Destinations, North America

A Weekend Guide to The Upper Keys

Growing up in Key West, I can’t count the number of times I drove by signs for restaurants, hotels and things to do in the Upper Keys, and didn’t think twice about them! Thankfully, after watching a few episodes of Netflix’s Bloodline, my boyfriend and I decided to plan a trip down to explore these beautiful islands and celebrate his birthday.

After our incredible weekend, I felt it was necessary to share the wealth of all the wonderful experiences we had. Below, you will find everything you need to know and more about visiting the Upper Keys!

Where to Stay

Banana Bay Resort, Marathon

Though the Keys have an abundance of wonderful places to stay, it wasn’t as easy to find ones that were in our price range and met our criteria for a dog friendly resort. Banana Bay exceeded our expectations. Upon arrival, we were given a room upgrade with a beautiful ocean view. Additionally, the free amenities were a huge perk. They included everything from free beach towels to free bikes!

Pro Tip: Use the bikes to ride to the Key’s Fisheries nearby, try to find some upstairs seating, and enjoy a refreshing drink with some famous Lobster Reuben!

Cheeca Lodge, Islamorada

Although we didn’t get to stay in at Cheeca, this is the hotel I would recommend for anyone who wants to stay a little further North in the Keys. Cheeca is tranquil, serene and upscale at an affordable price. It is also dog friendly, however, you will be paying a fee of $70 per night if you decide to bring you fur baby along.

The Best Eats in the Upper Keys

Not only are all of the places listed below some of the best in the Keys, they are all welcoming to dogs and other pets! We were able to bring Leilah along with us to every restaurant on this list besides the last one.

Mangrove Mike’s Cafe, Islamorada

Mangrove Mike’s is a great place to stop for breakfast/ lunch if you happen to be in Islamorada. They have a large menu full of delicious food, and large, affordable portions. The service we received here was the most wonderful we’d experienced during our time in the Keys.

The Buzzard’s Roost, Key Largo

We stopped at Buzzard’s on our way back up North to catch some dinner with a Sunset view. We got a beautiful table next to the water, however the heat made things a tad unenjoyable. Luckily, their GM was extremely kind and helpful. He came over to fix our umbrella and block out the harsh sun with some fun innovation. As soon as a table under the awning opened up, he moved us without question. We enjoyed delicious oysters and lobster bites (that were heavy on the lobster and so yummy) and the most delectable chocolate turtle cake for dessert. I’d give this place and A+ for food, service, and atmosphere!

Key’s Fisheries, Marathon

If you decide to take my advice and stay at Banana Bay Resort, you absolutely must take that bike ride over to Key’s Fisheries to try out some of the FRESHEST (I mean literally fresh off the boat fresh) seafood in the Keys. Next to it’s tasty seafood, Key’s Fisheries boasts a casual atmosphere with good vibes guaranteed.

Square Grouper Bar & Grille, Tavernier & Summerland

Whether you’re going to brunch, lunch, or dinner you can’t go wrong with this place. Square grouper has two locations in the Keys that are both thriving in business, and it’s not hard to see (or taste) why! They have a large menu full of mouth watering appetizers, and their fresh catch specials are any seafood lover’s dream!

Lorelei Restaurant & Cabana Bar, Islamorada

With rustic outdoor seating, delicious seafood, Sunset views and live music, Lorelei’s is a must-make bucket list stop to truly get a taste of life in the Keys. Seating comes at a first come first serve basis, so make sure you get there early!

Florida Keys Steak and Lobster House, Marathon

This was the only restaurant that Leilah (our dog) was not able to join us at, and also the only one that requires a reservation beforehand. This Dinner may be a little bit of a splurge, but we found the food to be 100% worth it. This is the perfect place to go for a romantic dinner or birthday celebration. Although it’s famous for it’s steak and lobster, I must admit that the “happy tuna” sushi roll we got took the cake for the best item we had (and possibly the best sushi roll I’ve ever had!)

Things to Do

Take a Snorkel Trip to Sombrero Reef

Located right in Marathon, FL, Sombrero Reef is the the 3rd Largest barrier reef in the world! This reef not only boasts vibrant and colorful coral, but some of the most beautiful underwater wildlife you’ll ever encounter. We had a wonderful experience with Spirit Snorkeling despite unfortunate weather conditions.

Important Tip: Plan your snorkel tour for a less windy day. If you aren’t an experienced snorkeler, the waters can get rough. And if you are faint of the stomach like myself, make sure you take your Bonine the night before!

Spend a Day at Bud n Mary’s Marina

You can’t go to the Keys without stopping by the “Sportsfishing Capital of the World!” From charter fishing boats to party boats, Bud n Mary’s has something for whatever kind of mood you’re in. When you get back from your sea ventures, stop by their lively bar for some great drinks and eats!

Visit Bahia Honda Beach

A little South of Marathon is my favorite beach in the Upper Keys, Bahia Honda. Although there’s an $8 entrance fee, you’ll find upon entering that it is more than worth the money. Bahia Honda is located right next to the 7 Mile Bridge, and boasts some of the most gorgeous views and clear waters in the Keys. The last few hurricanes did do their damage on this beach, but I can attest that it’s still just as beautiful as I remember.

Feed Tarpon Fish at Robbie’s in Islamorada

Although this may be labeled as a “touristy” thing to do, it’s hard to deny that it isn’t a fun time! Watching these big silver monsters munch down is an extremely intriguing spectacle, especially when the pelicans decide to come join the party! If you’re an adventure/ animal lover like myself, visiting Robbie’s is 100% worth the stop!

RELAX, you’re on island time.

Find a beach, a random mangrove, pull your car over and go for a swim and soak in the sun. It’s what the Keys are meant for 🙂

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