Siesta Key, FL / Birthday Trip

Oh travel, how I missed thee! If you know me and my family, you know we love to travel so COVID-19 has made us all a little stir crazy…who am I kidding? Made us A LOT stir crazy.

We were able to sneak away in March for a few days to Sedona, AZ, for Sawyer’s 9th birthday trip and keeping with the “s” theme, we booked Scout’s Sixth Birthday trip to Siesta Key, FL. Full disclosure, this was not our first choice. We actually booked an all-inclusive trip to Costa Rica but following the CDC updates and travel recommendations, we got nervous and backed out. Luckily, we were able to fully transfer our trip to a 6 day / 5 night trip to Siesta Key and even luckier two other families who we are close with were also going to be visiting at the same time. 

We are not new to Florida and have visited many locations in the state (Captiva, St. Pete, Miami, Key West, Orlando, Naples, etc.), but we are first-time visitors to Siesta Key. Multiple friends had recommended we visit, knowing how much we love the beach. We wanted to relax, sit on the beach, and not do much and this was exactly that trip. Our boys slept in every day, spent hours at the beach, and for the most part got along great (thank you Lord!) Our family absolutely loved Siesta Key and are already planning a trip back! 

Here is a peak into our family trip and our recommendations….just book it, you won’t regret it!

To see all our Siesta Key trip photos, visit our share site

Where we stayed

We booked a house through VRBO within walking distance (.4 miles) of the beach and with a private pool and hot tub. There are tons of condo and home options in the area. Be sure to book early because they sell out!

The adorable little yellow home we chose is here.

How we got around

Since we flew into Sarasota, we had about a 25 minute drive to Siesta Key. You can also fly into  Tampa but it is over an hour. We opted to rent a convertible mustang rental, I mean cause “Why not?” but also so we could enjoy the Florida sun and salt water air even on our drives. Highly recommend! Honestly, we walked everywhere since our rental was right in the heart of downtown Siesta. They also offer bike, golf cart, scooter coupes rentals, as well has have a free trolley so a rental car is not a necessity.

Where we ate and drank

While we definitely ate out a lot, we also picked up stuff to eat at home at least one meal every day. Luckily we were within walking distance of Morton’s Siesta Market that had all the staples (hello Dot’s pretzels!) When we weren’t eating at home, here are the places we checked out:

  • Owen’s Fish Camp – this is a must when in the area! Located in downtown Sarasota, there is always a wait because it is that good. We arrived when they opened and still had an hour wait. Which we didn’t mind because they have a super cool backyard area that serves drinks and apps, with a tire swing for the kids and usually a band playing. The time flew by! 
  • New Pass Grill and Bait Shop – This place has history, open since 1929 and it is another one of our top recs, we stopped here for a quick bite after the Aquarium to kill time before our flight out of Sarasota. It is right on the water where the kids can even play while you wait or when they are done eating. The bait shop is connected and the worker let Scout play with the crabs too. I opted for their fish sandwich and it did not disappoint! 
  • The Old Salty Dog – peel and eat shrimp are awesome, so are their house margs.
  • Meaney’s Mini Donuts – Not your typical donut, they are served hot and fresh on a skewer like a kabob with yummy toppings (my kids loved the peanut butter cup and chocolate delight). Their cold brew is also delicious
  • The Lobster Pot – delicious seafood, particularly the lobster (hence the name). I tried the Lazy Dutchess, which is New England lobster meat with seafood stuffing, splashed with Sherry wine, topped with parmesan cheese and then baked. Whoah, it was good!
  • The Hub Baja Grill – fun place to eat and hangout, they had a band the night we visited that even sang Happy Birthday to Scout.
  • Island House Tap and Grill – we were just wanting a snack after a late swim and they really hit the spot. The guys raved on the Duck Fat Fries with truffle aioli.
  • The Boatyard Waterfront – a great place to sit outside by the water, with great vies of the marina.

Drinks / Desserts

  • Daiquiri Deck – this is a must if you like frozen drinks. We opted for the souvenir cup on our first visit for discounted refills. We would fill before heading to the beach each day. Our favorite was the Voodoo Love Shake which is the less sweet option that is a mix of a Bushwhacker and Pina Colada topped with Peanut Butter Whiskey. The kids liked their non-alcohol Electric Lemonade which is bright blue.
  • Mojo Risin’ Coffee Co – great for your caffeine fix or a quick bite to eat. They have a super cool interior and patio out back for relaxing – any place that has a full wall of Kurt Cobain and Jim Morrison’s face is my kind of place!
  • Big Olaf’s Creamery – after dinner at the Hub, we promised the boys ice cream. They had been eying Big Olaf’s and were very happy with their homemade ice cream in waffle cones.
  • Sub Zero Nitrogen Ice Cream – John picked this up one night, so we all didn’t try but he was kind enough to let us sample his. It was delicious. Developed by two chemist, they use liquid nitrogen to freeze the ice cream. John ordered the Peanut Bond with Peanut Butter, Brownie, and Peanut Butter cups.


  • Village Café – just a traditional café with good breakfast for adults and kids
  • Bonjour French Café – The owners are from France so everything is authentic. We got to introduce the boys to crepes, and they were amazing and are now huge fans! I ordered the Baked Brie Croissant and it might be the best breakfast I have ever had …filled with baked brie, walnuts, baby spinach, and orange marmalade. 
  • Sun Garden Café – Super cute, music-inspired café! All their dish names are super clever, like what I ordered: The Baba O’Riley which was an omelet with broccoli, spinach, turkey, Boursin cheese, avocado, and bell pepper.

What we did

Since our #1 agenda item was relax at the beach, we didn’t do much else besides that or lounge in the pool and eat. We were close to Siesta Key Beach (.4 miles), but we also visited Turtle Beach one afternoon which is a bit further from us (4 miles). Thought it was worth checking out since it was named for its sea turtle nesting habitat. Our preference was Siesta Key Beach (Public Beach Access 6) because it had a less steep entrance into the water and had softer sand. We also found out it is listed as the #1 beach in the USA -which is warranted after our visit. It is beautiful! Sawyer made sure to mention “Mom, it took you this long to see the #1 beach but I am only 9 and I am seeing it.” 

Our rental house gave us access to a beach cart, chairs, and toys for us to bring with us, so if you visit and don’t have those things, I recommend picking them because it made it much more enjoyable! Just hit up the Beach Bazaar which has everything you need…we drop a pretty penny there on souvenirs and goodies. My parents bought the boys some full face snorkels for our trip and they were great for finding shells, clams, and sand crabs.

There are some great shells to find too, both boys came home with a bag full. I woke up before the boys a few days to get my run / walk in. Running down the beach was so refreshing from my norm. I always felt safe too since I was joined by many other locals and visitors out for their morning exercise.

We had booked a Dolphin and Drinks excursion through Fun Boat Tours with our friends who were also in town, but we only made it out a few miles before a storm came in. So, we headed back in, they reimbursed us, and we went and had dinner and drinks at the Daiquiri Deck instead. It actually ended up being a very fun impromptu afternoon.

Scout said all he wanted to do for his birthday was “fish!” So, we had booked an offshore trip with Chasin’ Tail Fishing Charters. Our captain called us about an earlier opening because he had a cancellation but it meant we had to do inshore instead. With two small boys, we figured it was probably fine and luckily we still had a great time. We caught flounder, snapper, salt water catfish, and grouper with enough to bring back to our house to cook that night. Scout loved helping Captain Alex and grabbing the shrimp for our bait and feeding the filleted fish guts to the pelicans. And we saw a dolphin which made up for our cancelled dolphin cruise the day prior.

We had an afternoon to kill between checking out of our house and the airport and heard the Mote Marine Laboratory Aquarium was a great place to spend our time. There is a lot to see and do including manatee, shark, sting rays, and we lucked out because they had a special exhibit, Wild Kratts Ocean Adventure which the boys loved. What is really cool about the Mote is it isn’t just animals but also interaction with the scientists who are working to ensure the safety of all marine life. 

John and I came to the conclusion that our boys might just be at the perfect age for beach vacations. We have taken them since they were little but this trip they didn’t complain and literally spent hours there entertaining themselves (even built a sand hot tub!). The only issue we had was some swim trunk chaffing from spending too long at the beach, but nothing a little Vaseline couldn’t fix. While we were bummed to cancel the all-inclusive since it had a kids club, this trip still felt like we had some adult time without the babysitters. We will definitely be back, Siesta Key…thank you for your amazing hospitality!

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