A Cheapskate’s Guide to Surviving South Beach: Entertainment

No, really, are you actually bored in South Beach? If so, take a deep breath and come back to your senses. You do not need to go to LIV to have fun on South Beach, nor do you need spend exorbitant money on Ocean Drive dinner and show traps, nor do you need to waste $ on an Uber to Wynwood.

To entertain yourself of South Beach, you can do a lot more with less if you’re up to walk around and hit up free shows when they’re available. In a post-COVID world, the slate of free and public shows is a bit slimmer, but that’s changing fast. Soundscape Park up on 17th street has music that coordinates with some sculptures to provide some fun for the senses while walking or sitting there.

You do sometimes have the almost dystopian mix of confused margarita-filled tourists and homeless verbalizing their opinions/rants over the sweet sounds of Soundscape’s audible art, but that’s life. Again, not boring, and always entertaining.

Are you NOT entertained?

If weird dystopian tech parks aren’t your thing, head on over to The Betsy Hotel, a mere few blocks away. There are nightly piano bar performances in the Betsy’s lobby that cost $0. Just splurge on an overpriced drink and enjoy the experience. People pay up to $600 a night to stay here, but not you. You are getting a world-class hotel lobby experience, live entertainment, and a beautiful place to enjoy a classic cocktail. Even if you spend $20-$30 per person on a two-hour experience, you’ve just done something unique for the cost of half a crab leg on Ocean Drive.

You’re in South Beach, go to the pool and take a million selfies

If it’s good enough for an Instagram influencer who’s moonlighting on OnlyFans back in the room later that day, it’s good enough for you, cheapskate. Find a hotel, and go to the damn pool. Act like you belong there, even if you don’t. Most nice hotels on South Beach have very experience-oriented pools, meaning that they cater to partying there as much as relaxing there. That’s good news for cheapskates, because it creates this grey area that toes the line between “Are you a guest?” and “Do we care if you buy drinks?”, which is ripe with opportunities. Trespassing is wrong, of course, but if a pool area has a bar and restaurant that is open to the public, using the pool is not trespassing at all. Hotels don’t advertise this, but it’s true.

There are some hotels that are exclusive and have all their pool and recreational facilities accessible by keys, sign-ins, etc. There are more that don’t. For a boutique experience, head to The Betsy Hotel rooftop pool (2nd mention!) and order some food/drinks. You can get there from the lobby via a small elevator, and just sit down or jump in.

Another great pool to check out is at the Bentley Beach Cub on 1st street. The pool there shares the patio with their in-house Greek restaurant “Santorini”, so you can sit outside all day, sunbathe, have drinks/food, and swim. As long as you’re buying drinks and food, you won’t have an issue, and probably 1/3 of the crowd is doing just the same. Oh, and Santorini has (as mentioned) an incredible happy hour with $5 drinks, and bar eats, so if you time it right, you’re cooking with gas, cheapskate.

The pool at the Moxy Hotel is another one you can jump into for free, but prepare to sacrifice cheap anything to do so. Drinks and food are overpriced at their pool bar/restaurant, and you can expect big crowds there and at the pool. You can always do any of this at your own hotel or apartment (if you live here), however since you’re a cheapskate, we can safely assume you have no pool in either. Don’t hate the player, hate the game.

Timing is everything

For anyone looking to get started on their own South Beach cheapskate journey, timing is one of the most important factors. South Beach is a resort town, and it’s seasonal. What time of year you visit South Beach can affect a number of variables with the cost of visiting there. Hotels and ride shares have the biggest price swings during the seasons, with food and booze costs remaining fixed. Where timing is truly important though, is planning a day that gives you what you need, without burning out your spending limit too soon.

Pace yourself, fellow cheapskates. Try to spend as much time outdoors as possible early on, don’t rush anywhere, and don’t be afraid to call it a day when you’re physically/emotionally spent. Don’t get too wasted at happy hour, even though drinks are cheap. Don’t be afraid to pop back into your hotel or home in the middle of your fun to take a disco nap, or a shower, or just sit on the couch in the A/C. If you stay on the weekends, you’ll find more crowds, and that can be good/bad depending on your energy. Time out your trip to fit your budget needs, but also something that vibes with your tolerance of people. Timing is everything here, and not factoring that in could make none of this worth it.

South Beach is a playground for the weird, wild, and wacky sides of all of us, but it’s also a city where people live and work. Enjoy it, don’t break the law, don’t be a dick, leave good tips, and let it inspire you to be whoever you want to be for however long you want to be it. You don’t have to be rich and famous, a Bitcoin bro, or an NBA player to enjoy this town, either. You can be a cheapskate, a modest spender, or a weekend splurger too. Just be you.

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Andy Jackson

Andy Jackson is a writer and freelance journalist based in Miami Beach, Florida. He's spent 12 of the past 15 years living and working in Italy, Argentina, and Panama, with a background in travel writing, digital marketing, and consulting. He is a graduate of the School of Journalism and Media Innovation at Northeastern University.