Key West Holiday Historic Inn Tour

Isle Style Salon on Simonton Street in Key West, Florida.
Isle Style Salon on Simonton Street in Key West, Florida.

Key West might not have the cold temperatures or the snow to make it feel like Christmas, but we do have the lights! On the first of the two lighted historic inn tours offered this holiday season, my friend Pam and I decided to join in and find some holiday spirit. At 6pm we headed over to Isle Style on Simonton Street which was one of the “inns” on the tour that evening. We easily found parking in this neighborhood, and with the Old Town Trolley’s offering transportation around the island to the other inns on the tour as part of the $30 fee, we were all set to go! 

Isle Style is not an inn; it is actually a high end spa offering all different types of services from hair and nails to massage and more. They even have a boutique! But the conch style house that the spa calls home is definitely worthy of being a historic inn. And frankly, it was one of my favorite stops that night. Partly due to the gorgeous foliage that decorates the outdoor courtyard, partly because of the amazing little boutique that I browsed and had to council myself not to buy anything, and partly because Better Than Sex owners Len and Dani were there to provide delicious snacks for the tour members. The Chocolate grilled cheese was so deliciously decadent.

A room at the Almond Tree Inn on Truman Ave in Key West, Florida.
A room at the Almond Tree Inn on Truman Ave in Key West, Florida.

Next, we took the trolley to Almond Tree Inn on Truman Ave. I have driven by this property a million times, but I had no idea how nice it was. The foliage is gorgeous and the pool looked so relaxing. They had a room opened to show tour members, and it was very updated and comfortable. It reminded me of an old hotel on St. Pete Beach that I once stayed at, but really nice and updated version. The snacks and wine were served near the main office, and it was nice relaxing by the pool for a bit.

Our next stop was the Wicker Guesthouse on Duval Street which we walked to. The wicker Guesthouse has a great location and a fierce following of regular guests. The inn is a bit older in looks, but the staff is incredibly friendly and they were quick to offer wine, water, and other snacks poolside for the tour members.

Next we again rode the trolley to Courtney’s Place which is a very small B&B on Whitmarsh Lane. The grounds were well manicured and the pool was very cute. Nyna, one of the employees and a friend of mine showed us around. We got to tour a couple of the unoccupied rooms which were more like little apartments. This place is pet friendly and would be a great, inexpensive place to stay for a family.

Santa taking a nap outside of the Mermaid and Alligator B&B on Truman Ave in Key West, Florida.
Santa taking a nap outside of the Mermaid and Alligator B&B on Truman Ave in Key West, Florida.

The last place on the tour for us was the Mermaid and the Alligator which is one of the most beautiful inns on the island located on Truman Ave. The Victorian House is very homey, and it was probably the best decorated for Christmas of all of the inns on the tour. The pool area surrounded by tropical foliage was just beautiful, and they offered wonderful hors d’oeuvres here. The guesthouse dogs were lounging by the pool too,and they seemed to like us, coming up to Pam and I for pets. The inn employees were super friendly and even told us about how the inn got its name. Hint: check out the pool side statue when you stay here!

Now, I mentioned that the trolley was part of the tour package, but, I neglected to mention how great these drivers are! They know the town inside and out, they are friendly, and they are full of knowledge. I suggest any visitors to Key West take a tour on the Old Town Trolley to learn more about the island and to get a better idea of what sites you really want to check out during your stay. Even I seem to learn something new every time I take one of these tours!

Would I do this tour again? Probably not because I am not a big drinker, and I think that besides showcasing some of the properties on the island, it is another reason to party. But for those visiting the island in early December that like their wine, this tour is a must. I am glad that we did it, and I got to see a few things that I had not seen before. For me, I thought $30 was a bit much for the tour, but if we had even had one glass of wine at each stop I would think that it was more than worth it!

See what else is happening on the island during your visit by checking out our Key West Events Calendar, and for other things to do and see in our island city, go to our Key West Web Site.

Before making your reservations for Christmas dinner or any other meal while in Key West check out our restaurant reviews!

Feel free to Email Me if you have any questions about Key West!!
Island Genn
Key West Concierge



About the author: Island Genn

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