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Home/Destinations/Key West/Old Town & History

Old Town & History Tours

Historic Key West: trolley and walking tours explore Old Town’s colourful lanes, from Duval Street and the Southernmost Point to conch houses and quirky history. The best way to see the island’s character.

184 tours · prices per person, book with partner

Shark and Wildlife Viewing Adventure in Key West
Key West
Shark and Wildlife Viewing Adventure in Key West
5.0(3,401)·2 hours
from$99/ person
via Viator
Guided Bike Tour of Old Town Key West
Key West
Guided Bike Tour of Old Town Key West
4.9(2,743)·2 hours
from$59/ person
via Viator
Southernmost Food & Cultural Walking Tour by Key West Food Tours
Key West
Southernmost Food & Cultural Walking Tour by Key West Food Tours
4.9(1,941)·3 hours
from$94/ person
via Viator
Key West Hop-On Hop-Off Trolley Tour
Key West
Key West Hop-On Hop-Off Trolley Tour
4.5(1,784)·1h 30min
from$56/ person
via Viator
Key West Ghosts and Gravestones Trolley Tour
Key West
Key West Ghosts and Gravestones Trolley Tour
4.4(1,399)·1 hour
from$40/ person
via Viator
Key West Ghost and Mysteries Guided Tour
Key West
Key West Ghost and Mysteries Guided Tour
4.5(1,132)·1h 30min
from$33/ person
via Viator
Key West Conch Tour Train
Key West
Key West Conch Tour Train
4.5(901)·1 hour
from$45/ person
via Viator
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Key West
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
4.9(846)·6h 30min
from$159/ person
via Viator
Key West Historic Seaport Food & Walking Tour
Key West
Key West Historic Seaport Food & Walking Tour
4.9(682)·3 hours
from$94/ person
via Viator
Ultimate Sea Doo Jet Ski Tour of Key West-Additional Rider Free!
Key West
Ultimate Sea Doo Jet Ski Tour of Key West-Additional Rider Free!
4.6(672)·1h 30min
from$151/ person
via Viator
Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
Key West
Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
4.5(620)·2 hours
from$32/ person
via Viator
Key West Glass-Bottom Boat Tour with Sunset Option
Key West
Key West Glass-Bottom Boat Tour with Sunset Option
3.9(615)·1h 45min–2h
from$64/ person
via Viator
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
Key West
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
4.9(595)·4 hours
from$143/ person
via Viator
Dry Tortugas National Park Day Trip by Catamaran from Key West
Key West
Dry Tortugas National Park Day Trip by Catamaran from Key West
4.6(529)·10 hours
from$260/ person
via Viator
Shallow Water Snorkeling and Dolphin Watching in Key West
Key West
Shallow Water Snorkeling and Dolphin Watching in Key West
4.6(476)·4 hours
from$109/ person
via Viator
Key West Parasailing - Next to Cruise Port with Amazing Views
Key West
Key West Parasailing - Next to Cruise Port with Amazing Views
4.8(447)·50 min
from$64/ person
via Viator
The Original Key West Island Jet Ski Tour from Barefoot Billy's
Key West
The Original Key West Island Jet Ski Tour from Barefoot Billy's
4.9(372)·1h 30min
from$156/ person
via Viator
Key West Dolphin and Snorkel Experience
Key West
Key West Dolphin and Snorkel Experience
4.4(372)·3 hours
from$70/ person
via Viator
Key West Historic Old Town Food Tour with 5 Authentic Tastings
Key West
Key West Historic Old Town Food Tour with 5 Authentic Tastings
4.8(317)·2h 30min
from$108/ person
via Viator
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
Miami
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
3.7(224)·15 hours
from$99/ person
via Viator
Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure
Key West
Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure
4.8(176)·2 hours
from$81/ person
via Viator
Southernmost Key West History and Culture Small-Group Walking Tour
Key West
Southernmost Key West History and Culture Small-Group Walking Tour
5.0(138)·1h 45min
from$50/ person
via Viator
Key West Haunted Pub Crawl Walking Tour
Key West
Key West Haunted Pub Crawl Walking Tour
4.4(113)·2 hours
from$35/ person
via Viator
Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
Key West
Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
4.3(85)·1h 30min
from$56/ person
via Viator
Florida Key West Self-Guided Driving Tour (7 Mile Bridge)
Key Largo
Florida Key West Self-Guided Driving Tour (7 Mile Bridge)
4.5(74)·2–3 hours
from$17/ person
via Viator
Key Lime Pie Walking Tour of Key West Historic Seaport
Key West
Key Lime Pie Walking Tour of Key West Historic Seaport
4.9(62)·1h 30min
from$70/ person
via Viator
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Key West
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
4.9(36)·7 hours
from$169/ person
via Viator
Marathon to Key West Private Tour of Florida Keys
Key West
Marathon to Key West Private Tour of Florida Keys
5.0(28)·8 hours
from$137/ person
via Viator
Key West Day Trip from Miami with Boating Options
Miami
Key West Day Trip from Miami with Boating Options
3.6(28)·15 hours
from$139/ person
via Viator
Key West Ghost Tours: Southernmost Shadows and Ghosts
Key West
Key West Ghost Tours: Southernmost Shadows and Ghosts
3.9(26)·1 hour
from$32/ person
via Viator
Key West Sweet Treats Food Tour: Sunshine & Sweet Times
Key West
Key West Sweet Treats Food Tour: Sunshine & Sweet Times
4.8(24)·1h 30min–2h
from$70/ person
via Viator
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
Key West
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
4.9(24)·2 hours
from$75/ person
via Viator
Miami to Key West One Day Roundtrip Shuttle
Miami
Miami to Key West One Day Roundtrip Shuttle
3.5(11)·15 hours
from$40/ person
via Viator
Key Largo/Islamorada to Key West Private Day Tour Florida Keys
Miami
Key Largo/Islamorada to Key West Private Day Tour Florida Keys
5.0(10)·10 hours
from$169/ person
via Viator
Six Passenger Golf Cart Rental in Key West - Downtown
Key West
Six Passenger Golf Cart Rental in Key West - Downtown
3.1(8)·1–30 days
from$185/ person
via Viator
Private Full-Day Tour of Florida Keys from Miami/FLL to Key West
Miami
Private Full-Day Tour of Florida Keys from Miami/FLL to Key West
5.0(2)·13 hours
from$147/ person
via Viator
A Snorkel Tour with a Twist of History, Marathon, Florida Keys
Key West
A Snorkel Tour with a Twist of History, Marathon, Florida Keys
5.0(1)·3 hours
from$70/ person
via Viator
Key West Attractions Pass with Trolley Tour
Key West
Key West Attractions Pass with Trolley Tour
3.0(1)·1h 30min
from$93/ person
via Viator

Old Town & History in Key West — FAQ

What is there to see in Key West Old Town?
Duval Street, the Southernmost Point, historic conch houses, Mallory Square and the Hemingway House.
What is the Southernmost Point?
A landmark buoy marking the southernmost spot in the continental US, 90 miles from Cuba.
How do you explore Old Town?
On a hop-on hop-off trolley, a walking tour or a food tour.

More things to do in Key West

Sunset CruisesReef SnorkelingDry TortugasWatersports