I have lived 34 years without ever visiting the Sunshine State! It seems like a destination that everyone has been to! Maybe it is the beautiful weather or the endless beaches. Somehow it has eluded me for so long until June 2019!

Long before kids, Kyle and I had always talked about driving the whole way to Key West. After going to Prague in April of 2019, I got the travel itch. I couldn’t wait to book another flight. I didn’t even care where it would be take us. My Mother-In-Law told me that they were heading to Florida in June to visit her brother. I began looking into flights out of CHO. It is a smaller airport so we always end up with at least 1 connecting flight to and from our destinations. I love flying through ATL. We prefer to fly Delta which is conveniently headquartered in Atlanta. There is a comforting and familiar feeling when I am there, which matters to me when flying. 

I was a bit torn. We had looked at flights to be in Florida around the same time as Kyle’s parents would be there. We wanted to visit with family but we were hoping this would finally be the chance to hit the Keys. I checked to see what flights to Miami were and they were also well within our price range so we opted to make our Keys dream come true! The cherry on top was that we could celebrate Asher’s 7th birthday there!

Never having been to the Keys before, I was afraid I would pick the wrong one! There are over 1,700 islands. Thankfully, only about 40 are populated so that narrowed it down a bit. Should we stay in the Keys the whole time? Maybe we should visit another area of South Florida as well? I have a bit of analysis paralysis while planning trips. When we travel to places that I have never been, I am always afraid that I will be making the wrong decision. I put the success of the trip on my shoulders since I am always the one planning it. I had booked a hotel and then backed out. I could have continued to do that up until we left but I figured I should commit. Since Kyle’s work-travel days, we have been able to rack up a lot of points at different hotel chains and car rentals. Our preferred hotel is Marriott. We looked into some others but they were a bit out of our price range. Since we are so familiar with Marriott Bonvoy Loyalty Rewards, we felt confident sticking with one the Marriott affiliates so we could accumulate more points on this trip!

Finally, I made a choice. We decided to stay at Courtyard Marathon – Florida Keys for half of our trip. I chose to pay using the Advance Purchase Member Rate which includes a discount for paying in full right away. This was great for two reasons: (1) I couldn’t change my mind any more than I already had! (2) I had a month to pay it off before arriving. Of course, this option might scare some away as it is nonrefundable.  

Overall, everything about Courtyard Marathon – Florida Keys was fantastic. The staff was friendly and the grounds were well kept! They had 2 pools, plenty of yard games and a few different options for food and drinks. The location was great as well because it is nearly in the center of the Keys. This made it easy to take day trips North and South of Marathon.

We were about an hour from Key West. We drove down there to do a Glass Bottom Boat Reef Eco Tour with Fury Water Adventures. The drive was beautiful and went by quickly. On the way down, we got to drive over the 7-mile bridge, see quite a few Key Deer, plenty of iguanas and found some delicious food and drinks! We gave ourselves plenty of time before having to board the boat, so we stopped at Two Friends Patio Restaurant. The Pirate Punch, a rum drink, was my favorite part!  I would recommend all of this and plan to take my family back there again. 

I opted to split our time between Marathon Key and Naples on the gulf coast. My parents used to visit Marco Island often. I wanted to see what was so exciting about it. I looked for a few hotels there but found that Naples would work better for us being a younger family. We did get to visit Tigertail beach on Marco Island! The sand was soft and the seashells were plentiful. I love an ocean where I can see my feet in the water. The calm waves crashing was great for kids. 

When I booked this trip, I didn’t realize a good friend of ours from years ago lived right in Naples. We had contacted him about 2 weeks before arriving to ask him where he lived, knowing it was somewhere in the state. We were willing to drive wherever it was so that we could visit. We didn’t have to go far, he lives right in Naples!! The last we saw them was about 6 years ago when our sons were both turning 1 year old. They had lived in PA and we had just moved back to PA briefly. The stars aligned back then and we were able to spend time with them at his son’s 1st birthday party. Shortly after, they moved to Florida! The universe must have known that we needed this reunion. It had been so long but everything fell right into place. Our kids loved playing together and we had such a great time catching up. When you find people who match your energy, hold onto them!

Our hotel was just a few minutes down the road from their house. This time, I opted for a hotel that was not one of our usual brands. We stayed at The Naples Grande Hotel. We walked in wondering what on earth I had signed us up for. We arrived late after spending the entire day with our friends! We stayed at the very top, on the 18th floor… what a view! It was on the corner of the building and had 2 balconies, so we could see the coast and the city of Naples! I don’t think that we have ever stayed at a place like The Naples Grande before. It was vibrant and beautiful. I chose it because when searching for hotels, I was looking for a place with a fun pool! Silly but necessary with kids! 

For us, it is as much about the journey as it is the destination. If we were to head back, I don’t know if I would change a thing. Except maybe staying 2 weeks instead of just 1 🙂 

16 comments / Add your comment below

  1. What did you think about the keys? Was it everything you dreamed of? Was the beaches nice? I would love to go! Would you rather stay on the keys or Naples?

    1. It was beautiful with plenty of things to do. I think when we go back, I will still split my time between the keys and Naples or another place. Some of the beaches had sargassum, which made them less desirable to swim at. We did find a few that were clear, it just takes some time. I would assume that is highly dependent on when you go also! If you are a boater, there are no limits!

  2. Glad you made it to the Keys. They are not what everyone thinks! Marathon is my favorite as well. We rent a house and a boat there so I can go fishing.

  3. You picked some great places for your first visit to The Sunshine State!! I moved to Florida 11 years ago, and we always said we should go to the Keys. Our only visit has been to Key West on a cruise.

  4. This is so neat to see Florida from a non-native’s perspective! I grew up in Naples and remember Tigertail beach when it was covered with horrible sandspurs. I’m glad you enjoyed my home state!

  5. We have only ever visited Florida for Disney World and that’s not really seeing Florida is it? We have always wanted to Visit Miami and the keys. Looks like it was definitely a great experience

  6. What a fun family getaway…we stayed in Key West last year and absolutely loved it. Will definitely go back…and would love to drive over the 7-mile bridge next time (we flew straight into Key West so didn’t get the opportunity).

  7. Awww. I am glad you finally got to go. It sounds like it was a great trip. My parents loved Marco Island. Thye said it was so peaceful. I have been to Key West a few times, but nowhere else on the Keys. I would like to drive it one day.

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