Sunset & Dinner Cruises in Islamorada
39 boats available
The best out of 39 deals in Islamorada - enter dates to check availability
Top Sunset & Dinner Cruises in Islamorada
Islamorada: 39 boats available
Island Ryder Charters
Islamorada • 23 ft • 6 persons
2 Hour Sunset Trip
2 hour trip • starts at 05:00 PM
Experience Islamorada Like Never Before!
There is no better way to immerse yourself in the natural beauty and vibrant marine life of Islamorada than by setting sail on a private charter. "Highest recommendation for Capt Jen! She was a great guide for a wonderful morning on the water for my wife and two daughters." — Zach, 2 Hour Sunset Trip
Instant confirmation
2 adults • 0 children
US $300
US $300
Islamorada Private Charters
Islamorada • 26 ft • 6 persons
SUNSET CRUISE
1 hour trip • starts at 04:00 PM
Islamorada Private Charters - Luxury Catamaran Experience (2019 Custom Build)
Set sail aboard the stunning Islamorada Private Charters, a custom-built 2019 catamaran offering an unforgettable adventure in the heart of the Florida Keys. "We booked our charter and as the day got closer we saw that it was supposed to be super windy." — Heather, SUNSET CRUISE
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2 adults • 0 children
US $295
US $295
Bamboo Charters
Islamorada • 25 ft • 6 persons
2 Hour - Private Charter Afternoon
2 hour trip • starts at 01:30 PM
Step aboard the 2022 Parker 25 SE Center Console, your gateway to the turquoise waters of the Florida Keys. "Matt was a great captain, allowed us to go to a quieter spot for snorkeling as it was a busy holiday weekend." — Christina, 2 Hour - Private Charter Afternoon
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2 adults • 0 children
US $350
US $350
Keys Aquatic Adventures
Islamorada • 25 ft • 6 persons
Uncover the Magic of Islamorada with Keys Aquatic Adventures!
"Captain Charlie is amazing! He asked us what type of experience we were looking for then took us to some beautiful spots." — David,
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trips fromUS $390
Nautical Tiki Islamorada
Islamorada • 23 ft • 6 persons
Private Charter Sunset cruise
1 hour trip • starts at 07:00 PM
Experience the ultimate island escape aboard the Nautical Tiki Islamorada, a stunning 2023 Beach Cat Tiki Catamaran, perfect for unforgettable adventures in the heart of Islamorada. "Captain Mervin was amazing! Great communication, and very accommodating." — Dana, Private Charter Sunset cruise
Instant confirmation
2 adults • 0 children
US $299
US $299
custom charters
Islamorada • 26 ft • 6 persons
Custom trip
6 hour trip • starts at 08:00 AM
custom charters is a 2017 Sea Fox 266 Center console based out of Islamorada. "We had a great time on the sandbar! The captain was amazing and helpful!" — Danielle, Custom trip
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2 adults • 0 children
US $700
US $700
Coral Sea Charters
Islamorada • 38 ft • 6 persons
1 Hour Trip – Sunset Cruise
1 hour trip • starts at 05:00 PM
Coral Sea Charters is a beautifully restored 1978 Harris Sportfish, reconditioned in 2016, offering a premium experience on the waters of Islamorada. 1 Hour Trip – Sunset Cruise
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2 adults • 0 children
US $400
US $400
First Choice Charters – Sunset Cruise
Islamorada • 37 ft • 6 persons
2 Hour – Sunset Cruise
2 hour trip • starts at 06:30 PM
Step aboard First Choice Sunset Cruise, a beautifully restored 1958 Merritt Sportfisher Sportfishing vessel, and experience the charm of classic craftsmanship paired with modern comforts. 2 Hour – Sunset Cruise
2 adults • 0 children
US $500
US $500
Wild Dolphin Tours
Islamorada • 25 ft • 6 persons
1 Hour – Sunset In The Bay
1 hour trip • starts at 06:30 PM
Set off on an unforgettable adventure with Wild Dolphin Tours aboard our sleek Sea Hunt Escape Center Console, located in the heart of Islamorada. 1 Hour – Sunset In The Bay
2 adults • 0 children
US $299
US $299
Deep Sea Scuba and Snorkeling
Islamorada • 27 ft • 6 persons
2 Hr – Private Tour (1-3 Guests) AM
2 hour trip • starts at 08:30 AM
Get ready for an unforgettable adventure aboard Deep Sea Scuba and Snorkeling, a beautifully restored 2001 Maycraft Pilot Pilothouse (refitted in 2024), departing from Islamorada. 2 Hr – Private Tour (1-3 Guests) AM
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2 adults • 0 children
US $350
US $350
KeyZ Charters
Islamorada • 21 ft • 6 persons
2 Hour – Sunset Eco Cruise
2 hour trip • starts at 05:30 PM
Set sail aboard KeyZ Charters, a 2005 Key West Oasis Deck boat located in the beautiful Islamorada, ready to offer you an unforgettable day on the water! 2 Hour – Sunset Eco Cruise
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2 adults • 0 children
US $400
US $400
Southern Tauk Charters
Tavernier • 23 ft • 6 persons
Southern Tauk Charters is a 2023 Sea Hunt Center console based out of Tavernier. "“What an incredible day on the water with Captain Mike! It was clear from the start that Mike knew all the lively and serene spots to hang out, have fun, and relax ." — BoatBooker Member,
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trips fromUS $450
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