Wes & Em

September 17, 2025 • Siesta Key, FL
117 Days To Go!

Wes & Em

September 17, 2025 • Siesta Key, FL
117 Days To Go!

Ways to Spend Your Days in Siesta Key

We cannot wait to have our family and friends experience our favorite place that brings us joy and comfort when we're looking for an escape. Below are different ways we've found ourselves spending our days in Siesta Key / Sarasota over the years, but always try something new and invite us so we can add it on the list!

Sunrise Beach Walk

Picture of Sunrise Beach Walk

Our favorite way to start the morning is taking a stroll on the beach as the sun rises. Fresh sea air and the sounds of the waves crashing on the shore is free therapy. Pro Tip: If you walk up all the way up to the north end of the beach, you can catch a local veteran raise the American flag and lead a ceremonial 'Pledge of Allegiance' if you're feeling patriotic.

Siesta Key Village

Picture of Siesta Key Village
5145 Ocean Blvd, Siesta Key, FL 34242, USA
(941) 349-2822

Besides the beach, Siesta Key Village is the downtown heart of the city. It includes so many mom-and-pop places to shop, eat, drink, and have fun. We highly recommend Beach Bazaar and Gidget's Coastal Provisions for keepsakes and gifts for friends, and for something sweet, Olaf's Ice Cream or Meaney's Mini Donuts & Coffee House.

Beach Day

Picture of Beach Day

TBH, we're beach bums the majority of our time during our Siesta trips, and we highly encourage you unplug and try it, too! We'll bring the Yeti, you bring the vibes.

Siesta Key Outdoor Activities

Picture of Siesta Key Outdoor Activities

Don't want to lounge on the beach all day? There's tons of outdoor activities to do, including jet ski, kayaking, parasailing, or renting bikes! Pro Tip: Don't try to ride the bikes on the public beach... easily one of our biggest arguments to date out of pure frustration from the chaos.

Website

St. Armands Circle

Picture of St. Armands Circle
300 Madison Dr, Sarasota, FL 34236, USA
(941) 388-1554

Raining or beach-bumming / day drinking not your style? Take around a 30 minute drive to St. Armands Circle in Sarasota for lots of shopping and casual/fancy dinning. S/O to Sam for recommending this gem of a spot to us, and she'll tell you, too, to go to Crab & Fin for dinner.

Daiquiri Deck Siesta Key Village

Picture of Daiquiri Deck Siesta Key Village
5250 Ocean Blvd, Sarasota, FL 34242, USA
(941) 349-8697

Need to take a break from the sun and heat? A refreshing daiquiri is your cure! Daiquiri Deck is a must-- whether it's for just a drink, food, or fun night on the town! 'Deck Diesel' and 'Bat Sh*# Crazy' are our go-to.

Siesta Key Oyster Bar

Picture of Siesta Key Oyster Bar
5238 Ocean Blvd, Sarasota, FL 34242, USA
(941) 346-5443

Daiquiris not the vibe? Our next recommendation is SKOB for a wide array of drinks, amazing seafood, and live music. Bring a signed dollar bill to hang on the wall, making yourself a true Siesta Key tourist.

Gilligan's Island Bar & Grill

Picture of Gilligan's Island Bar & Grill
5253 Ocean Blvd, Sarasota, FL 34242, USA
(941) 346-8122

We're embarrassed to admit that we discovered Gilligan's too late in the game, only on our third trip to Siesta Key per the recommendations of the Sinn's. Big Mike got us 'ship-wrecked' and we hope you have this out-of-body experience, too!

Liberty Tattoo Club

Picture of Liberty Tattoo Club
2430 Stickney Point Rd, Sarasota, FL 34231, USA
(941) 210-3461

Feeling adventurous and wanting to join us in making a permanent decisions this trip? Go see our guy, Trevor, at Liberty Tattoo Club for fresh ink. You don't have to persuade Wes to get another tattoo.

Sunset on the Beach

Picture of Sunset on the Beach

We highly recommend ending every day watching the sunset on the beach with your loved ones. Nothing compares to end your night by watching the painted sky reflect on the ocean, listening to the waves, and the soft sand between your toes.