Miami and Key West, FL

Introduction

Though Miami is synonymous with nightlife, this sun-kissed coastal metropolis has an even more exciting daytime scene. While the beach is an obvious choice, Miami is also home to numerous art museums and galleries, water sports, a popular zoo, fantastic art-deco architecture, and trails and parks you can access all year round. The city’s proximity to the Florida Keys makes for a fun day trip as well.

At the time I received my first Covid-19 vaccine shot in January 2021, I had not been on a plane in a year. The Miami trip kicked off a binge of “revenge travel” where I took 3 trips in 2 months. Like everyone else, I had been cooped up for so long I started spending all of my money on med-spa treatments to fix all of the things I hated about my face from staring at myself on Zoom. I knew I needed to get the hell out of my house ASAP!

The minute I set foot in Miami, I felt like a new person. It was like I was Jesse in El Camino trapped in the drug dealer’s cage and was set free. The weather was 77 degrees and sunny every day I was there, and people packed the beach and dined al fresco as though the pandemic didn’t exist. Miami in January was the perfect travel destination for my first post-vaccine excursion.

A few years after my initial post, I visited my sister in Boca Raton and we took road trips to both Miami and Key West, so any information here is updated as of 2023.

Can’t get enough of Florida’s beaches? Check out this post from Rock a Little Travel for 32 more options in the Sunshine State!

Getting Around

South Beach is fairly condensed, so the beach, restaurants, shops and galleries are mostly within walking distance of each other. If you are looking to branch out to other areas of the city or road trip to the Keys, a car is necessary.

I recommend flying into Fort Lauderdale and renting a car or even Ubering to Miami. The Miami Airport is one of my least favorite due to its vastness, high volume of travelers, and long lines and I will do anything to avoid it. Fort Lauderdale is much smaller but still offers a respectable amount of flights, and is less than an hour from Miami.

Where to Stay

Miami and Miami Beach are actually separate, distinct cities; divided by Biscayne Bay and connected by a long bridge. Miami is more urban, while Miami Beach is where you find the resorts, celebs, fancy cars and sand.

In 2021, I stayed at the Kimpton Palomar South Beach, which offered a decent location a few blocks from Lincoln Road’s shops and restaurants and down the street from Sunset Harbor. The beach was about a 15 minute walk. I booked a room with a balcony, which was a waste of money because the constant blaring of traffic in the street below made it unusable. If I had to do it again, I would have stayed at the beachfront Surfcomber or Redbury, or tried one of the boutique hotels in the Art Deco historic district a few streets over.

Fun Activities

• The Beach

South Beach features large swaths of sand stretching several miles. In spite of this it can still get crowded on nice days. The water is pretty warm year-round and perfect for swimming. Waves lap placidly against the shore. Miami Beach Boardwalk is a pedestrian pathway shaded by palm trees that runs from 5th Street to 46th Street at Indian Beach Park. It is perfect for walking, running, biking or (yes) in-line skating.

One thing you will notice is that everyone on the beach is trying to be an Instagram influencer. I’ve never seen so many people taking selfies or having their friends take photos of them sticking their butts out. I also watched an older woman with bleached hair wander around with no top on, and noted dozens and dozens of glistening, hairless chests and Speedos. The people-watching on Miami Beach is unparalleled.

• Wynwood Walls

This was probably the coolest thing I have done in Miami; I first went in 2021 and again when I returned in 2022. Wynwood Walls is located in what used to be a textile district, where old factories are now adorned with street art. It’s a hipster enclave with cafes, restaurants and galleries, surrounded by the skyscrapers of downtown Miami.

Wynwood Walls is an outdoor museum showcasing the works of famous graffiti artists from around the world, from Shepard Fairey (of Obey and Obama Hope poster fame) to up-and-comers like Vhils, who uses miniature dynamite to create detailed images on the sides of concrete walls.

Since I am not well-versed in the world of street art, I booked a tour to gain some background and insight into each of the exhibits. I ended up being the only person who signed up, and got my own personal tour. The ambassador who guided me was a young, tattooed art gallery owner from Italy who was in Miami working since his home country was under lockdown. He filled me in on both the street art scene and his experiences in the art world more broadly.

At the end of the tour you enter into the gallery, where the graffiti artists created pieces that patrons could buy. Many of them were listed in the $20-$50k range, which shows how valuable and mainstream street art has become.

• Little dogs

Everyone in Miami has a small dog. They are adorable and I wanted to kidnap them.

• Instagram Photos

South Beach is filled with people snapping photos for social media–so why not join them? If you need ideas for captions and quotes, check out these Miami quotes!

Key West

Each of the Florida Keys I passed through on my way to Key West reminded me of Delaware, but with palm trees. Basically a bunch of highway strip malls and car repair shops. The years-long marketing campaign launched by the “other” Keys–Isla Morada, Marathon, Key Largo–did a phenomenal job convincing me that I was going to find paradise. The reality is that if you are planning on doing something other than hanging out in your hotel’s swim-up pool drinking daquiris, there isn’t much for you in the Upper and Middle Keys.

Key West was a different story. It is reminiscent of Provincetown in Cape Cod, bustling with well-heeled tourists and filled with historic buildings, cute shops and great restaurants. There is a main drag, Duval Street, that splits the downtown area, as well as beaches at Fort Zachary Taylor State Park and historical landmarks such as The Hemingway Home and Museum. There are also chickens bobbing around the streets.

There are daily glass bottom boat tours offered at the end of Duval Street near Ocean Key Resort, which I took advantage of. A comfortable catamaran cruised a half-hour out from shore and provided us with an up-close-and-personal view of the local marine life. I spotted barracudas, pufferfish, and clown fish flitting among North America’s only living coral reef. The tour guide also regaled us with stories about stepping on fire coral–twice. It made me grateful to be in the boat and not in the water!

Fort Zachary Taylor State Historic Park has some hiking trails, but the real draw is the beach lined with trees and the clearest blue water rolling up onto the shore. During our stroll around the park we saw several yoga and fitness classes taking place under the canopy.

For any lover of history and literature, a tour of Hemingway House should be on your to-do list. Ernest Hemingway purchased and renovated this Key West estate in the 1950s, and wrote several of his greatest works here. The tour provided a fascinating window into the personal life of one of the most celebrated American writers in all of his talents and flaws.

In nice weather, sunset at the Southernmost Point can get crowded, but with good reason. An array of colors paint the sky as the sun dips below the horizon.

Key West is a top spot for snorkeling and diving, with its warm, clear waters and colorful, tropical fish flitting around the rocks and reef. Read more about Key West snorkeling and diving opportunities from our friends at The Traveling Something blog!

Food

I ate dinner twice at Taverna on Lincoln Avenue, one night for sliders and the next night for Argentinian empanadas. Both meals were on point. In Key West I stopped at a restaurant on Duval Street and ordered the obligatory conch fritters, which were fresh, crispy and delicious.

Running

The Miami Beach Boardwalk is a paved trail that runs parallel to the beach, taking you past the Art Deco Historical District and winding around to the waterfront in Sunset Harbor/Biscayne Bay. I headed out at first light to catch the sunrise. Miami Beach is an active city and the Boardwalk is pretty busy even in the morning, so the earlier you go out, the better.

Recovery Meetings

There is a 6pm outdoor AA meeting every night at Maurice Gibb Memorial Park in Miami Beach that is pretty well-attended. The view is so beautiful it’s actually a little distracting. There is also an 8:30am Sunday morning meeting on the sand in Miami Beach. The guy who chaired the meeting when I went was super tan and oiled up, and was wearing a Speedo swim brief and nothing else, which was the most Miami thing ever.

Here is the list for AA meetings in Miami!

In Key West, the land of never-ending fruity drinks, there are meetings all day, every day at the Anchors Aweigh club house. Located in the middle of town a few blocks from the Hemingway House, the locals are warm and welcoming and give newcomers and out-of-towners “worms” instead of chips!