• Facebook
  • Instagram
  • Pinterest

The 5 Things I Learned from City Hopping in Florida

Are you that kind of traveler that wakes up at dawn and plans out a full itinerary to make sure you capture every second of your trip? I believe in soaking in every moment that you can, but I do it with a twist. I am that traveler who wants to jump cities every day and find a whole new world just a short drive away. Let's go from point A to H within hours!!

I learned this about myself pretty quickly when I started traveling back in 2016 and one I decided to test to the limits. Why not stay in a new city each night I am traveling?? That was my goal and I was determined to fulfill this one!

So, I purchased round trip direct tickets from Concord, North Carolina to Punta Gorda, Florida for only $74. (No specific reason for this destination, I just found cheap flights.) I decided this would be a good trip to explore new cities every day because of only staying in Flordia for 3 nights 4 days. After making this decision, my next "to do" item was determined what cities to stay in and where to lay our heads at night. (Matt, my boyfriend, was with me on this trip!)

This link provided is an affiliate link and I may gain commission from you purchasing from these affiliate links. 

Going into this, I did not have any thoughts on what or what not to do and we truly winged it. That is how I learned firsthand what not to do when city-hopping.

The cities I decided to stay in:

  1. Cape Coral

  2. Siesta Keys

  3. Punta Gorda

I booked our 3 Airbnb's in each of those cities and waited patiently for our trip to arrive.

1. Distance from Airport to Destination

Something I learned day one of landing in Punta Gorda needing to drive to Cape Coral. The drive itself is only 43 minutes, but I learned quickly that I needed to account for time for getting the car rental and all the odd things you do after landing like eating. These small activities may seem like 30 minutes to do each, but when in a new city and not sure where you are going right away, time seems to add up easily on these small activities. And I happened to purchase the car rental from a location 5 minutes away from the airport which adds more time. (This saved me about $150 just for booking the car rental away from the airport.) So now I need to uber to the car rental, add some more time on.

By the time we got on the road, it was around 4 pm and still had a little less than an hour's drive to get to our first Airbnb. Another thing I learned is to research if you will go through any toll roads as this cost money and can take time off of your day. Make sure you take a coin purse full of change for Flordia tolls! If you do not have the money, you receive an IOU to mail the payment in which Flordia only accepted money orders. Money order costs more than the toll fee which is something I know, unfortunately.

This link provided is an affiliate link and I may gain commission from you purchasing from these affiliate links. 

We arrived at the first Airbnb location in Cape Coral around 5:30 pm and it was already starting to get dark. When we arrived, I felt like the day was spent actually traveling vs. exploring the beautiful city of Cape Coral and seeing what all it offered. Once the car was parked and we checked into the Airbnb which was actually a boat, we could hear music while sitting on the backend of the boat. Of course, I wanted to go exploring and we ended up finding a local restaurant with an outside bar facing the water (which was playing the music) and we decided to enjoy a few drinks before heading out for dinner. Well, a few drinks turned into conversations with the locals sitting around us and we ended up staying here for dinner. (Some of the best lobster, shrimp pizza I have ever had!)

2. Distance Between the City-Hopping Cities

This sounds like a no brainer, right?! Well, not for me! I learned while driving from Cape Corals to Siesta Keys that the distance between the cities can take a chunk of your day away. The distance between the two cities is about an hour and a half drive, but time can be added to that when stopping for gas, food, shop, etc as you drive.

Another thing to account for is needing to check into an Airbnb at a certain time (typically there is a set time when meeting the host for check-in) which can put time restrictions on you. So after the driving, eating, and checking in, it can be 3 hours later before you finally have time to explore the new city.

This link provided is an affiliate link and I may gain commission from you purchasing from these affiliate links. 

For Siesta Keys, I knew I wanted to lay on the beach as much as I could and not move a muscle unless it was to go from the ocean to my beach chair. Siesta Keys is known for its fairy dust sand and water being crystal clear that you can see crabs walking on the ocean floor. My kind of ocean water! And the sole reason for my wanting to stay in Siesta Key for the night.

Before this trip, I hadn't seen clear water since the Bahamas which was over 15 years ago. In North Carolina, our beaches have muddy water that you instantly lose the sight of your toes the moment you walk into the water. Yuck! I am beyond thankful to have visited this location because since this trip in May 2017, I have been to Siesta Keys every year and sometimes multiple times throughout a year.

3. Beach Supplies

When traveling by plane, you instantly become limited to what you can bring and pack which has no comparison like driving to the beach. Meaning, I couldn't lug my beach chair, umbrella, cooler, blankets, and everything else I usually take to the beach. Something to keep in mind when flying to a beach destination with hopes of laying out all day. Some people don't mind having all the bells and whistles when laying on the beach for the day, but that is not me when it comes to certain items!

I have fair skin so if I stay in the Florida sun all day even with wearing sunscreen (and reapplying every 30 minutes) I turn into a lobster. Crispy red! The fastest way to ruin a perfect trip is to become so sunburnt you can't get out of bed. Thankfully our Airbnb host had plenty of items for us to take like chairs and umbrellas. And if you didn't know, you can message the Airbnb host before booking that spot and ask if they provide beach supplies if not listed in their description. In general, the Airbnb's I have stayed at provided way more than I expected.

He doesn't always travel with me, so that's why I write in "I" and "we" approach.

(My boyfriend relaxing while on Siesta Keys beach and being able to enjoy himself by the beach supplies our Airbnb host provided.)

4. Research Local Events

One piece of advice I can give anyone traveling to a new destination is to look up the local events going on in that area(s) for all the dates you will be in the area. The reason I state this is that when we were in Siesta Keys, we had missed a huge boat/water show which seemed to be a hot topic when we were there. Our Airbnb host was telling us all about it and how fun it is when it comes every year. If I had looked up the events in the area I was thinking about visiting, I could have seen this and planned on visiting the show by staying in Siesta Keys the first night. Minor tweaks can enhance your experience by a thousand percent by doing a little research beforehand.

This link provided is an affiliate link and I may gain commission from you purchasing from these affiliate links. 


If you have been following my travel journey from the beginning then you know I am big on reviewing Airbnb reviews and like to see what kind of experience others had. Reviews can be a deal-breaker for me and one thing I have learned from a "not so good" Airbnb experience on this travel journey. Airbnb reviews hold weight with me when trying to decide on a place to stay. People are honest and let you know the minor details of issues with their stay. I am a strong believer in my own reviews as well, so these reviews hold value to me.

I prefer not to go into specifics on this place as my feedback was given to exactly who needed it and whether they listened or not, that's on them. I am not one to "blast" their business on a social platform.

And there you have it, folks, the things I learned from city-hopping the very first time in Florida! Each of these has helped me with other travel journeys and future ones I have yet journeyed too. I would love to hear from you on what you learned while trying something new with traveling on my Facebook page, That Travel Deal. Click the icon below to leave your comment!

17 views0 comments

Hello Everyone, my name is Sara Elizabeth and a full-time working mom and a full-time student!

Over the years I have fallen in love with  traveling and exploring the great states of the United States! This passion grew from understanding how to find good deals on airline flights which have been the reason for many of my travel adventures. This journey has led me to find "that travel deal" for domestic and international flights. These are those kinds of deals that have people asking "How did you find them so low?" ...Well, to those asking that question, follow along this adventure of mine to learn my methods for finding that perfect travel deal. 

  • Facebook
  • Instagram
  • Pinterest
  • Facebook
  • Instagram
  • Pinterest



  • Facebook
  • Instagram
  • Pinterest