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Cruises and boat trips in Key West

Free cancellation
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
2 hr4.74k reviewsMallory Square
from$75
Free cancellation
Key West Sunset Cruise: Dinner, Live Music & Drinks Included
2 hr4.32k reviewsFlorida Keys National Marine Sanctuary
from$93
Free cancellation
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
2 hr4.91k reviews
from$135
Free cancellation
Key West Dolphin Watch and Snorkel Tour - Eco Adventure
3 hr4.71k reviewsFlorida Keys National Marine Sanctuary
from$73
Free cancellation
Key West Sunset Sail with Live Music, Drinks and Appetizers
2 hr4.61k reviewsMallory Square
from$73
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
2 hr4.91k reviews
from$109
Free cancellation
Sunset Sail in Key West with Beverages Included
1 hr, 30 min4.9(989)Mallory Square
from$79
Free cancellation
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
2 hr4.9(893)Mallory Square
from$123
Free cancellation
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
2 hr, 30 min4.6(767)Mallory Square
from$80
Free cancellation
Key West Reef Morning Snorkeling with Breakfast and Mimosas
3 hr4.5(739)
from$54
Free cancellation
Key West Glass-Bottom Boat Tour with Sunset Option
2 hr3.9(617)
from$64
Free cancellation
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
4 hr4.9(596)Key West Historic District
from$143
Likely to sell outFree cancellation
Key West Champagne Sunset Catamaran Cruise
1 hr, 30 min4.7(596)Mallory Square
from$43
Free cancellation
Key West Reef Snorkel & Sail Adventure
3 hr4.7(569)
from$79
Free cancellation
Key West Afternoon Reef Snorkeling with Open Bar
3 hr4.5(489)
from$59
Shallow Water Snorkeling and Dolphin Watching in Key West
4 hr4.6(476)Key West Historic District
from$109
Free cancellation
Key West Signature Sunset Sail with Live Music, Open Bar & Food
2 hr4.5(418)
from$77
Free cancellation
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
3 hr4.4(397)
from$57
Free cancellation
Key West Dolphin and Snorkel Experience
3 hr4.4(373)Florida Keys National Marine Sanctuary
from$70
Free cancellation
Key West Sunset Sail Aboard Legendary Schooner Appledore
2 hr5.0(368)Mallory Square
from$89
Free cancellation
Sunset Sail Cruise in Key West
2 hr4.9(296)
from$102
Free cancellation
Classic Key West Schooner Sunset Sail with Full Open Bar
2 hr4.9(277)Mallory Square
from$109
Free cancellation
Key West Sailing & Snorkeling: A Reef Adventure
3 hr4.7(250)Key West Historic District
from$79
Free cancellation
Sunset Cruise
2 hr5.0(243)
from$89
Free cancellation
Key West's Favorite Afternoon Dolphin Sail
2 hr, 30 min4.5(219)Key West Historic District
from$50
Free cancellation
Key West Day Sail on Schooner America 2.0 with 2 Drinks
1 hr, 30 min4.9(213)Mallory Square
from$79
Free cancellation
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
3 hr4.7(210)Florida Keys National Marine Sanctuary
from$75
Free cancellation
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
3 hr4.7(209)
from$55
Free cancellation
Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
4 hr, 30 min5.0(208)Sand Key Reef
from$156
Free cancellation
Key West Sandbar Safari on One of a Kind Tiki Boat
3 hr, 30 min4.7(197)Key West Historic District
from$140
Free cancellation
Key West Mini Catamaran Eco Tour
1 hr, 30 min4.6(195)
from$285
Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar
2 hr4.9(185)
from$65
Free cancellation
Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure
2 hr4.8(176)Mallory Square
from$81
Free cancellation
Key West Historic Schooner When And If Sunset Cruise
2 hr4.8(144)Florida Keys National Marine Sanctuary
from$117
Free cancellation
Key West Kayak Rental
2 hr4.8(130)
from$40
Free cancellation
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
5 hr4.9(114)Key West Historic District
from$119
Free cancellation
Schooner Appledore Day Sail with Full Bar in Key West
2 hr4.9(113)Mallory Square
from$49
Free cancellation
Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat
2 hr4.8(68)Mallory Square
from$457
Free cancellation
Private Sunset Cruise around Key West
2 hr5.0(67)Mallory Square
from$400
Free cancellation
Cruisin Tikis Marathon - Sunset Tiki Cruise
2 hr5.0(60)
from$99
Free cancellation
Key West: Sunset Sail + Reef Snorkel & Sandbar
4 hr, 30 min5.0(56)Sand Key Reef
from$143
Private Key West Sunset Sail
2 hr4.7(52)Mallory Square
from$695
Free cancellation
Dolphin Watching Key West and Snorkeling
3 hr4.9(49)
from$149
Free cancellation
Day Sailing Adventure in the Florida Marine Sanctuary
3 hr5.0(45)Florida Keys National Marine Sanctuary
from$120
Free cancellation
Key West Dolphin Watch and Sunset Sail on Catamaran
3 hr4.7(43)
from$117
Free cancellation
Private Key West Sandbar and Paddle by Boat
3 hr, 30 min4.9(41)
from$600
Free cancellation
Key West Low Country Seafood Two Stop Snorkel Adventure
4 hr4.6(39)Key West Historic District
from$80
15% offFree cancellation
Florida Keys Sunset Cruise with Champagne Toast and Seafood
2 hr5.0(36)
from~~$85~~$72
Free cancellation
Half Day Private Boat Charter Key West: Dolphin, Snorkel, Sandbar
4 hr4.9(35)
from$966
Free cancellation
Key West Private 6-Person Sandbar & Snorkeling Charter
4 hr5.0(32)
from$749
Free cancellation
Sandbar, Snorkel, and Sunset Sail in Key West
5 hr4.7(29)
from$135
Free cancellation
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
2 hr5.0(28)
from$102
Free cancellation
Key West Ultimate Beach Pass with Parasailing
8 hr3.9(27)Smathers Beach
from$107
Free cancellation
Key West Private Luxury Charter Rental: Boat Tour with Captain
2–8 hr4.7(24)Mallory Square
from$899
Key West Private Charter: Sandbar and Snorkeling
4 hr5.0(19)
from$950
Free cancellation
Private 90-Minute Harbor Sailing Charter in Key West
1 hr, 30 min4.9(19)
from$425
15% offFree cancellation
Sandbar Adventure Cruise in the Florida Keys
4 hr4.8(18)
from~~$102~~$87
Free cancellation
Key West's Locals' Top Sandbar and Sailing Experience
5 hr4.3(16)
from$193
Key West Wreckers Race Aboard Schooner America 2.0
3 hr4.9(15)Mallory Square
from$116
Free cancellation
Key West: Dolphin Watching cruise & Snorkeling unlimited beer & soda
3 hr4.0(14)Key West Historic District
from$90
Free cancellation
Island Sandbar Tour Catamaran Cruise in Marathon FL
4 hr4.7(12)
from$130
Champagne Dolphin Sail and Reef Snorkel
3 hr4.6(11)
from$109
Free cancellation
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
2 hr5.0(10)
from$599
Free cancellation
Key West Nighttime Full Moon Sail
1 hr, 30 min5.0(10)
from$84
Free cancellation
Ultimate Key West Day: Dolphin & Snorkel Combo with Sunset Sail
6 hr3.3(8)
from$190
Free cancellation
Experience Florida Keys Boat Charter Private Tour
1 hr, 30 min5.0(6)
from$460
Free cancellation
Key West Christmas Cruise with Live Band and Drinks
1 hr, 30 min5.0(6)
from$98
Free cancellation
Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL
2 hr5.0(6)
from$89
Free cancellation
Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music
2 hr4.2(5)
from$120
Free cancellation
Key West Center Console Boat Rental With Sound and Seat Upgrade
4 hr5.0(4)
from$475
Free cancellation
Private Afternoon Snorkel with Sunset Sail in Key West
4 hr5.0(4)
from$995
Free cancellation
Half Day Luxury Boat Tour in Key West with Snorkeling
4 hr5.0(3)Southernmost Point of the Continental USA
from$700
Free cancellation
Key West Culinary and Catamaran Reef Tour Experience
4 hr3.7(3)Key West Historic District
from$80
Free cancellation
2 HR Key West Clear Kayak Rental – Discover Mangroves & Wildlife!
2 hr5.0(2)
from$50
Free cancellation
Key West 3-Hour Private Dolphin-Watching Boat Charter
3 hr5.0(2)
from$895
Free cancellation
Dolphin Watch, Snorkel, Open Bar & 1 Day Hop-On Hop-Off
1 day5.0(1)
from$150
Free cancellation
Tropical Drift - A Key West Sunset Cruise
2 hr5.0(1)
from$350
Free cancellation
Private Sunset Sail in Key West Florida
2 hr5.0(1)
from$750
15% offFree cancellation
Summertime Morning Swim in the Florida Keys Catamaran
3 hr5.0(1)
from~~$96~~$82
Free cancellation
Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
5 hr3.0(1)
from$160
Key West: Nautic Star 21 Ft Speed Boat 21ft 115 Horse Power Speedboat-6 Pass
4 hr
from$750
Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
2 hrKey West Historic District
from$130
Free cancellation
Key West Boat Rental with Seat, Sound and Fishing Upgrades
4 hr
from$475
Free cancellation
Key West Private Wildlife Refuge Eco Boat Tour
3 hr
from$995
Florida Keys Private Luxury Yacht Charter with Overnight Stay
4 days
from$4,500
Free cancellation
Key West Clothing-Optional Private Sandbar & Snorkeling Charter
6 hr
from$1,295
Free cancellation
Key West Private Bachelorette Yacht Party Cruise
6 hr
from$1,670
Free cancellation
Key West Private Sandbar, Snorkeling & Sunset Charter
6 hr
from$1,795
30% offFree cancellation
Marathon Seven Mile Bridge Sunset Cruise Tour
1 hr, 30 min
from~~$117~~$82
Free cancellation
Key West Custom Charter: Snorkel, Sandbar Sightseeing
4 hrFlorida Keys National Marine Sanctuary
from$1,050
Free cancellation
25' Cobia Center Console Boat Rental
1 day
from$475
Free cancellation
24' Hurricane Sundeck Boat Rental
1 day
from$350
Free cancellation
21' Hurricane Sundeck Boat Rental
1 day
from$300
Free cancellation
Full Day Kayak Rental in Key West
8 hr
from$40

See all 268 experiences in Key West

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