Ultimate Florida Keys Guide: 7 Rainy Day Bucket List Things To Do

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Photo taken on the GoPro HERO 12 Black

So you finally are setting out on your bucket list trip to The Florida Keys that you have been dreaming of… but it’s going to rain…? While it can be easy to feel like the trip is ruined, there is actually a TON to do throughout the Keys in the rain, from trying new sports to lots of amazing food, to cruising on the water at sunset.

We just finished a 5 day trip through the Keys, and got caught in a pretty crazy storm. Most of our water activities ended up getting canceled due to wind. Even though it was a little different from the original plan, we were able to pivot and find plenty of fun ways to enjoy the beautiful Florida Keys, and I am excited to share them with you for your trip!

1. Take a Jetski Tour in Key West!

While many of the underwater adventures may not run in the rain, we were able to instead book a Jetski tour with Barefoot Billys in Key West! You can rent a jetski for one or two people, and take a tour around nearby islands, ride through the mangroves, and learn more about the history of The Keys. Private tours are also available!

We weren’t totally sure what to expect on a “tour,” and this one turned out better than we could have expected! You don’t need any experience to hop on a jetski, and the guides will teach you everything you need to know. There is plenty of space for people who want to go a little bit faster, and those who are just learning, and we also got “free” time to ride around on our own and play in the water. After being really disappointed when our snorkeling tour got canceled, this was such a fun way to enjoy the beautiful Keys water and explore through areas we wouldn’t have seen otherwise.

2. Visit the Key West Butterfly and Nature Conservatory

Walk amongst the butterflies right in town in Key West! The Key West Butterfly and Nature Conservatory is home to hundreds of butterflies of 50-60 different species, and you can stroll right through their habitat. Day tickets for adults are $17.50 (you can save $2.00 by buying them online) and $12.50 for kids. You’ll start in the learning center, where you can explore the butterfly lifecycle, the monarch migration, and see close up caterpillars feeding and developing on their host plants.

Then, you’ll make your way into the main event. On each side of the pathway, there are towering leafy plants, flowers, waterfalls, and trees the butterflies, birds, turtles, and flamingos call home. You will instantly be filled with awe seeing all of the butterflies dancing throughout the conservatory. I couldn’t believe how many there were, and they often even landed on us! It is quite a unique experience, and it was a lot more engaging than I expected. You are truly transported to another world right in the middle of Key West. You’ll leave through the gift shop and art gallery with plenty of keepsakes to bring home to remember the trip.

3. Eat your way through The Florida Keys

One of the biggest highlights of our entire trip was how much amazing food we got to try! There really is something for everyone to try in The Florida Keys, and here are a few of our favorite spots:

  1. The Boat House: This Historic Waterfront restaurant offers a really fun atmosphere, great food and drinks, and the best happy hour around. From 4:30 to 6 pm every day, all appetizers and many of their wine, beer, and cocktails are half off. We ended up doing a whole dinner of appetizers, and it was delicious! The portions are plenty large, and for two very hungry people, we could get 4 to 5 of their apps and be stuffed. We’d recommend their conch fritters, buffalo wings, and calamari, and finished off with a slice of Key Lime Pie (because you know, you have to!).
  2. Half Shell Raw Bar: Right next to The Boat House is “The best raw bar in Key West.” Half Shell Raw Bar offers a ton of variety for raw seafood lovers and visitors trying it out for the first time. We really enjoyed getting a few raw plates to share, and loved their Baked Oysters Sampler and Bucket of Clams. Not so into the raw experience? There are plenty of meat and cooked seafood options too!
  3. Chef Michaels: If you are celebrating an anniversary or birthday, or are looking for a more upscale dining experience, Chef Michaels in Islamorada offers a high-end dinner menu with seasonal and local ingredients. The food was top tier, the service was really wonderful, and I would love the opportunity to dine here again! We split the Tuna Tataki, Conch & Shrimp Fritters, Grilled 8oz Filet Mignon, Smokey Bacon & Gorgonzola Cream, Fried Spinach, and “Juliette” Swordfish seared w/ shrimp, scallops, chardonnay butter & toasted almonds. Plus, their Key Lime Pie was the best we had in the Keys!
  4. Harbor Cafe 90: This very small cafe in Islamorada surprised us so much that we had to go back for seconds. Harbor Cafe 90 offers a menu filled with Latin flavor and cuban pastries. We both absolutely loved their Homewrecker breakfast burrito and their Spanish Lattes (the best coffee we had in the Keys!!).
  5. Key Largo Conch House: This restaurant offers breakfast, lunch, and dinner, and was definitely some of my favorite food we had the whole trip! We split their Conch Fritters, Mahi Panini, and Conch and Chips, and were really happy with how fresh and delicious it all was! Plus, we ended with Key Lime Pie (can you tell there was a theme?).
  6. The Fish House: This eclectic restaurant will transport you back in time. They offer a HUGE menu filled with fresh fish, crab, shrimp, and steak, all with unique preparation options you probably haven’t tried yet! We split their lobster ravioli and their black and blue mahi mahi, and were constantly going back and forth on which one was better because they were SO GOOD.

4.Try some Iguana Bait at Florida Keys Brewing

Florida Keys Brewing, located in Islamorada, offers a really fun atmosphere, live music, and great beer, all while transporting you to one of the most colorful places you’ve ever been. All of the beer is made right at their microbrewery down the street, and the beer garden is located right in the Morada Way Arts and Cultural District (which you should definitely check out while you’re there).

Their most popular beer is the Iguana Bait, which is a honey hibiscus kolsch made with local Keys honey and hibiscus. We loved getting flights to taste their wide variety of beers, and the bartenders and patrons all made for a really fun environment to hang out at day or night.

5. Enjoy the Outdoor Views of The Florida Keys

Photos captured on GoPro HERO 12 Black

While rain may feel like it’s going to force you inside, we actually felt quite the opposite. Even during a large December storm, the temperatures outside were still incredibly pleasant. While we were there, it never got below 65 degrees, which still felt very nice in a t-shirt and shorts.

We spent a lot of time walking around town and on the beaches in the rain! We loved walking around the Historic Seaport, along Smather’s Beach, and through the shops on Duval Street. Smather’s beach also has some beautiful covered picnic tables, which would be a fun spot to bring a picnic lunch or dinner to watch the sunset. Don’t forget to go by the Southernmost Point Buoy to take a photo at the southernmost point in the continental United States!

6. Try a new sport at The Lagoon Adventure Park on Grassy Key

When most of The Keys shut down because of bad weather, the Lagoon employees live for it! The ocean can get pretty intense in a storm, but the lagoon offers a closed in area that is thriving in pretty much any weather. This cable park was created for locals and visitors to learn and progress on a variety of wind, board and paddle sports. You can learn how to wakeboard, start hitting jumps on a wakeboard, learn to kiteboarding, and even start foilboarding all at one site.

The instructors are knowledgable and passionate about their sports, and are stoked to get you out on the water, whether you’re brand new or a seasoned rider. The lagoon also has a beer garden on site with a food truck concocting amazing meals for you to enjoy after your session. The Lagoon at Grassy Key will save your bucketlist trip adventures even if the weather tries to change things up!

7. Hop on a Tiki Cruise in Key Largo

Grab some drinks and set out for sunset with Cruisin Tiki’s Key Largo. These mobile tiki bars are a super fun way to get out on the water. You can book a private tour, but we enjoyed being on a group tiki cruise and chatting with other visitors. You can buy drinks at Snook’s Bayside (the restaurant where the cruises start), or you can BYOB and use their on-cruise cooler to keep them chilled.

The cruises last about 2 hours, and you’ll get to cruise around some small islands and next to the mangroves. We even got to see two manatees, so bring your GoPro’s for underwater shots while you’re on board!

Where to stay in the Florida Keys

Photos captured on GoPro HERO 12 Black

Key Largo:

Baker’s Cay: This upscale hotel offers beautiful views of the crystal blue water, a beach with great swimming access, and delicious waterfront restaurants right on the property! We loved coming back to the resort every night and having the most amazing view out our balcony.

Grassy Key/Islamorada:

The Resort at Grassy Key This is one of the most beautiful resorts we have ever stayed at. The resort has a stunning pool and beach right outside of the rooms, paddle boards and kayaks for visitors to use, and restaurants and bars on the property. We spent our afternoons watching kite surfers right out our patio, and it was our favorite place we stayed the whole trip!

Key West:

The Perry Hotel: This beautiful property on Stock Island is a great home base for exploring Key West. We loved the cleanliness of the rooms, the pool and outdoor area right on the harbor, and the access to nearby restaurants and bars. Definitely check out their on-site restaurant and bar, Salty Oyster! They had a great happy hour and we loved the easy access.

More about the GoPro HERO 12 Black

GoPro’s newest camera, the HERO12 Black, is their most stable, colorful, and user friendly camera yet. Most of these photos were taken as frame grabs from videos, which means we don’t have to choose between taking photos or videos anymore! We just start recording, and can get the photos later using the Quik app!

One of the biggest benefits to the new camera is Vertical Mode, which allows us to choose between shooting horizontal or vertical, and we can capture vertical videos that are ready to go on socials instantly (I cannot express how useful this is for time saving and getting higher quality videos). This new action camera can run for over 2.5 hours at 1080p30fps, utilizes voice control for hands free recording, captures up to 5.3K60fps video resolution, and is waterproof up to 33 feet.

Pair this camera with the new Max Lens Mod 2.0 and an Enduro Battery, and you’re going to be set to capture incredibly POV content in even the most intense conditions.

A vacation in The Florida Keys will be amazing, no matter the weather. While I hope you get a sunny trip on your next visit to The Florida Keys, I also hope that we have inspired you to find a little more to explore too! For more information on visiting the Florida Keys, best times to go, and more fun activities, check out their website here.