The Unknown Ahead

No passport needed, because we’re going to the “southern most point” of the United States – Key West! Yes, technically Hawaii is the most southern state in the USA, but Key West tends to claim the honor anyway. We’ve been down to Key West three times, and it’s always a blast. There’s a ton to see and do in the area for kids and grown ups alike.

Key West has a great vibe. It’s both a place for families to enjoy time in the sun, and it also has a vibrant nightlife with plenty of bars and live music. We went to Key West three years in a row over the Thanksgiving holiday in November. We were lucky enough to have an au pair at the time, so we brought her along. This allowed us to hang out with the kids, but also escape in the evenings to enjoy some adult fun. If your budget allows you to bring a sitter (or older niece?), it’s worth it.

We’ve gotten to Key West in two different ways. The first is to fly to Miami and rent a car to drive down to the Keys. It’s a gorgeous drive and gives you the freedom to stop in the various Keys along the way. But be warned, it’s a long drive. The Keys look really close on a map, but this is about a 4 hour drive. However, if you wanted to stay a few nights here and a few nights there, it’s an easy one-road trip. You can also fly right into Key West, but typically those flights are a little more expensive. There’s no wrong answer!

Where to Stay?

Weirdly, there aren’t a ton of beaches on Key West. If you’re yearning for some beach time, I’d recommend Casa Marina or The Reach. These are sister properties, so you can use both resorts during your stay. They’re just a short walk away from each other, and it’s really nice to have double the options. Both properties have a great beach with access to gentle ocean waves that’s great for kids of all ages. These are both private beaches, so you won’t have to fight off crowds either. I think Casa Marina has the better pool, but The Reach isn’t shabby. Casa Marina just had a full renovation too (2023), it’s like brand new. They’re both Hilton brands, so if you have points, get ready to cash in!

The hotels are also a great resource for booking day trips and experiences. You can see the list of options here. Want a massage? Sunrise yoga? In the mood to rent a kayak, bike or jet ski? Yearning for a dolphin encounter or snorkel trip? These hotels offer it all and more! There’s always something fun happening on property too. When we visited, they were hosting an international sand castle competition. It was amazing to see what could be made out of sand! There was a little treasure dig for the kids too where they could find coins hidden in the sand. Both hotels do a great job engaging guests young and young at heart.

Although there are certainly other fun hotels, these are some of the only ones centrally located with private beaches. There is a public beach nearby too which is worth a visit! You can check it out on my interactive Google Map, but you’ll need to bring your own towels, umbrellas, etc. If you’re traveling with kids and looking for sand, check out Casa Marina.

Kid-Friendly Exploring

You’re welcome to spend all day at the beach, but we usually get a little antsy and need to find some activities. The main drag in Key West is Duval Street, and it’s an easy walk from the hotel.

Side note – did you know there were roosters running around all over Key West? Back in the day, it was legal to have cockfights…yep, cockfights. People would gamble and bring their roosters to Key West. Evidently, it was a really popular “sport” for southern men. It was banned in the 1980s, but the roosters had nowhere to go. They’re actually protected now! As you walk around, keep an eye open for chickens everywhere – even in the trees!

The most iconic photo spot is a giant buoy that designates the Southern Most Point of the United States. Honestly, it’s just a big buoy, but I guess you need the photo to prove you were there. Sometimes there’s a line just to take a picture next to it. I dunno, you do you.

And now for a family favorite – the butterfly house! This glass-domed nature conservatory is a blast for kids. Not only are there a ton of butterflies, but there are also little birds and flamingos to see. It’s about $12 to enter and open daily from 9 to 5.

As you work your way down Duval Street, pop into The Happy Rooster for some souvenirs. They have a huge selection of kids clothes! A small detour off of Duval brings you to the Key West Lighthouse. You can climb the 88 steps to the top for great views of the island. Why this lighthouse isn’t on the water is a mystery to me, but it’s fun for the kids and great for some photos. The next stop is probably more fun for adults, but you should check out Hemingway Home and Museum. He lived in Key West in the 1930s and created the first in-ground pool on the island for $20,000.

At this point, your kids (and you!) will be clamoring for some dessert. Pop into Limes and Pies for some Key Lime Pie or ice cream. This is one of my all-time favorite pies. I like mine without the meringue, but if you love multiple inches of meringue on your pie, you’re in for a real treat. If it’s really hot outside, you’ll be ready for more dessert in a few blocks. Pop into Wicked Lick Ice Cream for some creamy heaven. Still hungry? A little further down is the Key West Key Lime Company. Also excellent.

Although not huge, Key West does have a great aquarium! Located in the north west near Mallory Square, the aquarium is a great stop if you need to get out of the sun for a bit. They feed the sharks at 11:45 and 2:45 daily. Right across the street is the Shipwreck Museum. If you have a little one that’s into old coins and pirates, it’s a great use of an hour.

As it turns to evening, check out Mallory Square. This is where the cruise ships dock, so it can be a little busy, but it’s chock full of street performers. Unicycles, fire eaters, acrobats, magicians and musicians gather here to thrill the crowds. There are also outdoor vendors selling everything from t-shirts to shark teeth to snow cones. It’s a really fun vibe and there are public restrooms available for the littles.

My other suggestion when roaming around Key West is to check out the marina. There are tons of restaurants here, but it’s also where the fishermen come to clean their catch. As they clean the fish, they throw the “left-overs” to the tarpon. Kids will love to watch from the Tarpon Feeding Deck. the fishermen are always eager to show off their catch to kids too.

Duval Street also has Trolley Tours. I haven’t done this personally, but it seems to be a popular option. I think it’s like a hop-on-hop-off bus, but a trolley. I find Key West to be very walkable, but if you need a break or have a fussy little one, it’s a great choice. There are also a zillion art galleries that line Duval Street. My kids actually love galleries, but it’s not every family’s cup of tea. You can find some weird antiques, super modern sculptures, and fun art everywhere.

Food

If you love seafood as much as I do, this is your island! Here are my top recommendations:

Breakfast

• Cuban Coffee Queen Waterfront – amazing coffee
• Banana Cafe – lots of crepes and breakfast options, outdoor seating
• Blue Heaven – outdoor seating with your toes in the sand, but a little pricey for breakfast
• Sarabeth’s – brunch from 9-2 with outdoor seating

Lunch & Dinner

• DJ’s Clam Shack – great fried seafood and lobster rolls with outdoor picnic tables
• Blue Heaven – awesome cocktails and live music in the evenings
• 915 – upscale tapas in an old house on Duval
• Conch Republic – amazing raw bar, cocktails, and gorgeous marina location
• The Jerk – Jamaican cuisine in a laid back local
• Caroline’s Cafe – lovely outdoor setting with Key Lime pie for days…
• A&B Lobster House – more upscale location in the marina for seafood
• Half Shell Raw Bar – amazing seafood and hermit crab racing!

I don’t think you can go wrong with most food options in Key West! There are also big name places here like Margaritaville, but I like the more local feel.

Activities

You can do some great snorkeling and glass bottom boats in Key West. We did a sunset snorkel with champagne that was delightful. I would say that you may want some Dramamine for the glass bottom boats. When they cut the engines and just bob in the water, I get a little green. Especially when staring down into the water for an extended time period. However, it was a lot of fun to see the fish, coral, sea turtles and starfish without trying to coax a 4-year old into the water. Fury has lot of family-friendly options and departs daily at noon, 2:00 and 4:30.

I’m not a huge jet ski fan, but my husband and son love doing these tours in Key West! You get to zip around the island in a follow-the-leader fashion and see all of Key West from the ocean. Fury does these trips too, but there are several great vendors. Sunset Jet Ski Tours in highly rated in Key West.

You can also rent a boat and tour the ocean on your own! My husband grew up doing summers at a lake house and driving boats. We even had a boat in Lake Michigan for years before the kids were born. However, Key West proved to be a little stressful in a rented boat. The area is known for shipwrecks for a reason – things get very shallow very quickly and without warning. There’s an app that you can download that is basically GPS for boating, and I would highly recommend it if renting your own boat. We got some tips from a bar tender at Blue Heaven and found an amazing sand bar in the ocean, but we never would have found it without his recommendation.

Adult Fun

If you have some time away from the kids, check out some nightlife!

• Hog’s Breath Saloon – This is one of my favorite bars on Earth. It’s an indoor-outdoor vibe with plenty of cocktails and beers. There’s also live music every night. Drink, enjoy the saltwater in the air, listen to some music, and be happy.
• Blue Heaven – I’ve mentioned this as a breakfast and dinner spot too. It’s an iconic location in Key West for good reason. The cocktails and live music in the evenings is great. Take the time to chat with the bar tenders here! They typically know everything about the island and are a great resource for your vacation!
• Green Parrot Bar – I had SO much fun listening to music here! They get great live bands with full brass sections and awesome energy. They basically had to kick me out at the end of the night.

Dry Tortugas

Our kids seemed too little to do this, but the Dry Tortugas are a popular day trip from Key West. Hop on a high speed ferry, and go 70 miles west into the ocean, to visit the Dry Tortugas. A day trip will cost you about $200. The snorkeling here is supposed to be amazing. The 100-square-mile National Park covers seven islands and is only accessible by boat or seaplane.

You can also camp here overnight! You’ll need a tent and camping gear, but it looks amazing. These camp sites sell out months in advance, so plan ahead! It’s $15 per night to camp.

Check out all of these locations on my interactive Google Map!