The Continental United States literally runs out of land at Key West. Mile Marker Zero. The End. Perhaps that kind of geographic location is why this tiny island paradise has an anything goes attitude in a good way. Pirates, rum runners and those seeking to disappear off the grid have always called this 4×2 mile spot of land home. Today however, Key West has become a special destination for those seeking flip flop casual luxury, watersport fun, bars, restaurants or nature lovers.
I was there with family and friends celebrating my birthday, which we kicked off in Miami. (ICYMI..check out my previous blog post featuring My Top 5 Miami Family Vacation Must Do’s.) Living in Miami for 18 years allowed me countless visits to Key West but it had been over 7 years since my last visit here. So much has changed and thankfully much has stayed the same. Before going, I highly recommend the following websites to help build your itinerary: https://fla-keys.com/key-west/ & https://keywestattractions.org/ & https://www.historictours.com/keywest/
The 3 to 4 hour drive down from mainland Miami is part of the fun. US1 South aka Overseas Highway is a gem. Shimmering Atlantic Ocean on one side and the famed Gulf Of Mexico opposite is amazing. Most of the drive is just one lane each way and that forces you to slow down and enjoy the simplicity of it all. The seven mile bridge is one of the most unique experiences anywhere in the world! Upon arrival at our hotel, we dropped of our bags, grabbed a drink by the pool and hit those iconic Key West Streets.
Since this day was my actual birthday, I thought why not do one of the signature Sunset Sails! My #HeighPartyof3 and 2 good friends took a 2 hour sunset sail with Sebago Watersports. Sebago offers a multitude of cruises, watersports and tours. Departing from The Historic Key West Seaport, this was truly a grand way to celebrate another trip around the sun! Open bar, delicious hors d’ouevres and live music set the festive atmosphere. The crew went out of their way to check on its passengers and we had a blast celebrating! We thanked Sebago Watersports for making a great memory for my family and friends.
SobeSavvy Tip: We enjoyed a great happy hour at Onlywood Grill prior to our sunset cruise. They are located right near the Historic Key West Harbor, so we simply walked over after happy hour in plenty of time to check in for the sunset cruise. If your kid loves pizza like ours, then definitely check out this spot!
We awoke to a brilliant sunrise and were ready to seize an entire Key West day. Aqua Yoga at the Southernmost Resort was a wonderful way to begin my day. I met up with my girlfriend and we enjoyed an hour of peace in their pool led by an awesome yoga instructor. How unique!
While I enjoyed yoga, my husband and daughter went to The Key West Butterfly & Nature Conservatory. They had an amazing time seeing dozens of varieties of butterflies, flamingos and birds. It has a education room and also a delightful gift shop. It is a must do for visitors looking to enjoy something different and beautiful!
Afterwards, it was time to eat breakfast. Our favorite is Blue Heaven in Bahama Village. This iconic spot has been everything from a bordello to hosting boxing matches refereed by Ernest Hemingway! Luckily since 1992, it has been a restaurant which serves a great breakfast. As always my husband ordered the banana pancakes, I went with a lobster benedict and my now 10 yr old enjoyed a simple but yummy pancake. Resident roosters just make the atmosphere a classic Key West experience. Be sure to save room for their infamous Key Lime Pie!
Afterwards, we all made our way to Harry Truman’s Little White House. President Truman spent 11 working vacations here, starting in 1946. He loved the warm winter climate and outdoor activities he could do here. The home still has many of the original furnishings and floorings. It was spacious and airy. Although not yet air conditioned, the design and famous Key West shutters made it bearable indoors during that time. One of his fully restored Presidential Limo’s is also on the property. A great place to tour and so informative. No photos are allowed inside for security reasons but you can purchase some cool souvenirs in the gift shop to remember your visit!
If you want an educational overview of Key West, I highly recommend The Old Town Trolley Tour. They offer a 13 stop, Hop on-Hop Off daily tour, which conveniently included a stop at our hotel! We could hop off at a particular stop to explore and once done, simply go back to the trolley stop. This is an awesome way to see the island while leaving your car parked. It is also fully narrated by one of their expert conductors.
Opened in 1934, the Key West Aquarium is a small gem that should not be overlooked. Located adjacent to Mallory Square, this aquarium was one of the first and largest open air aquariums in the nation. Alligators, sharks and a hands on touch tank are all here. Make sure you go for their outdoor tank feeding time. They narrate as you watch HUGE fish battle it out for their lunch being tossed in the water. Great fun for adults and kids alike.
I hope our itinerary gives you some aid in planning your next family vacation to Key West. We can’t wait to return and when we do we will be utilizing the complimentary hospitality support services of OurKeyWest! We had the opportunity to meet Sarah and learned how they provide free concierge services with a locals perspective. We can’t wait to return to see what fun ways we can enjoy more of Key West!
SobeSavvy Tip: Make sure you stop at Bahia Honda State Park on your way back to the mainland. It is a natural wonder. Literally a real life snorkel aquarium in flat crystal clear water. Our daughter LOVED this place. We laid out a blanket and umbrella and frolicked. Perfect way to end our Florida Keys stay.
We left Key West with fun family memories of sunsets, cruises and food. As always, we will be back!
👀WATCH my YOUTUBE video recap for more highlights from our family visit to Key West!
2 Day Itinerary of Kid-Friendly Family Fun In Key West, Florida
Featuring Key West attractions that are fun for the whole family!