Workcation in Naples, Florida: My Remote Work + Vacation Combo

One of the perks of my new job (okay, not that new, I’ve been there since October 2024) is that I get to work remotely most days. This summer, we decided to take full advantage of that flexibility and head back to a VRBO we previously enjoyed in North Naples, Florida.

We flew down on a Wednesday evening, right after I wrapped up my workday. My plan was simple: log in from the house for two days, enjoy the Florida sunshine from my laptop, and then roll straight into a vacation. The house has its own pool and hot tub, complete with a lanai, so I could set up my workspace in the kitchen overlooking the pool. While I worked, Travis and Jack lived their best pool life, hopping in and out of the water all day long.

By knocking out two full workdays remotely, I only had to take two additional days off to stretch a long weekend into a full week of Florida sun. We flew home early the next Wednesday, and I was logged back in that morning. So yeah, I’m loving the work/life balance!

What We Did:

When I say we had the laziest vacation ever, I mean it. Most days we alternated between reading on the couch (me and Travis), playing video games from a bed nest (Jack), checking out the local thrift stores, eating all the food, going in and out of the pool, and walking along the nearby beach. One night, we enjoyed both a rainbow AND a sunset at the Delnor-Wiggins beach.

Where We Ate:

We revisited: Turco Tacos, Michaelbobs BBQ and Kilwins for ice cream. New places we enjoyed: Steamers Seafood, Mystic Lobster Roll Company, and Naples Brunch Restaurant.

Where We Shopped:

Most of our thrifting luck was had at the nearby Goodwill locations. However, I also found a couple fabulous scores at the St. John’s Shoppe consignment store.

I barely changed out of my swimsuit all week and it was PERFECT. I actually ended the week feeling rested and refreshed!

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