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Mallory Square Tours

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439 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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19 Tours and Activities to Experience Mallory Square

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

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 70-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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$63.00
From
$63.00
Taking safety measures

Key West Sunset Champagne Catamaran Cruise

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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Guided Bicycle Tour of Old Town Key West

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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.81
From
$49.81
Taking safety measures

Secret Food Tour of Key West w/ Private Tour Option

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
$221.20
From
$221.20
Taking safety measures

Sunset Sail in Key West with Beverages Included

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
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Sunset Sail Aboard Schooner

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
$103.20
From
$103.20
Taking safety measures

Key West Scavenger Hunt Adventure Mobile Experience

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

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

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
Taking safety measures

Key West Island Helicopter Tour

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
  • Taking safety measures
From
$117.96
From
$117.96
Taking safety measures

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

star-5
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West. As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures. With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset. A chef’s selection of Tapas including shrimp cocktail and tuna poke are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
From
$79.00
Taking safety measures

2-Hour Private Sunset Cruise around Key West

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!
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  • 2 hours
  • Free Cancellation
From
$200.00
Price varies by group size
From
$200.00
Price varies by group size

Rum Runner Bar Boat Tour of Key West

Rum Runner Bar Boat Tour of Key West

star-3
We are the only floating bar on 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, snorkeling, water saddles and Reef viewers. 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

Key West Day Sail Aboard Schooner

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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$59.12
From
$59.12
Taking safety measures

Key West Luxury Sailing Catamaran in Florida

Key West Luxury Sailing Catamaran in Florida

star-5
The S/V Liberty is a luxurious 44-foot catamaran. Sailing with Bimini Charters is an experience of a lifetime at a very reasonable price. Enjoy a romantic sunset cruise, host a cocktail party, try stand up paddle boarding, all aboard this luxurious yacht. While there are a number of catamarans to chose from in Key West, Bimini charters is unique in that we limit the number of people on our boat to six, so you can have a comfortable and safe sail distanced from others with much room to spread out. You can also rent the entire boat out for 1/2 day (3 hour) or full day (6 hour) sails to host your family and friends on a private charter (up to 10 people.) The S/V Liberty offers five different seating areas, so you can spread out, enjoy different vantage points, and savor the coastline as we cruise by. Feel free to bring your own food and beverages to make the most out of your sail! You are welcome to view our customer reviews on our Saco, ME listing (our summer location) to learn more!
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$85.00
From
$85.00
Taking safety measures

GPS-Driven Self-Guided Audio Sunset Tour in Key West

GPS-Driven Self-Guided Audio Sunset Tour in Key West

Stroll along the Gulf of Mexico enjoying the island’s best happy hours then watch the famous Key West sunset. You’ll have historic photos as links to happy hour menus right at your fingertips. Cool off at a tiki bar with a gorgeous waterfall, then stroll along a hidden boardwalk with stunning ocean views. Find the best best happy hours with the tastiest seafood snacks. Stroll past Jimmy Buffett’s secret recording studio. Enjoy Key West’s most popular brewery, best mojito, or the world’s yummiest coffee. Learn where the locals watch the sunset. Sight-see at your own pace, avoid being herded in a crowd, and linger only in the places that truly interest you. Each tour is carefully researched to give you an authentic, immersive Key West experience with no tourist traps.
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  • 35 minutes to 2 hours
From
$8.99
From
$8.99

2-Hour Private Sunset Cruise in Florida Keys on Tiki Bar Boat

2-Hour Private Sunset Cruise in Florida Keys on Tiki Bar Boat

Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar catamarans. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Our boats feature a large thatch roof for shade, bluetooth tv and stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$456.88
per group
From
$456.88
per group
Taking safety measures

Private Tour of Florida Keys from Marathon to Key West

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
Taking safety measures

Private Walking Tour of Key West

Private Walking Tour of Key West

star-5
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.
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  • 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
Taking safety measures

Key West Christmas Day Brunch Sail

Key West Christmas Day Brunch Sail

star-5
A great way for families and friends to relax on Christmas morning! Enjoy a 2-hour sailing experience aboard the beautiful and classic Schooner America 2.0. Your ticket includes a special Christmas Day plated brunch served onboard including spiraled ham, bagels and pastries, meats and cheese, smoke salmon, crudite and more! Also enjoy complimentary beer, wine, Champagne, mimosas, bloody Marys and soft drinks. Sit back and relax as the crew raises sail and provides beverage service. As the boat sails along the majestic Key West waters, take-in views of Fort Zachary Taylor, Sand Key Lighthouse, Mallory Square and Sunset Pier.
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  • 2 hours
  • Taking safety measures
From
$124.70
From
$124.70
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?