Top things to do in Key West in Summer (Updated November 2026)

Key West, USA
142 Results
Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

Likely to Sell Out
Likely to Sell Out

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation
5.0 (10)
from
$89
Key West Boat Experience — Swim, Sip & Soak Up the Sun!

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a …More

Likely to Sell Out
Likely to Sell Out

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a...

4 hours Free Cancellation
4.9 (9)
from
$600
Island Sandbar Tour Catamaran Cruise in Marathon FL

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares …More

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares...

4 hours Free Cancellation
5.0 (9)
from
$130
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
Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll …More

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll...

1 hour 30 minutes Free Cancellation
5.0 (7)
from
$158
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 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
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
Private Sandbar Charter & Island Escape in Key West

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with …More

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with...

4 hours Free Cancellation
5.0 (2)
from
$800
Private Marathon Offshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and …More

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and...

4 hours Free Cancellation
5.0 (2)
from
$217
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
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
Key West Beach Elopement Intimate Wedding All Inclusive

Our beach elopement package is designed for couples who want a meaningful wedding experience without the stress an expense of planning a large celebration. Our …More

Our beach elopement package is designed for couples who want a meaningful wedding experience without the stress an expense of planning a large celebration. Our...

1 hour Free Cancellation
5.0 (1)
from
$1,350
Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering …More

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering...

4 days Free Cancellation
5.0 (1)
from
$40
Four Passenger Cart Rental

Our 4-passenger golf cart rentals are the perfect blend of convenience, fun, and flexibility for exploring Key West. With a smaller footprint than larger carts, …More

Our 4-passenger golf cart rentals are the perfect blend of convenience, fun, and flexibility for exploring Key West. With a smaller footprint than larger carts,...

1 to 7 days Free Cancellation
5.0 (1)
from
$134
Hire Photographer, Professional Photo Shoot - Key West

Professional photo shoot in unique Key West locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see …More

Professional photo shoot in unique Key West locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see...

4 hours Free Cancellation
5.0 (1)
from
$49
Key West Hop-On Hop-Off Trolley Tour

The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour …More

The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour...

1 hour 30 minutes Free Cancellation
4.6 (1,768)
from
$56
Key West Ghosts and Gravestones Trolley Tour

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the …More

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the...

1 hour Free Cancellation
4.4 (1,410)
from
$40
Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt

Unleash your inner ghost hunter! Embark on a spine-tingling 2-hour haunted walking tour through Bone Island's Old Town Key West. You'll first receive your commemorative …More

Unleash your inner ghost hunter! Embark on a spine-tingling 2-hour haunted walking tour through Bone Island's Old Town Key West. You'll first receive your commemorative...

2 hours Free Cancellation
4.5 (622)
from
$32
Ghosts of Key West: Haunted History Walking Tour

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost …More

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost...

1 hour 30 minutes Free Cancellation
4.6 (130)
from
$30
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