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
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

Ryan M.
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   NEW  Half Day Trip โ€“ Reef Fishing (PM) on September 23, 2025
We went reef fishing and to Stingray City. It was my 5-year-old daughterโ€™s first time fishing and we had a blast! Captain...
Ryan M. recommends Happy Day Charters
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Ryan M. 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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Seneca T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great afternoon at Stingray City and reef fishing

VERIFIED   Half Day Snorkel/Stingray PM on June 26, 2025
Captain Bobby and Travis were great!ย  We went to Stingray city and Captain Bobby and Travis got us up close and personal with...
Seneca T. recommends Happy Day Charters
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Seneca T. recommends Happy Day Charters
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William W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

The best on the island!

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on June 19, 2025
These guys are amazing!ย  Very knowledgeable and ran the spread correctly. We fish the OC MD tournaments every year (White...
William W. recommends Happy Day Charters
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William W. recommends Happy Day Charters
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