If you are planning a trip to Cuba it is good to plan ahead a little. Remember in Cuba can be a bit of a challenge for even the most experienced of travelers. You aren’t going to have easy access to the internet and if you are from the US you won’t have easy access to your money. So even if you aren’t normally a planner a little planning will go a long way in Cuba. In this post, I have mapped out a Cuba itinerary for 2 weeks.
2 weeks in Cuba is a short time but if you don’t mind moving through quickly, you can cover quite a bit of ground in the week. Or if you can squeeze 10 days even better but 2 weeks would be perfect.
If you like this 2 Week Itinerary for Cuba, save it in your Stipple trip planner where you will find destinations, things to do, and accommodation all in one place without juggling between several apps.

Day 1 Exploring Havana Cuba
Havana is impressive but my advice is to get out of Havana and spend your time in the capital city on your way back. As a seasoned solo traveler, this is one of my top tips for visiting the capital of any new country. Whether it’s Bogota or Bangkok, capital cities can be overwhelming, and in a new country, it can take a while to settle in and understand the culture and how things work. In my experience returning to the city after spending some time away from the city where things aren’t so chaotic helps. So if you don’t have much time do Havana on your way back.
Day 2-3 Get outdoors in Viñales
Vinales is a beautiful place to spend two days. I have written a guide on how to spend 48 hours in Viñales you can read here.
Day 4-5 Walk the Colonial Streets of Trinidad
Trinidad is second only to Havana for having beautiful colonial architecture. It also has some great hikes and a pretty nice beach. Take a read of my 48-hour guide to Trinidad here.
Day 6 Take a rest in Cienfuegos
I didn’t make it to Cienfuegos due to my budget and time not stretching. But I would have loved to spend the day here. Don’t worry though I have just the thing, a blogger friend Travels with Talek did get to hang out in Cienfuegos though so you can read about all the cool things to do on her post.
Day 7 Remember Che in Santa Clara
Okay, so there isn’t much here about from the Che stuff. But if you have 2 weeks in Cuba its worth a visit. Sadly I didn’t have the time but my friend Travels with Talek has written an excellent guide to help you plan your time in Santa Clara here.
Day 8-9 Chill on the Beach in Varadero
I didn’t make it here due to my budget not stretching. But I would have killed for 2 days here on the beach! But I found this interesting guide to Varadero so you can plan your three days. Although if you take my advice, then you will find a cheap all inclusive for three days and sit by the pool/ on the beach sipping Mojitos and eating the free food. You will need the rest before heading back to the craziness of Havana.
Day 10-14 Back to Havana
On returning to Havana, you should be much more relaxed and accustomed to the Cuban way of life. I have written a guide to help you spend 48 hours in Havana that you can read here.
Final Thoughts
Cuba is one of the most interesting and intriguing places I have visited and I am sure you will get as much out of visiting there as I did. If you have less time then I also have a guide to spend 10 days in Cuba and how to spend 7 days in Cuba.
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