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Mallory Square Tours and Activities

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445 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, Florida 33040-6634, USA
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18 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
922
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
$74.95
From
$74.95
Taking safety measures

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
197
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
$79.95
From
$79.95
Taking safety measures

Key West Sunset Champagne Catamaran Cruise

Key West Sunset Champagne Catamaran Cruise

star-4.5
292
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
$51.95
From
$51.95
Taking safety measures

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
149
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
201
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

Secret Food Tour of Key West w/ Private Tour Option

Secret Food Tour of Key West w/ Private Tour Option

star-5
61
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

2-Hour Private Sunset Cruise around Key West

2-Hour Private Sunset Cruise around Key West

star-5
16
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

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
64
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
$60.20
From
$60.20
Taking safety measures

Key West Scavenger Hunt Adventure Mobile Experience

Key West Scavenger Hunt Adventure Mobile Experience

star-3.5
6
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 Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

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

star-4.5
35
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
$79.95
From
$79.95
Taking safety measures

2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West

2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West

star-5
5
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 boats. 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. Keep your eyes on the horizon for a chance to see the famous Green Flash as the sun goes down.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$456.88
per group
From
$456.88
per group
Taking safety measures

Self-Guided Audio Sunset Stroll in Key West

Self-Guided Audio Sunset Stroll in Key West

star-5
1
Stroll along the Gulf of Mexico, enjoying the island’s best happy hours, then watch the famous Key West sunset. Download this multi-media, GPS-driven tour to your phone or tablet. It's like walking with your own local tour guide! Historic photos, recordings and videos plus links to restaurant menus and websites rest at your fingertips. In just 35 minutes of walking, you can 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 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. After purchasing, check your confirmation emails for instructions on how to download your tour to your phone or tablet.
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  • 35 minutes to 2 hours
From
$10.99
From
$10.99

Private Self-Guided Black History Tour of Key West

Special Offer

Private Self-Guided Black History Tour of Key West

Download this multi-media, GPS-driven tour to your phone or tablet. Tour the 2-by-4 mile island in your own vehicle (electric car/golf cart is ideal.) Nowhere on this tour will the speed limit exceed 35 mph! Drive for one hour for a quick tour, or stop, eat, and swim to spend a whole afternoon. Learn about Key West's deep ties to Bahamian culture and the city's pivotal role defeating the Confederacy during the Civil War. Discover why 250 Africans are buried by the beach, and what the colors of the buoy at the Southernmost Point have to do with segregation. Visit the island's oldest black church. Find the Keys' best conch salad, get a taste of Haitian and Cuban flavors and sample some Key Lime pie. Historic photos plus links to restaurant menus and websites rest at your fingertips. After purchasing, check your confirmation emails for instructions on how to download your tour. Electric car rental is NOT included. Recommended rental spots are listed at the start of your tour.
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  • 1 to 4 hours
  • Taking safety measures
From
$8.79
$10.99
$2.20 savings
From
$8.79
$10.99
$2.20 savings
Taking safety measures

Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Learn about how Old Fisherman’s Wharf has transformed into Yacht Harbor! Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car! Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$69.00
From
$69.00
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
2
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
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 Private Morning Sail on Schooner America 2.0

Key West Private Morning Sail on Schooner America 2.0

Enjoy a morning sailing experience and have Schooner America 2.0 all to yourself! Let us whisk you and yours away on a glorious morning sail across the beautiful waters of Key West on your own private yacht! This 1.5 hour charter aboard the America 2.0 grants you all the luxuries of yachting on your own private schooner. Let our crew do the work as you sit back and relax and take in the sights. Soda and water included. Alcoholic beverages and food are available for purchase onboard. Due to our licensing, guests are not permitted to bring their own alcoholic beverages on their sail. At this time, we do not offer swimming, snorkeling, or diving. After booking, you will be contacted by a Classic Harbor Line representative regarding more details about your trip.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$750.00
per group
From
$750.00
per group
Taking safety measures

From Miami: Key West with options like Snorkel with unlimited drinks

Special Offer

From Miami: Key West with options like Snorkel with unlimited drinks

star-4.5
4
Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. If you selected the snorkel option in Key West we will board a boat and go out to the reef where we will snorkel and experience Florida's underwater world. After the snorkel tour you will have some time to experience the highlights of Key West on your own. If you selected the transportation only tour option you can enjoy 6 hours of leisure to exploring the islands turquoise waters and white sandy beaches or the small white Victorian conch villas and lush tropical gardens. Stroll along Duval Street with it’s cute shops, galleries and cafes to the famous southernmost point monument only 140 km or 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation is included  
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  • 15 hours
  • Free Cancellation
From
$69.30
$99.00
$29.70 savings
From
$69.30
$99.00
$29.70 savings

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?