Top 25 – What to Do in Florida Keys So You’ll Want to Stay

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My memories from childhood flooded back to me as we drove from Palm Beach to the Florida Keys this summer. The clear water and laid back atmosphere remind me that luxury is an experience, not a price point. The Florida Keys has always been a relaxing getaway for me and this trip was no different. Today, I am excited to share what to do in the Florida Keys.

Eat Al Fresco

When you are in the Florida Keys, you must eat outdoors as much as possible. Eating outdoors is part of the luxurious lifestyle that having warm weather year-round provides.

Try Sea Grapes Wine Bar & Bistro with amazing food and wines. They served us our first meal in the Keys and I was blown away by the flavors! One of the tasty dishes was a peach salad with the perfect flavor and texture combination! The savory summer tarts were an explosion of flavor too. The first was an heirloom tomato & goat cheese tart and the second was smoked mozzarella, asparagus, and prosciutto tart. They have some fun events like “On Wednesday’s We Drink Pink” Rose’ Night and a delicious Sunday Brunch. Learn more here and follow them on Instagram @IslamoradaWineBar.

Another amazing location to check out is Square Grouper Bar & Grille and their new bar upstairs called My New Joint. At ‘My New Joint’ start with an oversized pretzel and some fondue. We tried nearly the whole menu and I am still dreaming about the flavors! Follow them on Instagram @MyNewJoint and check out the full menu here.

Fresh Catch

While you are dining al fresco, make sure to eat a freshly caught fish. The Florida Keys are surrounded by water with some of the best fishing in the world. Some restaurants in the Keys will cook up your fresh catch from a day of fishing. There is nothing like fresh fish in the Florida Keys!

Relaxing on the Beach with a Good Book

Part of being in the Florida Keys is taking time to do what you enjoy without the hustle and bustle of a city. To mean that means relaxing on the beach with a good book. Sunset Key has a lovely beach that is so very quiet and peaceful. Ocean Sotheby’s International Realty has several Sunset Key Cottages available for purchase. Sunset Key is right off the coast of Key West and can be accessed by ferry. The island does not have any cars on it and the only transportation allowed on the Island are nice golf carts. It is really cute to see the tiny garages for the fancy golf carts.

Boutique Shopping

Island Trendz tropical gifts is part of a group of boutiques own by Ocean Dayz(@OceanDayzShop) in the Florida Keys. You need to stop by one or all of them on your trip to the Keys. Island Dreamz is at Post Car Inn (follow them on Instagram @IslandDreamzFL), Island Trendz at Amara Cay Resort (follow them on Instagram @IslandTrendz), Sea Aire Boutique in Islamorada (follow on Instagram @SeaAireBoutique), Sandy Dreamz at Marriott Beach Key Largo (follow on Instagram @SandyDreamzKL).

The Ocean Dayz stores have this amazing brand called Pool to Party which is perfect for the Keys. They have kaftans that can easily go over a swimsuit. They also have fantastic hats that are crushable so you can pack them. Also, the jewelry and accessories fantastic!

Art Galleries

The Florida Keys is filled with art galleries Ocean Sotheby’s International Realty in Islamorada has a gallery in their office that is a must see. During our stay in the keys, we met Roberto Pasta Pantaleo (he goes by Pasta). He is an amazing local artist that focusing on the capturing of sea life in the Florida Keys. His work is displayed in the Ocean Sotheby’s International Realty Gallery in Islamorada and also in his Signature Gallery. Follow Pasta here on Instagram and on Art by Pasta where you can order a print!

Scooters & Club Cars

Part of the fun of being in the keys is that you can get around in a scooter or a golf cart. Sunshine Scooters has an awesome deal where you can rent club cars or scooter so that you can leave your car behind while you explore Key West. I absolutely love Key West in the Fall and Winter. That is why South Florida and the Florida Keys are on my list of Winter Travel Spots to Escape the Cold Weather. The absolute best time to visit Key West is from Halloween week (for Fantasy Fest) to the end of May. Here is my Key West Packing Guide.

Here are the awesome gals that I shared the trip with – Jessica from PB Social Diary, Heather Reinhardt, Jessica from Eat It Miami, Ellie from Espresso & Chanel, and Dana Peller from SoFloMoms and Pellerini Mom Blog.

Baby’s Coffee

There is a cute coffee shop on the way to the Key’s that I fell in love with. It is called Baby’s Coffee. They have an amazing selection of milk and coffee options that cater to a (mostly) dairy free girl like me. They also give you paper straws rather than plastic ones – looking out for the environment!

House Hunting in the Florida Keys

During your travels to the Florida Keys, you should also go house hunting for your own slice of luxurious paradise. It is the perfect place to get away from stress and just ease into a slower paced island life. Ocean Sotheby’s International Realty has an amazing selection of properties that you must see. Follow them on Instagram @OceanSothebysRealty.

Pen Key Club

One of my favorite homes is in the Pen Key Club in Upper Matecumbe Islamorada, Florida Keys. The home was built in the 1960s and each room is meticulously redone! I would like to move in right now! The entire house is surrounded by patios so that you can live an indoor-outdoor life of leisure! See all the info on the property here. It is being sold by Sabrina Wampler and Sarah Ewald (follow them on Instagram @flkeyssoldsisters_oceansir).

Southern Comfort

This beautiful home is called Southern Comfort with their own personal beach and wrap around patio. The view from the upstairs master bedroom is a dream of mine. I have always wanted to walk up to an unobstructed view of the ocean! Learn more about this amazing property here and follow the gals that are selling it on Instagram @LiveIslamorada (Cheri Tindall and Leslie Leopold).

Hidden Gem

The Ultimate home is this gorgeous fisherman’s dream home called the Hidden Gem that has a main house and guest house in Marathon Key! OMG this home is fantastic with 8 bedrooms and 10 full bathrooms! It is a beautiful corner lot that makes you feel like you are on your own island! Learn more about the Hidden Gem here. It is being sold by Bob Cardenas – Contact him at [email protected].

Villa Tenardier

This is another one of my favorite properties in the Florida Keys. Villa Thenardier is on 2 acres with a private beach. The wrap around porch is a dream which is somehow made even better with private outdoor showers for each bedroom. The outdoor covered living area is perfect for entertaining! The master suite has it’s own living room, brand new updated in 2018 bathrooms, and even a 3rd floor office with amazing water views!

Key West

While you are in the Florida Keys, you must visit Key West to experience some of the nightlife, art, food, and rich history.

Nightlife in Key West

The nightlife in Key West is like no other and really a must experience. There are so many famous spots that I could write all day. One of my favorite places in Key West is Irish Kevin’s.

Key West Gallery

The Key West Gallery is an amazing place filled with so much fun art from Salvador Dali and Roy Lichtenstein. I discovered some artists that are new to me! I also discovered that collecting art is actually possible when you have an easy to talk to women like Kellie Alpert helping you. She’s amazing!

Some of my favorite new artists are Jillian Lee, Adama Scott Rote, and Dmitri Danish. Jillian Lee has these amazing dresses that draw you in with their intricate detail. Adam Scott Rote’s art is extremely fun and modern realistic painting. The paintings of Madonna and Albert Einstein Peonies are my favorites! Dmitri Danish art is wild with their ability to seemingly glow in the dark. Learn more about the Gallery here and what they have available for purchase.

Papa Pillar’s

While you are in Key West, you must check out Papa Pilar’s Rum Distillery. The rum is named after Ernest Hemingway who’s nickname was Papa. The Rum is aptly named after Papa and the vessel, Pilar allowed Hemingway to reach beyond the shoreline, feast on life’s experiences and later regale us with his stories. I picked up a bottle of the blonde rum while I was there and I am very excited to start mixing fun drinks with it! Follow Papa Pillar’s Rum on Instagram @papapilar here.

Thanks to Ocean Sotheby’s for hosting us on this amazing Keys Adventure! Special thanks to @EatItMiami for taking a lot of these amazing shots of me. You are the best! 

What does your dream life in the Florida Keys look like?

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