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
(179 reviews)
West Bay
 Last booking: 7 hours ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 179 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (157)
Wonderful day on the water!
Wonderful day on the water!
Great family fishing trip
+154
Angler rating
165
5
4
0
0
Anglers claimed
Good experience
96%
Friendly captain
100%
Recommend this charter
93%
Appropriate for children
99%
Satisfied with the boat
100%
Caught fish
92%
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Showing:
5 of 179 reviews
Jeremy T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great time!

VERIFIED   Half Day Trip – Deep Sea (AM) on April 7, 2025
We had an amazing experience with Captain Bobby and Travis! They were both friendly, knowledgeable, and made sure we were comfortable...
Jeremy T. recommends Happy Day Charters
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Jeremy T. recommends Happy Day Charters
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Erich L.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Day Fishing

VERIFIED   Half Day Trip – Reef Fishing (AM) on February 4, 2025
5 of us when fishing with Captain Bobby and Travis. The wind and waves we’re rough that day, so we went reef fishing and...
Erich L. recommends Happy Day Charters
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Erich L. recommends Happy Day Charters
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Clinton G.
Excellent
4.7 / 5
Experience:
Very good
4.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic Fishing Trip with Happy Day Charters

VERIFIED   Half Day Trip – Deep Sea (AM) on July 23, 2024
My sons and I recently went on a fishing trip with Happy Day Charters, and I have to say it was a great fishing experience!...
Clinton G. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Clinton G. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

Robert K.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Wonderful day on the water!

VERIFIED   NEW  Half Day Trip – Deep Sea (AM) on July 14, 2025
Captain and helper were personable and the boat was great. We each caught a fish and had fun reeling them in. Would definitely...
Robert K. recommends Happy Day Charters
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Robert K. recommends Happy Day Charters
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Mark C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Terrific Family Fishing Charter

VERIFIED   Half Day Trip – Reef Fishing (AM) on June 1, 2025
Captain Bobby and Travis were truly exceptional. It was our 8 year Old and 3 year olds first fishing trip and captain bobby...
Mark C. recommends Happy Day Charters
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Mark C. recommends Happy Day Charters
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