Unique things to do over Thanksgiving in Key West (Updated 2026)

Key West, USA
Marathon Florida Keys Fishing Experience

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing …More

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing...

4 hours Free Cancellation
5.0 (39)
from
$995
Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Likely to Sell Out
Likely to Sell Out

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$98
Marathon Snorkeling and Sandbar Adventure

Discover the best of the Florida Keys with a thrilling snorkeling and sandbar adventure from Marathon Mermaid. Begin at the stunning Sombrero Reef, where vibrant …More

Likely to Sell Out
Likely to Sell Out

Discover the best of the Florida Keys with a thrilling snorkeling and sandbar adventure from Marathon Mermaid. Begin at the stunning Sombrero Reef, where vibrant...

4 hours Free Cancellation
4.8 (5)
from
$129
Key West Ghost Tours: Southernmost Shadows and Ghosts

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate …More

Likely to Sell Out
Likely to Sell Out

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate...

1 hour Free Cancellation
4.6 (30)
from
$32
Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure: Castaway (The Haunted Island), Mermaid Adventure or Gilligan's Island! Each private 3-hour charter includes a one-hour escape game played outdoors, on the …More

Likely to Sell Out
Likely to Sell Out

Choose your adventure: Castaway (The Haunted Island), Mermaid Adventure or Gilligan's Island! Each private 3-hour charter includes a one-hour escape game played outdoors, on the...

3 hours Free Cancellation
5.0 (5)
from
$500
Key West Private Sandbar Charter with Swimming & Snorkeling

This private Key West sandbar charter gives your group flexibility to swim, wade, float, snorkel, or relax at a pace that suits you. Rather than …More

Likely to Sell Out
Likely to Sell Out

This private Key West sandbar charter gives your group flexibility to swim, wade, float, snorkel, or relax at a pace that suits you. Rather than...

4 hours Free Cancellation
5.0 (3)
from
$1,195
Sandbar Excursions with Snorkeling and Sunset Cruises in Key West

Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning …More

Likely to Sell Out
Likely to Sell Out

Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning...

4 hours Free Cancellation
5.0 (4)
from
$700
38' Private Luxury Sunset Charter w. Music & Drinks, up to 13 ppl

Ready to explore Sunset Charter with drinks and Music? aboard a luxurious private boat charter, accommodating up to 13 guests. Sailing aboard a 38’ private …More

Likely to Sell Out
Likely to Sell Out

Ready to explore Sunset Charter with drinks and Music? aboard a luxurious private boat charter, accommodating up to 13 guests. Sailing aboard a 38’ private...

2 to 4 hours Free Cancellation
5.0 (2)
from
$899
Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

Likely to Sell Out
Likely to Sell Out

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$49
Summertime Morning Swim in the Florida Keys Catamaran

Start your day with a soothing adventure aboard Island Girls Excursions' 53-foot catamaran. The Summertime Morning Swim is a family-friendly experience designed to immerse you …More

Likely to Sell Out
Likely to Sell Out

Start your day with a soothing adventure aboard Island Girls Excursions' 53-foot catamaran. The Summertime Morning Swim is a family-friendly experience designed to immerse you...

3 hours Free Cancellation
5.0 (1)
from
$96
Sharkeys Glass Bottom Fish Feeding LED Night Tour Key West

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point …More

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$62
Hemingway Tour

You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street). …More

4.7 (13)

Hemingway Tour

You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street)....

1 hour 5 minutes Free Cancellation
4.7 (13)
from
$69
2-Hour Live Music Guided Tour in Key West

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for …More

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for...

2 hours Free Cancellation
5.0 (20)
from
$35
Dry Tortugas National Park Day Trip by Luxury Private Boat

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury …More

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury...

8 hours Free Cancellation
4.9 (10)
from
$250
Florida Keys Backcountry Eco Tour from Big Pine Key

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands …More

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands...

2 hours Free Cancellation
5.0 (35)
from
$399
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
Private Fishing Charter Florida Keys

Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone …More

Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone...

4 hours Free Cancellation
5.0 (9)
from
$800
A Snorkel Tour with a Twist of History, Marathon, Florida Keys

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat …More

Likely to Sell Out
Likely to Sell Out

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat...

3 hours Free Cancellation
5.0 (1)
from
$70
Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while …More

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while...

1 hour 30 minutes Free Cancellation
5.0 (8)
from
$460
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the …More

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours Free Cancellation
5.0 (13)
from
$599
Private Marathon Reef Fishing Charters

Explore the productive reefs of the Florida Keys on a private Marathon reef fishing charter into the Atlantic. Marathon provides convenient access to an incredible …More

Explore the productive reefs of the Florida Keys on a private Marathon reef fishing charter into the Atlantic. Marathon provides convenient access to an incredible...

4 hours Free Cancellation
5.0 (33)
from
$183
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