It feels really good to be traveling again. And I mean like, really traveling (on a plane and everything)! We managed a couple of road trips through Texas last year (read about those here), but I couldn’t wait to feel the excitement that comes with packing a rolling suitcase, hustling through a busy airport, and landing in a completely new destination. That new destination was Miami and The Florida Keys! 

Welcome to my latest Eat + Stay + Play travel guide! If you’re planning a similar trip to Florida, I’ve included all the places we had amazing food and views, plus where we stayed and a few things we did (aside from all the relaxing). 

Outfit details: Lace Maxi Dress | Tory Burch Espadrilles (similar style here) | Palmgrens Rattan Clutch

You can see all of my Eat + Stay + Play travel guides here!

Miami

We took a direct flight from San Antonio to Miami, but we only spent one night here. The focus of this trip was to get to The Keys and Miami made a great pitstop along the way. I’d never been to this part of Florida before and I love big exciting cities. Miami is definitely that! There is certainly a lot more to see and do in Miami, but we squeezed in some fun things.

Where To Eat

Bennijama – Some local friends brought us here for an authentic Cuban Colada. If you’ve never had one before, it’s Cuban espresso served in a styrofoam cup. It has a little sugary foam on top and they give you these tiny plastic cups to share. It’s so good and gives you quite the jolt of energy! It’s pretty much the tastiest rocket fuel I’ve ever ingested. LOL Seriously though, this little spot has a great atmosphere and the minute I saw it I said, now I feel like I’m in Miami!

Outfit details: Linen blend shorts (similar style here) | White Tank | Espadrille Wedges

La Mar – Two things to come here for – incredible Peruvian cuisine and amazing views of the city over beautiful Biscayne Bay. It’s exactly what you want when you think of fine dining in Miami. We started with an appetizer of octopus and cebiche (both amazing, and in Peru ceviche is spelled with a b). I had a fabulous branzino and Paul had Arroz Con Mariscos that was also perfect. He’s looking for a recipe to make this at home now, and I can’t wait! Don’t forget to keep the Pisco Sours flowing! After dinner, we had drinks on the terrace overlooking the Miami skyline. I tried the Piscojito – exactly what you’d think – a pisco sour and mojito mashup, and it was great! 

Greenstreet Cafe – If you’re looking for fun brunch vibes, Greenstreet Cafe in Coconut Grove is it. We came here for breakfast and loved sitting outside. There’s a vibrant energy here and plenty of people watching. It feels rather European, a bit artsy, and bohemian at the same time. The kind of place where great conversations happen. I loved the indoor/outdoor set up of the place and the service was exceptional. We sat outside under a white canopy covered in crawling green vines and enjoyed strong coffee and the occasional raindrop or two. 

Havana 1957 – A local friend recommended this place to get our Cuban fix. There are a few locations but we opted for the one on Española Way, as it has this great little outdoor courtyard off the busy street. Tables are shaded with umbrellas and it’s another excellent spot for some people watching. A bit touristy? Yes, but I enjoyed it all the same. The inside embodies all the beauty of Havana in the 1950s, with dark woods accentuated with brightly colored Tiffany lampshades and vintage items representing Cuba’s lively culture. There’s a full bar that looks plucked right from the Tropicana where you might expect to see Ernest Hemingway and Rita Hayworth among other members of the 1950s jet-set sipping mojitos. It’s really impressive and the food was delicious. We loved the traditional Cuban sandwiches here, and I had a pineapple soda that tastes exactly like white gummy bears (my favorite).

Outfit details: Dress | Espadrille Wedges | Sunglasses

Where To Stay

Conrad Hilton Miami – We only stayed one night here but it was a fine hotel. They have water view rooms and the service was good. Great location! 

Where To Play

Coconut Grove – This is a great area of Miami to explore. It’s very lush and tropical with lots of little shops, high-end boutiques, and restaurants. This was where we had breakfast at Greenstreet Cafe. Coconut Grove or just “The Grove” is Miami’s oldest neighborhood and has that old school elegance that I love. 

South Beach – Hmm, what to say here. I’m glad we went and at least saw it. We checked the box. Not sure we will go back, to be honest. There is some well preserved art deco architecture along Ocean Drive, however, that I always wanted to see. We went during the day and drove around, but that’s about it. I was a little disappointed. I try to keep it really positive here on the blog, so if you’re curious I recommend doing your own research on the area prior to visiting.

The Florida Keys

There are a lot of little islands making up The Florida Keys. We drove all the way to Key West, but spent most of our time in Islamorada. I highly recommend Islamorada if you’re looking for that low-key relaxing island vibe. We absolutely loved it there! 

Where To Eat

Morada Bay – We loved it here so much that we came back a second time. We ate here for our first and last meal in Islamorada and it was the perfect way to bookend our trip. This is a great spot for sunsets and sipping. The food is also just so dang good! The first night I had grouper tacos that were insane! We also had a snapper sandwich that was lick-the-plate good and of course, key lime pie! The colorful tables set on the sand and gas-lit torches made the perfect ambience when the sun went down. 

Chef Michael’s – Most restaurants we went to were on the very casual side, but we wanted a really nice dinner to dress up for, too. Chef Michael’s is a beautiful fine dining experience and is great for a romantic date night. The seafood here is also some of the best we’ve had. They have a variety of fish that is unique to the area that we don’t get back in Texas. We started with conch fritters which were just the absolute best. I had yellowtail snapper and Paul had cobia. At Chef Michael’s you’re given the choice of how you’d like your fish prepared, which is really fun. It was also right next door to our resort so we enjoyed a quick golf cart ride over. Make a reservation here if you can!

Key’s Fisheries – This was another great recommendation from our local friends. We love places that have a bit of a dive feel to them where you can order some fried seafood, cold beer, and sit on the water to watch boats go by. This is the place for that! We had the best coconut shrimp I’ve ever tasted as well as the lobster reuben sandwich. It sounds really bizarre but trust me on this one, it’s a MUST! So good! Key’s Fisheries is a market and marina with the freshest seafood on the water. It is super casual and fun. When you place your order they ask you who your favorite band is and then call it out when it’s ready. It was funny hearing, “Fleetwood Mac, your order is ready!” They also supply fish to all the Whole Foods in Florida. I highly recommend coming here! 

Lorelei – Speaking of cold beer and waterfront eating, Lorelei is a fun restaurant and cabana bar that is extremely casual with live music. We went without any expectations and had a very fun night. We ended up having to wait about a half hour for a table but you can grab a drink at the bar and sit on the dock while you wait. The food was good but the atmosphere is what you really come for, I think. The cover band playing under a tiki hut backlit by the setting sun is basically what beach vacations are all about. 

Nikai Sushi Bar – After a relaxing day by the pool, we opted to stay “on campus” and try the sushi restaurant inside Cheeca Lodge, our resort hotel. It’s highly rated and has one of the best views on the property. We opted to dine on the upstairs terrace overlooking the beach. The wind was pretty fierce that night but it made for a good laugh as we tried to keep our menus and napkins from flying away. We started with a tuna stuffed avocado and then had some really yummy sushi rolls. 

Where To Stay

Cheeca Lodge & Spa – I cannot say enough wonderful things about this resort! When you arrive, the resort takes on a bit of a hidden treasure feel to it. It’s tucked away amongst lush tropical trees and winding sandy paths. Cheeca Lodge is a resort that’s been hosting Islamorada guests since 1946. The overall feel is one reminiscent of a simpler time, but with today’s modern conveniences. We opted for one of the bungalows (get bungalow #517 if you can – it’s on the end and has a corner view). What’s great about a bungalow stay is that you’re right on the beach. We loved our covered screened in terrace with spiral staircase down to the sand. It really felt like we were on our own private island. There are so many palm trees and plenty of spots for photos. The staff was the most accommodating, offering to take you anywhere you needed to go and insisting that you not lift a finger while you’re there. Even the food at the pool was some of the best we had on our trip. There are three pools, including an adults-only option, plus lots of fun water toys included like kayaks, water bikes, and more. You can do as much or as little as you’d like. Fishing is a huge attraction here. There’s a massive pier where fishermen cast their lines all day and night. But if just lounging in one of the many white chairs along the shoreline with your toes in the sand is more your thing, that’s ok too. It’s very comfortable and I hope to come back soon! Grab a reservation as early as you can. Cheeca Lodge tends to book up quickly.

Outfit details: Hat (similar style here) | Swimsuit | Sandals

Outfit details: Raffia Headband | Dress | Longchamp Filet Market Tote (similar style here) | Espadrille Wedges

Outfit details: Dress | Espadrille Wedges

Outfit details: Halter dress | Palmgrens Rattan Clutch | Espadrille Wedges

Where To Play

Robbie’s – You cannot come to The Florida Keys without going to Robbie’s. It’s an adventure! Robbie’s has a restaurant and bar plus dozens of open-air shops. There’s something for everyone, but we came to hand feed the tarpon. That’s right – for a small fee you get a bucket of dead fish to dangle over the water hoping (or fearing) that one of the “Silver King” monsters will leap from the water and snatch the tasty snack right from your hand. Hopefully you don’t lose a finger or two. Kidding…but they do get rather aggressive. I opted to drop the fish into the water and watch them scramble to eat it. The tarpon are massive with huge eyes that stare up at you, just waiting for a bite. Hungry pelicans wait nearby, but you have to be careful or they will steal your fish. It was quite an exhilarating experience! 

Rain Barrel Village – You can’t miss this place with its giant sculpture of Betsy the Lobster out front! She’s 30 feet high and 40 feet long, took 5 years to complete, and is a biologically correct sculpture of a Florida Spiny Lobster. And she takes great selfies. 😉 This place has been around for over 40 years and is a must stop. Rain Barrel Village is a large outdoor garden with boutiques, souvenirs, art galleries, and snack stands. We came here to poke around and I left with a watercolor piece done by a local artist. It’s a fun way to spend the morning. 

Day trip to Key West 

Key West is a very easy day trip from Islamorada. Having seen it, I’m very glad we chose to stay in Islamorada instead. While Key West has it’s attractions, I’m not sure we will return. Another check the box kind of thing. If you’re looking for a party scene that pretty much mirrors New Orleans, then Key West is what you’re looking for. Not that I don’t like to have a good time, but I just didn’t see the uniqueness to it like I did with Islamorada. But I’m glad we saw it and we did manage a couple of fun things while there.

The Hemingway Home & Museum – As a huge reader I wanted to come here for some time. The home is pretty amazing given its age, and the garden and pool around it are like an oasis. Also throughout the property are cats with six toes, some or perhaps all, being descendants of Hemingway’s own six-toed cat. I loved the history here and learning even more about Hemingway’s life. For architectural buffs the home has many design elements to admire.

Outfit details: Tiered Color-block Dress | Espadrille Wedges

Southernmost Point in the Continental U.S. – I managed to get a single photo of this point but it was fun knowing we were there. The line to stand next to it and take a photo was extremely long, and I just didn’t think it was worth waiting in the 90+ degree heat and humidity for it. As we drove past, I rolled down the window and snapped. Sneaky, I know. But it’s a great photo op if you’re willing.

Other than the above, we spent time just driving south and exploring along the way. It’s important not to have too much of an agenda and just let yourself relax. See what you see. Stop along the way and check things out. Get absorbed into that island life!

Have you been to The Keys? What are some of your favorite spots? We look forward to a return trip, so let me know in the comments! 🙂

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xo – Erin

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