I’m finally sharing my 2 weeks in Cuba plan, after returning from the trip of a lifetime earlier this year. I shared a gallery of my favourite images which you can see here, but I wanted to share what you can do for 2 weeks in Cuba and also how to plan it.

This was our first time visiting the beautiful country and furthermore, our first time in this part of the world so a lot of prep went in before we left. I promise there is no other article you will need, this is a detailed one 🙂 

Some think 2 weeks in Cuba is not nearly enough time, some may say it’s perfect. I would say if I had all the time and money in the world, I would have travelled every width and breadth of the island. But when ya got responsibilities, 2 weeks in Cuba is the perfect escape. 

When to Go

If you are going all the way over to spend 2 weeks in Cuba, please do your research on when not to go. I have a dear friend who decided to go in September of 2017, which is when Hurricane Irma hit the Caribbean. Besides this type of weather spoiling your holiday, it is also obviously very dangerous, so it’s best to not go between July and October.

The further south you go, the hotter the weather. However, the ‘main’ cities that we (and most people) wanted to visit as first timers meant that we were staying only in the more northern half of the island. We went at the end of April to mid May and we definitely saw the change of season towards the end of our trip. So, I would say the perfect time to go is probably March. I always always use Skyscanner to get a feel for the best flights.

Don’t forget that the ‘hottest months’ do not always equal the best months to go, as this sometimes indicates the ideal time for thunderstorms and definitely humidity. Climates to Travel is a great weather reference to check out if you are really worried about the weather. 

2 Weeks in Cuba | Bekah Molony

Getting There

I can’t speak on behalf of people going through the US (I know you definitely need to pay for a visa into Cuba), but what I do know is that from Europe, going through Canada is a good option as you don’t need a visa to get into Cuba. 

When we realised our connecting flight was definitely going to be through Toronto, we took the opportunity to see Canada for the first time and tried to find the longest stop over possible on Skyscanner (download the app here and keep track yourself on pricing!). If like us, you are easy going about stopovers, you will find a great price. You will find an even better price if you plan way, way ahead.

Between first looking out of interest in around November, to actually booking at the very end of January: the prices/ quality of flights had changed slightly. Nonetheless, I am the queen at finding deals so I found us €495pp return flight Brussels – Havana (on a Saturday!), including 24 hours in Toronto on the way over and 9 hours on the way back. Sure, stopovers aren’t for everyone but we were more than happy to hang out in Toronto for a steal of a price.

If you are flying through Canada you now need an ETA which is so easy to apply for online, you can do so here. It’s $7 CAD (€4.65 / £4) and takes seconds to approve, but you might as well do it after you booked your flights just incase.

When I was planning my 2 weeks in Cuba I kept reading that you need travel insurance to get into the country. We personally did not get asked at airport security if we had it or not, but it’s not expensive and definitely worth it for peace of mind. A popular travel insurance is World Nomads, but we went with the Irish Insure and Go as it was only €37pp for the Worldwide Gold Insurance Cover. They also have a UK version of Insure and Go.

Most people fly in and out of Havana, but that does not mean you have to stay there. Next is how to create your 2 weeks in Cuba itinerary.

Where to Go and Where to Stay?

We were first timers so we decided to go a route that was well documented. As you may have heard by now, internet is rare and it’s not a place that we were going to risk just showing up to and hope for the best. We went with Havana (including a day trip to Vinales) to Trinidad to Varadero and back to Havana (for one night for our 7:30am flight the next morning). The only thing that you can’t predict is bad weather when you’re on the beach and falling in love with a place (and therefore not wanting to leave). Both of these things happened to us during our 2 weeks in Cuba, but I’ll get to that.

I highly recommend booking accommodation in advance and this will make your itinerary more solid. We are not ‘resort’ people so hotels were never on our agenda. You may have read that a ‘Casa Particular’ (private house) is the way to go and these are essentially the original Airbnbs, which is what we used for each place we visited. Click for our Havana Airbnb, for our Trinidad Airbnb or for our Varadero Airbnb

Trinidad Casas - 2 weeks in Cuba - a little bit of b

Yes it is true that you can arrive at a place and find casas. But I much preferred the idea of being able to see the place, read the reviews and get the payments out of the way before we got there. What made the trip so special for us was the hospitality of these people you stay with. It is truly like nothing we’ve ever experienced, so if you’re spending 2 weeks in Cuba you absolutely have to do it staying with the locals. 

Our Favourite Place 

This was by far Trinidad. We took a taxi collectivo from Havana to Trinidad (around 4-5 hours, $35pp) and loved this little town from the moment we arrived. After spending 5 nights in the busy Havana, this was a beautiful change of scene. The Airbnb with amazing hosts and a beautiful rooftop terrace that we stayed in, was just one of the many reasons that we had a perfect time.

This along with the little square that we went at night to drink $2 mojitos and hang out with dogs, being 15 minutes taxi away from a paradise beach, great food and the most memorable thing for me: our rain forest hike to the waterfall. Because this was my favourite place, I will write a little separate post for it, because it deserves much love.

Trinidad, 2 Weeks in Cuba - Bekah Molony

Our Least Favourite Place 

The only reason I am naming Varadero as our least favourite is just comparing it to the rest of the stops during our 2 weeks in Cuba. This is not to say that we didn’t have a lovely time there. We were unlucky to get the thunderstorms and it is true what they say, it is literally just a peninsula of one main road, strips of beach and touristy restaurants.

We met people who were on their 10th return to Varadero because they absolutely loved it! For us, it was more of a family friendly location or Canada’s equivalent to the Canary Islands for example. Still, it was great to be a 1.5 minute walk to the silky sand, we had the best toasties everyday, had probably the best nights out in the Beatles Bar (out of the whole 2 weeks in Cuba!) and found a tattoo studio with the most G local lads.

More Tips:

• They use 2 currencies: CUC (for us tourists) and CUP (for locals), we heard it can be useful to have CUP but we found it absolutely unnecessary 

• I have a whole post scheduled on what to pack for Cuba because this was the one thing I couldn’t find online without long posts just linking to products 

• When you get WiFi, look up places on TripAdvisor for where you want to eat and drop a pin on Google Maps 

• When someone asks you to buy milk for their child, kindly say no. These ladies will bring you into a supermarket and try their hardest to guilt you into buying them a huge amount of groceries that they have waiting behind the till

• Remember to leave reviews for your Airbnb hosts or restaurants that you loved. They really need the positive reviews to keep their businesses strong, so take the time to say something nice

• Enjoy it while you can because word on the street is that place is going to change. So go see the beauty while it lasts. 

I hope that was helpful for anyone planning their 2 weeks in Cuba (or more if you’re lucky!). Please don’t hesitate to contact me with any questions you may have about visiting this beautiful paradise.