Of everywhere I've been, one of the places I get the most questions about is Cuba. Old Havana is filled with tons to explore—colorful buidings, cobblestone streets, so much history—and, if you're like me, you're going to want to walk every inch and explore every last plaza and paladar. So you're going to want to make sure you pack well.
Cuba has a pretty perfect Caribbean climate with hot, sunny, breezy days but it can get humid certain times of year. Pretty much anything goes but it is a laidback place so there's no need to get fancy. Assuming you always take a sun hat and a light scarf, this is pretty much everything else you'd need for exploring Old Havana.
Easy and breezy is the name of the game when it comes dressing for Cuba's warm days. If you're going out exploring midday, you'll want something that'll protect you from the sun but that is still super lightweight and breathable (in say linen or cotton).The ideal long dress is one like this Lemlem number, which is chill enough for hanging with locals along the Malecón but classic enough for sipping a Mojito under the palms at the historic Hotel Nacional.
A shift dress that's roomy is key to surviving the Cuban heat and humidity (and to hide your food baby if you've had too manyChocolate Frappes). But rather than pack just another LBD, pack something light and airy and fun enough to match Cuba istelf like this vivid &Other Stories dress.
The best way to get to know every inch of Old Havana is to spend an afternoon (or three) exploring by foot. Enter easy, walkable shoes like these smoking slipper-style espadrilles from Soludos. And, since you're wearing coco-clad slipper, you'll obviously have to hail a Coco taxi!
Of course, you should always pack a few plain tees, but also bring something with a little extra style like this minimalist, structured, but still very summery tee from IRO. A style like this is perfect for going gallery hopping and exploring Cuba's burgeoning art scene.
Depending on when you go to Cuba, it may be way too hot and humid to even think about wearing pants. But pack at least one pair (if only to wear on the plane there and back) like these sunny Enza Costa linen pants that have major Carribbean vibes.
You totally can and should at least once take a vintage taxi to get around Havana. But the majority of time you're going to want to walk so you can explore and discover all the gems. The streets of Old Havana can be uneven and lots have cobblestones, so pack a comfortable flat even for night like these L*Space by Cocobelle sandals.
Cuba is hands-down the most vibrant place I've ever been—bold-colored buidlings, animated people, and liveliness everywhere. So, if there's ever a time to pull out an eclectic clutch (like this one by JADEtribe), Cuba is it.
The only time you'll need to get dressed up in Cuba is for nicer dinners or if you go out to a show. An airy, slightly fancy blouse like this white gauzey Zara top is a winner as its old world lace-look would be as good with a flowy skirt as over a pair of shorts.
Speaking of shorts, take at least one pair along with—preferably a longer pair in a lightweight, flouncy fabric like these bermuda shorts from Zara. Do know that you often can't wear shorts in nicer restaurants and at various religious sites, so these are best for a day of wandering around.
If you like a good Daiquiri, you're going to want to spend at least one night doing Daiquiri research. That could lead you from a posh paladar to a touristy (but still requisite) bar, so you'll need a dress that can go the distance like this mini dress from Mikoh.
When it comes to heels, leave anything that isn't a wedge at home. You're going to want something that is comfortable enough to dance all night in (be it onstage at the Tropicana or at a hole-in-the wall bar) and sturdy enough to tackle the cobblestones of the old city, so a wedge with a solid ankle strap like this one by Matiko is key.
You may want to just go straight from a day of touring to rooftop drinks at the Hotel Saratoga (where JayZ and Bey stayed, FYI) so a sundress with a little flare, like this red one bydRA, should go in your suitcase.
I love wearing dresses while traveling (less to pack, less to think about when getting ready). And, while most of the time in Cuba, you can go with a super simple sundress, I'm all for having one totally over-the-top piece for a nicer night. This Ulla Johnson is the perfect statement dress for Cuba since, like Havana, it has classic lines and old-school vibes and doesn't try to hard.
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