Wondering how to spend 48 hours in Havana? Way back in November (at least, it feels like a really long time ago now) I travelled to Cuba for 10 days. It was the first time I’ve taken a ‘winter sun’ kind of holiday and was definitely one of the best holidays I’ve ever been.

Despite being one of my favourite holidays to date, it wasn’t exactly what I expected. Not that I expected much… before I stepped on the plane, all I really knew of Cuba was the colourful backdrops I’d seen of of fashion shoots and travel magazines, it’s an incredibly poor country and that it’s the home of one of my favourite rums.

The first couple of days were spent in Havana – before we moved on to Varadero for some beach + chill – and, during those 48 hours or so, I learnt so much about Cuba and its people. And at the same time I didn’t really learn anything at all.

Havana is one of the most mysterious, magical and mesmerising cities I’ve ever been to. It reminded me of several places I’ve been before (Vietnam, Jordan and even Europe) but was unlike anywhere else. Perhaps it’s because the city and its buildings have somehow maintained a real sense of glamour despite mostly looking like they’re about to fall down. Or perhaps it’s because the city looks like it could be a ghost town if you removed all the people, but still has more energy than anywhere else I’ve been.

Whatever it is, I completely fell in love with the place and know for sure that I’ll be going back again.

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Where to Stay

Cuba is pretty much the original Airbnb, with guesthouses, called casas, on pretty much every street. These can be booked online in advance, or you can just turn up and look for buildings with the casa symbol outside. We didn’t stay in a casa but it’s certainly something I’d love to do if when I go back. It’s a great way to travel deeper and see how the locals live because you’re actually staying in someone’s house!

There aren’t many hotels in Havana and the ones that do exist aren’t exactly what we’re used to. If you choose to stay in a Havana hotel, even though the rooms will probably be very spacious, you might find there are no ceiling lights, the upholstery doesn’t match and only 1 of the 3 lifts in the building works… on a good day. I heard a few horror stories about the 3* hotels so this is one place where it’s best to stick with a 4* or 5*.

We stayed in the 4* Riviera hotel in Verdado, which is the newest and richest part of Havana, and it was definitely a new kind of hotel experience! That said, our hotel still had a unique charm about it and I loved experiencing everything from the 50’s diving board to the strange breakfast menu (spaghetti carbonara at 7am, anyone?).

Where to eat

Speaking of food, Havana may be the biggest struggle for foodies or anyone with a strict diet. Nobody goes to Cuba for the food and every day is a culinary surprise dictated by what arrives on the island’s shores.

But it isn’t all bad! I’d prepared myself for 10 days of chicken, rice and beans, but I didn’t eat any of those things once. Cuba actually has some really delicious food, especially the croquettes, which are available almost everywhere. The seafood is also great as it’s all really fresh and super affordable – even at tourist prices. The only thing I would leave is dessert.

Restaurants are pretty hard to come by in Havana – not because there aren’t any but because they’re not always easy to spot. I had lunch with Anoushka on my second day there because we happened to be in Havana on the same 2 days (but didn’t even tell each other until the week before!). The first place we found was tucked away down an alley along the side of a house, but was still packed. It was so packed that we had to look for another place and the second one we came across was on a roof. It’s amazing that they get any business being hidden away so well, but like most things in Havana, word probably spread in the old-fashioned way.

What to Do

Since there’s no guarantee of internet, a trip to Cuba is a great opportunity to completely switch off. No phone, zero emails and definitely no social media! I knew it was the only way I’d ever have a full, 100% digital detox so I made the most of it and (whisper it) really, really enjoyed it.

And it’s not hard at all to fill all the time you gain from not being connected to the online world because Havana has so much to offer for everyone. The streets are so full of colour, live music and life that you could easily spend a couple of days just wandering around. We found the best way to see the city in such a short period of time, however, was by guided tour – either walking or in a classic American car. We did both, walking around Old Havana and seeing the wider city in a 1956 Ford Thunderbird.

Read next: Looking for more things to do in Cuba? Check out this 2-week Cuba itinerary.

If you don’t want the full guided tour, there are plenty of classic cars being used as taxis. They’ll probably charge a little more than a ‘regular’ taxi, but prices are always negotiable and the car is an absolute MUST.

Havana is also a must-visit for literature buffs as it was the home of Ernest Hemingway for many years. We took a taxi to his house, which is just outside central Havana, and also passed Floridita, one of Hemingway’s favourite bars.


A photo posted by Jodie Marie Dewberry (@alajode) on

What to Wear

Being pretty much cut off from the rest of the world, fashion isn’t really a thing in Cuba. Sure, the Chanel resort show took place there, but the locals were more excited about the trade it brought with it from the sudden influx of tourists than than the fact the king of fashion was in their  country.

Still, you’ll want to choose what you wear in Cuba carefully.

Locals mostly wear jeans and shorts so there’s no real need to dress any differently from how you would back home, but it’s definitely a good idea to pack layers. We went at the beginning of November and I mostly lived in denim shorts, culottes and dresses, but could have done with a jumper for the evenings!

Alajode UK travel blog and vlog by a female digital nomad
Jodie Marie Dewberry

Jodie has been travelling the world full time since 2017, sharing the most unique places in the world along with tips for living as a digital nomad. She is a passionate wildlife photographer and has worked with a number of prominent travel brands, including airlines, tourism boards, hotels and tour operators.

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