Best Things to Do in Old Town Key West
The best way to explore Old Town Key West is with the Conch Tour Train. This world-famous sightseeing tour covers the most popular historic locations and iconic landmarks, providing an easy way to sightsee. Choosing the Conch Tour Train guarantees a reliable and fun vacation experience for all ages.
Old Town Key West with the Conch Tour Train
- Front Street Depot Boarding: Board and finish your tour at 303 Front Street, located steps from Mallory Square and historic harbor piers.
- Expert Island Narration: Listen to your tour engineer share fascinating local history, trivia, and humor about the Conch Republic.
- Open-Air Seating: Relax in shaded, open-air train cars that allow you to enjoy the ocean breeze without walking under the intense sun.
- Stress-Free Sightseeing: Travel through narrow streets safely without the burden of driving through traffic or finding parking in busy districts.
- Continuous 60-Minute Loop: Enjoy an uninterrupted narrated tour covering major historic corridors across Old Town from start to finish.
Key Features of Your Old Town Key West Visit
- Southernmost Point History: Hear stories about the island’s coastal geography and the famous marker, then walk down Whitehead Street to see the buoy after your tour.
- Key West Lighthouse Views: View the 73-foot historic brick beacon along Whitehead Street as your tour engineer explains its 1848 construction.
- The Ernest Hemingway Home & Museum: Travel aboard the Conch Tour Train toward Whitehead Street to view the author’s residence and meet resident polydactyl cats.
- Mallory Square Sunset Celebration: Finish your train tour near the waterfront to watch evening street performers and magicians gather at dusk.
By Day
Conch Tour Train
The Conch Tour Train is the perfect way to get the lay of the land in Old Town as they whisk you around the island where you’ll learn about Key West’s fascinating history, the quirky characters that shaped Key West and its eye-catching architecture.
Ernest Hemingway
Ernest Hemingway, the Nobel and Pulitzer Prize-winning author, lived in Old Town throughout most of the 1930s in a beautiful home that still stands on Whitehead Street today. You can visit the home-turned-museum to learn all about the author’s life and times in Key West. You’ll also encounter descendants of Hemingway’s beloved six-toed cat Snowball that roam the property today.
Southernmost Point
The most popular photo op in Old Town is the Southernmost Point where you’ll find a buoy that exclaims ’90 Miles to Cuba.’ You might have to wait in line, but it’s well worth it to have that coveted Instagram of you with this famous landmark.
Mile Marker 0 Sign
Once you’ve snagged your Southernmost Point selfie, head to Whitehead Street and Fleming for a photo by the Mile Marker 0 sign. It marks the end of the road and embodies everything that makes the island such an offbeat, quirky destination.
Key West Lighthouse
The Key West Lighthouse was erected in 1825 to offer ships a safe harbor. Today, you can scale the 88 steps of the steel spiral staircase for one of the best bird’s eye views of Old Town. You can also tour the Lighthouse Keeper’s Quarters to get a glimpse at what life was like centuries ago.
Fort Zachary Taylor State Park & Beach
Arguably the most beautiful beach in Key West, Fort Zachary Taylor is the most convenient beach to Old Town found at the end of Southard Street. You can relax on the rocky beach, hike nature trails and discover the historic fort. The park boasts a concession stand for snacks and a kiosk to rent snorkels so you can splash around and discover fish swimming right offshore.
By Night
Mallory Square
A visit to Key West simply isn’t complete without taking in the sunset. Head to Mallory Square where every night the sunset is celebrated with tightrope walkers, musicians and magicians all with the backdrop of the setting sun. Vendors sell conch fritters and mojitos, and the whole atmosphere is festive and fun.
Sunset Pier
Another great perch to enjoy the sunset is at Ocean Key’s Sunset Pier. This colorful tiki bar serves delicious bar bites (lobster rolls, fish tacos, conch fritters) and frozen cocktails (pina coladas, Miami vice, rum punch) on a spacious deck overlooking the harbor with live music and a chill vibe.
Green Parrot
The Green Parrot is easily Key West’s most iconic and beloved bar. Located on Southard Street just a block off Duval, it’s a brooding biker bar meets tropical oasis. The walls are covered with psychedelic posters and Key West mementos. Order a cold beer and a round of root beer barrels (their proprietary shot made with root beer schnapps and Miller Light) and find your place on the dance floor. It gets crowded with live music most nights and there’s also billiards, darts and free freshly popped popcorn.
Duval Street
A night on Duval Street involves the extreme sport of bar hopping, locally referred to as the Duval Crawl. This mile-long street in the heart of Old Town is Key West’s nightlife and entertainment corridor. From classic spots like Sloppy Joe’s to Rick’s, and Irish Kevin’s to more sophisticated options like The Other Side and Point 5, there are more bars to choose from than we can count. Our best advice is to start at one end and pop into any watering hole that tempts you.
Ghost Tour
You may not realize it, but there are many ghost stories and haunted houses around the island, from Robert the Doll to the Key West Cemetery. There’s even a story involving the Victorian mansion that currently houses the Hard Rock Cafe. The best way to experience haunted Key West is on a Key West Ghosts & Gravestones Tour held nightly.
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Conch Tour Train Tickets
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Since 1958, the Conch Tour Train has treated guests to a close-up view of the Southernmost City’s most popular places including Mallory Square, The Harry S. Truman Little White House, Overseas Railroad Museum, the Key West Aquarium and more. While on the tour, your engineer offers an interesting and amusing narrative filled with historical facts, trivia and humor, and recounts fascinating stories of the colorful people that make Key West so unique.
- 60-minute tour of the Conch Republic
- One full loop through Old Town Key West
- Open-air sightseeing perfect for taking pictures
- 2 FREE Self-Guided Walking Tours Included
- FREE coupons filled with valuable discounts to use all over the island
- FREE Full color map
Save up
to 9%
to 9%
TOUR KEY WEST AND TWO MUSEUMS
Since 1958, the Conch Tour Train has treated guests to a close-up view of the Southernmost City’s most popular places. While on the tour, your engineer offers an interesting and amusing narrative filled with historical facts, trivia and humor, and recounts fascinating stories of the colorful people that make Key West so unique.
Visit Florida’s only presidential museum at the Harry S. Truman Little White House built on the waterfront of the harbor of Key West.
Journey back to the mid-19th century in the Key West Shipwreck Treasure Museum. Highlights include displays and video presentations on the history of wreck salvage in the Florida Keys and the sinking of the legendary Isaac Allerton.
- Conch Tour Train:
- 60-minute tour of the Conch Republic
- One full loop through Old Town Key West
- 2 FREE Self-Guided Walking Tours Included
- FREE coupons filled with valuable discounts to use all over the island
- Harry S. Truman Little White House:
- See the home Harry S. Truman came to relax and rest
- Visit where Eisenhower recuperated from his heart attack in 1956
- Thomas Edison resided here during World War I
- Key West Shipwreck Treasure Museum:
- Discover the world of Shipwrecking
- Hear the story of the Isaac Allerton which wrecked off Key West
- Climb a 65' Captain's Observatory
- Attraction tickets do not have to be used on the same day
Save up
to 5%
to 5%
TOUR KEY WEST AND TWO TOP ATTRACTIONS
Since 1958, the Conch Tour Train has treated guests to a close-up view of the Southernmost City’s most popular places. While on the tour, your engineer offers an interesting and amusing narrative filled with historical facts, trivia and humor, and recounts fascinating stories of the colorful people that make Key West so unique.
Discover the undersea world at the Key West Aquarium. A Window of Wonder comes alive as expert guides explain the mysteries of the water surrounding the Florida Keys.
Journey back to the mid-19th century in the Key West Shipwreck Treasure Museum. Highlights include displays and video presentations on the history of wreck salvage in the Florida Keys and the sinking of the legendary Isaac Allerton.
- Conch Tour Train:
- 60-minute tour of the Conch Republic
- One full loop through Old Town Key West
- 2 FREE Self-Guided Walking Tours Included
- FREE coupons filled with valuable discounts to use all over the island
- Key West Aquarium:
- Daily turtle feedings
- Touch Tank offers guests hands on experience
- A wide variety of fish including grouper, moray eels, barracuda, tropical fish and more
- Key West Shipwreck Treasure Museum:
- Discover the world of Shipwrecking
- Hear the story of the Isaac Allerton which wrecked off Key West
- Climb a 65' Captain's Observatory
- Attraction tickets do not have to be used on the same day
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