Key West Family Vacation: 25+ Popular Things to Do

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Looking for a fun-filled, adventurous family vacation in Florida that’s a little different than the typical theme park experience? Then, Key West is the perfect option.

The island city at the southernmost tip of Florida is known as the fishing capital of the world and is home to world-class diving and snorkeling in lively coral reefs. But there’s more — a unique culinary scene, plenty of pirates’ history, and a colorful and playful vibe.

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Key West, Florida, offers plenty of activities to entertain the entire family. Take the kids to the beach to search for shells, partake in exhilarating water sports, or book a sunset cruise. If you want to learn the city’s layout and a bit of history, hop on the Old Town Trolley Tour, visit the Key West Butterfly and Nature Conservatory, or go on a pirate ship adventure.

There’s also the Mel Fisher Maritime Heritage Museum and the Aquarium Encounters to explore. And don’t miss the famous Ernest Hemingway Home and Museum. For the adults, there are plenty of bars and restaurants to enjoy, as well as shopping, sightseeing, and people-watching (one of my favorite activities).

Key West has something for everyone. Here’s our list of over 25 best things to do in Key West on a family vacation.

Key West Family Vacation: Culinary Edition.

1. Grab a Cuban Cafe Con Leche or Cafe Americano at Cuban Coffee Queen to start the day.

There’s no better way to begin a day exploring Key West than with a strong Cuban coffee from Cuban Coffee Queen. My favorite is the cafe americano, black and unsweetened, but you can also get traditional Cuban Coffee, Cafe con Leche, or Cortadito.

These coffees are the perfect pick-me-up before exploring all the things Key West has to offer, whether you’re touring on a Conch Train or strolling through the historic Old Town on foot. Grab a cup and prepare for a fun-filled day in Key West. And who knows, you might even find yourself coming back for an afternoon caffeine fix to energize you for the evening festivities.

2. Indulge in a Cheeseburger in Paradise at Jimmy Buffet’s Margaritaville Restaurant at 500 Duval Street.

Jimmy Buffet’s Margaritaville Restaurant is the perfect destination for anyone who wants to indulge in a delicious meal, and I mean INDULGE. This restaurant has some of the most tempting food items, especially burgers — double stacked, cheddar cheese and bacon, garlic aioli with onion rings, or the OG Cheeseburger in Paradise.

In addition, they have booze in the blender, boat drinks, and of course, the perfect margarita.

It’s 5 o’clock somewhere, y’all.

3. Try the chocolate-covered Key Lime Pie on a stick at Kermit’s.

Lunch at Kermit’s is tasty. Try the fresh BLT, the perfectly crispy wings with Kermit sauce, or the fish sandwich. I hear the hot dog is perfection, too, if you are into that kind of treat. But the dessert is as decadent as it gets, and the real star of the show, frozen chocolate-covered Key Lime Pie on a stick — delightfully refreshing on a hot day.

4. Host a Family Key Lime Pie Tasting Contest.

Key lime pie is a Key West specialty, a delicious dessert made with Key lime juice, egg yolks, and sweetened condensed milk. My vote is Kermit’s, although the Key Lime Pie at Mangoes is simply decadent.

5. Taste fresh caught local seafood.

Key West is a foodie’s paradise, and there’s no better way to experience the local cuisine than by indulging in some fresh seafood. Recently caught wahoo or Mahi are both delicious choices, and luckily there are plenty of fantastic restaurants to choose from. Louis Backyard, Little Pearl, Seven Fish, and Martin’s are all popular options for seafood lovers.

But, if you’re looking for something a little different, check out First Flight Brewery. It’s the southernmost brewery in the US and the exact spot where Pan Am began operations in 1920.

6. Explore the enchanting world of rum tasting.

Key West is known for its rum distilleries and tasting rooms. Papa’s Pilar Rum Distillery, nestled in a historic tobacco warehouse at Greene and Simonton Street in Key West, offers rum lovers an immersive experience featuring samples of their delicious rums. From light blonde to smoky dark — each sip will be as smooth as silk with a delightful sweetness that’ll remind you of a birthday cake pop. This unique scene allows you to learn about Key West’s rum-making history and taste some of the island’s best rum.

7. Go on a Foodie Tour.

Key West is a mecca for foodies and is home to various bars and restaurants offering many cuisines and atmospheres. And it’s also home to many watering holes where you can enjoy drinks with friends or take in the colorful and vibrant atmosphere.

Learn Something New On Your Key West Family Vacation.

8. Combine family fun with learning something new by touring the Key West Aquarium.

Key West is home to many unique creatures above and below the water. Combine your love of learning with your sense of adventure by touring the Key West Aquarium. Discover the fascinating world of marine life and get up close and personal with some of the most beautiful fish in the sea. The aquarium also offers fun educational programs for all ages, making it a great learning destination for the whole family.

9. Check out the Key West Butterfly and Nature Conservatory.

Suppose you’re looking to continue your education on all things winged and wonderful. If so, then a visit to the Key West Butterfly and Nature Conservatory, home to over fifty species of butterflies from all over the world, is a must. Stroll among hundreds of butterflies and birds in a dome-shaped rainforest setting. Observe as they flit and dance through the air. Enjoy the splash of color they provide as they land on colorful flowers. And don’t miss the gift shop full of unique souvenirs and gift ideas for the lepidopterist on your Christmas list (that’s what they call a lover of butterflies).

10. What better way to spend a rainy day than with pirate-themed museums?

If your kiddos are into shipwrecks and pirate treasures, stop by the Mel Fisher Maritime Museum and the Key West Shipwreck Treasure Museum. The Mel Fisher Maritime Museum has exhibits on historic ships, is a great place to learn about the history of pirates and their stolen loot, and displays plenty of kitschy trinkets.

Next, uncover the secrets beneath Florida’s waters at The Key West Shipwreck Treasure Museum.
Take a journey through time with fascinating exhibits that explore Florida’s rich maritime history. From artifacts of sunken wrecks to tales of looters and salvagers, you won’t want to miss this immersive treasure trove!

11. Take a ride on the Old Town Trolley.

Known for its orange and green color scheme and friendly and informative conductors, the Old Town Trolley is a hop-on hop-off bus tour with multiple stops, including The Hemingway House, Mallory Square, Key West Aquarium, and The Audobon House. The Old Town Trolley winds through the city street while you learn the island’s history and layout. Purchase your ticket for the day and see how many sights you can fit in.

Tours! Tours! And More Tours!

12. Tour Key West at night and discover why Key West is known as one of the top ten most haunted cities in America.

Learn about the haunted mansion of Dr. Porter, Florida’s first Public Health Officer, known for his research and treatment of people with yellow fever. And you’ll inevitably hear the story of Robert the Doll, a creepy character who has been haunting Key Westerners for over a century. You can even visit Robert the Doll at the Fort East Martello Museum, but be sure to ask for permission before you take a picture. He’s known for tossing out hexes and curses for those who don’t ask first.

13. Go dolphin watching with the Key West Dolphin Watch and Snorkel Eco-Tour.

Get up close and personal with the bottlenose dolphins. They will delight and amaze you as they playfully romp in their natural habitat, the crystal blue waters of the Gulf of Mexico. You will then get a bonus snorkel trek to the shallow backcountry waters of the Florida Keys — perfect for an up-close look at life in the sea.

14. Book a historic Jimmy Buffet tour; yes, it’s a thing.

Grab your blown-out flip-flops and your Margaritaville state of mind, and book a Jimmy Buffett Tour. Jimmy spent many years living in Key West, and he drew inspiration for many of his hit songs from his time spent there.

15. Visit the Ernest Hemingway Home and Museum, a must-see tour for families interested in Key West’s literary history.

The museum is home to a collection of Hemingway’s personal belongings and artifacts — kids will love seeing the writer’s life up close. The five-toed Hemingway cats are the stars of this home, and the architecture and grounds will take your breath away with their beauty.

16. A Visit to Key West would not be complete without the Conch Train Tour.

The Conch Train Tour is a must-see for any visitor to America’s southernmost city. This unique tour guides you through Key West’s most scenic areas and provides an immersive experience with history, landmarks & culture that you cannot find anywhere else.

17. Book a Key West ghost tour or, even better, a ghost hunt.

Explore some of Key West’s notorious haunted locations with an experienced tour guide. An entertaining mix of thrilling ghost stories and historical knowledge will make this experience fun for the whole family.

Try These Activities to Stay Active and Fit While on Your Family Vacation in Key West.

18. Go kayaking in the mangroves.

Nestled in the mangroves of Key West is a hidden world awaiting exploration full of tropical fish, sea birds, jellyfish, crabs, and sponges, maybe even sharks and manatees. Take a kayak tour through this serene landscape and discover all that nature offers. Glide through the waters, surrounded by lush greenery and wildlife — this is an experience you won’t soon forget.

19. Plan your own art walking tour.

20. Spend the day on Smather’s Beach, where you can enjoy a variety of water sports.

You may prefer to sunbathe and swim in the beautiful waters or kayak through exotic landscapes with breathtaking views. But, if the weather is right, head out on a Hobe Cat or parasailing.

21. Spend a few hours strolling Duval Street.

Duval Street is the main street in Key West, full of artsy boutiques, restaurants, galleries, bars, and an epic spot for “people watching” (they are rather interesting down there). Just know that as the evening progresses, the vibe becomes more adult. It’s vibrant, colorful, and lots of fun. But, it may not be appropriate for the kiddos.

22. Play Pickleball.

Test your skills on the picturesque pickleball courts at Higgs Beach. Whether new to the game or an old pro, each day offers something unique for players of all levels.

23. Try out some watersports.

If you’re looking for an adrenaline-filled experience, there’s no better way to get started than parasailing, jet skiing, or scuba diving. Although first-timers should try snorkeling, it’ll give them something refreshing without being too intense. Other activities on the water in Key West include banana boat rides, sunset cruises, sailing, fishing, or swimming with the dolphins.

24. Experience the Lighthouse and Keeper’s Quarters on Whitehead Street.

Climb the 88 steps of the Lighthouse and Keeper’s Quarters on Whitehead Street to experience one of Key West’s most stunning vistas. Built in 1826, with a few upgrades and a complete restoration in 1987, this unique attraction will give you views like none other — especially around sunset.

25. Rent a bicycle and explore the island.

Renting a bike is one of the best ways to experience this beautiful island — plus, it is a great way to cover a lot of ground without worrying about parking or traffic and get some exercise, too. Take in the breathtaking scenery and explore hidden gems. Also, wear your helmet to avoid a situation that may dampen your adventure. Immerse yourself in local culture as you peddle around; who knows what secrets are waiting for YOU?

26. Enjoy a little piece of paradise and take a dip in the ocean at Higgs Beach.

One of the best ways to cool off during the humid summer months in Key West is to take a dip in the refreshing waters of the Gulf of Mexico at Higgs Beach. The gentle waves and bright turquoise waters are a perfect way to relax and forget your troubles.

And Now For the Epic Photographic Moments.

27. The Quintessential Key West Picture.

Snap a quintessential Key West Picture at the Southernmost Point of Florida, although not really the southernmost point, but a must-stop at this iconic bright red and yellow buoy.

28. And US Mile Marker 0.

You can also find US Mile Marker 0, where it all begins. And, yes, another quintessential Key West Picture.

29. Enjoy the sunset on Mallory Square while sipping your favorite adult beverage and taking in local artists and street performers.

Experience the unparalleled delight of Key West’s beloved Sunset Celebration. Every evening, locals and visitors join at Mallory Square to revel as a vibrant sunset paints the sky. It’s not just an eye-catching sight but also provides plenty of opportunities for mingling with others, sipping your favorite adult beverage, and discovering the talents of local artists and street performers. Bring your family along for an incredible memory at this unique gathering spot.

30. Book a sunset cruise.

Watching the sunset is one of the most popular things to do in Key West. And for a good reason — the sunset in Key West is extraordinary. There are lots of ways to experience the sunset in Key West. Head out on an adult-themed Booze Cruise with a band and the alcohol flowing, book a peaceful sailboat with unlimited champagne or take a private tour with just you and your family. No matter how you experience it, watching the sunset should be at the top of your list while visiting Key West.

Last But Not Least, a Quick Day Trip

31. Take a day trip to Dry Tortugas National Park.

Dry Tortugas National Park is a hidden gem in the Florida Keys that awaits discovery. You will be blown away by miles of crystal clear waters, abundant marine life, and stunning, untouched beaches.

Key West is the ideal spot for an unforgettable family getaway and the perfect destination for families looking for a fun and unique vacation. Take a sip of island culture with rum tastings, or set sail on a high-seas pirate adventure with a glorious sunset finale. Enjoy exhilarating water sports, discover hidden gems and local lore via haunted tours, and sunbathe at its beautiful beaches, all while indulging in the delicious culinary delights that Key West has to offer.

This guide provides over 25 best things to do on a family vacation in Key West. So, what are you waiting for? Key West has something for everyone, so start planning your Key West family vacation today.