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Mallory Square Tours

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438 Reviews
Mallory Square
Overflowing with Key West quirkiness, Mallory Square draws a crowd at sunset thanks to its many restaurants, street performers, and daily Sunset Celebration. During the day, visitors come for some of Key West’s best shopping and to admire the open-air sculpture garden, which pays tribute to famous local residents.
 
The Basics 
Mallory Square has been one of Key West’s social and commercial hubs since the 1820s and is now one of the town’s top destinations for shopping, dining, and sightseeing. The square is a stop on many city tours, and sunset cruises pass by on their way out to sea. To enjoy the Sunset Celebration, head to the area in the evening; you’ll find oddball performers, street artists, and a friendly crowd enjoying the evening light.
 
Things to Know Before You Go
  • The sunset-viewing area is wheelchair and stroller accessible.
  • Street performers put on shows for tips, so it’s ideal to have some small bills on hand.
  • Dockside restaurants fill up quickly during sunset hours; reserve a table in advance, or visit one of Mallory Squares many food vendors.
 
How to Get There
Mallory Square is located at 400 Wall Street in Key West. The area is hard to reach by private car due to narrow streets and limited parking. You can reach the area easily on the Key West trolley or by booking a hop-on, hop-off bus tour; both have stops adjacent to the square.
 
When to Get There
Mallory Square’s restaurants and shops draw a steady crowd throughout the day, and the Sunset Celebration kicks off about an hour before the sun sets. If you’re hoping to find a prime spot for taking photos, plan to arrive on the early side and stake out a place by the water.
 
Mallory Square Restaurants
There are dozens of great dining options in or near Mallory Square. For upscale seafood, Hot Tin Roof, which offers everything from poke to poached lobster, is a local favorite. Other top picks include Bistro 245, Terrace Roma, Rooftop Café, and the lively Hog’s Breath Saloon. For something more casual, check out the Sunset Celebration food carts, which offer fruity drinks, seafood, conch fritters, popcorn, and more.
Address: 1 Whitehead Street, Key West 33040-6634, USA
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16 Tours and Activities to Experience Mallory Square

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details
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Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvresSailing

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-5
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 60-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
...  More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$63.00 
From  
$63.00 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Key West Sunset Champagne Catamaran CruiseSailing

Key West Sunset Champagne Catamaran Cruise

star-4.5
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
...  More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
$45.00 
From  
$45.00 
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures

Guided Bicycle Tour of Old Town Key WestMountain Bike Tours

Guided Bicycle Tour of Old Town Key West

star-5
Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.
...  More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From  
$49.81 
From  
$49.81 
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  • 3 hours
  • Free Cancellation
  • Taking safety measures

Secret Food Tour of Key West w/ Private Tour OptionPrivate and Luxury

Secret Food Tour of Key West w/ Private Tour Option

star-5
From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.
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  • 2 hours 30 minutes
  • Taking safety measures
From  
$91.09 
From  
$91.09 
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  • 2 hours 30 minutes
  • Taking safety measures

Sunset Sail in Key West with Beverages Included Day Cruises

Sunset Sail in Key West with Beverages Included

star-5
Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
$61.46 
From  
$61.46 
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  • 1 hour 30 minutes
  • Free Cancellation

Schooner Key West Day and Sunset Cruises with Full BarSailing

Schooner Key West Day and Sunset Cruises with Full Bar

star-4.5
Set sail on the schooner Appledore for a scenic cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail.. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$38.95 
From  
$38.95 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Key West Sunset Sail Aboard SchoonerDay Cruises

Key West Sunset Sail Aboard Schooner

star-5
Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$81.70 
From  
$81.70 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Key West Scavenger Hunt Adventure Mobile ExperienceHalf-day Tours

Key West Scavenger Hunt Adventure Mobile Experience

star-3.5
Discover Key West in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure from the Historic Seaport at Key West Bight to Duval Street, Mallory Square and other real-life locations around town. Discover both well-known and overlooked locations, solving clues and completing challenges via smartphone while learning the local history of this popular island city. Teams of 2- to 5-people are welcome.
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  • 3 hours
  • Free Cancellation
From  
$20.84 
Price varies by group size
From  
$20.84 
Price varies by group size
Learn More
  • 3 hours
  • Free Cancellation

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full BarSailing

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$75.95 
From  
$75.95 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

Key West Island Helicopter TourAudio Guides

Key West Island Helicopter Tour

star-5
Take in the views of Key West from above on this scenic, small-group helicopter tour. Circle 20 miles (32km) around the island, passing over popular landmarks including Smather’s Beach, Fort Zachary Taylor State Park, Sunset Key, and Duval Street. Find a time that works best for you with convenient departure times offered throughout the day.
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  • 10 minutes
  • Free Cancellation
From  
$117.96 
From  
$117.96 
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  • 10 minutes
  • Free Cancellation

Key West Sunset Sail with Premium Wine, Champagne and Tapas PairingsSailing

Key West Sunset Sail with Premium Wine, Champagne and Tapas Pairings

star-4.5
Our Captain’s Choice Sunset Sail is limited to an intimate number of passengers for an awesome experience! It’s more like a private cruise than a tour and is one of the top things to do in Key West. A chef’s selection of Tapas is served during the sail, prepared fresh daily by Sebago’s own catering kitchen. Delectable shrimp cocktail and tuna poke are Sebago’s signature dishes. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour! As the sun sinks lower, your captain carefully positions the boat to capture a perfect view of the fiery sky. As we leave behind the Historic Seaport, look for Key West landmarks like Mallory Square’s Sunset Celebration with its jugglers, opulent Sunset Key and the historic Fort Zachary Taylor. On reaching open water, the sails are unfurled to provide you with an authentic sailing experience. A sunset cruise Key West style with Sebago will forever linger in your memories.
...  More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$79.00 
From  
$79.00 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures

2-Hour Private Sunset Cruise around Key WestPrivate Sightseeing Tours

2-Hour Private Sunset Cruise around Key West

star-5
This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter. Feel free to bring food or beverages of your choice. Price is $375 TOTAL and includes up to 6 people. Looking forward to seeing you on the dock!
...  More
  • 2 hours
  • Free Cancellation
From  
$200.00 
Price varies by group size
From  
$200.00 
Price varies by group size
Learn More
  • 2 hours
  • Free Cancellation

Rum Runner Bar Boat Tour of Key WestDay Cruises

Rum Runner Bar Boat Tour of Key West

star-3
We are the only floating bar in the island and we take you to places that normal tours do not, 100 year old Shipwreck, Movie boat set of Beach Bum, and we provide swimming if you book the whole boat. You will see Castaway Island a.k.a. Christmas Tree, Sunset Key and the crazy wildlife in, under, and around the waters of Key West.
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  • 1 hour
  • Free Cancellation
From  
$35.00 
From  
$35.00 
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  • 1 hour
  • Free Cancellation

Key West Day Sail Aboard SchoonerDay Cruises

Key West Day Sail Aboard Schooner

star-5
Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
...  More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
$47.30 
From  
$47.30 
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures

Private Tour of Florida Keys from Marathon to Key WestDay Trips

Private Tour of Florida Keys from Marathon to Key West

star-5
Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
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  • 7 hours
  • Free Cancellation
  • Taking safety measures
From  
$200.00 
Price varies by group size
From  
$200.00 
Price varies by group size
Learn More
  • 7 hours
  • Free Cancellation
  • Taking safety measures

Private Walking Tour of Key WestPrivate Sightseeing Tours

Private Walking Tour of Key West

Walk through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide for only $1 per person** It's air-conditioned with several convenient stops throughout Old Town. These tours are private so you can ask questions and we can customize the tour to your interests. Your tour guide is knowledgeable about everything Key West, so don't hesitate to let us know what interests you and what you want to know about Key West.
...  More
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures
From  
$69.00 
Price varies by group size
From  
$69.00 
Price varies by group size
Learn More
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What's the best way to experience Mallory Square?