The Florida Keys*, especially Key West, are known for eccentric, talented characters with a bit of a wild side (think Ernest Hemingway and Humphrey Bogart in Key Largo). For some people Key West is one big party that goes on and on and on. But the Keys have a quieter side filled with beaches, water activities and casual restaurants with fantastic local food.

There’s plenty for families to do and ample opportunities for them to chill out and relax, too. Here’s what you need to know for a family week in the Keys:

First Stop: Key Largo 

You have to eat key lime pie in the florida keys

Key Largo is the biggest key and nearest to Miami. If you fly into that city and drive down you’ll be ready to get out of the car and take a break here. Luckily there’s the too-bright-to-miss Key Largo Chocolates and Ice Cream. Everything is homemade and I was pining for it (and talking about it) long after I got back home to New York. Everything is good, and you can get into the local spirit most with the key lime and coconut rum truffles and frozen key lime pie.

Getting around Key West

Our first stop was the Key West Visitors Center for free maps and coupons we were glad to have — all the attractions add up.

Key west in the florida keys has handy trolley tours

Key West is very walkable. But, if it’s hot, consider the Old Town Trolley tours. Once you pay the fee you can hop on and off all day. It passes through the historic waterfront, Duval Street where the restaurants, bars, and shops are, the Bahamian Village Market, and some legendary mansions. The narrators are full of both information and corny jokes.

Note: Children 12 and under can ride for free. Tickets are about $30 a day if you buy them on the spot but $38 for two days if you buy ahead online.

Glass-bottom boats are popular in the florida keys
Enjoy the Water

There is no shortage of beaches and water activities off of Key West. I liked South Beach at the end of Duval Street because the water is shallow, making it great for kids.

I didn’t get there, but locals say the best beach is Fort Zachary Taylor, an 87-acre state park with a pre-Civil War fort. It has food and drink kiosks, chair rentals, picnic tables and BBQs.

I saw people parasailing, kayaking, jet skiing, and heading out to snorkel, and on glass-bottoms boats and dinner cruises. I confess I didn’t get around to trying most of these things. The glass-bottom boat is a nice option if your kids are not old enough yet for snorkeling.

Celebrate the Sunset

Make time on at least one evening for the Sunset Celebration at Mallory Square. There are street performers, musicians and singers. Vendors sell roasted corn, guacamole and chips and ice cream, along with art, crafts and jewelry. Hundreds of people gather to watch the fading sun sparkling on the waters as boats pass by. It was a simple and joyous few minutes as the sun went down, and highly memorable.

Rainy Day Options

There are fun things to do off the beach as well, for those cloudy days or when you and your kids need a break from the sun.

Explore our seafaring past in the florida keys

At the Key West Aquarium I got to pet a shark, hold conchs and starfish and feed stingrays. At the Shipwreck Treasures Museum I got a history lesson from characters in 1850s costumes and watched more daring visitors climb a 65-foot lookout tower.

I was impressed with the Key West Butterfly & Nature Conservatory, a glass-enclosed tropical habitat with more than 50 types of butterflies and 25 exotic birds from around the world.

Tweens and teens might like to the Ghosts & Gravestones “Trolley of the Doomed.” I was scheduled to try this tour and but it was cancelled at the last minute. That’s fine because I’m a bit of a chicken. But I think older kids will get a kick out of exploring “haunted” locations at night, handling cursed Spanish treasure and hearing ghost stories.

Key West Dining

Blue Heaven in the Bahama Village neighborhood is a winner for breakfast. The pecan, blueberry and pineapple pancakes all looked good. I prefer my breakfasts on the savory side and so went with Key West Pink Shrimp with grits. If you’re not so hungry, the banana bread and a cup of Joe will do you.

Outdoor dining is the thing to do in the florida keys

I also enjoyed the food and atmosphere at the busy Conch Republic Seafood Co. at the Historic Seaport. People come for the view of the docks and boats, as well as for the plates of crispy conch fritters, grilled mahi-mahi, and blackened grouper.

It was tempting to overdo it, but I managed to save room for everyone’s favorite local dessert at Kermit’s Key West Key Lime Shoppe nearby.

A Day in Islamorada

I got a kick out of my afternoon at Robbie’s marina, a funky gathering spot with outdoor shops, the Hungry Tarpon Restaurant, and food and crafts vendors. If your kids are daring buy a few fish to feed the tarpon that swim around below. Dangle them over the water and watch tarpon jump up for their lunch! The marina is a base for local eco-tours, fishing charters and to rent jet skis, kayaks and paddleboards.

Islamorada is renowned for fishing. If your kids have the patience to be out on a boat for a few hours waiting for a nibble you might be rewarded with a sizable Mahi-Mahi or even a shark! If not, consider an afternoon at Theater of the Sea, which offers live sea-animal shows, tours and glass-bottom boat tours.

I ended my trip at Marker 88, which provided beachside dining and an awesome sunset. Like most everywhere in the Keys, it was casual, cool and unforgettable.

Sheryl Nance-Nash is a freelance writer specializing in travel, business and personal finance. Her work has appeared in national magazines, newspapers and websites. She’s based in New York. You can connect with.her on LinkedIn.

*Our writer was a guest of The Florida Keys & Key West and received complimentary or discounted admission to some venues. We did not agree on any particular coverage of the destination in exchange for the trip. Our opinions are always our own.


This blog is part of Weekend Travel Inspiration. Visit our partners:

• AlbomAdventures
• ContentedTraveller 
• TheCrowdedPlanet
• Malaysian Meanders
• ReflectionsOnRoute 
• Safari254

Previous post

8 Fun Baltimore Activities for Parents and Kids

Next post

Family Weekend Getaway To Dutchess County