We’re going to share our top picks — tours we love, things for cruise ship stops, what we recommend for visiting with kids, touring on the cheap, hanging with your girlfriends, or managing a rainy day.
Grab your favorite fruity drink, and let’s get planning your Key West, Florida vacation!
Head out on the clear Gulf of Mexico waters to see Key West’s magnificent dolphins. This is a family-friendly outing that allows guests to observe dolphins and other Key West wildlife mingling in their natural habitat. Be sure to take advantage of the opportunity to dive in and snorkel Key West’s warm, gentle waters. The Seabreeze Dolphin & Snorkel Tour will take your vacation up one gigantic notch.
Take a guided bicycle tour from Key Lime Bike Tours and explore this amazing city. The leisurely ride focuses on the history, architecture, and culture of the southernmost city in the US. Get a little bit of exercise while hitting all the local hotspots. Plus, this tour includes a complimentary slice of Key Lime Pie at the end!
OUR TOP KEY WEST PICKS
These are our absolute favorite things to do whenever we're lucky enough to be visiting Key West.
CONCH TRAIN TOUR
The Conch Train is an absolute must-do! It's been around since 1958, and it's still one of Florida's most popular attractions.
The open-air Conch Train takes you around Key West, with hop on/off options allowing you to explore and learn simultaneously. We recommend making this your first adventure so that you get a lay of the land, and an understanding of the culture and history of the island.
Skip the Line: Key West Conch Train Tour
FURY WATER ADVENTURES
There are just so many options with Fury Water Adventures, from snorkeling to sunset rides. Our favorite experience was opting for BOTH on the Rum & Reggae Snorkel Sunset Combo.
We rode out to the reef, enjoying antics from the crew the entire way! Such a fun group. Then we snorkeled the reef -- even seeing a lemon shark! Great music was blaring and everyone was dancing and cutting up.
After rounding up all the snorkelers, the crew poured copious amounts of Rum Punch, plus beers (and sodas for the kiddos). About a half-hour from hitting shore, the boat slowed and we experienced a glorious sunset on the water!
Whether you are a couple with no kids (like most everyone on this excursion) or you have kiddos yourself (we were one of about 4 other families) this is SUCH a fun experience! Heck, this is the ONLY coral reef in the U.S., and the 3rd largest in the world. You must, must, must head out to experience it.
Need to knows: You can bring your own gear, but unless you're a professional, their gear will be better. Trust me. Bring towels and a sweatshirt, the wind gets cold when the sun goes down and you are wet. Bring snacks for the kiddos. You're onboard for 3 hours total...and snorkeling is hard work. Bring a cash tip for the crew (about $10 per person is customary). You will want to tip them - they are amazing and make this one of the best businesses to work with in Key West.
But Your Tickets Now: Rum and Reggae Afternoon Snorkel and Sunset
The Hemingway House was the residency of Ernest Hemingway when he lived in Key West, and is now a museum. Because of the stories about 6-toed cats...and The Old Man and The Sea being one of my favorite books of all time, well we HAD to visit!
With the kids, we opted to forego the guided tour and roam around ourselves. I wish the boys had the patience for the full tour, but it was a late afternoon and I was already pressing my luck. We still learned quite a bit by reading placards and eavesdropping on other tours.
The stories about the 6-toed cats are true! Descendants of Hemingway's original 6-toed feline roam the property (there is even a cemetery for those who have passed). Some are shy, but others will take all the affection you can offer.
Featured Tour: Hemingway's Life and Local Food Walking Tour
KEY LIME PIE
Having Key Lime Pie is a must when you are in the Florida Keys, and there are a lot of options available. I wish I could tell you that I had time to nosh my way through the city, ranking each option as I progressed...but in all honesty, we only visited Kermit's - as recommended by Facebook readers and friends.
There are a few locations -- including one in DeLand, which is where our 18-day Florida road trip began -- but we opted for the original in Key West. It did not disappoint! We had a slice of key lime pie, a key limonade, key lime taffy, and a frozen key lime drink!
Featured Tour: 3-Hour Guided Bicycle Tour with Key Lime Pie
THINGS TO DO IN KEY WEST WHEN IT RAINS
Florida is known for getting a lot of rain, but that doesn't mean there still isn't plenty to do! Here are our favorite places to go when the rain starts falling.
KEY WEST AQUARIUM
At Key West Aquarium, you'll find sharks, stingrays, an alligator exhibit, jellyfish, and a sea turtle conservation tour, too!
Plan your trip to Key West Aquarium at the right time of day so you can feed the sharks! They also have a touch tank, and multiple shows that go on throughout the day.
The aquarium is pretty small as aquariums go, but all the fun offerings make it a great place to visit -- whether it's raining outside or not.
Skip the Lines: Key West Aquarium Tickets
KEY WEST BUTTERFLY AND NATURE CONSERVATORY
When it's raining outside (and even when it's not) you'll find nothing but sunshine in the Butterfly Conservatory. Stroll through the conservatory where hundreds of butterflies and birds fly among tropical plants, waterfalls, trees, and you!
Don't miss the short film before you go in! My boys adored the bright gift shop with so many interesting items for nature-lovers.
TRUMAN'S LITTLE WHITE HOUSE
In the late 40s/early 50s when Harry Truman was president, The Little White House served as the White House for him during the winter months. The home then continued to be a place of relaxation for presidents and dignitaries after that. In fact, it's called a "living museum" because it continues to host functions for government officials today.
You can tour the Truman Annex area of the house every 20 minutes or so, getting a look into his private life and politics in America during his presidency.
Skip the Lines: Truman Little White House
FIRST LEGAL RUM DISTILLERY
When it rains in Key West, you drink! Key West's First Legal Rum Distillery runs free tours every 20 minutes from 12 p.m. to 5 p.m., and your kids and pets are welcome, too. If you miss the guided tour, you are welcome to tour on your own.
The real fun, though, comes at 4:30 Monday - Saturday. They offer a free Mojito class and tasting. These guys trained in Mojito-making in Cuba, and they want to teach you how to do it right!
THINGS TO DO IN KEY WEST KEY WEST WITH THE KIDS
Key West is not just a place for adults to have fun -- there's plenty to do for the littlest members of your party too!
SHIPWRECK TREASURE MUSEUM
Arrrrgh! No trip to Key West with kids is complete without a visit to the Shipwreck Museum, where kids can learn all about the Key West Pirates!
Take a guided tour, or just walk at your own pace through the museum to check out all of the artifacts. The museum has actors, films, and actual artifacts from a vessel that sank in the reef in 1856! You can also go into the basement where you are actually below Sea Level. Spooky!
Our favorite part about the museum was climbing to the top of the tower so we could look out over all of Key West. Buy Tickets Now!
Skip the Lines: Key West Shipwreck Treasure Museum Tickets
KEY WEST TROPICAL FOREST & BOTANICAL GARDEN
The Key West Tropical Garden is the only frost-free, natural conservation habitat, botanical garden in the continental United States.
After you watch the short video, pick up a garden guide that describes the eight self-guided information tours, two wetland habitats and two butterfly gardens! Kids are free with an adult ticket.
LAGERHEADS BEACH BAR
I won't lie - Lagerheads saved the day for us. If you travel with kids, you know that you can only cram so much into one day. Just as the boys reached a breaking point -- you know, they were weary and hangry -- we came across Lagerheads.
It's tucked in a backstreet, so there weren't many people there. Grab a lawn chair on the sandy beach and relax while the kids frolic in the water.
We ordered some snacks and a few drinks, and relaxed here for a good hour or so...with no hurry and no schedule...giving everyone time to re-energize. We didn't do this, but you can also rent hydro-bikes here -- which would be a super fun way to end a day.
Good food, a great atmosphere, live music, and fun activities for the whole family? No wonder it's Key West's favorite beach bar.
LUCY'S RETIRED SURFERS BAR
Lucy's has a few locations around the world, but don't let that stop you. It's still a spot the locals adore - and so did we!
Go in the evening and get a table outside where you can enjoy the Key West vibe and live music. The musician the night we were there was Ike Kanakanui, and he was amazingly talented! He even gave the boys a tambourine and maracas to play along with him!
I highly recommend you stop here - it was the best food and the best prices we experienced in Key West. Get the Tsunami Tuna Salad, for sure...and a Flamingo Punch! Yum!
FREE AND CHEAP THINGS TO DO IN KEY WEST
Want to know a secret? Some of the best things in Key West are free (or almost free)! Here are our favorites.
SOUTHERNMOST POINT OF THE US
When people think of what to do in Key West this always comes to mind. Is it exciting? No. But do you have to do it? Yes!
We planned to stop by on the way back to the hotel one day, but the line was so long! Like...around-the-block long. Why? Cruise ships! The best thing to do is go early in the morning, so that's what we did - the second time. We were in the area about 8:15ish -- you're close to White Street, so stop there and grab a Cuban coffee to go -- then drive over to the point.
Before 8:30 there is plenty of street parking available, and no lines. We had one person in front of us, and then almost immediately 2 people behind us. You don't want to be by yourself anyway - someone has to take the photo! Just swap cameras with the other people in line.
ECO DISCOVERY CENTER
The Key West Eco Discovery Center is a 6,400-foot environmental facility where visitors can experience the underwater eco system of the area - all without getting wet!
The Eco Discovery Center features interactive exhibits, films, a reef tank, and a mock-up of Aquarius -- the world's only underwater ocean laboratory.
It showcases the local underwater habitats and upland barriers, and gives you special insight into the nearby living, contiguous barrier coral reef. It's a great place to visit before the Fury reef tour we mention above! And it's free!
MALLORY SQUARE SUNSET CELEBRATION
Come down to Duvall Street and Mallory Square about an hour before the sunset (give or take ) to catch the street performers, watch the sunset, and celebrate with the locals and tourists at Sunset Celebration.
There are performers swallowing swords, walking on tight ropes, and doing all sorts of tricks - it's tradition. Once the sun starts going down, find a place along the wall to sit and take it in!
While you are there, be sure to walk over to the Memorial Sculpture Garden. It features 36 cast bronze busts of the men and women who have had the greatest impact on Key West.
FORT ZACHARY TAYLOR STATE PARK
Fort Zachary Taylor State Park is an old fort that you can walk around and explore. It's a cool experience to see and imagine how the soldiers used to live here. You can also climb the stairs to the top of West Martello Tower to get a great ocean view.
There is a big area at the back of the parking lot where you can tailgate or set up your own picnic looking out over the ocean. This is also an amazing place to catch the sunset. As the sun sets, you get to see all of the sunset cruise sailboats trying to give their passengers the best view.
Smathers Beach is located on the Atlantic side and is off of A1A. Key West isn't generally known for its beaches, but this is a nice one - and the largest, and a half-mile. If you only do one public beach while here, make it this one.
You can rent chairs and umbrellas and water toys here. Plus there is a nice bike trail/sidewalk right off the beach. You could easily ride your bike here, hang out at the beach, then get back on your bike to ride to a restaurant or to head into Key West.
Higgs Beach Park is truly unique on many fronts as it hosts the only shore-accessible underwater marine park in the United States and is also the terminus of the Florida Overseas Heritage Trail, one of only 31 nationally designated All American Highways in the United States.
HISTORIC SEAPORT AT KEY WEST BIGHT
The Seaport is just a great place to walk around, do some shopping, and grab a bite.
There are catamaran and tall ship sailing excursions that leave from here, so the boat-watching is beautiful. There is also a neat museum highlighting the island's history!
COMING OFF A CRUISE SHIP
Take advantage of the time you have away from the ship with these awesome stops.
Find a local coffee stand and purchase a Cuban coffee. You're only 90 miles from Cuba -- now's the time to do it!! I guarantee once you have one, you will want to have another one. They really are addicting - and oh-so-good!
You can sign up for a pub crawl excursion with your cruise ship -- but why not go on your own?
Start at Schooner Wharf Bar for their morning happy hour. It's where you will get a taste of true old Key West.
Captain Tony's is another stop you need to make. It was established in 1851 as an icehouse, and then Key West's first morgue! It also includes the "hanging tree," which was used to kill 16 pirates, plus a woman who killed her family. After several other transformations, it finally became a bar - said to have been frequented religiously by men who need no first name introductions - Hemingway, Capote, Silverstein, Williams and Buffet.
Green Parrot was voted the best bar in Key West. You'll want to check out any events going on - like a Poetry Slam or a Divorce Celebration. Leave your pretense at the door.
Finally, muster up to the bar at Hog's Breath Saloon. You'll love the live music and a Hogarita!
KEY WEST SCAVENGER HUNT
How did Old City Hall become one of the city's oldest treasures? Which world-famous writer hung out on Duval Street? Find out on a scavenger hunt around Key West -- it doesn't require a tour guide, and you can do it at your own pace!
We adore Let's Roam for their scavenger hunts, and their Key West hunt is no exception. It's by far the easiest way to learn the MAX about this awesome place while mastering your own schedule.
Visit the Audubon House, and its glorious tropical gardens, ride the Conch Train, or climb the 88 steps at the Key West Lighthouse Museum. Word on the street is that parasailing and the Conch Train Ride are the most popular options for cruisers.
RECOMMENDED FOR TOUR-LOVERS
When we travel, our FAVORITE way to explore a new city is with a tour. We couldn't take all the tours on our 3-day visit to Key West, but here are some from a partner we know and trust.
These are great ways to explore the island (and save some money)!
Key West Cocktail Crawl : Sip, stroll, and party your way through Old Key West as you sample some of the best drinks in town.
Guided Old Town Bike Tour: Take a leisurely bike ride on this guided tour that will hit all the local hot spots, provide great photo opportunities, and ends with a slice of Key Lime Pie.
Tropical Fruit Bike Tour: This is a tropical bike ride tour down quiet streets and hidden alleyways. You'll also have a chance to taste fruits right from the trees -- like coconut, mangoes, and key limes.
Southern Food Tasting & Cultural Walking Tour: Your guide will take you to six of the best local eateries, while explaining the history of the city along the way.
Seafood Lover's Tasting & Cultural Walking Tour: Explore the beautiful city, making stops at five eateries along the way. You'll enjoy fish tacos, a Cuban sandwich, and other local delicacies.
Private Harbor Day Sail Aboard the High Tide: This 90-minute, private sightseeing cruise is a great way to experience the beauty of Key West with your family and friends.
Half Day Deer & Wildlife Tour: This 3.5 hour tour takes you to explore the world-famous Bahia Honda State Park & walk on a historic railroad bridge, photograph endangered Key Deer on Big Pine Key, and search for alligators in the Blue Hole.
DAY TRIPS AND FULL-DAY FUN
DRY TORTUGAS NATIONAL PARK
When putting your list together of things to do in Key West, this should be at the top. It is expensive and will take all day, but my friends at Crazy Family Adventure say it's totally worth it.
The Dry Tortugas are located 70 miles off of Key West and is a true paradise. You have to take a 2-hour boat ride to get there - and it is choppy - so bring your Dramamine. But once you pull up to the island -- it's all worth it!
There is an old fort on the island that you can explore (Fort Jefferson), beautiful beaches, snorkeling, and a ton of conch shells to find (you can't keep them - but they are still fun to find).
You can either go for a day trip or you can plan on camping there for a few nights. Plan to catch the YANKEE FREEDOM III FERRY from Key West Historic Seaport. Head out on the open deck, or take a seat in the air-conditioned cabin.
Planning a National Parks road trip? The America the Beautiful Pass covers entrance for an entire year to all the US National Parks and over 2,000 federal recreation fee sites. Fees are covered for everyone in the car for per-vehicle sites and for up to 4 adults for per-person sites. This is a no-brainer, friends. While fees vary, you'll likely break-even after two visits. Plus, REI will donate 10% of pass sale proceeds to the NPS Foundation.
FURY ULTIMATE ADVENTURE
This Fury Ultimate Adventure trip should NOT be missed! It is a 6-hour catamaran boat ride that will take you snorkeling, jet skiing, parasailing, and to an inflatable playground in the middle of the ocean. It is all you can drink (soda and water - then beer and wine after you are done jet skiing,) and they provide breakfast, lunch and snacks. You can get a ton of adventures marked off your bucket list in one day!
You may think that 6 hours sounds like a long time, but when our trip was done, we weren't ready to get off and could've stayed on longer! The crew does an amazing job making you feel comfortable, and with all of the activities -- you are never bored.
You do have to sail to the snorkeling destination, and then go for a little ways to get Fury's "island," where they have the jet skis, parasailing, and water playground. So be prepared for that.
Also bring tip money for the parasailing crew, and know that the food they provide is OK but nothing to special. So if you have dietary restrictions, you may want to bring your own food. As a side note -- kids under 6 get on the boat for FREE, but you have to be at least 6 to go parasailing.
If there is one trip I would recommend doing with your family to get out on the water when you are in Key West -- the Fury Ultimate Adventure is it. Pick a day, book it, and enjoy!
OUR ACCOMMODATION PARTNERS
While hotels are abundant here, we cannot recommend Havana Cabana more highly! They are spectacular! Great rooms, great location - and Key West's largest pool!!
MORE INFORMATION FOR YOUR TRIP TO KEY WEST
- WHERE TO EAT: Where to Eat in Key West [including local favorites]
- HOTEL LAUREATE: Review of Hotel Laureate Key West: Family Suites in the Florida Keys
- SUNSET CRUISES: THE BEST FLORIDA KEYS SUNSET CRUISES
- MORE THINGS TO DO: 4 Can’t Be Missed Fascinating Places To Visit In Key West
- SEA ANIMALS: 3 Places To See Enchanting Sea Animals In Key West, Florida
- FLORIDA BEACHES: 25+ Best Family Vacation Destinations
- BEST OF FLORIDA: 20+ Things To Do In Florida On The Ultimate Sunshine State Road Trip
- NPS ROAD TRIP IDEAS: 6 EPIC NATIONAL PARK ROAD TRIP IDEAS [MAPS INCLUDED]
- FLORIDA ROAD TRIP: 31 AMAZING PLACES YOU WON’T WANT TO MISS
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