For many travelers there is a certain Mystique that Cuba and in particular Havana holds. The largest Island in the Caribbean is a treasure of Spanish Colonial architecture, breath taking beaches, classic American Cars and being one of the final bastions of communism. Frozen in time is one of the descriptions I use to convey the feeling and emotion of being in Havana. Every where you cast your eyes you cannot be but reminded of being in a place that has changed little since the late fifties.
Getting to Havana may be the most expensive part of your getaway. Flights at reasonable prices are available through gateway cities in Canada and you can catch a flight daily on Cayman Airways from Grand Cayman, which is well served from Miami, New York, Atlanta and other airline hubs.
For a short break Havana will entertain you and leave you wanting much much more. Location of your accommodation is the key to maximum absorption of Havana’s sights, sounds and smells. My choice is Old Havana or La Habana Vieja. Here you are in the beating heart of Havana and you’ll be using the best mode of transport, your feet. Hotel Florida provided reasonably priced rooms that are clean and comfortable with a great location on Obispa/Obispo Street. For an authentic experience you also may choose to stay at a Casa Particulare. These are family homes that operate like a Bed and Breakfast. For the equivalent of $25-30 us you can have a room where the home owners can also cook you breakfast for 2-3 CUC and an evening meal for $7 to $10.
The street of Obispo is a narrow and busy pedestrian thoroughfare abuzz with tourists and locals alike. Designated as one of the areas for restoration by the government the look and feel of this street is slowly changing and becoming more sterile. However there are plenty of street vendors and market areas keeping the old feel and vibe of the area alive. Peso pizza and Ham Sandwiches (bocadito de jamón) are the staple street foods. For 1 or 2 convertible (1CUC = 1USD) you will have yourself an authentic taste of Cuba. Meat is a scarce commodity and the street vendors and food outlets aimed at the locals don’t always have access to meat supplies, so some times the only thing on the menu is Cheese Pizza and Cheese Sandwiches. Further up the scale of eateries there are plenty of places aimed squarely at tourists and they have tourist prices, but it is safe to say that for 10 CUC you can have a hot meal and a beverage if you don’t feel up to the street food. Prices vary so brows around. The parallel streets of O’Reily and Obriapia are quieter and contain many wonderful bars and restaurants.
Wandering the local markets and streets here is enough to occupy a full afternoon. Havana is a photographers dream with stunning colors and contrasts that will quickly fill your memory card.

For one of the best panoramas of the city I recommend you make your way to the rooftop bar at Hotel Parque Central. It seems as this bar is for hotel guests only but if you walk through the lobby confidently to the elevators and take them right to the top, you will be rewarded with stunning views from this Pool Bar perched atop one of Havana’s most historic hotels. From outside the Parque Central one can find many of the remaining Classic American cars that operate as Taxis. These are a tad more expensive than the more modern air-conditioned tourist taxi fleet but to indulge yourself in the nostalgia of being in such a beautiful automobile it is worth the little extra. Take a ride to Plaza de la Revolution where you can see the José Martí memorial and the iconic Che mural on the side of the Ministry of the Interior, (previously the Havana Hilton Hotel) For a more cost effective means of transport within the city the Coco taxis are a fun and exciting, they look like a giant yellow helmet on three wheels powered by a small motorbike engine. A unique and cheap way to get around with fares being 2-3 cuc.
Returning back to Old Havana get dropped off at the Capitolio Nacional which is one of the landmarks of Havana and immediately recognizable from it’s similarities to the US Capitol Building. A short stroll across the plaza here and you will find the terrace of Hotel Inglaterra, a perfect perch for having an evening cocktail and people watching as you unwind from your whirlwind day of sight seeing.
Heading out on the town is an experience and Cubans really know how to have a good time. The city is alive with the sounds of live music during the day but this really intensifies once the sun goes down. Worthy of a cab ride is visit to the popular El Aljibe restaurant. A popular restaurant with the tourists staying at the more upscale hotels in Havana, the pollo asado El Aljibe (CUC$12) house specialty is a must have. This restaurant is more up scale than your typical Cuban eateries and also attracts some of the movers and shakers in Havana but for less than 25cuc you will wine and dine like a king.
The European tourists flock to La Floridita, home of the Daiquiri and a favorite of the late Ernest Hemmingway, it retains some of the old world charm with bartenders in their signature red evening jackets, but even better is Bar Monserrate around the corner, which has a good mix of locals and tourists, live music and reasonably priced beverages approx $3-$4 US.
An authentic old Cuban pub in the form of Bar Bilbao is a must for the adventurer (on O’Reily St). Sparse in its furnishing and limited in it’s beverage selection this gem is decorated with soccer memorabilia and is one of the cheapest bars in Havana. This is a local bar and as such doesn’t carry the Cuban Premium beers of Buccanero or Crystal. Here they have lower grade of beers and rums, and, and if you manage to get your hands on local pesos the drinks here cost the equivalent of 20 cents, albeit they have an acquired taste.
If the music and atmosphere of Bar Monserrate has left you wanting more then continue your evening at the Casa de la Musica. There are two, one in the Miramar district of the city which is the better of the two and one in Centro Havana which is still a fantastic night of Salsa, with big name Cuban Artists playing regularly. Entry can be between $5 and $15 depending on the time you go (Earlier is cheaper for 6pm-9pm) but the 10pm will have you meeting colorful Cubans who love to dance and meet the tourists, the music is sublime with 10-12 piece bands showcasing Cuba’s rich musical heritage. For those looking for a more up beat “club” like experience I suggest the Salón Rojo at the Hotel Capri in Vedado. The Cabaret/Variety show has a little of everything and attracts quiet a younger crowd than perhaps the more traditional Tropicana.
Words of caution however. In the bars and primarily ones like the Casa de la Musica, and Salon Rojo, there will be advances made by pimps and prostitutes. Generally speaking once you mind your own business and tell anyone offering you companionship etc to leave you alone they generally do. If you do wish to buy anyone a drink or drinks I advise that you pay on consumption and know how much you are paying. In some of the less well-known bars there are scams that involve you thinking that it’s ok to run a tab and four drinks later you may be forced to pay the equivalent of $100 us. The Cuban people are wonderfully warm and sociable people, however there are those that will take advantage. Do not let this deter you from engaging with any one but do exercise caution with all your interactions. From any of my trips to Havana I have always felt safe but trust your instincts and do not let any one on the street guide you or bring you to a restaurant, club or a bar at night.
About the author:
Brendan O’Connor is an hotelier with many years experience in Luxury Travel and Accommodation. For personal pleasure he discards the suit and dons a backpack veering off the beaten path in search of authentic travel experiences and local cuisine. Having left his native Ireland he has worked and traveled extensively in Europe, US and Caribbean, and currently is traveling around Australia. He Tweets random Hospitality and Hotel insights @brendanoconnor_
I was lucky enough to be able to go to Cuba last year. I had 7 days in Havana, and while I didn’t fall in love with the place I am so glad that I went. La Floridita was a sight, and I enjoyed walking around the streets, popping in for a Havana club on ice and a Romeo y Julieta cigar at some pretty cool bars, and cruising along the promenade in a moto. I decided to spoil myself on the last night, so after 7 days of staying in casa particulars I splurged on a night at the Ambos Mundos Hotel, where I was treated to a tour of Hemmingway’s pad (room 511), great hotel though I did manage to get the worse food poisoning I’ve ever had from their restaurant – beware of the club sandwich.
Cuba is definitely an exceptional place. Having been there several years ago I can attest to the beauty of the island. With the economy going the way that it has, it seems that vacations to the Caribbean are cheaper than ever. If you are looking for summer travel deals, I know that the Caribbean has some great deals for the fall as well. I saw the other day that the US Virgin Islands has a fantastic flight package. The details were posted on Travelzoo. Having been to the Caribbean I can definitely attest to the beauty of the islands.