plaza de la Catedral, Habana, (537) 8013332

Wonderful, delicious place to eat for around $5.

Day #1 – Friday: Jazz at La Zorra y el Cuervo

Ready for some Cuban jazz? Head to the classic choice. It’s going to be a taxi ride from old Havana, but so worth it. If you like jazz this is your place. Check it out. It’s amazing live jazz Cuban music. Every day a different band. Saturdays that they host a radio show in the afternoon and have a happy hour.


Read Trip Advisor review La Zorra y el Cuervo.

Avenida 23 | Entre N y o, Havana, Cuba

Day #1 – Friday: Jazz at Bertolt Brecht Cultural Center

Want to explore another jazz scene? Try out this one! For a $5 cover, you get 2 incredible hours of salsa/funk/fusion with Interactivo, one of the most exciting and funky bands in Cuba. Considering the quality of musicianship and the level of hype in the audience, $5 is really worth it. Arrive around midnight and get ready to stay out late!

Read Trip Advisor review and info.

13 Street 258, Havana 10400, Cuba

Day #2 – Saturday: Explore Callejon de Hammel

Explore the amazing street art and creativity here.

Read Trip Advisor review Callejon de Hammel.

Avenida 23 | Entre N y o, Havana, Cuba

Explore this arty part of Havana, perfect for a Saturday morning.

Day #2 – Saturday: Lunch at El Del Frente

Did you make a reservation? I hope so! This place is delicious and amazing. If the weather is nice, ask to sit on the terrace. If this place is booked, make a reservation and do the full lunch at Cha

Read Trip Advisor review on El Del Frente.

Their Facebook:
Visit their Facebook link here.

303 O’Reilly, Havana, Cuba
+53 7 8630206

Day #2 – Saturday: Hotel Rooftops

We really enjoyed visiting the grand hotels in the middle of old Havana. We went to the roof tops and enjoyed a beautiful late afternoon hangout / sunset chat with drinks.

Pop over to the Hotel Inglaterra, which is the oldest hotel in Havana and a fun spot for pictures if you enjoy retro signage! Go upstairs and see view from the roof.

Hotel Inglaterra, the oldest hotel in Havana and a fun spot for pictures.

Grab a drink on the rooftop of Hotel Inglaterra, the oldest hotel in Havana.

Sunset view from Havana Cuba downtown hotel roof.

What to do in Cuba? Enjoy sunsets and write a novel like Hemingway.

Day #2 – Saturday: Fabrica Des Artes Night Visit

La Fábrica de Arte Cubano — this feels like a mix of CBGB, Art Basel Miami, a community center, a coffee shop, a bar (or two or three) and a bomb shelter. Arrive for folk dancing, and you may end up lost, in a good way, listening to reggaeton or staring at sculpture, huge canvases of colorful paintings, or black-and-white photography. “It’s an urban experiment,” said Inti Herrera, a member of the artists’ collective that runs La Fábrica with permission from the government, which owns the building.

Cost & Caution:
There’s a 2cuc cover and you’re given a card to resemble their ration book that you’ll have stamped for every purchase. No money is exchanged at the beverage bar or infusion-snack bar, you pay on your way out. However, don’t lose that booklet or you’ll pay a flat rate of 30cuc.

Visit their Trip Advisor review page here.

Calle 26 | Corner 11, Havana 10400, Cuba (Calle 26 Corner 11, Vedado)

What to do in Havana Cuba? Do NOT miss Fabrica Des Artes!

What to do in Havana Cuba? Do NOT miss Fabrica Des Artes!

What to do in Havana Cuba? Do NOT miss Fabrica Des Artes!

What to do in Havana Cuba? Do NOT miss Fabrica Des Artes!

Fabrica Des Artes is a mecca of amazing modern art in central Havana. It is a MUST see on your Havana Cuba itinerary!

What to do in Havana Cuba? Do NOT miss Fabrica Des Artes!

In the middle of Fabrica Des Artes you’ll find the Cuban version of Anthropologie — except all the dresses are made by crazy talented old seamstresses from Havana.

Amazing food in a shipping container attached to Fabrica des Arts – Havana Cuba things to do!

Fabrica Des Arts – Havana Cuba (Hip poster art and best Cuban Sandwich EVER!)

Enjoy modern art in Havana Cuba – put this on your 4 day itinerary for Cuba!

Fabrica des Arts – artsy fun in Havana Cuba – put this on your itinerary!

Check out Havana’s modern art scene at Fabrica des arts!

Day #3 – Sunday: Beach or Pool Day (You pick!)

This will depend on you. Santa Maria beach is about 1 hour (they say 30 minutes, but it’s an hour with traffic.) This will cost you $20 each way. If you prefer pool, go to the nicest one.

A cab to the beach at Santa Maria beach  will cost you $20 each way from Havana Cuba.

Beach about 30 minutes to 1 hour from Havana. Nice beach day trip.

If pool is more your style, visit one of the downtown pools for the day in Havana Cuba.

Beach view from the top of Hotel Parque Central Havana, Cuba

Either beach or a nice hotel rooftop is a great way to spend a day in Havana Cuba – make sure you have a day of lounging by water in your itinerary!

Day #3 – Sunday: Enjoy Old Havana at Night

Old Havana, Havana Vieja, has a certain charm at night. Walk around and absorb this.

What to do in Cuba? Enjoy the culture or Old Havana at night. It feels like a Vincent van Gogh painting with the lights and the old buildings.

Havana Cuba at night – Americans in Cuba.

Day #3 – Sunday: Grab a Drink at El Floridita

Want to be a tourist? Grab a daiquiri at Hemingway’s old joint, or at least take a picture. (Supposedly famous for the daquiri and still unmatched.) Visit their website here.

Head to El Floridita —the old Hemingway hangout.

Day #4 – Monday: Chill at Air B&B  and Head Home…

Pack up your things, say enjoy a nice coffee and breakfast at your Air B & B and head out for your flight.

We loved the quiet garden outside of our Air B and B. Great for chilling.

We loved our Air B and B hosts in Havana Cuba!

Cuba Itinerary – Havana Cuba – Weekend in Havana

Other Thoughts:

  • But I like to “wing it” on vacation. Isn’t this itinerary kinda too planned?
    • Sure, go ahead and “wing it” in Cuba. But just a head’s up, when we went to restaurants with no reviews, they weren’t great. We got paella in one place and it was practically rotten. We had to send it back. Americans know what Americans like (on some level). I love finding out of the way, hole-in-the-wall places too. But sometimes, it’s just nice to have others with similar interests help you discover those spots.
  • I want to visit a fancy pool but not stay in a fancy hotel. How does that work?
    • Ah-hemm… There is a $20 “pool fee”, but we found if you pay cash for your drinks, it’s not really a question we’re asked. Again, call the hotel for the official policy. (And no hotel elevators have swipe cards to get to the roof in Havana.) You can kinda just visit any pool you like in any hotel you like. If you do pay the pool fee, we were told they give it back to you in mojito credit on the roof.
  • How do I change my money when I leave Cuba?
    • Try not to. At the airport, the line to change money was insanely long. (Not worth missing a flight.) And the airport attendants say “just change it in the terminal area.” But when you get in there, the machine is conveniently broken. Yep. Lesson learned. Don’t be one of those New Yorkers (we saw a few) running around trying to hustle some arriving party to change cash because they needed to get rid of $300 in CUC.
    • Change only the money you’ll use. And try to get rid of it with a friend or fellow traveler before you leave.

I Want MORE Cuba!

Want to spend more time in Cuba and see other areas? Fantastic idea! You might consider horse back riding in Trinidad, about 4 hours away from Havana Cuba. There are beautiful coffee plantations and tours there.

Beach in Trinidad:

Beach in Trinidad Cuba. A four hour trip from Havana.

Coffee plantation tour in Trinidad:

Awesome authentic tour of Trinidad Cuba.

During the tour, they bring out coffees for you to sample and play live music. A little touristy? Yea, but still a lot of fun!

Ride horses in Trinidad Cuba.


  1. Ruthie

    April 24, 2017 at 4:45 pm

    Thank you!! Really appreciate your post!

  2. Neeta

    August 26, 2017 at 8:10 pm

    Thanks for this terrific itinerary idea. It sounds great- considering a trip to Havana and will definitely borrow a lot of these ideas:)

  3. K Stevenson

    December 25, 2017 at 10:31 pm

    How were you able to make the reservation at the air b/b having an American credit card?

    1. iamvioletta

      April 16, 2018 at 3:23 am

      We paid through Air B&B with our American credit card. Yes.

Share your thoughts!

This site uses Akismet to reduce spam. Learn how your comment data is processed.