Fort Myers

If a friend invites me to Florida in the dead of a Chicago winter I am an easy yes. Especially when it involves hanging with her cool, fun parents for the week.

After being picked up from the airport, we headed to downtown Fort Myers where we spent the rest of our day.

Her parents were staying there to feel out if they wanted to retire there so our first stop was an open house. I’ve never spent much time Fort Myers so it was news to me that there was a cute little downtown that was pretty popping, and it wasn’t just retirees and spring breakers on the beach. The place we toured overlooked a marina and if I ever win the lottery might be a prime spot to retire at the ripe age of 26.

The relator who showed us the place recommended Downtown House of Pizza for authentic New York style pizza by the slice. It did not disappoint, especially for someone who flew on the red eye from California the night before (me) and hadn’t had anything to eat. Post pizza we went on the hunt for a rooftop bar that would be the perfect spot for her parents to frequent once they were Floridians.

We did exactly that. On top of the Luminary Hotel there’s a fairly new rooftop bar called Beacon Social Drinkery. My friend and I both got the Grand Light Parade to drink. It was a tequila based drink with a little spice which in my opinion is the best way to start a beach vacation. We also split and appetizer which was eh but the drinks and view of the water made our experience worth coming back.

For dinner we stopped at an Italian restaurant, Cristof’s on Mcgregor. The calamari, Caprese salad, and pasta dishes we all got were amazing, not to mention the bread- but as great as the food was it was still overshadowed by the view of the sunset. We got a great spot on their patio facing west and it couldn’t have been a better spot to enjoy the last bits of daylight.

The next morning we went for a run on the beach. When we’d both had enough of exercising, which wasn’t much, we walked to a fun breakfast spot. MoJoe’s Coffee Cafe had a big outdoor patio that had great spots to sit in the sun or shade. The food was great, I saw the fattest cat I’ve ever seen, and the espresso got us buzzing and ready to take on the day.

On our next endeavor we made a bit of a whoopsies. After finishing what responsibilities we had to bring with us, we got beach ready and decided to walk the beach to a bar. Halfway there (probably a mile walk) we realized we forgot our ID’s. Couldn’t let the minor setback kill our vibe though, we trekked back grabbed those pieces of plastic and left for Shucker’s.

You could say we’re suckers for Shucker’s. It sits right on Fort Myers beach and some days has live music. It’s a great spot to enjoy a margarita on the beach. At night, it’s easy to head right upstairs to The Cottage which also has live music and offers and offers an outside-inside type of bar space.

The next day we headed with her parents’ to Punta Gorda to visit some of their friends from back home who’d already retired. We spent the day lounging by the pool and going for joy rides on their boat. They lived right on the water so we got to go through back channels of homes out to the open ocean. If you do go on a boat ride during your time in Florida I’d recommend putting your hair up before jetting off, which I failed to do and spent a good twenty minutes ripping knots out of my hair.

We made it back to their place in time to see the stunning sunset that sold them on their home. On the ride home, which is about an hour from Fort Myers Beach, my friend and I both slept like the dead weight we are for her parents.

For our last day we started off with a beach run which turned into a walk and picked up coffees from MoJoe’s Coffee Cafe again. On our walk back, we stopped at the Beach Baptist Farmer’s Marker. For a Wednesday, this farmer’s market was poppin’.

Everything from fresh produce, to swimsuit coverups, to fresh pressed juice was there. My personal favorite spot was the Crepe stand. You get to pick exactly what you want in your crepe and then watch him make it right in front of you. I got a crepe with mushrooms, chives and goat cheese and I wish I would’ve gotten two. One of the best I’ve ever had, easily. We also both walked out of there with some fresh fruit to snack on later.

It was a nice day but not super warm so we decided to do a little impromptu bar crawl. To save some time, since time is money on vacation, we rode bikes into what’s called the “Times Square” of Fort Myers Beach. My friend had a coworker who who was also in Fort Myers Beach (they’re both vaccinated) so we all met up at Mango Rita’s. No, we didn’t get mango-ritas since I guess we’re amateurs, but we did get mojitos which were delicious.

Next on the agenda was the Salty Crab Bar & Grill. Another great spot for a Mojito, especially when the sun is setting. It sits right on the beach and has a ton of space, perfect spot to enjoy the view or feel like you’re in a sports bar with all TVs. Personally, I didn’t eat but when I saw some of the food I almost wish I did. Looked like a great spot for some deep fried shrimp or seafood tacos.

With our bikes to get us home, we made it back to her parent’s place just in time to join them for dinner. When we got to the restaurant they were taking us to- I can assure you, we were both happy we hadn’t already ate.

We went to dinner at Cōste Island Cuisine. This was quite the step up from where my friend and I had been spending our time on our trip. The restaurant sits in the DiamondHead Beach Resort and overlooks the beach. I ordered a pear martini and went with the Snapper for dinner and felt fancy as hell. The fish I had was so flaky and fresh and served with a wasabi béarnaise. TO DIE FOR. We closed out the flawless culinary experience with Fort Myer’s signature key lime pie. Cōste had an incredible menu and is the perfect spot if you’re looking to treat yourself to something a step up from the typical beach dining.

Then after having a great dinner with her parents, my friend and I closed out the night at Shuckers like the degenerates we are.

If you want to see a highlight from my Fort Myers adventure click here and click through my pictures below!