Spend one day in Havana, Cuba's vivacious capital that's stuck in a bygone era, and you'll understand why Hemingway was so inspired there. With gorgeous (if a little crumbling) architecture, vibrant culture (there really is tons of dancing in the streets), and relaxed travel restrictions, the island city is poised to be American travelers' next frontier. And we've got your packing list covered.
Blessed with breezy tropical weather, Havana is made for cheerful sundresses and rich brights, like this sprightly pink and white striped style by Lem Lem ($248) and saffron linen top with pretty embroidery ($140.01) Pack a few extras to change up your vacation look. A gray modal-silk blend scarf ($29.99 at Muji), cat-eye gold shades ($40), and pink stingray belt (as an homage to Havana's Caribbean seaside) for $29.99 at Ann Taylor can all change up an outfit without taking up much luggage space. For walking around cobblestoned streets, stick with flats or a sandal with a solid low '60s type heel, like this brown and gold pair by Sam Edelman ($100). Add a touch of glam with these gold and labradorite stud earrings by Alexis Bittar, which are glitzy and fun while being basic enough for daytime ($95).
Flirty and feminine are standouts for night, and a couple frocks, like this tropical print dress with high-low hem ($188) or this chic muted floral print silk number ($398). Pair either with this antique green stone ring, a steal for just $4) or crocodile box clutch in deep orange ($325). If you're looking for a saucy heel, this strappy python-print design, aptly named "Cuba," by Tory Burch ($134.99) is a stunner. And bring along a ruffled cashmere wrap ($164) for nighttime breezes—it'll serve double-duty on the plane for chilly air cabins.
Go for a casual-cool vibe in this handy travel hoodie in a muted brown ($225), while adding some footwear flair with these turquoise Margiela sneaks ($485). Try a light blue jean like these Levi's ($48) with a cotton short ($65 in green by Bonobos). T-shirts are always a good choice for day, but if you're planning lunch in a swankier setting, go for a short-sleeve henley ($49.50 in dark blue by Denim & Supply) in a super-soft slub-knit. Top it off with a straw fedora ($28) and slather on the SPF.
The Guayabera is a traditional short-sleeve button down which you can pick up at local markets, or you could bring your own modern version with a bright papaya hue ($64.50 by J. Crew). A few tops will pad out your wardrobe, like this baseball-inspired design in gray with white trim ($14 by Topman). Crisp white linen trousers are always in season for island-wear ($255) or skip the iron with these summery cotton-stretch trousers ($201.50). For accessories, go with neutral colors like this leather belt with nifty stitch detailing ($106), striped wood ring ($85), and leather shoes with crafty side detail ($114 by Volta).
Where to Stay
It's not a bad idea to go to Cuba with a tour or group trip; they'll help you avoid any tricky travel situations. We like Insight Cuba, which coordinates legal trips to the country with different itineraries and lengths of stay. (You can also customize your own, for a fee.) And Marazul Charters, one of the larger licensed companies, also arranges its own charter flights, direct to Havana from Miami.
Once there, you'll find an assortment of international hotels, like the Iberostar Parque Central with great city views, especially from the rooftop swimming pool. For a trip back in time, head to the Hotel Nacional de Cuba with plenty of local lore—Winston Churchill, Ava Gardner, and Frank Sinatra used to stay here in its heyday—but older rooms. The setting is pretty special though (the hotel has been declared a national monument). If you don't stay here, we at least recommend grabbing drink in the historical and bustling lobby bar.
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