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
(192 reviews)
West Bay
 2 bookings in the past week.
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 192 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (188)
We had a great time!
We had a great time!
Excellent!
+185
Angler rating
177
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 192 reviews
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   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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Joseph U.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fun Day!

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on June 25, 2025
Capt Bobby made the experience special. From explaining the Cayman waters to finding the fish, Capt was spot on!ย  Also, we...
Joseph U. recommends Happy Day Charters
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Joseph U. recommends Happy Day Charters
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Mike P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great day on the Ocean

VERIFIED   Trip for Mike on August 28, 2025
Captain Bobby and his first mate were extremely knowledgeable. My son and I had never been on a charter before and had a wonderful...
Mike P. recommends Happy Day Charters
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Mike P. 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   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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Jeremy O.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Deep Sae

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on June 24, 2025
Rough day on the water in terms of catching a lot of fish but the Captain and First Mate never gave up and ended up landing...
Jeremy O. recommends Happy Day Charters
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Jeremy O. recommends Happy Day Charters
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