5 Days in Florida: A Last Minute Trip Using ONE Day of PTO!

The first vacation day of the year is always a struggle because I try to wait as long as possible. Once I start traveling, it usually sets off my #wanderlust and opens the floodgates for time off. I try to be smart about planning out my travels well in advance, but hey, even I'm not immune the temptations of a last minute trip!

This year, I made it until February 20th before caving. In my defense, Wisconsin's winter has left us with polar vortexes, feet of snow, and literal ice storms. I think you'll be hard-pressed to find someone who didn't want to escape. In need of sunshine and warmer temperatures, I headed down to Clearwater Beach (Tampa, FL area) for 5 days.

I played a little flight roulette on Skyscanner, my favorite airfare-finding site, and figured out that the cheapest nonstop, roundtrip flight from a nearby airport was the Tampa area. I flew Rockford to St. Pete's on Allegiant, leaving Wednesday morning and coming back Monday morning. There were plenty of flights for around $100 or less on multiple airlines from the Milwaukee/Chicago area to various cities in Florida. Cheap tickets always make me happy.

I spent Wednesday afternoon through Monday morning in sunny Florida - all with using only ONE DAY of PTO. I was planning to only use half a day of time off, but I felt a little run down after the flight home and decided to take the full day. How did I swing it? Taking advantage of the flexibility I cleared with my boss ahead of time.

I front-loaded hours the days before leaving by coming into work a little earlier, working over lunches, and staying later at night. This got me one free day off (Wednesday), which I used for flying and settling in.

Thursday and Friday I worked remotely. Trust me, it still felt like a vacation! I was able to work from the pool, hotel balconies and rooftop lounges, beachside coffee shops - it was the most relaxing working environment. I purposely saved less demanding tasks for these days, too. I found it easier to start my day earlier so I could unplug by midafternoon and enjoy the rest of the day/evening doing fun stuff.

The only day I took off entirely was Monday. And again, I could have worked in the afternoon - yielding more vacation day savings - but I was coming down with a cold of some sort so my body needed rest.

Most hotels around the Clearwater Beach area are expensive and booked out in advance. I opted to venture further out and stay in the Palm Harbor/Dunedin area, which is just north of Clearwater, at the new Fenway Hotel. This hotel is a former speakeasy nd faces the ocean. Some of the hotel highlights included the rooftop lounge - which got very popular over happy hour - and live music in the lobby at night. They also offer free bikes for guest use, making it easy to get to the nearby restaurants or to hop on the expansive waterfront biking trail.

Each room was bright and breezy and clean. My favorite touch was the Alexa in each room, which could call the front desk, tell you the WiFi password, or even order room service for you. I wouldn't be surprised if this concept grows over the years. My room, while facing the water, was right over the main entrance so the guests coming and going got noisy. My only other complaint was that the curtains were sheer, which let the bright Florida sun into the room a little earlier than I would have liked. Overall, this boutique hotel was charming and the perfect place for a little weekend retreat.

While most of downtown Dunedin is easy to walk or bike around, you do need some transportation plans to get to Clearwater Beach or other surrounding areas, like Palm Harbor. Lyfts and Ubers are easy to catch, but it's not a bad idea to splurge on a rental car for the weekend. Pro Tip: schedule your pickup from a rental place that ISN'T at the airport. The lines are so long and move slowly with all the snowbirds and families coming in. It makes more sense to rideshare to a location a few miles away!

Parking is a bit of a mess in the Clearwater Beach area. There's really only one public parking lot and you have to feed the meters often. While I never suggest criminal activity, it was worth paying the small ticket for an expired meter instead of running back to put change in every hour. If you can rideshare to the beach, you'll avoid all the hassle from the get-go.

While I spent my days working in warm and scenic locations, I made sure to unwind and have some fun in the evenings. My top suggestions on things to do for the area are:

Clearwater Beach - voted one of the top beaches in America, this is the main draw for coming to the area. The water is beautiful and it's easy to lose a day sitting on the beach. Make sure to walk along the shops nearby when you need a break, and hit up the pier for great views and tons of vendors selling their wares. You have to pay to go to the very end of the pier - not worth it, in my opinion.

Tarpon Springs - Head even further north and wander around this Greek-influenced city. You'll find tons of Greek eateries and gelato shops along the way, but make sure you leave with a natural sponge souvenir. The interactive aquarium is worth a visit - it's small but you can feed stingrays and sharks!

Honeymoon & Caladesi Island - Honeymoon Island is a state park in Dunedin with four miles of beach and plenty of nature trails to explore. The real draw is to take the ferry to Caladesi Island, an offshore beach with white sand and crystal waters. You'll need a pass to get into the state park and admission to the ferry ($14), but the secluded beach filled with sea turtles and dolphins is worth it.

Catamaran Cruise - You can truly take your pick on which cruise and from which marina, but spending time on the water is a must when visiting. Clearwater Beach offers dozens of cruises - one is even a pirate ship - but you can find smaller, cheaper options leaving from Dunedin as well. Most will offer up complimentary rum punch, so make sure you're indulging!

Do not miss out on some fresh seafood while you're visiting. Grouper tends to be the local catch and worth ordering if you see it on a daily specials menu. My top eats, broken down by area, are:

Clearwater Beach:

-The Bait House Tackle & Tavern - this dive is hidden in the back of a tackle shop, but those in the know are rewarded with seaside views and some of the freshest fish. Get whatever seafood they've caught that day and don't skip on the sangria or chips, either.

-Island Way Grill - for those looking for something upscale, this is your place to go. The outdoor dining is first-come, first-serve, but hit up the bar for drinks while you wait for a table. The sushi never disappoints and the crab cakes are delish. The service can be spotty, especially if it's busy, but the food is worth it.

-Columbia - this Spanish restaurant has been around since 1905 and serves up a delicious, if not overwhelmingly large, menu. Start off with a pitcher of the sangria - made right in front of your eyes - and indulge in the Cuban bread. I've never had a bad dish here so order whatever calls your name.

Dunedin:

-Olde Bay Cafe - another seaside dive, this restaurant offers fresh seafood and dishes that change daily. Order something from the specials menu (grouper tacos are always my pick if they're available) and take in the stunning view.

-Ohana Cafe - switch things up with some healthy Hawaiian fare. The owner is the sweetest lady who hugs every customer, truly warming your heart. The popovers get five stars in my books.

-Frenchy's Outpost - soak up some live music in this open-air restaurant. Seafood is once again the name of the game, but I prefer to order a bunch of starters to share with the table instead of a main dish. The crab fries and fire island tacos are personal favorites.

This trip was thrown together in about two weeks and truly was a spur-of-the-moment thing to restore my sanity. I needed the sunshine and fresh air after weeks of bitter, extreme winter weather in Wisconsin. Heading to the Palm Harbor area wasn't costly - flights were a steal and staying away from larger, touristy cities meant lower prices - and I was able to swing an extended weekend getaway without sacrificing more than a day of vacation time.

To some, having to work remotely, even while traveling, is a drawback. To me, I think it's undervalued. I got to work in paradise while still having tons of time to explore and have fun.

Would you ever try to work remote for a day or two to get away? If you need advice on how to juggle work while vacationing, or just suggestions on how to have a conversation about working remotely with your boss, let me know in the comments! If there's enough interest, I'll make that an upcoming blog post!