Romantic Things to Do in Siesta Key

What makes an ideal romantic day out? Is it a basket full of flowers or chocolates? Is it a memorable and exciting activity between two or a nice dinner overlooking the water? Or, is it all of these things? Find out for yourselves during your next stay in one of many gulfside Siesta Key vacation rentals.

On Siesta Key, you can make just about anything into a romantic activity. With the beach as your backdrop and the warm weather all around, there’s a constant air of romantic energy on Siesta Key. We cover our top six favorite romantic things to do when visiting this popular southwest Florida key. 

What makes an ideal romantic day out? With the beach as your backdrop and the warm weather all around, there’s a constant air of romantic energy on Siesta Key.

Dual Massages at the Spa

What better way to relax than with a massage? Infinitely comforting and worth every penny, a dual massage is a romantic way to relax for an afternoon. Also known as a couple’s massage, a dual massage can make you a little healthier while also providing you extra emotional energy to have an amazing vacation. 

While there are many providers in Siesta Key, we can’t help but recommend Siesta Healing at the Holistic Spa and Wellness Center, as well as Hands of Light Massage Therapy. Both manage to provide an ethereal atmosphere, with soft music, comfortable lighting, and calming smells like lavender and eucalyptus. You can round out either selection with a stop at Massage Heights, which focuses on massage as a regular part of your self-care regiment.

Fudge and Ice Cream Shop

It doesn’t take much to satisfy someone who loves sweets. A simple bowl of ice cream soaked in hot fudge gets the job done. Maybe a bowl of gelato or a good vintage candy does the trick. Overall, Siesta Key is filled with romantic places to shop for some phenomenal sweets. 

The Fudge Factory: Exclusively homemade fudge, ice cream, and chocolate- 5263 Ocean Blvd, open 12 p.m. to 9 p.m.

Big Olaf Creamery: Relax on the patio by the water at the famous St. Armand’s Circle shopping plaza- all with amazing ice cream in hand- 5208 Ocean Blvd, open 11 a.m. to 10 p.m.

Stefano Versace Gelato: Authentic Italian gelato, complemented with coffee, pastries, and smoothies- 5212 1/2 Ocean Blvd, open 10 a.m. to 9 p.m.

Dulcifina Chocolate and Sweets: All the candy, vintage or otherwise, you could ask for- 4221 S Tamiami Trail, open 11 a.m. to 5 p.m.

There’s no shortage of fantastic little spots to grab a sweet or two (or 200). Every sweet tooth is satisfied on Siesta Key.

Spend a romantic vacation in Siesta Key with your special someone.

Dinner at a Nice Restaurant

Just about all daytime Valentine’s Day activities can be capped by a romantic dinner in Siesta Key. Even in the center of the key, you are just a few short miles from the beach. This gives you so many possible places to dine. We love The Cottage for its impressive mix of contemporary American dining and classic Japanese. We also can’t recommend Café Gabbiano enough. It manages to make Old Italian dining feel fresh, authentic, and intoxicating. We love its rustic charms and inventive wine selection.

For a look at Old Florida, we suggest the Summer House Steak and Seafood. Housed in a classic-styled summer home, the restaurant is both a place to eat and a museum.

Its 1,000 gallon fish tank is a spectacular sight and worth visiting whether you actually take a seat or not.

Live Theatre Performance

There’s something really special about excellent live theatre. The energy of a theatre performance is immediate, inescapable and enthralling. You can go see a show at the Florida Studio Theatre in Sarasota. Ranging from popular jukeboxes to contemporary classics, you can always expect to see a solid local performance. 

For a more upscale performance at a renowned theatre, we suggest visiting The Mertz. This Italian-styled performing arts theatre is maintained by a repertory company and features a number of astonishing Broadway classics.

Stroll Along the Beach

No romantic visit to Siesta Key is complete without a walk on the beach. Take a stroll along miles of Siesta Key Beaches. Keep your shoes or sandals off- you can feel the famous white sands between your toes, made up almost entirely of crystal-clear quartz.

Watch the Sunset

Closeout your holiday romp with a view of the iconic Gulf of Mexico sunset. Most of the coastline of Siesta Key closes after sundown, so you can spend some time admiring the glowing sun and reflecting on your experience. There’s no better way to wrap up a romantic evening before retreating to your Siesta Key vacation condo.

Looking to soak in the Siesta Key’s local culture? For more information on places to stay and things to do, reach out to our team. We can help connect you with exactly what you need to have a phenomenal stay on Siesta Key. 

Contact Us

Peppertree Bay Association
6056 Midnight Pass Road
Sarasota, Florida USA 34242

T 941.349.7777
F 941.346.0371


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