The Perfect Five Day Cuba Itinerary

I know from experience that planning a Cuba trip can be intimidating. If you want to travel to Cuba but haven’t done much research yet, check out a few general tips here. Figuring out the travel logistics can be complicated and confusing, and itinerary planning isn’t much easier. There is not much information out there on Cuba. Websites are sparse or nonexistent. Figuring out just how to get from point A to point B isn’t easy. After A LOT of research, Britton and I went to Cuba and had an incredible time during our five day trip. From a show in Havana to waterfalls near Trinidad, we got a great taste of what Cuba has to offer. Here is our itinerary:

Day One: Arrive in Havana and stay the night.

Day Two: After breakfast in Havana, drive 2.5 hours to the beaches of the Bay of Pigs. Go scuba diving with a local dive company. There is beautiful shore diving and you’ll get a chance to see deep blue water and a vibrant reef. If you have your own mask, I highly recommend bringing it, as most of the dive shops have worn out gear and the masks are scratched and not easy to see out of. Stay the night in Cienfuegos. Cienfuegos is relatively small, and food options are limited.

Day Three: Drive one hour to El Nicho waterfalls. Spend a few hours hiking and swimming around this lush, tropical paradise. There are several spots where you can take photos and go swimming, and I recommend taking your time and visiting all of them. Try to get to El Nicho early, as it is a popular tourist spot that gets very crowded by mid morning.DSC09543 After El Nicho, drive one hour to Trinidad and stay the night. Trinidad is my favorite city in Cuba! The colonial old town and cobblestone streets have a historic charm and I could have easily spent hours aimlessly wandering around. For dinner in Trinidad, go to Cafe Bistro Madeley. It is hands-down the best food we had in Cuba. The chef told us that he developed his menu by asking guests what they would like to eat and working with the limited ingredients available in Cuba to come up with something similar. The food options are diverse and creative, which is hard to come by in Cuba. Better yet, there are labeled vegan options!img_1649-1

Day Four: Drive back to Havana. Have a late lunch at El Cafe – an open-air cafe in Old Havana with healthy food and vegan options. In the evening, go to a show at Buena Vista Social Club. Buy your tickets as soon as you get back to Havana, as shows often sell out. Buena Vista Social Club is a world-famous ensemble of Cuban musicians established in 1996 to revive the music of pre-revolutionary Cuba. The show is excellent; the food, not the other hand, is subpar. But the exceptionally talented performances will make you quickly forget how terrible your dinner was.

Day Five: Start the day driving around in a 1950s convertible in the morning, before it gets too hot.

Spend the rest of the morning and early afternoon wandering around Havana before you fly out.

Six Things You Should Know About Cuba Before You Visit

  1. If you plan on paying for anything, bring cash. Cubans do everything in cash. And I mean everything. Want to buy a car? Better bring bags of cash. A house? Cash. So don’t plan on using your credit card at any restaurants, hotels, or stores.
  2. Cuba is communist. Almost everything – from hotels to restaurants to stores to taxis – is owned by the government. Government rations are low, and often not enough to live comfortably. Therefore many Cubans count on tips for a better lifestyle. Despite this, many Cubans are highly educated and very intelligent, even, and in some cases especially, in what would usually be considered less desirable jobs. While a lawyer or a doctor will work for the government on a government wage and can be sent to live wherever, a tour guide has more control over his or her life and because of the ability to earn tips, will likely be better off financially than a lawyer or a doctor. Therefore you can expect to meet incredibly intelligent tour guides.
  3. Grocery stores have about 6 items. if you’re looking to buy liquor, milk, water, tomato sauce, beans, or rice…you’re in luck! If you want anything else, sorry, but Cuban grocery stores probably won’t have it. I expected to at least find soy milk, but had no such luck. Markets sell tomatoes, avocados, onions, garlic, and peppers. And most restaurants have menus based off of this very limited food selection. It wouldn’t be a bad idea to bring a few bars and maybe some hot sauce for added flavor.
  4. WiFi is difficult to come by. It’s not like other countries where you’re likely to have free WiFi in your hotel, hostel, or bed & breakfast. No such luck in restaurants and cafes either. WiFi is relatively new to Cuba. There are certain areas throughout the cities that have WiFi connection, typically town squares and hotels. However, WiFi is controlled by the government and you’ll need a WiFi card with a username and password to use the WiFi. You can buy a WiFi card at various stores for about 1 CUC for an hour of connection. The card will only work on one device. The WiFi is slow. I highly recommend doing the majority of your research and planning prior to arrival.
  5. Hotels are expensive, and most tourists stay in Casas particulares. Expect a nice hotel in Havana to put you back about 500 USD per night. An average hotel – and I really do emphasize the word “average” – will cost about 300 USD per night. Casas particulares are bed & breakfasts that range in price from about 20 USD to 50 USD. Casas particulares can vary greatly in terms of cleanliness and comfort; however, they are much more reasonably priced than hotels. And if you’re from the U.S., you need to be careful with hotels because staying at certain hotels is a violation of OFAC sanctions. I’d recommend staying at casas particulares because it’s a great way to immerse yourself in Cuban culture and hotels are just so expensive. Having said that, be aware of what you’re getting into and don’t expect high-end accommodations.
  6. The U.S. has sanctions against Cuba. While travel to Cuba is at the time of this post allowed under twelve categories of general licenses, it is restricted and you do need to make sure your trip is allowable based on current regulations. As an attorney in the US, I’m going to refrain from interpreting the law or giving legal advice on my personal blog, but make sure you do your research.

If you decide to go to Cuba and want some advice on what to do when you’re there, check out my five day Cuba itinerary here.