TNTP Travels: Miami – South Beach & Little Havana

A travel guide to 48 hours in two of Miami’s most iconic neighborhoods: South Beach & Little Havana.


Tuesday night, Sam and I returned home from five festive days in the Miami area. The main reason for our visit was to celebrate his grandparents’ 65th wedding anniversary (!!) in Aventura. Since our own wedding anniversary (our very first!) fell on the Monday following their anniversary weekend, we decided to extend our trip two days and enjoy a little getaway in nearby Miami Beach.

In classic Jewish grandparent fashion, all of Sam’s grandparents live in south Florida so we make it a point to spend a handful of days down there each winter. That being the case, we’ve done our fair share of exploring Miami neighborhoods like Key Biscayne and Wynwood (Grandma Harriett loves showing us around the design district 🙂 ), so we wanted to switch it up this trip and explore neighborhoods in which we don’t usually spend too much time. Though we’ve enjoyed a number of meals in South Beach and have gone dancing at Little Havana’s iconic live music bar Ball & Chain, limiting our brief visit to these two neighborhoods allowed us to really explore them.

Here is our complete itinerary including all of our favorite spots from South Beach and Little Havana (important reccos in bold!). If you’re looking for an idea for a fun 48-hour escape or are interested in a mix of trendy and culturally-rich Miami, this itinerary is for you.

WHERE WE STAYED: Kimpton Surfcomber Hotel, South Beach


I had a few requirements when looking for a hotel: fun, a bit trendy, in South Beach (preferably with beach access) and under $200/night*. Surfcomber checked all these boxes and so many more:

  • Central location on the boardwalk
  • Beach club
  • Beautiful pool with outdoor bar/restaurant, pool floats, plenty of chairs with umbrellas and Sun Bum sunscreen on tap
  • Free rental bikes
  • Outdoor games in the sand including ping pong, Connect Four and corn hole
  • Free wine hour everyday from 4-5pm
  • Classic art deco architecture with modern interior design

The service was also some of the best I’ve ever experienced. We were greeted warmly (especially since we arrived during free wine hour!) and when we tipped our valet for bringing our bags to our room, he returned promptly with a complimentary bottle of rosé. All of that really set the tone for our stay and our trip in general!

*Weekday prices are $178~/night for a king room vs weekends which are $300~.


Sunday Night


Free wine hour, outdoor games and more drinks at the pool bar with friends followed by food and dancing at Ball & Chain in Little Havana in time for free salsa lessons, every Sunday at 9pm! (Be sure to check Ball & Chain’s events page for up-to-date schedule of free salsa lessons and live music.)

Monday Morning (our anniversary day!)


A bike ride down the boardwalk, around the tip of the island and back north towards our hotel, stopping for a casual breakfast at The Daily (we sat outside to keep an eye on the hotel’s bikes, which didn’t come with locks).

Monday Afternoon


Beach day! We hardcore lucked out with the weather so we took full advantage of the beach club, rented an umbrella, ordered lunch to our chairs from High Tide, Surfcomber’s poolside restaurant, and just chilled (which for me meant working on an embroidery for a friend). Later on we cooled down by jumping in the heated pool.

Monday Night


This was our big night out so we got dressed up and went to drinks at the magnificent Faena Hotel (the best way to enjoy this extravagant establishment on a budget).


Before cozying up at the bar, we walked the hotel to visit its many artistic attractions: the lobby aka “The Cathedral,” Damien Hirst’s gilded woolly mammoth outside in the back (they’re real woolly mammoth bones, people!!!!); and the colorful, oversized chandelier made from fishing lures at Tierra Santa, the hotel’s 3rd floor spa. At the bar we enjoyed a delicious tequila-mezcal-jalapeño cocktail, a Peroni and some complimentary bar snacks, ringing in at under $40 for a totally grand experience.


After drinks, we walked seven minutes south to The Freehand, a hip, hideaway-like hostel featuring one of the city’s best outdoor bars, Broken Shaker, and 27 Restaurant, a funky, eclectic eatery built in an old house, featuring an internationally-inspired menu, crazy good cocktails and an upstairs that’s basically a living room-meets-bar-meets-restaurant. We ate dinner at 27 Restaurant, walked around the premises and made note to get drinks at Broken Shaker next time we’re in Miami, as we were simply too pooped from our very active day.

Tuesday Afternoon


After a slow morning grabbing breakfast tacos and burritos across the street at casual eatery Maxine’s, our main activity for the day was a food and culture tour of Little Havana. This amazing tour is through Miami Culinary Tours and I cannot recommend it enough. Below is a breakdown of the places we visited and what we ate, all of which are within a four-block stretch of SW 8th Street aka Calle Ocho.

You can certainly visit any number of these establishments yourself, however there are numerous benefits to the tour. We zipped through all of these authentic establishments in only 2.5 hours, plentiful food and drinks were ready and waiting for us at each establishment, and, of course, we received such a wonderful cultural history of the area from our lovely, knowledgeable guide Marie. You can find more info including the tour schedule here!


Cafe Cubano & savory snacks (beef empanadas & vegetarian tostones) at El Pub Restaurant, 1548 SW 8th Street // Cigar shop & live cigar rolling at Cuba Tobacco Cigar Co., 1528 SW 8th Street


Back at Ball & Chain for more mojitos! 1513 SW 8th Street


Aforementioned tostones at El Pub // Guava pastelito at Yisell Bakery1356 SW 8th Street


Scoping out local produce and enjoying fresh mango juice at Los Pinarenos Fruteria, 1334 SW 8th Street


Delicious small lunch at Old’s Havana (chicken croquetas, Cuban sandwiches, black bean soup & yucca fries), 1444 SW 8th Street // Learned the incredible story behind Cubaocho Museum & Performing Arts Center1465 SW 8th Street


Watched older locals spend their afternoon playing dominos in Domino Park, SW 8th Street corner of SW 15th Avenue (also below left)


Ended the tour with a scoop of Abuela Maria ice cream (vanilla with guava and biscuits) at Azucar Ice Cream Company1503 SW 8th Street

The 12:30pm tour ended around 3pm, then it was back to the hotel to grab our bags and head to the airport. Though we were in Miami only 48 hours, our fun-filled itinerary in South Beach and Little Havana made it feel like so much longer! If you have any questions about our stay, feel free to leave them in the comments below and be sure to check out TNTP’s other travel guides here in the travel section of our blog!

Peace, love & neon,

Leave a Comment