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
(216 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 216 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (213)
Fishing with Bobby
Fishing with Bobby
Fishing with Bobby
+210
Angler rating
201
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 216 reviews
Kate M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Super Day! On the fish.

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on May 15, 2025
Bobby and Travis worked very hard to get us on the fish and succeeded.ย  They are a great team and Iโ€™d recommend anyone to...
Kate M. recommends Happy Day Charters
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Kate M. recommends Happy Day Charters
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Wendy R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Much more than we expected

VERIFIED   Half Day Trip โ€“ Reef Fishing (PM) on March 16, 2025
Super time with Bobby and Travis.ย  We caught lots of fish, learned tons of great interesting ecological facts, and it was...
Wendy R. recommends Happy Day Charters
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Wendy R. recommends Happy Day Charters
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Michael O.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Captain

VERIFIED   Half Day Trip โ€“ Deep Sea (PM) on December 30, 2025
Fun, safe, & Outstanding Day!
Michael O. recommends Happy Day Charters
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Michael O. recommends Happy Day Charters
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Amy M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Reef fishing

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on November 30, 2025
kids loved fishing with Bobby and Travis!
Amy M. recommends Happy Day Charters
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Amy M. recommends Happy Day Charters
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Daniel B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Wonderful

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on June 2, 2025
Bob and his mate were great. Did some trolling without any luck , but stopped at a reef and caught some nice trigger fish....
Daniel B. recommends Happy Day Charters
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Daniel B. recommends Happy Day Charters
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