“This post may contain affiliate links, which means we may receive a commission, at no cost to you, if you make a purchase through a link. Please see our full disclosure for further information. If not otherwise stated, all prices are intended in US$.”
Arriving in Havana:
Welcome to Cuba! If you have landed and made it through customs, congratulations, you managed to complete the list of entry requirements and are on your way to an amazing adventure. To make your arrival to your Airbnb as smooth a process as possible, we highly suggest asking your hosts to set up a private car or taxi for you so that they are waiting once you exit the airport. Taxis to old town Havana run about 30-35 Euros for a 20-30 minute ride.
Exploring Havana:
Old Town Havana is full of charm and beautiful architecture. It is easy to spend a few hours strolling the streets and just taking it all in. From live music spilling out of paladars (family owned restaurants) to locals dancing in the streets, the energy of this city draws you in and will leave a lasting impression. Start your day with a coffee and an amazing local breakfast at El Dandy Cafe. We came here our first morning and quickly became regulars due to the excellent food, great drinks, and amazing hospitality (Do keep in mind that everything moves a little slower in Cuba, people aren't in a rush and that means meals are a much longer experience. Don't expect to get in and out while eating and enjoy the laid back experience). Also don't forget to stop at El Floridita for Ernest Hemingway's favorite Daquiri and La Bodeguita de Medio for his favorite mojito.
Classic Car Tour:
You cannot visit Cuba without taking a classic car tour! The best way to find one is to head over to Parque Central where you will have your pick of shiny convertibles and a few different tour options ranging from 1-3 hours, expect to pay 40-50 Euros per hour. You will be approached by many different drivers, all offering the same tours for the same prices, so it really comes down to if you like the driver and which car you want. The 2 hour tour is a great option which includes a drive through the city center, then out to the forest where you will stop for a pina colada with unlimited rum, followed by a drive past the old mansions of Miramar, and finishing up with a cruise along the Malecon. The other option is also 2 hours but goes over to the other side of the bay where the fortress and military memorabilia are, so if you are a history buff then this would be the best option for you.
Malecon/Nightlife:
Come evening time, the heart of Havana really starts to beat and the Malecon is where most of the locals flock. It is amazing to see so many people gathered around just catching up with friends and family along the seaside, enjoying some live music and a taste of some local fare. It is an experience not to be missed!
If you are looking for some other activities to liven up your evening, you can take in the sunset at the Hotel Nacional, watch the firing of the cannon at 9:00 PM over at the ancient Fortress of San Carlos de Cabana (or enjoy it from a restaurant rooftop such as La Moneda Cubana where you will have the perfect view from across the Harbor).
You can then finish off your evening with a visit to Fabrica de Arte Cubano, an art factory turned social hangout, nightclub, and art exhibit. Each room features something unique and different, for example when we were there, the exhibits included a DJ, salsa dance lessons, a pop up fashion show and an outdoor seating area for food and cocktails and each room is covered in art from local and famous artists. Our favorite way to get to areas outside of old town was by Coco Taxi's, adorable helmet looking scooters that whiz by in entertaining fashion. They run anywhere from $5-$10 for a 10 minute ride.
Still looking for more to fill in your Havana itinerary? Don't be afraid to chat with the locals, especially at your accommodations or in the restaurants. There are always events, festivals, and celebrations taking place and they are the perfect resources to help you discover them.
Exploring Vinales:
After a few days amongst the hustle and bustle of Havana, it is time to sneak off to the countryside for a more laid back experience and what most people travel to Cuba for.... cigars! While there are some bus routes that can get you there, we found it easiest for our Airbnb to set up another private car/collectivo (private taxis that fill all the seats with anyone wanting to ride in that direction to help keep costs lower). For 2 passengers, the 3-hour private car was 40 Euros per person or a collectivo would be about 30 Euros.
Vinales is a very quaint town consisting of one main street, nestled in the hills of the Cuban countryside, but don't be fooled, there is still plenty to do, starting with the market that pops up along main street each day. Here you can find local artists, crafts, souvenirs, etc. Take a stroll down Salvador Cisneros to check it out and make sure to stop at 3J Bar de Tapas for a meal, or all of them during your stay! Another great option is Plaza Cafe for their awesome Lobster dinner!
Tobacco Plantations:
Let's be honest, if you have made the trek out to this part of the country, you are really here to experience the tobacco plantations. There are many different tour options available, some that you can pay for with a credit card through Airbnb prior to arriving in the country (note that once in Cuba, sites like Airbnb won't be able to process your requests so make sure to do all bookings in advance) or you can have your Airbnb host set up a tour for you! Simply chose which time of day you wish to go and they will pick you up in front of your casa by a horse drawn carriage and bring you to the tour guide.
The tour is about 4 hours and includes a ride from town out to the plantations on well fed and cared for horses. Once out on the plantations, you will be able to experience local honey, rum, and of course cigars! Enjoy smoking a cigar and sipping rum while learning about the tobacco process and watching them roll cigars right before your eyes.
Varadero:
Voted the best beach in the world back in 2019, Varadero is the perfect white sand beach with clear blue water to end your vacation! Once again you will be finding either a private car or collectivo to get from Vinales to Varadero and since you will be backtracking through Havana to get there, you are looking at a full day of travel with usually a car change in the capital before continuing on your way. Estimate about 50-60 euros per person for the ride.
The reason to visit Varadero is of course for the beach. The town is very touristy, with many large, all inclusive hotels for non-American travelers, more expensive restaurants with food that wasn't quite as good as it was in other parts of the country, but it was worth the trip to relax for a few days on that beach!
There are a few stands that rent umbrellas and chairs for the day, but make sure to get there early on the weekends because they sell out quickly. If you enter the beach near Calle 54, there will be a few restaurant stands selling simple plates of fish or chicken with rice, perfect for lunch. Their hours vary though so we suggest trying to eat before 2.
After a day of soaking up the sun, it will be time to go out and explore for dinner. For a more laid back "cheaper" option, El Rancho on Avenida Primera is a good spot for a meal and if you are looking for something a bit more fancy then head over to Varadero 60 on Avenida Tercera for some excellent seafood and Italian style past dishes. If you are lucky, there will be live music to enjoy with your meal.
Time to head home:
The last day of your trip has arrived and after a little over a week of new memories, being immersed in culture, and a few delicious mojitos, you will hopefully be heading home with a greater appreciation for the Cuban culture. To get to the airport, make sure to give yourself plenty of time! We recommend getting to the airport 3 hours prior to your flight as customs leaving could take a while (we waited in line for over an hour). The collectivos usually have set times that they leave each town so check with your host and get scheduled on one if you plan on using that over a private car and keep in mind that they can run up to 30 minutes late. If you miss it, there is a good chance that there won't be another one until the evening or the next day.
Copyright © 2024 The Itinerary Investigator - All Rights Reserved.
All photos are taken by the itinerary investigator team
We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.