13+ Things to Do in Siesta Key on a Rainy Day

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Looking for things to do in Siesta Key on a rainy day? Rainy days in Siesta Key might seem like a damper on your beach plans, but fear not! This charming Florida paradise has plenty of indoor activities that will keep you entertained while the rain pitter patters outside. And since you probably drove from the airport to Siesta Key, you’ll have a car to help you get around when the weather isn’t ideal.

We travel in Florida often during the rainy months, and I’ve discovered that most days you’ll enjoy at least a few hours of sunshine even in the rainy season, but instead of just waiting for those times, why not enjoy ALL of your vacation time? You might need to leave the island for some of these fun ideas, but at least you’ll stay busy and still have a terrific time. Ready for inspiration?

street in Siesta Key Village

1. Siesta Key Village

Siesta Key Village is a fantastic place to visit on a sunny day when you need a shopping or dining break, but it’s also a great option for a rainy day. Yes, you’ll be ducking raindrops while hopping from shop to shop, but the area is so walkable that you can easily park your car and spend a few hours strolling with an umbrella.

When you are ready for a shopping break, there are plenty of dining options ranging from excellent breakfasts to fresh-off-the-boat seafood. And, several restaurants have covered outdoor seating so you can still enjoy the fresh air while avoiding the rain.

💥 Pam’s insider tip: several restaurants have amazing Happy Hour specials. On our last visit, we indulged in $1 oysters & tasty drinks at SKOB (Siesta Key Oyster Bar).

2. Siesta Key Wine Bar

Another fun option, just on the outskirts of the heart of Siesta Key Village is Siesta Key Wine Bar. It’s in the same strip center as the Siesta Key Visitors Center (which you should also visit!).

Although I love a good winery or wine bar, I’m not about to waste a day of sunshine inside if I can avoid it. However, if it rains? Perfect time to check it out. This cozy little wine bar serves wine by the glass or you could get a flight of wine. Next time we are in Siesta Key and it rains – this is where I’m headed!

Siesta Key Wine Bar, 5138 Ocean Blvd. Siesta Key, FL

inside of Mojo Risin' in Siesta Key Florida

3. Game time at a local coffee shop

This is something we’ve done multiple times while on vacation when it rains. We’ll search for the best local coffee shop, grab some cards or dice (or one of the games we’ve brought with us), and spend an hour or so enjoying drinks and games.

It’s a fun way to spend a rainy afternoon and something we don’t often have time for at home which makes it feel special. On Siesta Key, although there are several lovely coffee shops, my favorite is Mojo Risin’ Coffee Company. It’s in the village and has a fun, funky vibe.

Mojo Risin’ Coffee Company, 5251 Ocean Blvd. Siesta Key, FL

4. Movie marathon

Sometimes it’s raining so hard and you are feeling so lazy that you don’t even want to leave the room, am I right? On these occasions, it’s time for an in-room movie marathon! These days, many rentals have either a smart TV where you can use your own Netflix or Amazon Prime membership to watch movies or a DVD player.

We’ve done this on several trips – a very memorable one was when my daughter and I were traveling just the two of us and we borrowed all three Iron Man movies from the check-in desk and watched them in a row. Add popcorn, snacks, and blankets and you’ve got a wonderful way to spend a rainy day in Siesta Key!

Sniki Tiki in Siesta Key Florida

5. Hang out at a Tiki Bar

Okay, this is a fun thing to do ANYTIME on Siesta Key. On our last visit, we had a blast listening to live music and sipping on cocktails at the Sniki Tiki, and that was just a lovely winter evening. However, it would be something you could enjoy if it was raining while you were visiting Siesta Key too.

There are several Tiki Bars on Siesta Key, and all of them have party atmospheres, live music, and strong drinks. Many of them also have covered patios, so the fun can continue even if the weather isn’t cooperating. If you head to either Siesta Village or Captain Curt’s Village, you’ll find plenty of options. And, since there is a free shuttle service on Siesta Key, you don’t even have to worry about driving back to your rental – just remember cash to tip your driver.

Sniki Tiki, 1204 Old Stickney Point Rd. Siesta Key, FL

Things to Do Near Siesta Key on a Rainy Day

The rest of these fun ideas for rainy day activities when visiting Siesta Key will require you to leave the island, but as you need a rental car when visiting Siesta Key anyway, it shouldn’t be a problem.

6. Siesta Key Rum Distillery

It’s always fun to tour a distillery, and although I’m not a fan of rum myself, I still find these tours interesting and well worth my time. The Siesta Key Rum Distillery tour takes about forty minutes, and you’ll get to learn how their specialty rums are made.

There is also a gift store and place to purchase cocktails made with the Siesta Key Rum, so plan on spending a few hours (the perfect amount of time for a Florida thunderstorm) at the distillery. Sign up for your tour before you arrive, because they do fill up. There are two tours most days of the week.

Siesta Key Rum Distillery, 2212 Industrial Blvd. Sarasota, FL

7. Ringling Museum

The Ringling Museum in Sarasota is a super cool destination, especially on a rainy day in Siesta Key. Known for its vast collection of art, the museum showcases an eclectic mix from Renaissance paintings to contemporary works. The grandeur of the Ca’ d’Zan mansion, a part of the museum complex, offers a glimpse into the luxurious life of circus magnate John Ringling and his wife Mable.

Visiting the Ringling Museum is not just about admiring art; if you love the circus, it’s a fascinating look into its history along with that of the Ringling family. On a rainy day, the museum’s indoor galleries provide a perfect refuge, allowing you to wander through history and art, making it an enriching and educational experience for everyone. Plus, the lush gardens, even under a light drizzle, are a sight to behold, blending natural beauty with artistic elegance.

Ringling Museum, 5401 Bay Shore Drive. Sarasota, FL

8. Mote Marine Aquarium

We always try to visit an aquarium if there is one where we are traveling, and the Mote Marine Aquarium is a great option if it’s raining when you are visiting Siesta Key. Plus, it’s fairly near The Ringling and St. Armands Circle so if you encounter an entire day of rain you’ll be set!

The Mote Marine Aquarium offers a fascinating glimpse into marine life, featuring a diverse array of sea creatures from sharks to manatees. It’s not just about viewing; the aquarium provides educational insights into marine research and conservation efforts. This makes it an ideal spot if your family wants to combine fun with learning, all while staying dry and entertained on a rainy day.

The Mote Marine Aquarium, 1600 Ken Thompson Pkwy, Sarasota, FL

Restaurant in St. Armands Circle in Sarasota Florida

9. St. Armands Circle

St. Armands Circle, a unique shopping and dining hub near Siesta Key, is a splendid choice for a rainy day activity. Its charming layout, reminiscent of European town squares, is lined with a variety of boutiques, galleries, and specialty shops, offering a delightful shopping experience regardless of the weather. Whether you’re in the mood for fashion, art, or even gourmet treats, St. Armands Circle caters to all tastes.

Beyond shopping, St. Armands Circle is a haven for foodies, boasting an array of restaurants and cafes that serve everything from casual bites to upscale dining experiences. Whether you’re ducking in and out of shops or sitting down for a meal, St. Armands Circle offers a delightful escape from the drizzly weather.

When we visited St. Armands Circle it was before Christmas and the decorations were lovely! It felt magical and was a great opportunity to pick up some special gifts for the holidays. One of the things I like best about St. Armands Circle is the variety of unique shops along with standard upscale options. Next time you visit Siesta Key add a visit to St. Armands Circle to your trip.

St. Armands Circle, 300 Madison Drive. Sarasota, FL

10. The Artful Giraffe

Looking for something a little unique (and creative) to do next time it rains during your trip to Siesta Key? Check out The Artful Giraffe. The Artful Giraffe is an enchanting art gallery and studio nestled in the heart of Sarasota, just a short drive from Siesta Key. It’s part gallery, part art studio. The gallery showcases a delightful array of handcrafted art and gifts created by local and national artists, which are lovely to look at, but if you really want to have fun head over to the studio.

The studio offers a variety of workshops and classes, suitable for artists of all skill levels, including fun pottery painting sessions. It’s a perfect activity for a rainy day, allowing you to immerse yourself in creativity and maybe even craft your own souvenir. Whether you’re browsing for unique art pieces or getting your hands dirty in the studio, The Artful Giraffe offers a delightful and inspiring experience.

The Artful Giraffe, 1861 Fruitville Rd. Sarasota, FL

11. The Cookie Cottage

Ready for another fun and unique thing to do when it rains in Siesta Key Florida? Head over to The Cookie Cottage in Sarasota. It might seem a bit weird to consider visiting a bakery as a fun thing to do, but The Cookie Cottage is not your normal bakery!

In addition to yummy treats (maybe plan on taking some home to enjoy with coffee later), they also offer drop-in cookie decorating. How fun is that? Now they recommend that you avoid Saturdays (lots of birthday parties) or at least call ahead to see how busy they are, but most of the time, it’s a great rainy-day option.

The Cookie Cottage, 335 Gillespie Ave. Sarasota, FL

Palm trees outside the Mall at UTC in Sarasota Florida

12. Mall at UTC (University Town Center)

If it’s raining really hard, the indoor mall at UTC is a terrific choice. On our last visit, it wasn’t raining, but I spent several hours enjoying a drink and appetizer at a restaurant and then walking the mall. We did walk outside too, but the indoor part is large enough that you could easily spend a rainy afternoon shopping.

The Mall at UTC has pretty much every store you could imagine along with plenty of restaurant choices. And, if the rain stops, head over to the nearby Popstroke to play a little miniature golf. (We had a blast playing at the Popstroke in Peoria – read all about it here).

Mall at UTC, 140 University Town Center, Sarasota, FL

13. Sarasota Trolley Tour

Do you love history? Exploring a new place? If there is just a light rain during your trip, then the Sarasota Trolley Tour would be one of my top picks for things to do in Siesta Key on a rainy day. This guided tour offers a comfortable and insightful way to discover the best of Sarasota from the cozy confines of an air-conditioned vehicle. As you traverse the city, you’ll see several key points of interest, including the culturally rich Ringling Museum and the historic Sarasota Opera House.

The tour is more than just sightseeing; it’s a learning experience. Your knowledgeable guide shares fascinating details about Sarasota’s vibrant history and culture, enhancing your understanding and appreciation of the city. I’ve found that these tour guides also offer invaluable tips on where to eat, drink, and explore, helping you plan the rest of your stay. The Sarasota Trolley tour is an ideal rainy-day activity during your visit to Siesta Key, especially when the weather isn’t beach-friendly.

👉 Book your Sarasota Trolley Tour HERE!

Siesta Key Beach

More Ideas for Things to Do in Siesta Key When it Rains

Need more ideas? Hopefully not because you are getting plenty of sunshine during your Siesta Key vacation, but just in case, here are a few extra suggestions.

Bowling Fun

Bowling is a classic rainy-day activity, and Siesta Key’s nearby bowling alleys offer the perfect blend of fun and competition. Whether you’re with family, friends, or even solo, hitting the lanes is a great way to pass the time. Many alleys also offer food and drink, making it a complete entertainment experience.

Catch a Show

If you enjoy cultural experiences, catching a show at one of the local theaters is a must. Sarasota’s vibrant performing arts scene boasts a range of shows from Broadway-style musicals to intimate plays. It’s a perfect way to immerse yourself in the local culture and talent.

Escape Room Adventure

Escape rooms have become a popular group activity and Siesta Key’s vicinity has several to choose from. These interactive games challenge your problem-solving skills and teamwork as you decipher clues to ‘escape’ the room. It’s an exhilarating and fun way to spend an hour or two, away from the rain. My daughter especially loves these so we tend to search them out if you need something fun to do during icky weather.

Explore Sarasota Museums

Aside from the well-known Ringling Museum, Sarasota is home to other fascinating museums. Whether you’re interested in classic cars, science, or history, there’s a museum to match your interest. These museums offer a chance to learn something new and enjoy a day of exploration indoors. When the kids were little, a science museum was always our top pick.

Siesta Key Florida

Map of Things to Do in Siesta Key on a Rainy Day

Where to Stay on Siesta Key, Florida

Siesta Key’s charm is partly due to its lack of traditional hotels, offering a more intimate and home-like stay. Visitors typically rent condos, which adds to the island’s unique appeal. A personal favorite is the Sarasota Surf & Racquet Club. This spot is perfect due to its direct access to the beach, breathtaking views, and an atmosphere that warmly welcomes families. We loved the extra space and the cleanliness of our unit when we last stayed there – it had everything we needed for a beach vacation!

🌴Check out the rates for your dates at the Sarasota Surf & Racquet Club HERE.

For those seeking a touch of luxury, the Beach Residences on Siesta Key, also known as the Hyatt Vacation Club is a standout choice. This upscale property marries the comfort of a private home with the plush amenities of a premium resort. The condos at the Beach Residences are generously sized and elegantly furnished, featuring awe-inspiring views of the Gulf of Mexico (according to our son, our friends’ condo there even had a fancy bidet!). It’s an ideal option for those who desire a sophisticated yet comfortable beachside experience.

🌴Check to see if the Beach Residences are free on your dates here.

Ocean at Siesta Key, FL

FAQs: Siesta Key Rainy Day Activities

Does it rain a lot in Siesta Key?

It often rains in the afternoon in June, July, and August.

What is the best month to visit Siesta Key Florida?

Any month! Although the weather is probably best from April to May or September to October.

What is the least crowded beach in Siesta Key?

Crescent Beach is the least crowded beach in Siesta Key.

What is the best way to get to Siesta Key?

Fly into Sarasota or Tampa and then drive as you’ll want a car to get around.

Palm trees by Siesta Key Beach Florida

Conclusion: Rainy Day Activities in Siesta Key

It’s clear that Siesta Key, with its beach location and diverse range of activities, shines even on a rainy day. From the immersive experiences at local museums and galleries to the fun of indoor activities like bowling and escape rooms, there’s something for everyone. Whether it’s relaxing in a luxurious condo or exploring the rich culture of Sarasota, your time here is sure to be memorable – I know every time I leave the island I’m already plotting my return trip!

Remember, a little rain doesn’t have to put a damper on your adventure. Siesta Key and the surrounding Sarasota area offer a wealth of experiences that prove just as enriching indoors as they are under the sun. So, pack your bags (and maybe an umbrella) and get ready for an unforgettable getaway, rain or shine.


Is it raining on your Florida vacation? Here are 13+ great things to do in Siesta Key on a rainy day. Check them out and don't let the weather ruin your fun!
Rain or shine, Siesta Key never fails to entertain! Dive into our latest blog post for a list of 13+ exciting activities to enjoy on a rainy day. From indoor crafts to fascinating museums and cozy cafes, there's something for every member of the family! Grab your umbrellas and let the adventures begin! 🌴🌧️ #SiestaKeyFlorida #RainyDayFun