Key West Weekend Getaway

My sister and I had a blast on our Key West Weekend Getaway!  It was our first time to travel to the southernmost city in the continental United States, a subtropical paradise.  We stayed at The Gates Hotel Key West, helped a local artist create a driftwood Christmas tree for the lobby, and had a lot of fun exploring the unique blend of history, climate, natural beauty, cultural diversity, and architecture…the Key Lime Pie wasn’t bad either!

Fort Zachary Taylor Historic State Park

After a night’s stay in Miami we traveled down ‘Ocean Highway’ from Miami to Key West, an island city that has been a refuge to writers and presidents for many decades.

Key West Weekend Getaway @ItsOverflowing

We had the privilege of staying at The Gates Hotel Key West, a comfortable and stylish hotel.

unlockthekeys @ItsOverflowing

Another view of the lobby, we loved the furniture and wall treatments.  Beyond the lobby is the main stage with live music, pool and bar.

Driftwood Table @ItsOverflowing

Succulent plants are always in style, love this great little arrangement of Rosette Succulents atop the table.

Key West Succulents @ItsOverflowing

In the guest room, I loved the wooden paneled wall, rustic headboard and ocean art, but my favorite feature was the high-quality flooring.  The room felt extra clean without the typical hotel carpet.

Gates Hotel Key West Headboards @ItsOverflowing

At The Gates, we rented Key West style, chic bikes from Martone Cycling Co. – the bikes were amazing!  They required no gear shifting – gears adjust and change automatically based on your riding speed.  It was a ten minute water view ride to get to Old Town Key West.

unlockthekeys @ItsOverflowing

There are so many parts of the island to explore and there’s beauty around every bend.  Exotic-looking Bougainvillia is fairly common in Florida, but this one was beautifully displayed against a white picket fence.

Key West Island Flowers @ItsOverflowing

Key West is known for great local restaurants!

The Blind Pig, a food truck that’s permanently parked at the Gates Hotel serving food throughout the day, the mahi-mahi tacos were so good.

El Siboney, off the beaten path, this no-frills restaurant serves up generous portions of the best Cuban food on the island at reasonable prices.

Blue Heaven, the private courtyard (once home to Hemingway’s boxing matches) is filled with roaming chickens and lounging cats soaking in the sun.

Hogfish Bar & Grill, for a taste of a true local’s joint just five minutes away from Old Town (below).

Hotfish Restaurant Key West @ItsOverflowing

Key West has lots of MUST SEE Historical Sites.

Duval Street is Key West’s main tourist strip, with restaurants and shops designed to entertain.

Ernest Hemingway was one of the first important writers to call Key West home.  Take a tour of his 1851 Spanish Colnial house with a lush tropical garden and salt-water pool.

Harry S. Truman Little White House, still used as a vacation retreat for United States Presidents.

Audobon House and beautiful gardens containing a variety of tropical plants including birds of paradise, hibiscus, and different palms.

Fort Zachary Taylor protected this part of Florida’s coast during the civil war and today it is a historic park well known for its well-maintained, sandy beach with chairs, umbrellas and water sports equipment for rent. This 54-acre state park is also home to several nature trails, a stunning coral reef for snorkelers, picnic tables and a beachfront café.

Key West Lighthouse was built in 1847 and stands 86 feet high.  It offers great views from the observation deck near the top.

Mallory Square Dock is a former warehouse area that is now the location of a nightly sunset-watching ritual with live entertainment.  Tourist gather on the dock for a nightly Sunset Celebration. Jugglers, musicians, vendors, and street performers create a carnival-like atmosphere.

royal-street-key-west @ItsOverflowing

Old Town is lined with beautiful historic homes.

Key West Homes @ItsOverflowing

A picturesque canal that offers easy gulf and ocean access.

boat dock island key-west-travel

You may have seen this on my instagram feed!?!  Three years were spent restoring this Alsbury Mansion in Key West.  The owners paid meticulous attention to detail and historic preservation.

Key West Home @ItsOverflowing

Key West’s best kept secret.  Make a reservation in advance to have dinner (or just drinks) at Latitudes on Sunset Key and enjoy a complimentary ferry from the pier at Mallory Square out to Sunset Key.  The ferries depart from the harbor at Key West every half hour and return with the same frequency.  We planned our reservation time for 5:15 to correspond with the sunset, the view was amazing!

unlockthekeys @ItsOverflowing

I did a whole lot of relaxing and site-seeing, but I also had a fun opportunity to work with local artist Billy, from COAST to build a Driftwood Christmas Tree for The Gates Hotel Key West lobby.  I’ll write about that on Wednesday…tomorrow I’m sharing my family room Christmas Decor!

#coastprojects @ItsOverflowing

DIY Driftwood Christmas Tree

Favorite Vacations



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  1. Patricia says:

    I love those beds…what kind of wood was used!?!

  2. Stacey says:

    I am going there this Spring with my college roommates! Thanks for the tips!

    • You are going to love it! Make sure you check out Rum Rowe at The Gates Hotel, it’s such a fun atmosphere! XO, Aimee

  3. Jessie says:

    I haven’t been to Key West in years! Looks like you had a wonderful getaway!

    • I loved it! You’ll have to plan your own Key West Getaway soon! XO, Aimee

  4. Mary says:

    I’m still curious about that Driftwood Tree. Saw pics on FB can’t wait to see the reveal.

  5. Kelly says:

    We’re thinking of going somewhere this Christmas, but haven’t made reservations. I wonder if there’s still availability!? Do you think it’d be a good fit for us and the kids!?

  6. Loved this post! I was just in Key West as well over Thanksgiving weekend. Stayed at the beautiful Ocean Key Resort right on Duval. It’s such a cool little town with so much character! They key lime pie wasn’t too bad either 🙂

    xx, jen

  7. Rebecca says:

    It’s freezing here…jealous of your summer attire!

    • Oh my gosh, I know! Such a fun treat to visit sunny Key West in the winter! XO, Aimee