Resources for Planning A Trip to Cuba


We recently got back from a fun and very interesting trip to Cuba.

Cuba is probably one of the most talked about destinations to visit for Americans. The country has a sense of mystique due to the fact that we haven’t been allowed to freely visit for over 50 years.

Planning a trip to Cuba isn’t much different from planning a trip to any other destination. There just happen to be more questions and unknowns prior to visiting.

For our trip to Cuba we used a variety of resources to help come up with our itinerary and plan all of the important details before arriving.

In my post 14 Things We Learned From Visiting Cuba, there were a few readers asked questions related to visiting the island.

I had planned to share some more details about how we did our pre-trip research and that was pretty much what reader bluecat was curious to find out.

Bluecat asked:

What travel books and websites did you find the most helpful in setting up your trip?”

Here are some of the things that we used to help plan our trip.


After booking our flight, the first thing I did was order a copy of Lonely Planet Cuba. While many of you might not like print, I still prefer a physical copy of a guidebook. I bought it from Amazon and found it to be a great resource.

The book helped us build our itinerary, read a bit about the history of the country and gave us ideas related to things to do. We also loosely followed a few of the walking tours during our visit.

(The link above is an affiliate link. If you make a purchase, I may receive compensation from


We visited a variety of websites to get info and book some things for our trip. Here are a few that we used.

  • Wikitravel– I usually stop by Wikitravel for all of my trips to get some quick, basic info about a destination.
  • VirtualTourist Skimming around VT can be useful to find out tips and ideas from members. You can also leave a question about a place you are planning to visit.
  • Cuba Junky was useful for reading about casa particulars (homestays). The site has other info about Cuba too but we didn’t really look at it.
  • HavanaCasaParticular is a good site for casa’s in Havana. The big problem we encountered though was not being able to book any of them through the site.
  • Airbnb– We ended up booking 3/4 of our stays through Airbnb. Although some casas said instabook, that never seemed to work but the site came through overall. (If you don’t already have  an Airbnb account you can sign up through my link and get $20 off your first stay. I’ll get $20 too when you complete your stay.
  • GoogleMaps– I used Google Maps to see where casas were located, as well as the distance to key sites and attractions.

Ask people who have been there:

I don’t typically seek out info from people related to destinations we’re visiting. However, for Cuba I had a variety of questions that I preferred to ask someone that had been (more than once) rather than just read it online or in a book.

I reached out to Lee Abbamonte, (the youngest American to visit every country in the world). Check out my interview of Lee from 2014 here. I knew that Lee had gone to Cuba recently and I chatted with him about visiting at NYC Travel Massive over the summer.

I sent Lee an e-mail and he was happy to answer a variety of questions that I asked. He also shared his most recent Cuba trip report from June 2015. (I had read it way before I booked my flights to Cuba.)

Twitter travel chats can be a lot of fun. I even won $500 in an #ExpediaChat! The chats are a great way to meet (virtually) many people with a similar love for travel.

In recent months, I’ve exchanged tweets with Rachel Rudwall (@RachelRoams)– explorer, tv host and producer in the travel industry. When I found out that Rachel had been to Cuba, I mentioned that we were going and asked if she had any tips and advice to share.

We exchanged e-mails including some info about her itinerary and our upcoming itinerary.

Rachel also shared a few blog posts that she had written. Here they are:

Otherwise, when it came to researching Cuba, I also read random articles both online and in print and came across other info on the web.

If you have questions about Cuba, feel free to ask me and I will try to answer any questions as best as I can.

Related Posts:

Leave a Reply

Your email address will not be published.