Considering A Remote-Working Vacation? Don’t Book a Place Without Reading These Handy Tips

I couldn’t get comfortable, no matter what I did. The stool had no cushion and was definitely not meant for sitting for long periods; the counter where my laptop sat was not at the proper height. I moved the laptop to the coffee table and sat at the futon and tried working from there, but the futon cushion was as flat as a pancake, almost non-existent and there was no back support; I didn’t last more than a half hour. There I was, in Florida, working remotely from one of the most popular cities in the country, and miserable.  

In 2022, I started taking “remote work vacations,” something The New York Times has reported as one of the new opportunities in this post-Covid world, with one story suggesting six popular cities to consider. It’s a great concept and one that’s here to stay. While it’s good to know what cities make great work destinations, Woman Around Town goes a step further by providing a list of what to consider in your search for suitable accommodations, especially if you’re staying for a week or more. 

Some background before we start. This trip was my third. My first two were remarkably successful experiences, but this time, I was not so lucky.  In 2022, I visited Florida and Georgia, and worked from upscale lodgings. This time, I planned a second Florida visit and opted for a lesser priced Airbnb guest apartment. It was a comfortable half-hour drive from the oldest city in the United States – St. Augustine.  The price was right and came with a private entrance, a parking space for my rental, a fully equipped kitchen, and with a futon and air mattress, should I wish to invite family and friends looking to escape the New York January weather. I inquired about the consistency and strength of the Wi-Fi/internet and was told it was fine, and that “there hadn’t been any complaints from previous guests.” I thought I had it all figured out, but I was wrong. You know the saying, about “the third time being the charm?”  Well, for me, this was the complete opposite. Rather than moan and whine, I took this as a learning experience and began making a list of what I was experiencing and what I’d change next time.  

Here’s what I learned. 

  1. Don’t let price be the deciding factor on the accommodations. I hadn’t considered that Airbnbs do not necessarily include a comfortable workstation. I have an ergonomic set-up at home, with a standup desk, and have been lucky with the other places I’ve chosen, but this one was lacking. As someone who does have back issues, I had to locate a chiropractor during my stay to work on some new kinks in my lumbar area.  

Lesson Learned: look for accommodations with some sort of desk/chair availability. Ask if you’re not sure. You may be able to find a local coffee shop to work from, but do you really want to pack up each morning to go somewhere else to do your remote work?  I didn’t.  

  1. The ability to control the temperature. It wasn’t until after I was in the unit, and temperatures dropped significantly to the 40s’ when I noticed there was no baseboard heating, no radiators. This was a unit built above the garage, hence, there wasn’t even the potential for heat rising from the first floor. I was freezing while I worked in this unusually cold January spell in St. Augustine. A small, dated heater was in the closet which did very little unless it was right at my feet. I did text the owner about it and in two days Amazon delivered a unit that circulated a strong wave of heat. Still, it was an uncomfortable aspect of the stay and one that could have been avoided. Same with air conditioners. Ask if they’re on site and working.   

Lesson Learned: make sure that the place has the ability to heat and cool as YOU need it to be.

  1. The car rental decision. I wanted to be able to come and go as I pleased and be able to grab milk or fresh fruit from the market as needed. The price of the car rental took a big piece of my budget, and next time, I would opt to stay closer to the city and add a walk into my day to pick up any needed groceries and save the high-ticket price of a car rental. Plus, one has to consider having to deal with any damage to the car, or worse, any injuries. I’d rather put that money into the accommodations, (taking care of tip #1 as well). Plus, there’s no wasting time looking for and paying for parking, or better yet, figuring out the parking meter apps as you go sightseeing.   

If you’re choosing a more suburban experience, you may need a car since public transportation and ride sharing opportunities like Lyft and Uber may be limited. When booking a car rental, ask for the “industry rate” as you may be able to save a few dollars by letting them know you are coming to the area on business.

Lesson Learned: really consider whether or not you want to rent a car.

  1. Wi-Fi strength. I’m not sure how to get an absolute guarantee on this one. I found that despite my owner’s reply to my Wi-Fi inquiry, it was inconsistent, and to make a cell phone call, I had to stand by the window. The owner suggested I unplug the Wi-Fi-extender and plug it back in, but it didn’t do the trick. An Airbnb rental may not have the best Wi-Fi because the service is typically shared with the rest of the host family occupants; rarely will an owner supply a guest with their own connection. More upscale lodging is probably the way to go especially since reliable Wi-Fi is key to the working remote experience.  

Lesson Learned: research the Wi-Fi strength of the place you’re considering, read reviews, speak with the manager/owner about your need for strong Wi-Fi. 

  1. Stocking the kitchen/supermarket shopping. Look for accommodations where you can prepare your own meals. With that said, rather than shop at the market and using up precious “free” time, see if the supermarket has a shopping service where you can either pick up your items (should you have a car rental), or be delivered to you (if you don’t).  What you pay in service fees for these conveniences is better on your budget than having meals delivered each night from the local pizzeria or going out to restaurants. Just purchase enough food for the week and plan accordingly so you’re not throwing out uneaten bananas.  Oh, and always add a roll of toilet paper to the list for obvious reasons. 

Consider buying items that can be packed up for lunch when sightseeing.  With a cooler bag borrowed from your host and a storage bag of ice from the freezer, you’re all set for a day of wandering.

Lesson Learned: Take the time to plan your food shopping and meal prep. 

While what I’ve listed above are the top items on my list, here are a few honorable mentions: 

  • Look for free events at museums, libraries, bookstores, parks, and coffee houses for things to do in off-hours.  Some cities have free walking tours. Enjoy the local talent, authors, entertainers, and get to know your workplace city.  In my case, since Flagler College was located in the heart of St. Augustine, I went onto their calendar for free events or sporting events open to the public.
  • Look up sites like Groupon for discounts on local attractions. In my case, I was able to book a very reasonably priced massage from a highly regarded and nearby Licensed Massage Therapist.  
  • Make a note of the nearest urgent care office for any emergency that may arise during your stay.  
  • Find the nearby gym and see if you can purchase a monthly guess pass (or however long you’re staying) so you have the option of working out during your stay.  If you play tennis, see if the local club provides lessons with a pro; they can typically loan you a racquet.
  • Take advantage of your temporary worksite location to see if there are other places to visit on weekends. Savannah, Georgia, for example, is less than three hours away from St. Augustine by car and would make a fun city to visit. (Worth the car rental price for the day.)
  • Give back a little. If you’re fortunate to have a job that allows you to work remotely in a fabulous city, consider showing gratitude by dropping off groceries at a food pantry in town, or gift cards at homeless shelters.  
  • Look for accommodations with a washer-dryer so you don’t need to stuff the suitcase with too many clothes. 
  • Lastly, I always pack a pair of slippers to make my time away feel comfy and cozy. 

The author knows there’s always room for more good ideas.  Readers are welcome to send any of their remote working vacation tips to

Top photo: Bigstock

About MJ Hanley-Goff (160 Articles)
MJ Hanley-Goff has been contributing to Woman Around Town since its inception in 2009. She began her career at Newsday in the early 90’s and has continued writing professionally for other New York publications like the Times Herald-Record, Orange Magazine, and Hudson Valley magazine. Former editor of Hudson Valley Parent magazine, she also contributed stories to AAA’s Car & Travel, and Tri-County Woman. After completing her novel and a self-help book, she created MJWRITES, INC. to offer writing workshops and book coaching to first time authors, and also college essay writing help to students. MJ has recently made St. Augustine, Florida her home base, and is thrilled and honored to continue to write for WAT and the amazing adventures it offers. Despite the new zip code, MJ will continue to keep a pulse on New York events, but will continue to focus on the creative thinkers, doers, and artists wherever they are.