Over the last few years traveling, nothing has sparked more interest from followers and friends than my trip to Cuba. How to get there. What to do. Where to stay. So without further ado, here’s my ideal 7-day itinerary including a detailed Google Map with notes that should keep you busy and happy on your trip!
As the capital of Cuba, Havana (also known as “La Habana”) is the largest city and most popular tourist destination in close proximity to the international airport. Founded by the Spanish in the 16th Century, the city is now divided into three main sections: Old Havana (“Habana Vieja”), the area from which you’ll see most photographs of Cuba, Vedado (more of the urban business district), and then the more affluent area of the city which includes neighborhoods like Miramar.
It’s common for people to book accommodation upon arrival in Cuba if staying at casas (translation: local people’s homes), but if you want to book ahead, there are plenty of reviewed listings here.
Head straight to Obispo Street in Old Havana to experience the most exciting part of town — and also the area you’ve likely seen in all of the photos. Take in the colors, architecture, live music inevitably being played in the streets, and enjoy some churros or fruit from a cart to keep your energy levels high.
Lunch at El Chanchullero
Make your way over to this 3-level restaurant that serves up yummy versions of classic Cuban dishes. Depending on where you’re sitting, you’ll be in perfect positioning for a bird’s eye view of the comings and goings of the local crowd below.
Stroll the Plaza de Armas
Stroll around the Plaza de Armas for some souvenir and book shopping. If you want a little bit of Cuban film history, scope out one of the guys selling film poster/prints and prompt them with a few questions — just be warned, you may not get a swift exit from the conversation!
Mojito Break at NOA
Move towards the Malecon to NOA Bar Paladar for some mid-day mojitos — because those are required in Cuba! This spot is set in a cute little alleyway close to a wifi source with an ocean breeze, so you can cool down with a drink and check-in with life back home (although, when you’re in Cuba why would you want to)?
Rooftop Views From Hotel Ambos Mundos
Just before sunset, make a visit to Hotel Ambos Mundos, a pink hotel in the center of Habana Vieja (Old Havana) which has stellar rooftop views overlooking the entire city.
Important: Cuba is an incredible destination, but it’s best to protect yourself in case anything goes wrong. I use World Nomads for travel insurance to give myself peace of mind while on the road, and they’ve reimbursed me over $1,000 to date from travel mishaps.
Dinner at Habana 61
For dinner, Habana 61 is a great modern option for fresh and healthy food (some of the best we had during our stay in Cuba).
Drinks at Ernest Hemingway’s Watering Hole
End the night at El Floridita, a must-do for Ernest Hemingway fans as the writer frequented this now 100-year-old bar.
Start the morning with breakfast and coffee at your casa (most casas provide this, so make sure to ask if this is included in the price when booking).
The Oldest Hotel in Havana
Pop over to the Hotel Inglaterra, which is the oldest hotel in Havana and a fun spot for pictures if you enjoy retro signage! Across the street is an easy stop for the Habana Bus Tour which will take you all around the city.
See The Sights Via the Habana Bus Tour
Ok, let’s get one thing out of the way. I’m not one to normally suggest doing the tourist bus, BUT I particularly enjoyed this one for a few reasons. First off, it’s a super cheap way to cover a lot of ground around the city in a place where public transport is not readily accessible. Also, after a day on foot walking all around Old Havana, we enjoyed resting our legs and getting a different perspective from above. As a photographer, I especially loved this because there are so many cool buildings with intricate details to shoot from a higher vantage point. You can hop on and off the bus whenever you please and they don’t talk over the loud speaker the entire trip, so it’s quite relaxing especially on a nice sunny day — wear a hat or sunscreen!
Stop for Pictures at Revolution Square
Along the Habana Bus Tour, make sure to hop off at Plaza de la Revolucion where the famous Che Guevara mural is located.
Coffee Break at Cuba Libro
At the Colon Cemetery stop, hop off for pictures and walk five minutes to Cuba Libro, my favorite coffee shop and bookstore in Cuba with hippie vibes and a great selection of English books and magazines.
Dine at One of the Privately Owned Paladares
Paladares are the non-government run restaurants in Cuba and typically have better food than the latter option. Take the bus back into town and hop off to make your way to Atelier for dinner, a beautiful restaurant in the newer part of Havana which is consistently listed as one of the top paladares in the city.
San Cristobal is also a famous locale (make reservations ahead). It didn’t blow us out of the water, but the history behind this place (the Obamas made it famous) and atmosphere alone is worth checking out.
Socialize at the Fabrica de Arte
Don’t miss Fabrica de Arte open 8 pm – 3 am Thursday to Sunday each week. We sadly missed this because it was closed while we were in town, but I’ve heard so many great things about this hip cultural center which showcases art, photography, music and more.
The Parisien Cabaret at Hotel Nacional
End the night at the Hotel Nacional for the Parisien Cabaret show, one of the highlights of my trip. Many people decide to see the pricier show at the Copacabana as it’s more reputable, but my friend and I decided to go with this show instead and I’m so glad we did. It was entertaining, hilarious, impressive and cheesy all at once. Loved every minute.
Trinidad is a colonial town about four hours South East from Havana. It’s a beautiful, colorful town with a more slow-paced way of life and was named a UNESCO World Heritage site in 1988.
First thing in the morning, pack up and get a car to Trinidad (about a 4 hour car ride) with a stop for lunch in Cienfuegos, a small seaside town along the way.
Find a Casa with Rooftop Views
In Trinidad, it’s easy to arrive and ask around for accommodation on the spot (such is the way in Cuba). We stayed at Casa Amparo (see map for details), which is a spacious home in central Trinidad run by two very sweet ladies (they don’t speak much English but are extremely accommodating) and it has gorgeous rooftop views.
If you prefer to book accommodation ahead, check out Booking.com’s listings of over 500 properties in Trinidad.
Take a Salsa Lesson
Salsa dancing is a must while in Cuba. Call your casa ahead (if possible) to have them book a salsa lesson for you on the roof on the afternoon of your arrival.
Dinner at La Botija
Satisfy your hunger at La Botija for dinner, which is open 24 hours but commands quite a line around dinner time, so make sure to arrive before starvation sets in. They have quite a large selection of tapas style food — definitely one of the better meals we ate while in Cuba.
Salsa Dancing in the Square
After dinner, head to the Plaza Mayor to watch the salsa dancing commence. It costs about 1 CUC to get a seat inside the square. If you’re a lady, be forewarned that you will probably be asked to dance — so this is the perfect opportunity to put your new salsa skills to good use!
End the Night at Rincon de la Salsa
If you still haven’t had enough salsa, walk down the street to Rincon de la Salsa to get your groove on with the locals.
Explore the Streets of Trinidad
After breakfast at your casa, spend an hour or two wandering around the colorful streets of Trinidad (we spent most of our time wandering between the Plaza Mayor and Plaza Carillo).
Beach Bum it at Playa Maria Aguilar
Pack up a beach bag and grab a taxi to Playa Maria Aguilar which is only about 20 minutes by car for a couple hours of sunbathing and cooling off in the turquoise water. Just note: the food at the restaurants here is not great and there are no bathrooms, so just be aware going into it, but the beach is worth it!
Horseback Riding Tour Through the Trinidad Countryside
Head back into Trinidad in time for an afternoon horseback riding adventure that the casa can book for you. We did a tour for about four hours that took us through the gorgeous countryside to a waterfall, however, it started storming heavily and we turned right back around soaked without ever going into the falls. Make sure to check the weather for the best outcome! 2-3 pm is a good time to set off on this excursion.
Dinner at La Raddicion
Get back into town for dinner at La Raddicion, which has great lobster and vegetarian options as well. Their service can be slow (an expectation in Cuba), so make sure you’re not on a tight schedule before dining here.
Dance the Night Away in a Cave
End the night at the Disco Ayala, a semi-cheesy but have-to-see-once kind of nightclub, inside a cave. Check with locals about the best night to go because sometimes they do a show earlier in the night as well.
Visiting Viñales feels like seeing the real Cuba. It’s still a tourist town (and depends quite heavily on visitors), but with a local population of only about 10,000 Cubans, you get the feeling that it’s the kind of place where everyone knows each other’s names. Located in the Pinar del Rio region on the West side of the island, Viñales is the best place to experience the natural beauty of Cuba.
This will be the longest travel day, so strap in and get ready to nap during the 7-8 hour car ride — at least you won’t be driving! Cars are easy to hire around town in Trinidad. Your casa can either set this up for you or you can ask locals where to schedule a car and you’ll undoubtedly get steered in the right direction.
Check in to Your Casa
Arrive in Viñales around 5 pm, and check into Villa Farner’s, a modest little casa run by Lisette and Jimmy that sits in convenient proximity to the main drag in town (see map for details). Plus, the breakfast and rooftop views are to die for.
If you prefer to book accommodation ahead, Booking.com has over 300 properties in Viñales to choose from.
Grab Dinner in Town
Dinner. Be warned, there’s not much (if anything) in the way of good food in the main center of town in Viñales, so expect very basic and you may be pleasantly surprised.
Take in the Views of Viñales
Head to the rooftop of your casa (many in the area have them) for a sunset viewing overlooking the Viñales Valley. We spent a memorable night drinking wine and chatting it up with our casa hosts on the roof while each sampling our very first Cuban cigar — not a regular thing for me, but when in Cuba!
Dancing in the Square
Walk a few minutes to the main square of town for salsa dancing in the square and to mingle with locals.
Viewpoint at Hotel Jazmine
Start the morning off by hopping onto the local Viñales bus which has multiple stops at tobacco houses, the Hotel Jazmine (great views overlooking the Viñales Valley, but terrible food) and other local tourist attractions. It’s the most convenient way to get around and often cheaper than taking a taxi, so if you’re looking to explore the area outside the main square this is the way to go. You’ll find the bus stop right in front of the main square.
Lunch at Finca Agroecologica El Paraiso
Once you’ve worked up an appetite, head over to the best lunch in town at Finca Agroecologica El Paraiso, which is a family-run organic farm with incredible food. The views are unreal overlooking the Viñales Valley, but it can be quite the tourist destination as it’s the #1 rated restaurant in the area on TripAdvisor and surpasses everything else by a long-shot. Try to go when the tourist buses are gone for a more enjoyable meal. Also, word to the wise — these are the largest portions I’ve ever encountered in my life (seriously, ever) and they won’t wrap them up in takeout boxes for you unless you bring your own. Bring tupperware — you’ll seriously get three extra meals out of it!
Drinks at Palenque de los Cimarrones
For drinks and dancing, finish your night at Palenque de los Cimarrones which is another Cuban cave club (I preferred this one over the Disco Ayala in Trinidad). This club also comes with a history lesson, as the caves were a main escape for slaves. If you’re lucky enough to be in town on a Saturday night, you’ll witness a weekly performance here and chances are if you’ve met any locals around town, you’ll run into them here for a dance session!
Explore Cuba’s Largest Cave
Rise early for a cave spelunking tour at the Cuevos de Santo Tomas, Cuba’s largest cave system. We enjoyed a 90-minute tour with a small group as this location is not overrun with tourists. It was a nice respite from the heat to duck into the cool interior of the cave while learning about the stalactites and other geological formations. My favorite part, however, was the local pup who joined us on our tour — quite impressive as we climbed stairs and ladders to get there!
Pack Your Bags for Havana
Pack up and hire a share car back to Havana (about a two hour drive) to catch your flight out of town!
Hire a Vintage Convertible for Your Airport Transfer
For your final few hours, give yourself plenty of time before your flight and hire a 1950s convertible (the drivers act as tour guides as well) to take you to any spots you may have missed during your previous time in Havana. This is the perfect way to go out in style and also saves you money on an airport transfer!
Try The “Best” Pina Colada in Havana
Our driver took us through Miramar and more residential sides of Cuba to get a different feel for the local way of life. My favorite stop was to the Anfiteatro Parque Almendares, a park where our driver brought us to a spot where he claimed they made the best pina coladas in the city. As you can see, they came with an unlimited bottle of rum!
Make your way to the airport and say goodbye to this beautiful and lively country that I loved so much this year. Hope you get to enjoy a fabulous trip to Cuba soon!
Planning a trip right now? These are all the websites and services I love for booking everything from flights, tours, accommodation and more:
- Booking.com for the best hotel deals
- World Nomads for travel insurance
- Airbnb for awesome home rentals
- Intrepid Travel for group travel
- Skyscanner for finding the best flight deals
- Hostelworld for budget accommodation
- Rentalcars.com for easy car rentals