Travel Florida: Luxury Christmas Key West Style

Christmas in Key West, Florida

Luxury Christmas in Key West, Florida by Diane Leone

Travel Florida: Luxury Christmas Key West Style

By Diane Leone

Once the decision was made to spend the week of Christmas in Key West, Florida we were excited. Every previous Christmas had been spent enjoying family and the children as they opened their gifts. The children were now grown and we felt we needed a getaway after a hectic year. If you want to wear flip-flops, lie in the sun, and feel the sand beneath your toes at Christmas, Key West is where you need to be.

There are two ways to get to Key West: Drive the long US1 route through all the Keys to get to the most southern landmass in the US: Key West, or you can choose to fly. The airport is Key West International Airport and is two miles east of Key West, in Monroe County, Florida. We drove as we live in Florida. It’s a beautiful, scenic drive through the Keys on your way to Key West.

Christmas Key West Style

Christmas Key West Style

Once we arrived at the Casa Marina Resort & Beach Club, part of the Waldorf Astoria Collection, we breathed a sigh of relief, we were there, and we were in Key West for Christmas! This property, with 1,100 feet of private beach, meets the laid back yet luxurious standards we wanted. We had lunch by the pool and the best part of the stay: was the Christmas day brunch. The weather on Christmas day was warm with the slightest drizzle of rain but no one cared. There were families with young children, couples, grandparents and more. Everyone was enjoying the tropical weather and the amazing food, unlimited champagne and incredible entertainment. It was a perfect way to relax on Christmas. I can imagine Jimmy Buffett and Kenny Chesney celebrating Christmas Day the same way. Speaking of Jimmy Buffett, go to Margaritaville and have a “Cheeseburger in Paradise” and a Margarita. It’s a fun experience and the food is good.

It was tough to choose where to have Christmas dinner, as there are so many wonderful places to choose from in Key West. We decided to have dinner Christmas Eve at a charming restaurant called Nine One Five, located at 915 Duval St. right in he middle of downtown Key West. It’s a stylish old house with a big patio and serves delectable globally accented American fare, and has a secluded late-night wine bar. We sat on the patio and had a great time and amazing food. Ask to meet the owner, Stuart Kemp; you’ll want to tell him how amazing the food is.

Christmas Eve Dinner at Nine One Five Restaurant in Key West, Florida

Christmas Eve Dinner at Nine One Five Restaurant in Key West, Florida

We love Italian food and we found a fabulous Italian restaurant, La Trattoria. It’s not downtown but sits across from the ocean so the views are wonderful and the food is incredible. We ate there three times during our stay!

As I went off for a relaxing, tropical facial, my husband left to play golf at the Key West Golf Club. He loved the course and met great people from across the country also spending their Christmas Holiday in Key West. The golf club is located at the entrance of Key West on more than 200 acre of tropical foliage and wildlife. It’s an 18 hole, 6,500-yard course designed by Golf legend Rees Jones. Tom enjoyed it so much he played a second day. This was okay with me as I stumbled across something unique and wanted to try it.

Ernest Hemingway's Home in Key West, Florida

Ernest Hemingway’s Home in Key West, Florida

I am a huge fan of Ernest Hemingway so I found his Key West home. It’s open for tours and there was a line to get in. As you would expect, it is a lovely Florida style home with literary works on the shelves and a large inviting yard. Don’t miss it if you love Hemingway.

We felt like a part of a special group, being allowed to have this amazing tropical Christmas. If you decide to experience the delight of a luxury, laid-back Christmas in Key West, make your travel arrangements as early as possible, as you can imagine, it’s a popular place anytime and especially at Christmas. We were able to book some restaurants and experiences while we were there, but I would book as much as you can early.




Diane Leone

Diane Leone

Diane Leone is a freelance travel and lifestyle journalist and photographer who lives in Florida. Diane travels nationally and internationally. She is the author of two published books, is an award-winning Interior Designer, and a professional speaker. Diane usually travels solo and her travel blog is called One Woman’s Travels.

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Note: Disclosure – The author received a comped dinner at Nine One Five excluding alcohol, and a hosted lunch at Casa Marina.


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