Key West Vacation Ideas Guide: 9 Top Things To Do For Families

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Don’t miss this Key West Vacation Ideas Guide for families that I wish I’d had before our Florida beaches tour part #5. Especially since I totally prejudged this city and I know a lot of other vacation-planning women probably do too. I mean, Key West is nothing more than a bunch of bars and party animals, right?! Key West is so much more than that – families just need to know where to go and what to do! Check out my list of 9 favorite things to do in Key West for lots of family fun.

view of Havana Cabana Lagoon pool as top 9 Key West Vacation Ideas for Families
Havana Cabana Lagoon Swimming Pool – Largest pool in Key West

Key West vacation ideas

How about all the details of the best things to do in Key West with kids with practical and memorable Key West vacation ideas?! I’m thrilled to share after my family traveled on a week-long media trip to the Florida Keys for Okefenokee Living Magazine. My thanks go to The Florida Keys & Key West Visitors Bureau and the venues below for hosting us. As always, my opinions are my own.

I don’t remember much about living in Key West, Florida as a military kid except the beautiful homes and the incredible weather. Oh yeah, and the lizards. Lots of lizards. Now that I’m all grown up with a family of my own, I wasn’t so sure if Key West would be a good choice for a family vacation stay. To my surprise, Key West turned out to be even more beautiful than I remember and we had an incredible time sightseeing and eating our way through this jam-packed, city.

Here’s what you must do while visiting with your people:

view of smathers beach - one of the Key West Vacation Ideas

1. Stay at Havana Cabana Resort

As the name hints, Havana Cabana’s vibe plays on nostalgic influences from the culture of Cuba, 1950s era.  I’m a huge fan of retro, so I was thrilled to be greeted by a mid-century cruiser in the parking lot and to step back in time when we entered the gorgeous lobby of vintage furniture and oversized images, and two staircases leading to the second floor.

The Cabana part of the title couldn’t be more perfect because this resort is truly a lush escape from reality. The spectacular lagoon pool gives feelings of a tropical island retreat as sweet sounds of Flamenco guitar music wafts in the background.  We swam in that amazing pool morning, noon and night!  With the concierge assistance, free shuttle service around town (one of the best secrets!), and a couple dining choices, Havana Cabana Resort could be a fulfillment of a dream for all inclusive Key West vacations for your family too.

9 Top Key West Vacation Ideas for Families - Havana Cabana Hotel Room
Our beautiful room at Havana Cabana Resort

2. Take an Old Town Trolley Tour

To gain the ‘big picture’ of a new destination, there’s nothing better than a tour of the city – especially with so many Key West vacation ideas to see and do.  An Old Town Trolley Tour, a sightseeing tour designed to let you hop on and off and explore at your own pace all day long, is the perfect way to see all the Key West attractions jam-packed into this lively city.

With frequent free stops and pickups, this comprehensive, 90-minute tour on an enclosed bus was full of fun facts and entertainment by our driver with an elevated view of the 100 or so Key West points of interest. This may be one of your favorite Key West vacations ideas so that you don’t have to walk the entire city with the fam in tow.

view of Old Town Trolley Tours & best Key West Vacation ideas for families
Key West Trolley Tour

3. Eat at Turtle Kraals 

When it comes to the best places to eat in Key West Florida, there is one restaurant that we enjoyed a lot.  Turtle Kraals Bar & Restaurant has been a staple since 1980 and thankfully was right in the midst of the downtown action.  This energetic hot spot blends Key West’s colorful mix of food and culture and the food is influenced by generations of settlers from the nearby Caribbean islands.

Turtle Kraas’ lower level was alive with excitement and noise below, perfect for some, but we entered in the front by the marina and headed straight upstairs for a quiet table with an incredible waterfront view where we watched an infamous Key West sunset take place.  This upper deck is covered so it’s enjoyable rain or shine.  We received impeccable service from our waitress and learned a lot about the history of Key West and this historic restaurant from her.

view of Table food at Turtle Kraas & best Key West vacation ideas for families
Our dinner at Turtle Kraals Restaurant

4. Soak up best Key West beaches

I’d heard that Key West beaches were scarce and surrounded by rock.  Someone told even my husband that it was hard to get in the ocean.  My normal, stubborn side took over and I said, “Oh, there has to be a beach.  And this is a Florida beaches trip anyway.  We’ll figure it out.”  In my mind, one of the top Key West vacation ideas would be to find the beach!

As it turns out, we found the beach but I never got around to researching ahead of the trip so we wasted a little time, but there are definitely rumors that simply aren’t true.  There were several places on in Key West to visit beaches, but here’s my guide to three of the best to save you time!

Higgs Beach – The county-owned Clarence S. Higgs Memorial Beach Park has a pier and monuments from the site of a 1800s African slave cemetery, as well as “Salute! On the Beach” beachside café, and a beach concessionaire that offers water sport and beach accessories for rent including beach chairs, umbrellas, kayaks, and paddle-boards. This beach also has a tennis court, beach volleyball and a place for pickleball.  There is also a nice playground and a dog park with separate areas for small and large dogs.

Entry to the water from the shoreline here was full of shells, so water shoes are definitely recommended, but the area of clear, shallow water was fantastic. This beach was best for snorkeling and that made my crew very happy!

Smathers Beach – The sand and water were breathtaking at this location. The shoreline is only two miles long but was a popular spot for sunbathers and those looking to buy food items, drinks, chairs, and even rafts from vendors located there.  Parking is free in several spots and there are public restrooms and several vendors for renting water sports gear and equipment.

view of Smathers Beach - Key West vacation ideas for families
Smathers Beach, Ulla Moilanen, cc

Fort Zachary State Park Beach – This park and Key West beach are hidden gems. There aren’t big signs about this park and since it’s behind the Truman Annex, most people don’t even know it exists.  The admission is cheap and just beyond the beach sand, the Atlantic Ocean meets the Gulf of Mexico in a marvelous sight to behold.

view of Fort Zachary Taylor Beach - Key West vacation ideas for families
Fort Zachary Taylor State Park Beach, Matt Kieffer, cc

5. Take Southernmost point & mile marker 0 selfies

You can’t travel all the way to Key West, Florida and not do two of the most popular Key West vacation ideas – take iconic photos with the southernmost point and mile marker 0. Be sure though, friend, to get your pictures in the wee early hours or in the dark to avoid standing in line with other tourists doing the same.

view of Key West Southernmost Point Buoy - Key West vacation ideas for families
Southernmost point buoy in Key West, Florida, istolethetv, cc

6. Jetski around Key West adventure

One of the most memorable Key West vacation ideas on this entire trip was a Jet Ski tour that circumnavigated the entire island of Key West.  If your family wants to discover the natural beauty of Key West while also adding adventure, then you’ve found the perfect solution.  Barefoot Billy’s Yamaha Waverunners allow you to cruise around the island on a 2-hour guided jetski tour.

Barefoot Billy’s offered a free pickup and return to our resort.  Once at the adventure location, it begins with time for safety instructions from expert guides.  Next, it was adventure time on a 27-mile course lead by an expert guide, completely circumnavigating Key West.  Can you say, “Adrenaline thrill and beauty of a lifetime?!”

view of Key West Jetski Tour - Key West vacation ideas for families
Barefoot Billy’s Jetski Tour Adventure
view of Key West Jet Ski Tour - Key West vacation ideas for families
Princess on jet ski tour AROUND Key West!

7. Eat Key Lime Pie at Kermit’s

Kermit’s key lime pie is so famous that a St. Augustine, Florida local was talking about it while we were on a St. Augustine day trip recently.  You can’t travel to Key West and not try the key lime pie.  Even if you think you don’t like it, try some anyway!

We were greeted at the door of this adorable little shop and cafe’ with Key Lime pie samples. You can buy a little bit of key lime “anything” inside.  The pie was wonderful, by the way and the store had many key lime lover souvenirs!

view of Kermit's Key Lime Pie - Key West vacation ideas for families
There’s Kermit! We loved being able to meet him in person. Yes, this is him, not a statue 🙂

8. Shop & love history on Duval Street

Although “the Duval Crawl” refers to the multitude of bars of Duval, shopping in Key West is fun during daylight hours on Duval Street.  It’s fun to jump in and out of all types of stores, mainly trying to find the best souvenirs and mementos to take home from this memorable family vacation destination.

There were so many beautiful, historic buildings in this area and another great reason to ride the trolley tour first so you’ll know the story behind them all.  Just off Duval, you’ll find a life-sized replica of Marilyn Monroe’s famous pose from her film, The Seven-Year Itch, just outside the non-profit, retro-style, Tropic Cinema.

view of Duval Street Key West vacation ideas
view of Duval Street Key West shopping
view of Key West Marilyn Monroe statue near Duval Street - Key West vacation ideas
A life-size statue of Marilyn Monroe outside the retro theater called the Tropic Cinema

9. Be entertained at Mallory Square

No Key West vacation is complete without a trip down to Mallory Square for the unique entertainment. Definitely go right at sunset to see a variety of performers, people, and chickens wandering around.  Yes, chickens.  They are protected by the city too!

view of Mallory Square performer in Key West vacation ideas
Entertainer at Mallory Square, Key West

Expectation vs. Reality: Need to know before you go

Here’s the part where I talk about hits, misses and the surprises of the Key West vacation ideas that we experienced.

A. Festivals – Don’t go taking your kiddos on the last Saturday in October.  That’s when Fantasy Fest happens and trust me, it’s not for kids.

B. Chickens & lizards – I had no idea about the Key West chickens that roam the city and are protected by law.  There aren’t a ton of them, but sometimes we saw large iguanas as well, both minding their business.

C. Key West beaches – There aren’t waves and there are few natural beaches.  The sea bottom can be sharp on the feet when going in the water so water shoes at all times are advised. The clear shallow water that stretches out for quite a bit at these beaches and the lack of waves were actually great for snorkeling and would be great for young people.

D. Mallory Street –  To be honest, we weren’t sure what to expect from Mallory Street.  Surprisingly, it was really clean and the vibe was very chill.  I enjoyed it a lot.  The hilarious performer that was there during our sunset arrival was a hoot with his tricks and jokes. He made a couple innuendo that only adults would understand and I never heard him say anything inappropriate for kids. My advice would be to ride a free shuttle that your resort offers, like ours, or you’ll end up parking in crazy, tight, and expensive little spots.

Believe it or not, there are several more Key West vacation ideas like Ernest Hemingway’s home, the Florida Keys Eco-Discovery Center, and the Shipwreck Museum, but there’s only so much one family can see and do.  I hope this travel guide is helpful in vacation planning your own Key West family vacation soon.


What is the best time to go to Key West?

According to one of the tour guides, a great time to visit is in March and April, which is right after the busy winter season and before the spring break and summer visitors. Not only will all the winter bird crowds be gone but the hotel prices will drop and the weather is normally in the blissful 70s.

What celebrities have been in Key West?

President Harry S. Truman frequented his winter White House during the 1940s, and Ernest Hemingway, Robert Frost, and Tennessee Williams have all called Key West home as well.

What are the free things to do in Key West (or super cheap)?

  • Key West beaches
  • Duval Street window shopping
  • Be entertained at Mallory Square
  • Selfies with southernmost point & mile marker 0
  • Photograph the famous sunset
  • Bike ride the city (it’s only four miles by two miles
  • Visit art galleries
  • Try all the key lime pie

I hope these Key West vacation ideas are super helpful to take your family to a unique vacation experience that I think everyone should experience at least once!

Which of the Key West vacation ideas are you most excited to experience? Do you have Key West tips to add?

More info for Key West vacation ideas mentioned

Havana Cabana Resort: 3420 N. Roosevelt Blvd., Key West, FL

Old Town Trolley Tours: 1 Whitehead St, Key West, FL

Turtle Kraals Bar & Restaurant : 231 Margaret St., Key West FL

Higgs Beach: 1000 Atlantic Blvd, Key West, FL

Smathers Beach: 2601 S Roosevelt Blvd, Key West, FL

Fort Zachary Taylor State Park: 601 Howard England Way, Key West, FL

Southernmost point buoy: Whitehead St & South Street, Key West, FL

Mile Marker 0: 501 Whitehead St, Key West, FL

Barefoot Billy’s: 700 Waddell Ave, Key West, FL

Kermit’s Key Lime Shoppe: 200 Elizabeth Street, Key West, FL

Mallory Square: 400 Wall St, Key West, FL

For more Islamorada Florida Keys information, visit The Florida Keys & Key West



Published on HuffPost, Okefenokee Living Magazine, and more, Shan is a Family Travel Journalist with a passion for helping women lose the overwhelm of planning family-friendly trips in the south. She shares travel reviews & insider secrets that Women REALLY want to know about Georgia, Florida, & the Carolinas vacations.

☕️ It’s THE REAL DEAL around here ☕️



  1. Sabrina
    August 24, 2018 / 9:48 am

    I’ve always wanted to go to the Keys! The Christmas before J was born, we had decided our Christmas gift to the family would be a trip to the keys. However, when J made his appearance in October that year, we just couldn’t see driving that far with a 2 month old. And I haven’t been brave enough since. I’m tucking this away for later! 🙂

  2. Megan
    August 28, 2018 / 4:02 pm

    I adore Key West, it’s such an eclectic unique town. Definitely not like any place else I’ve been in the United States. It was totally not what I expected, but fun none the less!

  3. jenna | the urben life
    August 30, 2018 / 12:28 pm

    I love Key West and need to plan a trip back out there! My family took a trip there for spring break once and it was a blast. We parasailed, took a sunset cruise, went snuba diving, and ate awesome food! I loved the roaming chickens and pink taxis 🙂

  4. Erin Haigerud
    August 30, 2018 / 3:33 pm

    Love these ideas!! I’ll have to save this!

  5. Gina
    August 30, 2018 / 9:38 pm

    I want to go and do EVERYTHING! It looks like a fun place to go. I am all about good food and shopping! 🙂

  6. Andrea
    August 30, 2018 / 10:24 pm

    Taking my picture at the southernmost point is on my bucket list. I’m glad to know that I should go early to avoid the lines. Thanks!

  7. Jasmine Hewitt
    August 31, 2018 / 8:18 am

    looks so pretty there, and like there’s a lot of fun for a family to have!

  8. karen
    August 31, 2018 / 9:20 am

    LOVE IT! I have had this urge to travel lately and the keys sounds like a great place for me to check out.

  9. Cassie
    August 31, 2018 / 12:04 pm

    Looks like a fun place to be! We’ve never been to key-west before, but have hear a lot of great things about the food, atmosphere, and of course, the weather!

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