Celebrate Valentine's Day in Key West (Updated 2026)

Key West, USA
Florida Key West Self-Guided Walking Audio Tour

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the …More

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the...

2 to 3 hours Free Cancellation
4.7 (26)
from
$8
Self-Guided Driving Audio Tour in Florida Keys

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road …More

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road...

1 day Free Cancellation
4.8 (99)
from
$20
Key West Clear Kayak Eco Tour

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak, …More

Likely to Sell Out
Likely to Sell Out

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak,...

2 hours Free Cancellation
4.7 (50)
from
$60
The Hemingway Experience in Key West

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour …More

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour...

4 hours Free Cancellation
4.9 (74)
from
$189
Dolphin Watching Key West and Snorkeling

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; …More

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away;...

3 hours Free Cancellation
4.9 (49)
from
$149
iWitness Key West True Crime Walking Tour

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and …More

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and...

1 hour 30 minutes Free Cancellation
4.8 (19)
from
$49
Key West: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most …More

Likely to Sell Out
Likely to Sell Out

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most...

1 hour Free Cancellation
4.9 (7)
from
$45
Key West Cooking Show Chef Demonstration with Meal

Step inside one of Key West’s most storied historic buildings and settle into our stunning, state-of-the-art open kitchen for an unforgettable culinary journey. Sit back, …More

Step inside one of Key West’s most storied historic buildings and settle into our stunning, state-of-the-art open kitchen for an unforgettable culinary journey. Sit back,...

1 hour Free Cancellation
4.9 (50)
from
$91
Private Key West Morning Sail, Snorkel & Kayak Excursion

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

Special Offer
Special Offer

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4 hours 30 minutes (approx.) Free Cancellation
$2,399
$2,270
Key West 4th of July Tipsy Tiki Fireworks Sail

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Likely to Sell Out
Likely to Sell Out

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3 Hrs (approx.) Free Cancellation
5.0 (1)
from
$170
Private Looe Key Snorkel from Big Pine Key

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef …More

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...

3 hours Free Cancellation
5.0 (446)
from
$569
Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes Free Cancellation
4.9 (20)
from
$425
Key West Shore Excursion: Conch Tour Train

Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958. …More

Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958....

1 hour 30 minutes Free Cancellation
4.6 (42)
from
$45
Mel Fisher Maritime Museum Admission Ticket

Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story …More

Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story...

1 to 2 hours Free Cancellation
4.3 (127)
from
$18
Skip the Line: Mel Fisher Maritime Museum Admission Ticket and Audio Tour

Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story …More

Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story...

1 to 4 hours Free Cancellation
4.4 (28)
from
$20
Key West: Private Vacation Photoshoot with Photographer

⭐ Top-Rated Vacation Photoshoots 2025 & 2026 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of …More

Likely to Sell Out
Likely to Sell Out

⭐ Top-Rated Vacation Photoshoots 2025 & 2026 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of...

1 hour Free Cancellation
5.0 (6)
from
$77
Key West - Museum Culture Pass

The Key West Museum Culture Pass is an excellent way to explore the rich cultural history of this vibrant city. With the pass, you can …More

Likely to Sell Out
Likely to Sell Out

The Key West Museum Culture Pass is an excellent way to explore the rich cultural history of this vibrant city. With the pass, you can...

4 to 5 hours Free Cancellation
4.3 (26)
from
$45
Private Luxury Sandbar Excursion in Key West

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether …More

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether...

4 hours Free Cancellation
4.9 (621)
from
$1,200
Key West Smather's Beach All Day Pass with Parasailing

The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the …More

Special Offer
Special Offer

The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the...

All Day (9am - 5pm) Free Cancellation
4.7 (19)
$109
$100
Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Likely to Sell Out
Likely to Sell Out

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation
5.0 (5)
from
$89
Key West PADI® Advanced Open Water Diver Scuba Certification

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training. …More

Special Offer
Special Offer

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training....

2 days (approx.) Free Cancellation
5.0 (2)
$699
$659
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