Our one year date-versary was in November 2025! So what did we do to celebrate? First, Jason took me out to dinner, and since we had so much fun the first time, we decided to make it an annual thing and take a ride back to the Keys!
First, Jason changed out the seat and installed the tour pack on the bike. He ordered armrests for me, and cup holders for both of us. Then, we loaded up the trunk, saddlebags and also a duffle bag since the weather was supposed to be hot during the day and chilly at night. The forecast was perfect. Our first ride to the Keys was super chilly and not as beautiful, but this time it was perfect weather, making the ride much more fun.
Last time, we arrived after dark and it was super chilly. That was not the case this time! Since we left much earlier in the morning and the weather was nice, we had more time to make stops and take pictures along the way. If you know me, then you know that I take a lot of pictures because they are memories that you can document so that you never forget them.
On the way down, we stopped at Gilbert’s in Key Largo for lunch and a cold beverage. The weather, water and my date were perfect! Jason is very thoughtful and sentimental. He is always happy to amuse me by playing along with all of my photo sessions and pulling over so I can get pictures along the way.
The ride to the Keys is just so beautiful, scenic and serene. If you haven’t been then you have to make the trip, and if you can do it by motorcycle it’s even better! The sounds and smells, along with the views are almost majestic! There are so many places to stop in the different Keys along the way, with each one so different from the last.
We arrived at our hotel, Hilton Garden Inn, the same one we stayed in the prior year, and we still had plenty of daylight left this time. Our room had a huge bathroom, fridge, microwave, sofa and desk. We hoped to be able to enjoy the hot tub this time since we weren’t able to during our first trip. (If you haven’t read about that trip, consider this your que to go back and catch up.) Unfortunately the pool and hot tub were under construction and getting updates, so we weren’t able to enjoy them again this trip. The hotel is not on the main strip and away from the tourist areas of Duval Street but the hotel has a shuttle service that runs from morning until evening. We prefer the golf cart, but also like knowing that the shuttle is available. There were roosters everywhere again! The hotel provided earplugs as a cute little welcome gift in our room. We had breakfast at the hotel buffet and then walked over to the coffee shop for some bougie coffee.
We spent the first day just chilling out with cocktails and a sunset ride on the bike. Key West has some of the most spectacular sunsets, so we made sure to watch the sunset from a different place every night. The southernmost point buoy was under renovation and a temporary one was erected down the street, so we didn’t get to take a photo like we had the prior year. Hopefully the renovation will be complete by our next trip.
Jason rented a golf cart from Sharky’s Golf Cart Rentals and we spent the next day driving around and sightseeing with cocktail stops and photo ops. If you’re heading to Key West and need a golf cart, you definitely have to get in touch with Marc. Jason always rents from him at Sharky’s. They have different size carts and are very personable and super easy to work with, even dropping off and picking them up.
We tried to eat at different restaurants than last time, so that we can eventually say we’ve tried them all. 🙂 That way, when we move there, we will know which ones to frequent. Yeah, I wish… We took the golf cart to Mac’s Place for a late lunch one day and I didn’t think it would be much, but it was on the water with an outside tiki and actually surprised me. It was next door to the Dancing Finger Massage. Yes, seriously!
We both love sunsets and are always looking for the best places to view them. We lucked out on this trip! We took the golf cart to the far west tip near the aquarium and Spa at Sunset Key. We pulled over on a sandy trail next to the main road and there wasn’t anyone there except for us. We witnessed an absolutely gorgeous sunset! Sunsets are beautiful in the Keys!
We spent a day driving and walking around taking photos everywhere. We walked out to the end of the pier and took a bunch of daytime pictures. There was also a popular and huge farmer’s market within walking distance of the pier. The pier is also a great place to watch the sunset, but note that there are a bazillion people there to do the same thing.
This trip wouldn’t have been complete without a visit to the Key West Shipwreck Treasure Museum, just a few blocks from the main drag, Duval Street! There was so much history there about shipwrecks and wreckers. Jason was surprised and excited to see so much history that surrounded Maine, where he’s originally from. We learned that there was at least one shipwreck per week along the Florida Reef, dating back to the 16th Century. The museum itself is a setting around the year, 1856.
The museum shares history through a video within the museum, as well as a vast collection of original artifacts from shipwrecks and personal items from those wreckers. After touring the museum, we climbed to the top of the 65 foot lookout tower for a bird’s eye view of the island. The tower mimics observation towers that wreckers would erect and climb to patrol the reef. The Shipwreck Museum also houses a web cam at the top of the observation tower. You can check it out on their website.
Jason likes to be in control of things and I usually just go along with it, but not always. Such as… he doesn’t like to let me drive the golf cart. But… on our last night there, after a few too many celebratory cocktails, he might have gotten a little too tipsy & goofy. So, guess what?! Yep, I had to take the keys from him and I got to drive the cart back to the hotel! But before we made it to the hotel, he might have almost fallen out of the cart. I made a turn from a stoplight onto the road leading to our hotel and he wasn’t paying attention or holding on. Out flew his insulated tumbler, but not him, he managed to hold on! I did have to stop however, so that he could retrieve his tumbler. Jason gets a little sappy when he’s tipsy. It’s cute. 🙂 {Check out the video snippet on our Videos page, using the link at the top.)
There was so much more to do and see, but unfortunately, we were only there for a long weekend. We spent most of our time sightseeing & exploring on the golf cart, while stopping to grab food and cocktails along the way. Jason loves making plans and does a wonderful job. We were celebrating our one year together and we hope to take the camper down for our second year celebration.
Until next time,
Val
