Siesta Key

Places to Eat:

  • Summer House: My favorite. Steak house, pricey. I’d recommend going at least once for a nice dinner out
  • The Cottage: Right next door. Sit out back and listen to live music, great food.
  • Cafe Gabiano: It’s located in a strip mall but you’d be surprised at how cool it is inside. Feels like you’re eating in a wine cellar. 
  • Libby’s: Bistro over the bridge (Sarasota). Amazing ribs. $10 bottomless mimosas. 
  • Ophelia’s: Waterfront, GORGEOUS restaurant. More $$ but worth it even just for an app. Definitely go while it’s still nice out (4 PM-6 PM). Might want to call ahead for a resy. 

Places to Shop:

  • Siesta Key Village – 5 minutes walking from the house. 
  • Saint Armen’s Circle – about 10-15 minute drive. Great boutiques and restaurants.


Places to Hang:

  • Beach – need to get the name of the big beach. It’s not walking distance, 5 min car ride. It has a sushi chef and bar. Usually food trucks and festivals on the weekends. 
  • Patriot’s Pier – closest beach, really beautiful sunsets. Quiet vibe. 
  • Sarasota Farmer’s market: Every Saturday. It’s MASSIVE. Really good food/drinks/crafts. 
  • Gilligans – SO fun at night, always a live band and cheap drinks.
  • Big Tiki: I think it’s kind of weird but my parents are obsessed with this place. Every Saturday, their friend “Casey on the Key” plays here
  • Crescent Club: Dive bar but you can smoke cigs inside 😉 It’s owned by one of the people on the show Siesta Key
  • Local Bean: Coffee shop, good for posting up to work. Good breakfast sandwiches. Try the macadamia nut coffee 
  • Gilligan’s Coffee Shop: I forget the name of the coffee shop attached to Gilligan’s but it’s sooo cute, really great place to work. 

Potentially Helpful Tips:

  • The Frogger – Service that’ll pick you up anywhere on Siesta Key and bring you anywhere. Totally free but tips are encouraged (I’ll usually tip a few dollars per ride).  I use it when it’s raining and I don’t want to walk into the village – it’ll get you right from the house
  • Call: 844-376-4467
  • Turn on the hot tub like an hour before you want to use it – takes some time to warm up.
  • There’s an outdoor TV attached to the Tiki Bar – my favorite thing ever is bringing a glass of wine to the hot tub and watching my show.