Amazing Sights to See During a Weekend in Key West



This post is a little different because it’s a guest post- written by my mom! My parents got me hooked on traveling as a kid, and I got my mom hooked on photography. We took a girl’s trip to the New Orleans last year and took tons of photos between us! My mom recently took a trip to Key West with my dad and some friends, and she wrote a guide for a weekend in Key West for my blog! 🙂

Amazing Sights to See During a Weekend in Key West, Florida

Weekend in Key West

Last spring we had the chance to take an overnight trip to Key West. We moved to Fort Myers, Florida a few years ago and were intrigued by the chance to ride the Key West Express, a ferry boat that leaves for Key West every morning at 8 arriving at the port in Key West a little over 3 hours later. Better than driving, to be sure! We set off with some friends and had a nice relaxing ride! The ferry was set up with indoor and outdoor seating, comfortable tables and chairs, a bar, and movie screens.

Key West architecture

Key West statues

Once we arrived we walked to a restaurant to eat lunch and then caught a ride to our hotel. After we checked in, we took the hotel shuttle to the downtown area where most of the sightseeing and touristy places were. Our first stop was Truman’s- plenty of indoor and outdoor seating and a huge movie screen, bar, and tables with an awesome view.

During our walk we saw a new statue being delivered, the famous picture of the sailor kissing the nurse in NYC when World War II ended, and it’s now a statue in Key West!

Key West architecture

Custom House

The Little White House in Key West

The Little White House

Since 1890, the Little White House has served as the naval station’s command headquarters during the Spanish-American War, World War I, and World War II. In 1946 the historic building served as President Truman’s winter White House and a site for the Cold War response by later presidents. It is now used as a museum filled with historical artifacts.

The Little White House in Key West

White orchids in Key West

The Little White House in Key West

Roosters in Key West

Hemingway's house in Key West

Hemingway’s house in Key West

The southernmost house in the US

The Southernmost House in the US

The southernmost house in the US

Southernmost Beach in the USA

Stained glass dome in Key West

Architecture in Key West

One thing I loved to see during our weekend in Key West was the beautiful historic architecture. In my previous trips, I hadn’t explored the island very much at all- it was mostly just one little stop at Sloppy Joe’s, the famous bar, or the Southernmost Point of the USA. I felt like we thoroughly explored so many more parts of the island on this trip, even just staying one night.

We saw ornate Victorian homes, learned some more historical facts, saw lovely flowers, and saw plenty of roosters and chickens! It is illegal to kill these wild animals that roam the streets of Key West. It seemed funny to see them in trees, bushes, or standing on street corners.

Roosters in Key West

Greek statue on Florida house

Southernmost point in the USA

Pineapple gate topper

Purple orchids in Key West

Strand in Key West

Clock tower in Key West

Toward the end of the afternoon, we happened upon a French bakery that we wanted to check out. As it turned out it was the end of the day and the pastries were half price. We just could not resist, so I bought some Chocolate Almond Croissants from La Grignote that were amazing!! (Sorry I forgot to take a photo of them, but trust me, they were delicious!) We had them for a late snack that evening. Had I known how delectable they were going to be, I would have bought them all!

Captain Tony's Saloon in Key West

The Oldest Bar in Florida

Key West pier

Everyone tends to head to the pier for sunset, and it did not disappoint! We saw a spectacular sunset and met some friendly people as we awaited the sun setting in brilliant colors!

Sunset in Key West

Sunset in Key West

Sunset in Key West

Sunset in Key West

WeCycle in Key West

Biking around Key West

The next morning we stowed our luggage with our hotel. They offered a service where they would bring it to you downtown later before you catch the ferry back. It worked out great! Our first stop was breakfast and then a bike rental place, WECYCLE.

>My husband and I got a tandem bicycle for $18 for the entire day. It was a very well maintained bicycle, and we were able to explore so much more than we would have otherwise by foot. The bikes also came with a lock, so you were free to stop and do sightseeing without worrying about losing your bike. I was able to sit on the back and snap pictures to my heart’s delight! Thankfully, we only wobbled a few times 🙂

Key West historic house

Key West historic house

Key West historic house

Plumeria in Key West

Key West historic house

Key West historic church

Key West historic house

The Oldest House in Key West

We toured the Oldest House in Key West. It was built in 1829 by Richard Cussans. It has survived many hurricanes and tropical storms, but is in remarkable shape. Richard was a boat builder and used those skills to build a very sturdy home as well. It is in a slightly different location now, but is well preserved and serves as a museum.

The Oldest House in Key West

The Oldest House in Key West

Key West pier

Lighthouse in Key West

Our next stop was to the lighthouse. We had a wonderful view of the island from the top! The current lighthouse was constructed in 1848 after a hurricane destroyed the former structure.

We dined along the water for lunch and headed off for some quaint shops for souvenirs. We found Mile 0 of Route 1 and saw the Vietnam Memorial. After a day of biking and beautiful sites, we stopped to cool off at Duetto’s for some tasty gelato- it was a welcome treat!

View from Key West lighthouse

Mile 0 in Key West Gelato in Key West

Key West pier

Key West Vietnam Memorial

Key West historic restaurant

Key West sunset

At the end of our day, we walked back to the ferry to catch the return ride home. The sun set during the boat ride- it was a beautiful end to a wonderful weekend in Key West! 🙂

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Blog, Florida, North America, Photography, Travel, USA

  1. Kathleen says:

    I can see I’m going to have to plan a trip to Key West one of the times I’m in Florida. I go at least once a year, so it shouldn’t be too hard. I have a picture in Martinique of a chicken just like the one here, except he was at a restaurant I was eating, begging for food. So weird. I love all of the things you were able to see. The history of Florida is really interesting. I didn’t know that President Truman had a winter Whitehouse there. Very smart if you ask me. Great post.

    • Julia says:

      I hope you can go to Key West the next time you’re in Florida! It must have been so funny to see a chicken begging for food!

  2. Mari says:

    I have to make plans to get down to Key West soon! I’m so close in Marco Island all the time. I’ll definitely be following your tips!

  3. I really need to get back to Key West!! It looks so amazing from your pictures! I haven’t been in like 10 years

  4. Amy M Dent says:

    Such a fun time! 🙂 Thanks for letting me try out blogging for a day!

  5. Eric says:

    I love the guest-blog idea! That way you can feature more geography than you can travel to yourself.

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