Street Wise: A Stop-by-Stop Guide to Calle Ocho, Little Havana

Looking for a place to stay? Just a few blocks from Calle Ocho, this 1920s hotel matches urbane vintage Miami with the lush tropical vibe of Cuba. The boutique property brims with exotic curios and souvenirs brought from the original owners’ international expeditions. You’ll want to spend plenty of time on its plant-filled rooftop, where you can wine and dine overlooking the Miami skyline. When it’s time to turn in, return to your room, choose from the pillow menu and slip between luxury linen sheets.

Although set a few blocks before what many consider the “start” of Calle Ocho, Versailles Restaurant has been a benchmark for Cuban dining – and Little Havana community hub – for 50 years. Inside, you can enjoy fine Cuban cuisine in elegant surrounds decorated with etched glass and neoclassical flourishes. Alternatively, walk up to La Ventanita and grab a coffee and snack to go, also a popular spot for locals engaging in their favorite pastime of talking politics.

For the locals of Little Havana, there’s no better sandwich than the Cubano – a variation of a ham and cheese, packed with pork, melted Swiss cheese, pickles and mustard – and you’ll find it prepared to perfection here. With its floating tables and Cuban tiles, the interiors are a homage to early 20th-century Cuban architecture. The best seats in the house are at the counter, where you can chew the fat with friendly staff. In a hurry? Rock up to their ventanita and get your sanguich to go.

Another Cuban staple is La Frita, a burger topped with crispy shoestring fries in a fluffy white bun. In this American-diner-meets-Cuban-cantina, you’ll find the very best in town. El Rey De Las Fritas has been a family-run business for over 40 years and is a well-established fast-food landmark among the Miami-Hispanic community. If a burger’s not your thing, the menu extends to plenty more traditional Cuban bites, each sure to fill your belly with a minimal dent in your wallet.

This iconic piece of Miami Art-Deco architecture opened in 1926 and endures today as one of the city’s oldest cultural landmarks. It used to be a popular haunt for newly arrived exiles who would watch American movies to learn English. It’s been sensitively restored, complete with marquee sign and vintage seating, making it a great place to kick back with popcorn and enjoy anything from art-house movies to blockbusters – shown in both Spanish and English.

Just opposite Calle Ocho’s quintessential meeting place of Domino Park (named for the board games played here beneath shady trees), the Cubaocho Museum hosts some of the city’s finest performing arts, often with a focus on the history and experiences of Cubans. There’s a large collection of Cuban artworks, too, while by night things heat up with live jazz and salsa dancing. If that wasn’t enough, the bar boasts one of Little Havana’s best rum collections.

If you’re looking for a souvenir of your stroll down Calle Ocho, this is the ideal spot to pick up something totally tack-free. This cute store is brimming with a variety of creative pieces made by local artists and artisans. You’ll find everything from one-of-a-kind jewelry, footwear and handbags to books, perfumes and original art pieces. It’s also a great place to pick up some Miami-made Cremo Cigars, if you’re that way inclined.

If you prefer a vitamin hit, then this fabulously authentic fruit and veg market is worth a visit. They’ve been selling fresh produce, both locally grown and imported, to the community for five decades – and it hasn’t changed much in that time. Made-to-order smoothies are a great way to get your five-a-day, or chilled coconut water straight from the source to rehydrate on a sweltering Miami day.

If you’d rather stay in downtown Miami, but still have easy access to Little Havana, this skyscraper-set hotel is a five-minute cab journey from Calle Ocho. It distinguishes itself with Philippe Starck-designed interiors, an impressive art collection and seriously upscale facilities. An extensive rooftop terrace affords spectacular views over Biscayne Bay, plus a series of three pools. Spa treatments are state of the art and the dining options will make you think twice about heading out for dinner.