Key West Cruises, Sailing & Water Tours

96 Results
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Key West Private Charters three years running. See the …More

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Key West Private Charters three years running. See the...

2 hours (approx.) Free Cancellation
5.0 (1,718)
from
$3,499
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
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
Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation
5.0 (4)
from
$1,070
Half Day Private Boat Charter Key West: Dolphin, Snorkel, Sandbar

Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches …More

Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches...

4 hours Free Cancellation
4.9 (35)
from
$966
Key West Private Charter: Sandbar and Snorkeling

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a …More

Likely to Sell Out
Likely to Sell Out

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a...

4 hours
5.0 (20)
from
$950
Key West 3-Hour Private Dolphin-Watching Boat Charter

This three-hour private Key West dolphin safari combines wildlife searching with the flexibility of a private boat charter. Rather than following a fixed group-tour route, …More

Likely to Sell Out
Likely to Sell Out

This three-hour private Key West dolphin safari combines wildlife searching with the flexibility of a private boat charter. Rather than following a fixed group-tour route,...

3 hours Free Cancellation
5.0 (2)
from
$895
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 Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation
5.0 (1)
from
$750
Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the …More

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the...

4 hours Free Cancellation
5.0 (22)
from
$700
Explore the Waters of Key West

Explore the vibrant & diverse underwater world of the Florida Keys with Salty Paws' Reef Snorkel Trip! Our experienced & knowledgeable crew will take you …More

Explore the vibrant & diverse underwater world of the Florida Keys with Salty Paws' Reef Snorkel Trip! Our experienced & knowledgeable crew will take you...

4 hours Free Cancellation
5.0 (15)
from
$700
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
Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours
4.9 (50)
from
$693
Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More

Likely to Sell Out
Likely to Sell Out

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$600
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
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 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 Sandbar Adventure in Key West Backcountry

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle …More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle...

3 hours Free Cancellation
5.0 (54)
from
$500
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
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
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

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