Family Holiday in Key West, Florida

We curated this trip for our multigenerational family of 11 people (from 16 to 74 years old) during the holidays in December 2023.

If you’re driving to Key West from Miami, I highly suggest taking advantage of the Florida Key West Self-Driving Tour. This GPS-enabled app starts in Key Largo and continues for the 100-mile scenic drive. The tour automatically highlights points of interest, such as the iconic riverboat, ‘African Queen’, and the history of the Overseas Railroad as you approach each area of interest. This tour made our drive so interesting and it was a huge bonus that it kept the teens off their phones as they took in their surroundings! Contact me for a link on Viator!

If your time allows, and you have an affection for sea turtles, stretch your legs for a bit and visit the Turtle Hospital and Rehab Center in Marathon, Florida. The Turtle Hospital is a non-profit organization committed to the rehabilitation of endangered sea turtles. Tours last between 70-90 minutes. Our tour started with a brief educational talk followed by a behind-the-scenes, guided tour of the hospital and grounds. The tour included the history of how the Hidden Harbor Motel became the Turtle Hospital, the turtle rehabilitation center, and an opportunity to feed the hospital’s permanent residents. This was a favorite activity from the teens to the grandparents! The Turtle Hospital highly recommends making advanced reservations.

Visit Fort Zachary Taylor State Park Beach for some history and fun in the sun! The beach is known for offering the best swimming on the island! The state park is open 365 days a year and the entrance fee is approximately $6 per vehicle. There are tons of activities available on the grounds of the state park, such as bike trails, birding, fishing, hiking, swimming, paddling and more. On the day we visited, our group toured the Civil War era fort (included in the park entrance fee) and visited the beach. It was a windy day, but that didn’t stop our teens from running into the crashing waves of the Gulf of Mexico! From the picnic tables in the beach area, we spotted a pod of dolphins playing in the water too. If you’d rather sit closer to the water, there are beach chair and umbrella rentals at the concessions located in the picnic area. Additionally, they have snorkel gear for rent or purchase. I highly suggest wearing water shoes since it’s a rocky beach. Finally, there are showers for rinsing off the sand before you leave.

Relax on a Sunset Dinner Cruise and enjoy one of Key West’s spectacular sunsets. This was an incredible highlight of our trip! We were entertained by live music and drank rum punch as we set sail on this two-hour cruise. We opted to be seated in the first dinner seating of the evening and I would highly suggest choosing the second seating, if possible. This allows you to fully enjoy the sunset views. The dinner buffet had plenty of choices for everyone. We enjoyed Caribbean pork, plantains, chicken, fish, mixed vegetables, salad, dessert and more! Additionally, this cruise included an open well bar. You can purchase premium drinks if desired. The cruise back to the dock was just as fun with more music, dancing on the deck, and beautiful views of the moon rising over Key West. Contact me for a link on Project Expedition!

The Old Town Trolley Tour is a terrific multigenerational family tour! We purchased a one-day ticket and boarded the trolley at a stop near our hotel (you can start your tour at any of the stops along the route). The tour is narrated by a live guide who shares many interesting facts about Key West and adds some humor too. The trolley stops at many of the major points of interest in Key West, such as the Southernmost Point, Earnest Hemingway's home, Mallory Square, Duval Street, and more. This tour reduced the amount of walking for our older family members and kept everyone entertained with fun facts about the city. Contact me for a link on Project Expedition!

Enjoy the Sunset Celebration at Mallory Square. If the spectacular sunset wasn’t enough, there are also performers, music, shops, and food in this one location. It gets pretty busy during sunset, but it’s well worth the view, especially if you don’t have plans to take a sunset cruise. We enjoyed watching a stunt performer toss knives in the air while balancing on a barrel, listening to live music performed by local musicians, and the sun slowly fade into the Gulf of Mexico as boats streamed in and out of the marina.

The Earnest Hemmingway House is a fantastic tour, even if you’re not a fan or never heard of him. Seriously! The house docents hold tours every day, and you can only purchase tickets at the gate, using cash only. Ask about discounted entrance fees if you have a group of 12 or more people. While we waited for our tour time, we strolled around the grounds of the Hemingway House and enjoyed the gardens and many of the six-toed cats that live there. Our tour guide gave us an overview of Hemingway’s life as we moved from room to room in the house. She added some colorful and humorous stories that made it fun and interesting for everyone in our group.

Dare to visit the Fort East Martello Museum where Robert the Doll resides. This was the most unique tour during our time in Key West. During the Civil War era, troops constructed the fort, which has an interesting history. The Key West Art & Historical Society runs the museum and there is an eclectic mix of items that shows the colorful history of Key West. When we visited, we saw Civil War relics, learned about the cigar industry that shaped Key West, and some of the ghostly tales of the Keys, including Robert the Doll. The grounds inside the fort had lush landscaping and intriguing metal art.

The whole family enjoyed the tour of the Harry S. Truman Little Whitehouse. Our group found the history of the house fascinating. Our guide told us about the historical events of the home, personal stories about Truman and his family, and many of the famous leaders who visited or stayed in the house, such as President Eisenhower, President Kennedy, President Jimmy Carter, and more. Contact me for a link on Project Expedition!

Dinner at First Flight Island Restaurant & Brewery – Well known as the birthplace of Pan American Airways. They sold their first tickets out of this very building. Today, it’s known for being the southernmost brewery in the U.S. They serve original beers, brewed on the premises, that we ordered by the glass and by the flight. Their food was just as delicious as their beer. Some of our favorites were the brisket mac and cheese, deviled eggs, fish tacos, and fried peanut butter and jelly dessert.

Breakfast at Bistro 245 – Waterfront dining at the pier where cruise ships dock. This restaurant is part of the collection at the Opal Key Resort & Marina. The breakfast dishes were just as amazing as the views. Some of our favorites were the lobster benedict, Caribbean French toast, and turkey cheddar wrap.

Dinner at Boat House Bar & Grill at Turtle Kraals – The Boat House sits in Bight Marina at Historic Seaport, which is the site of a 200-year-old maritime trade base in Key West. You have gorgeous views from this restaurant that was voted “Best Happy Hour” by the Bubbas Key West People’s Choice Awards. The restaurant had a lively atmosphere and the nautical pennants hanging from the ceiling gave it a great vibe. Some of our favorite dishes were the blackened shrimp salad, the Commodore specialty prime rib, Chinatown steak (this received a double thumbs up from multiple people in our party), and sticky toffee pudding.

Lunch at D.J.’s Clam Shack, Key West – This quick-service restaurant with outdoor dining appeared on Guy Fieri’s Diners, Drive-Ins, and Dives (video). Before we visited Key West, we heard the lobster rolls here were better than in Maine, so we had to give them a try! The restaurant lived up to the hype and the lobster rolls were amazing! We also loved the fish fingers and generous portion of chicken fingers for the kids.

Dinner at Sunset Pier – This open-air restaurant is part of the collection at Ocean Key Resort & Spa. Voted one of the best bars in Key West by Conde’ Nast Traveler. It’s attached to Mallory Square and tables are at a premium during sunset. We enjoyed the Sunset Celebration at Mallory Square and then walked down to the end of the pier where the entrance to Sunset Pier restaurant is located. Our party found an open table within minutes and received great service, since the crowd was thinning as the sun went down. Some of the menu items we enjoyed were the strawberry lemonade, non-alcoholic monkey mango mania (which came in a hand-carved coconut pirate), pork belly tacos, and grilled mahi-mahi tacos while we listened to the live daily music.

Kermit’s Key Lime Shoppe – This 30-year-old tradition in Key West has two locations. The original location is on Elizabeth St and a second location opened on Duval Street. I truly appreciated that they had key lime pie with gluten-free crust, so I could enjoy this Key West staple dessert with the rest of my family. Other favorites were their traditional key lime pie, key lime pie on a stick (dipped in Belgium chocolate), and strawberry key lime pie.

Wicked Lick – Liquid Nitrogen Crafted Ice Cream – This location on Duval Street uses liquid nitrogen to freeze small batches of their ice cream made with fresh ingredients at 321 degrees Fahrenheit. Watching the process as we waited for our ice cream made the experience so fun! We enjoyed this sweet treat later in the evening since they’re open until 11 PM every night. Some flavors we enjoyed were the cookie butter caramel, pistachio, and coffee.