Captain
Bobby Rose

Member since August 2019 West Bay, Cayman Islands
Background
Owner and Operator Bobby Rose has been fishing the beautiful Grand Cayman waters since 2005. He's passionate about fishing and guiding his clients through the Cayman Islands and introducing them to the world-class fisheries that this region has to offer. Having worked with some incredible anglers throughout the years, Capt. Bobby knows the Cayman waters extremely well. Whether you're a novice or professional angler, he'll make sure you enjoy your trip, create memories, and come back again for another exciting adventure!
Techniques
Depending on your wishes, Captain Bobby will guide you to your preferred catch. Of course, this depends on the time of year and which fish are running at the time. He typically targets Blue Marlin, Wahoo, Mahi Mahi, Snapper, Tuna, and many other species. It's common to cast lines as close as 1 or 2 miles from the shore, about 12 miles out. Happy Day Charters strives to meet the needs of all anglers and are prepared to help you with all types of tackle, fishing inshore or offshore for big game. Please note, all Billfish and any smaller species will be strictly caught and released.

Hey, I'm Captain Bobby Rose

West Bay, Cayman Islands
Background
Owner and Operator Bobby Rose has been fishing the beautiful Grand Cayman waters since 2005. He's passionate about fishing and guiding his clients through the Cayman Islands and introducing them to the world-class fisheries that this region has to offer. Having worked with some incredible anglers throughout the years, Capt. Bobby knows the Cayman waters extremely well. Whether you're a novice or professional angler, he'll make sure you enjoy your trip, create memories, and come back again for another exciting adventure!
Techniques
Depending on your wishes, Captain Bobby will guide you to your preferred catch. Of course, this depends on the time of year and which fish are running at the time. He typically targets Blue Marlin, Wahoo, Mahi Mahi, Snapper, Tuna, and many other species. It's common to cast lines as close as 1 or 2 miles from the shore, about 12 miles out. Happy Day Charters strives to meet the needs of all anglers and are prepared to help you with all types of tackle, fishing inshore or offshore for big game. Please note, all Billfish and any smaller species will be strictly caught and released.

My Charter Listing

Excellent
4.9 / 5
(186 reviews)
West Bay
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 186 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (175)
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+172
Angler rating
171
6
4
0
0
Anglers claimed
Good experience
96%
Friendly captain
100%
Recommend this charter
94%
Appropriate for children
99%
Satisfied with the boat
100%
Caught fish
92%
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Showing:
5 of 186 reviews
Patrick S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing dream comes true!

VERIFIED   Full Day Trip โ€“ Deep Sea on June 11, 2025
We checked off a bucket list goal today and caught a blue marlin! Without Captain Bobbyโ€™s maneuvering of the boat and the...
Patrick S. recommends Happy Day Charters
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Patrick S. recommends Happy Day Charters
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Mark P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic!!!!

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on December 10, 2024
I donโ€™t normally comment online but I feel compelled to do so this time. Bobby is one of the nicest people we have...
Mark P. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Mark P. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

Daniel T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great time, great crew

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (PM) on July 21, 2025
While the weather impacted our haul, we managed one Tuna and two Barracuda, one which was huge. Then a great time at Stingray...
Daniel T. recommends Happy Day Charters
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Daniel T. recommends Happy Day Charters
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Keely B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Best fishing trip ever !

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on June 3, 2025
Captain Bobby and crew were exceptionally great. We have visited the Caymans since 2018 almost yearly and this is the best...
Keely B. recommends Happy Day Charters
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Keely B. recommends Happy Day Charters
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Brandon B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Wonderful Wahoo!

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on July 20, 2025
We had a great time deep sea fishing with this crew. Landed a good Wahoo and, at the recommendation of the captain, ate the...
Brandon B. recommends Happy Day Charters
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Brandon B. recommends Happy Day Charters
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