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

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 212 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (211)
Fishing with Bobby
Fishing with Bobby
Tough time on the water but caught fish
+208
Angler rating
197
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
93%
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Showing:
5 of 212 reviews
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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Norman E. F.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic Trip and Great Crew

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on June 16, 2025
Bobby and Travis were a lot of fun. They took us to several different spots while reef fishing. We were not able to take any...
Norman E. F. recommends Happy Day Charters
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Norman E. F. recommends Happy Day Charters
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Jared D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Stingray City, Starfish Point and snorkeling.

VERIFIED   Half Day Snorkel/Stingray AM on June 10, 2025
Bobby and Travis are great. Took us to some great spots for snorkeling, stingray city and starfish point. We have a family...
Jared D. recommends Happy Day Charters
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Jared D. recommends Happy Day Charters
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Chris W. J.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great captain and crew

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on November 26, 2025
Bobby was the most welcoming captain showed everyone how to fish.
Chris W. J. recommends Happy Day Charters
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Chris W. J. recommends Happy Day Charters
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Temple R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

July fishing trip

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on July 2, 2025
We had an amazing time with Captain Bobby. This was our second time with him and wonโ€™t be our last! We caught several fish...
Temple R. recommends Happy Day Charters
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Temple R. recommends Happy Day Charters
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