Sunset & Dinner Cruises in Key West
18 boats available
The best out of 18 boat rental deals in Key West - enter dates to check availability
Top Sunset & Dinner Cruises in Key West
Key West: 18 boats available
Kilo Whiskey Charters - Sunset and Snorkeling
Key West • 33 ft • 6 persons
3 Hour Trip – Sunset Harbor Tour
3 hour trip • starts at 05:30 PM
Welcome to Kilo Whiskey Charters, the premier destination for unforgettable aquatic adventures in the pristine waters of Key West, Florida. 3 Hour Trip – Sunset Harbor Tour
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2 adults • 0 children
US $500
US $500
Sandbar/Snorkel/ Dolphins/Sunset Trips
Key West • 27 ft • 6 persons
Step aboard a beautifully restored 1985 SeaVee Ocean Center Console, meticulously updated in 2010, and get ready for an unforgettable adventure.
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trips fromUS $350
Tiki Boat Adventures - Key West
Key West • 20 ft • 6 persons
2 Hour Trip – Sunset Cruise
2 hour trip • starts at 06:00 PM
Ditch the ordinary and immerse yourself in a tropical escape with Tiki Boat Adventures in Key West! "What fun and relaxing way to spend a few hours out in the water!" — Susie, 2 Hour Trip – Sunset Cruise
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2 adults • 0 children
US $425
US $425
Key West Boating Connection
Stock Island • 22 ft • 4 persons
3 Hour – Sunset Trip
3 hour trip • starts at 05:30 PM
Key West Boating Connection offers intimate and customizable trips on their 22-foot Lake and Bay Inshore center console boat, perfect for groups of up to 4 passengers. 3 Hour – Sunset Trip
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2 adults • 0 children
US $400
US $400
Blind Squirrel Charters
Stock Island • 63 ft • 38 persons
3 Hour Trip – Burial At Sea
3 hour trip • starts at 06:00 PM
Blind Squirrel Charters is a 2000 custom built sportfish based out of Stock Island. 3 Hour Trip – Burial At Sea
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2 adults • 0 children
US $1,650
US $1,650
Outta Line Charters
Stock Island • 23 ft • 5 persons
Sunset Sandbar Trip
2 hour trip • starts at 06:00 PM
Discover the ultimate adventure with Outta Line Charters, a sleek 2024 Contender 21 Open Center Console based in Stock Island. "We booked a last minute cruise with Armani & he gave us lots of good information to decide on the best day for us weather wise & he was spot on!" — Terri, Sunset Sandbar Trip
Instant confirmation
2 adults • 0 children
US $400
US $400
SeaEO I – Key West
Stock Island • 38 ft • 13 persons
2 Hr – Boating Adventure
2 hour trip • starts at 08:00 AM
Experience the ultimate adventure on the 2021 Axopar 37 XC, a sleek and versatile vessel based in Stock Island. 2 Hr – Boating Adventure
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2 adults • 0 children
US $799
US $799
Purple Heron Charters
Key West • 18 ft • 3 persons
Step aboard Purple Heron Charters for a personalized adventure on the water in Key West.
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trips fromUS $475
Live Like a Local, Off the Beaten Path
Stock Island • 21 ft • 3 persons
Sandbar Like a Local, 2.5HR, 1PM
2 hour trip • starts at 01:00 PM
Key West Custom Boat Charter – Sandbar, Snorkeling, Eco Tours, Lobstering, and More!
Sandbar Like a Local, 2.5HR, 1PM
Instant confirmation
2 adults • 0 children
US $449
US $449
Choose Your Excursion Aboard the Dauntless
Stock Island • 32 ft • 6 persons
Custom Combo Trip - 4hrs AM
4 hour trip • starts at 08:00 AM
Private Boat Charters – Adventure, Relaxation & Celebration on the Water! Custom Combo Trip - 4hrs AM
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2 adults • 0 children
US $850
US $850
Strawhat Charters
Key West • 32 ft • 6 persons
Embark on an unforgettable journey aboard Strawhat Charters, a beautifully restored 2006 Intrepid 323 Center Console (refurbished in 2024), departing from the vibrant shores of Key West.
trips fromUS $850
Goliath Charters
Cudjoe Key • 25 ft • 6 persons
1 Hour Trip – Sunset On The Water
1 hour trip • starts at 05:00 PM
Meet Captain Craig, a fishy dude who’s been fishing his whole life. 1 Hour Trip – Sunset On The Water
Instant confirmation
2 adults • 0 children
US $40
US $40
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