2 week itinerary for Cuba
Images taken from my trip to Cuba in 2018

2 week itinerary for Cuba

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.

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.

48 hours in Viñales

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.

Exploring Cuba | How to Spend 48 hours in Trinidad

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.


2 week itinerary for Cuba


This post was proofread by Grammarly

Book your trip now

Are you ready to book your trip?  To help you get the best deals and service here are the companies that I personally use to book all of my travel online. I always shop around before booking anything, but these are my tried and tested starting places.

  • Skyscanner – I’m a bit fan of Skyscanner, it is who I use to book all of my flights. I often will check other like Google Flights or Momodo, but I always go here first and it is who I book 99% of my flights with. 
  • Booking.com – I LOVE booking.com especially when I can book and cancel free up until a certain point, mostly because my plans are forever changing. It’s easy to use and has one of the widest selections. 
  • Airbnb – I’m not a huge user of Airbnb, but sometimes I do like to use it, and I ALWAYS check it before I book anything else. You can get some really cool places to stay here, and it is especially good in places like Cuba. If you don’t have an account and you click on this link then you will get $36 off your first booking.
  • Hostelworld – If you are looking for hostels then this is a great place to check first. They often have additional places that you won’t find on Bookin.com.
  • Agoda – Although I don’t use it as much as booking.com, Agonda is especially good if you are traveling in Asia as they really do dominate there. 
  • Worldpackers – If you want to travel on the cheap and save money on accommodation then you need Worldpackers in your life. You can read more about it here. If you click this link to sign up and use the code CLAIRESITCHYFEET then you can get a 40% discount on your membership! 
  • Book a Way – If you are traveling in Asia and want to pre-book your transportation then bookaway.com is a fantastic site to do so. They have buses, trains, and cars.
  • RentalCars – Looking to rent a. car while you are away? I always book through Rental Cars as they do a search of all of the big sites and find the best deals. 
  • Welcome Pickups – Very occasionally getting from the airport to my accommodation is a total pain in the butt, or I’m traveling in a group and it makes sense to arrange a pickup. When I do I use Welcome pickups.
  • World Nomads – If you are looking for flexible travel insurance then it’s World Nomads all the way. I wrote all about insurance here if you want a more thorough review. 
  • SafetyWing – AsI’m a Digital Nomad and not moving around quite so much anymore I personally use SafetyWing now for my health insurance. I wrote a full review here
  • Viatour – Sometimes it can be a little expensive, but I like Viatour for somethings, especially if you can get a discount code! It’s also great for inspiration. 
  • Klook – If you are traveling in Asia, then Klook is great! You can book all kinds of tours, activities, and train tickets, plus they even have sim cards and WiFi.

Claire Summers

Dancer, producer, traveller, photographer, cake maker, dog lover and knitter of Christmas scarfs.

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