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!
The Hable Way is an affiliate of Marriott and Get Your Guide. If you click through any links and make a purchase, we may earn a commission at no extra cost to you.
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 30 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 for this trip was 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 🙂