One of Ryan and my favorite places to vacation is the Florida Keys! Our first trip down there was in 2015 and we’ve gone every March since. Ryan proposed to me in Islamorada in 2020 and we were married in Key West in 2021! It’s one of our special places and we love to experience new things down there every year. We are constantly asked about our favorite places to stay, restaurants and bars and stuff to do so I wanted to put together a typical itinerary of things we like to do when we’re down there.
When we go to The Keys we always fly into Miami and make the drive down. We do this for two reasons: it’s much cheaper to fly into Miami rather than Key West and the drive is absolutely stunning. We typically stay for about 10 days and split our time between Sunset Villas on Conch Key and Key West.
Marathon – Islamorada
It is definitely a more relaxing, slower vibe around Marathon as compared to Key West. We have a lot of favorite restaurants and stops that we hit up yearly when we stay here.
Food: Lorelei, Sparky’s Landing, Island Fish Co, Herbie’s Bar & Chowder House, Lazy Days Restaurant, Keys Fisheries
Drinks: Florida Keys Brewing Company & Islamorada Brewery & Distillery
Fun: Robbie’s. You can rent jet skis or boats, snorkel, parasail, fish and more out of here. Kind of a one-stop-shop for all things on the water in the Florida Keys. Coco Plum Beach & Sombrero Beach, Florida Keys Aquarium Encounters (this is your chance to pet stingrays!), fishing charters with Captain Jeff Malone. We’ve snorkeled out of a few locations in the Keys and have enjoyed them all. We also parasailed out of Robbie’s this year for the first time and I think this will become a regular activity for us.
Where we stay: We stay at Sunset Villas on Conch Key. We’ve stayed here every year since 2015 and we absolutely love this spot. It’s centrally located and it’s right on the water. We get beautiful views of sunsets every night and the owners are fabulous.
Key West
Key West is another animal when it comes to vacationing in the Keys. It is definitely more of a party atmosphere and we are constantly on the go when we stay down in Key West. We try to do something new-to-us each year, so this list is far from comprehensive. These are all things we have done or places we’ve gone that we love. Happy Hour is a big deal in Key West and it typically starts at 4PM every day. Happy Hour is a great opportunity to try a ton of seafood for very little money. Absolutely take advantage of it!
Food: Two Friends Patio, Sarabeth’s Key West, Blue Heaven, Conch Republic, Bagatelle, Garbos’ Grill, Mangia Mangia, Caroline’s, Amigos Tortilla Bar, White Tarpon, Alonzo’s Oyster Bar
Drinks: Irish Kevin’s, Sloppy Joe’s, Hogsbreath Saloon, Waterfront Brewery, First Flight Brewery, Jack Flats Sports Bar, Willie T’s, Durty Harry’s, Captain Tony’s Saloon, Green Parrot Bar, World’s Smallest Bar, Hank’s Hair of the Dog Saloon
Fun: Papa’s Pilar Rum Distillery, Key West First Legal Rum Distillery, Hemingway House, Key West Ghost Tours, sunset celebration at Mallory Square, Hop-On Hop-Off Trolley Tour, Key West Shipwreck Museum, Key West Food Tours, Lazy Dog Adventures kayak tour, Key West Lighthouse
Where we stay: We’ve stayed in a few locations when down in Key West. It really depends on what kind of trip you’re looking to have. When Ryan and I visit Key West, we usually stay out late and enjoy the nightlife that Duval Street has to offer. We’ve found that the best location for us to stay is right on Duval Street at the Smallest Bar Inn, right behind the World’s Smallest Bar. However, if staying out late isn’t your thing, we’ve stayed in several cottages around Key West that we’ve really enjoyed. We’ve found a lot of great options on VRBO and Airbnb.
Have you been to the Florida Keys? Where is your favorite place to go or eat? Let me know!
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