BEST TIME TO TRAVEL: Most people visit January – May. I visited during August and it was super hot, but it also meant fewer crowds, so we were able to stay and eat in better places. Just keep in mind that May – October is the wet season, so the chances of it being rainy are higher.

WHERE TO STAY: Generally, stay in Old Havana. More specifically, try to stay here. The owner is so helpful and friendly and the space is probably the most STUNNING Airbnb I’ve ever stayed in. if this isn’t your first time, or you want something less touristy, Vedado is cool too.

day 1.

Start your trip off in picturesque, Plaza Vieja. You’ll be surrounded by all of the colorful colonial architecture that you have probably pictured for this trip. Afterwards, head to the Capitolio for a tour. They often have weird hours for tours, so try to plan in advance if possible. For an early dinner, make sure you have a reservation at La Guarida. It will likely be far from where you are staying, so I recommend taking a taxi.

Afterwards, head to see the Cannon Blast (Cañonazo Ceremony). The ceremony begins at 8, so go a little early to catch the sunset. The area overlooks the water, so it is a beautiful spot for pictures.

To end your first night in Havana, embrace being a tourist and Head to Bodeguita del Medio. It just happens to be both mine and Hemingway’s favorite bar in Havana. Expect strong mojitos and lively dancing! There is live music every night of the week, so don’t worry about what night you visit.

day 2.

Start your morning with a walk through Habana Vieja. Most other tourists will be sleeping, but it’s nice to walk around and experience a busy Tuesday morning as locals head to work. After picking up breakfast along your walk, flag down a taxi driver in a traditional car to give you a driving tour of the city. In our case, our driver only spoke Spanish, so if there is a Spanish speaker in your group, have them sit up front. Also make sure to check out the standard prices online so that you can bargain with them.

Next, head to this cooking class for the BEST lunch you will have in Havana. This was probably one of my favorite parts of the trip. You will prepare all of your food (and drinks!) with people from around the world and learn about what it is like to live in Havana. The home that it is hosted in is beautiful and historic as well. If you have room afterwards, head to Helad’oro for some ice cream.

Take an afternoon siesta, and then head to El Chanchullero for dinner. The portions are massive, prices are reasonable, and the cocktails are wonderful as well. After dinner, you can check another Hemingway bar off your list at El Floridita. They are known for their daiquiri. It’s nice to have a drink or two here while listening to the live music, but if it’s out of the way, it might be worth trying to find a spot closer to you.

day 3.

If you aren’t American, and you have a day to spare, head to Veradero Beach for the day. A friend from Havana said that his family always vacationed here and it looks incredible. On the way, be sure to check out Cueva de Saturno as well. It is one of the coolest swimming spots ever—tucked away in a secluded open-air cave. I promise it’s safe and legit. DON’T MISS IT.

day 4.

Back in Havana, grab breakfast at the Hotel Amobos Mundos rooftop. Selections are limited before noon, but the views are beautiful. The coffee is very good. To stay on theme, you should then head to Hemingway’s Cuban home, Finca Vigía. The home is pretty well preserved, so you really get a feel for his personality. My favorite part was getting a glimpse at his library and seeing what other authors he read. Just note, some people there will try to take your picture, give you a flower, or tell you additional information about the house. They will expect a tip, so politely walk away if you aren’t interested.

For lunch, head to the rooftop of La Makina. I just stumbled across this place, but the ropa vieja was the BEST that I had the entire trip. Next, head to Hotel Nacional. This place is super boujee, but worth the cost of drinks. Lay on the plush sofas, sip a piña colada, and watch the parade around the garden. Just before sunset, walk down to El Malecon and walk along the sea wall. The walk is SO scenic and lively with locals. This is also on my do-not-miss list.

For a late dinner, head to Doña Eutemia. You need to go in person (probably a day or two in advance) to make reservations. If you are in the mood to continue on and party, head to Museo Fabrica Arte Cubano. It’s an art museum by day, club by night, and in former cooking oil factory, so it’s a cool vibe.

day 5.

Of all the things we did in Havana, Viñales was hands-down my favorite. Start early and head to Viñales for your cigar tour by horseback. This is the tour that we did and I cannot recommend them highly enough. The guides take you to visit friends and family to learn about agriculture in Cuba (particularly rum and tobacco) and then end the tour with the best meal that we had during our trip. All of the ingredients for the meal are grown in the garden that houses the restaurant. I believe this part of the tour is extra, so make sure you include it when you are booking. The views and food are INSANE. Then head back to Havana to enjoy your last night in town!