Old Town
Key West Guide

What Makes Old Town Key West Worth Visiting?

Old Town Key West is the island’s most historic neighborhood, filled with charm, color, and laid-back energy. It’s the perfect place for families who want to explore at their own pace, with endless family-friendly things to do in Key West just steps apart. 

When planning a trip, Old Town makes an ideal starting point. You can walk, bike, or hop aboard the Old Town Trolley Tours® to reach top attractions, beaches, and restaurants without needing a car. Parents will find plenty of things to do in Key West with kids, from visiting marine life exhibits to catching the famous sunset at Mallory SquareSM Festival Marketplace. Families often stay nearby so they can start each morning with a stroll down Duval Street or a short ride to the waterfront. Every corner of Old Town offers a mix of history, fun, and friendliness that makes it easy to see why so many families return.

How Did Old Town Key West Become the Island’s Cultural Center?

The story of Old Town begins at the waterfront. In the 1800s, ships from around the world arrived here to trade goods, fish, and refuel. Over time, the area developed into a lively seaport community filled with workers, artists, and musicians who gave the island its creative spirit. It quickly became known for its welcoming attitude and mix of cultures, especially those from Cuba and the Bahamas, whose influence still shapes daily life in Key West.

Today, the same streets tell that story through their colorful architecture and historical sites. Wooden homes built in the early days of Key West still stand strong, with tin roofs, shaded verandas, and bright shutters that reflect the island’s tropical weather. This “Conch” style of architecture is one of the reasons families love exploring the area, as every block feels like a piece of living history.

Visitors looking for family-friendly things to do in Key West often stop at landmarks like the Southernmost Point Buoy or the Mile Marker 0 sign for a quick photo. These small moments tie modern visitors to the city’s long past. Families can also stop by the Key West Museum of Art & History inside the Custom House to see how the island grew from a small port into a vibrant community. Old Town’s blend of history, culture, and nearby attractions makes it one of the most enjoyable areas for anyone visiting Key West with kids.

What Are the Must-Do Old Town Attractions?

Old Town is where you’ll find many of the island’s best-known landmarks and experiences, making it a great base for family-friendly things to do in Key West. The area’s mix of tours, museums, and outdoor spots keeps families busy without feeling rushed. 

The Conch Tour Train is one of the most popular things to do in Key West with kids. It’s a comfortable and entertaining ride through Old Town’s narrow streets, led by friendly conductors who share local stories, fun trivia, and interesting details about island life. Kids love spotting colorful houses and hearing about famous residents, while parents appreciate the easy pace and live narration that makes history enjoyable for everyone.

For families with older kids, the Ghosts & Gravestones® Frightseeing® Tour adds a bit of spooky adventure. The covered trolley travels through Old Town at night, passing haunted spots like the East Martello Museum and the Key West Cemetery. It’s a mix of history, storytelling, and just the right amount of mystery for families looking to experience a different side of the island.

No visit to Old Town is complete without a stop at the Key West Lighthouse. The climb up its 88 steps rewards visitors with a sweeping view of the island and the ocean beyond. It’s one of the most memorable family-friendly things to do in Key West, especially for those who enjoy a little exercise and adventure. Nearby, the Ernest Hemingway Home & Museum draws visitors of all ages. Kids enjoy meeting the famous six-toed cats, while adults appreciate the peaceful gardens, personal memorabilia, and connection to one of America’s greatest writers.

Families interested in history should also visit the Harry S. Truman Little White House, where Truman spent nearly six months of his presidency. It offers a fascinating look at mid-century life and politics, presented in a way that’s approachable and easy for kids to understand.

To mix in some marine life and interactive fun, stop by the Key West Aquarium, one of the island’s oldest attractions. It’s filled with touch tanks, educational displays, and feeding sessions that help kids learn about the island’s marine ecosystem. Finally, the Fort Zachary Taylor Historic State Park and Beach give families the chance to explore a real Civil War fort before enjoying swimming, snorkeling, or picnicking by the water. The nearby Mallory Square Festival Marketplace adds a festive finish to the day with its nightly Sunset Celebration, complete with jugglers, musicians, food vendors, and a view that’s become one of the most famous in the world.

Where Should You Stay in Old Town Key West?

Finding a good place to stay in Old Town makes exploring much easier. Families who plan to experience many things to do in Key West with kids will appreciate how walkable and compact the neighborhood is. Staying in Old Town means you can leave the car behind and still be within a short walk or Old Town Trolley Tours ride of the main attractions, beaches, and restaurants.

There’s no shortage of options, from charming bed-and-breakfast inns to modern boutique hotels. Many properties are housed in restored historic homes that reflect the island’s distinctive Conch architecture, complete with porches, gardens, and tropical details. Families who value extra space can look into Key West Vacation Homes, which offer full kitchens, laundry access, and room for everyone to spread out while still staying close to top attractions.

Parents traveling with young children often choose smaller inns and guesthouses for their quiet, friendly atmosphere and personal service. Larger hotels like The Marker Key West or the Pier House Resort & Spa provide pools, on-site dining, and waterfront views that make it easy to unwind after a day of sightseeing.

Old Town is a favorite among returning visitors because it strikes the right balance between convenience and character. Staying here keeps you close to everything, including Mallory Square, Duval Street, and the waterfront. Families can walk out their front door and find breakfast spots, souvenir shops, or beach access within minutes.

Where Should You Eat in Old Town Key West?

Old Town has some of the best places to eat on the island, offering plenty of family-friendly things to do in Key West for every taste and budget. The area is filled with casual cafés, seafood shacks, and historic restaurants where families can enjoy a good meal together. Many spots are easy to reach on foot or by Old Town Trolley Tours, making dining simple after a day of exploring.

Along Duval Street and Mallory Square Festival Marketplace, you’ll find many restaurants that use local ingredients and offer a welcoming atmosphere. Southernmost Beach Café is one of the best-known oceanfront spots. It serves breakfast, lunch, and dinner with views of the clear water. Popular dishes include fish tacos, shrimp and grits, and tropical fruit parfaits. The open-air tables make it easy for families to relax while kids watch boats in the distance.

Nearby, El Meson de PepeSM brings authentic Cuban flavors to Old Town. This family-owned restaurant has served locals and visitors for decades, and its menu celebrates Cuba’s rich food traditions. Guests can enjoy dishes like ropa vieja, picadillo, black beans, and the signature Cayo Hueso Cuban Mix sandwich made with roast pork, ham, and Swiss cheese. Live music often plays in the background, giving diners a taste of both Cuban culture and island energy.

For something quick, B.O.’s Fish Wagon is a local favorite known for its conch fritters and fish sandwiches. The open-air setup, picnic tables, and friendly service make it a great lunch spot for families. Schooner Wharf Bar, located by the Historic Seaport, offers fresh seafood baskets, sandwiches, and a relaxed atmosphere. Families often stop here during the day before it becomes a popular live music venue in the evening.

Parents who want to unwind can stop by the Green Parrot Bar, one of the oldest bars in Key West. The building dates back to the late 1800s and has long been a gathering place for residents and travelers. It’s known for its easygoing atmosphere and connection to the island’s past.

Old Town’s dining scene blends the island’s Cuban, Caribbean, and southern roots. Many restaurants have been family-run for generations, keeping recipes and traditions alive. 

Why Is Old Town Key West the Best Place To Stay and Explore?

Old Town Key West is the center of island life and the ideal place for visitors to begin their adventure. The narrow streets, pastel-colored houses, and warm breeze create an inviting setting that families notice right away. Most things to do in Key West with kids are close together, making it easy to explore without needing a car. Many visitors stay in Old Town so they can walk or ride with Old Town Trolley Tours to beaches, museums, and restaurants.

Families can start their day with a ride on the Conch Tour Train, which offers an entertaining and educational look at the island’s history. Guides share stories about local landmarks, famous residents, and the island’s culture in a way that keeps both kids and adults interested. The Old Town Trolley Tours provide another easy way to get around, with friendly and knowledgeable guides giving live narration that highlights the best of Key West’s history and character.

There’s something new to enjoy each day in Old Town. In the morning, you might visit Duval Street for coffee or shopping. By midday, you could head toward the water for a beach visit or a stop at a museum. As evening approaches, Mallory Square Festival Marketplace fills with performers, artists, and food vendors celebrating the sunset. Families gather along the waterfront to enjoy the show, making it one of the most well-loved family-friendly things to do in Key West.

Old Town connects visitors to the heart of the island. Every block holds pieces of its story, from the old seaport to the gardens tucked behind quiet guesthouses. It’s a place that invites exploration and rewards curiosity. For families planning their first trip, staying in Old Town means being surrounded by the culture, color, and warmth that define Key West.