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

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 166 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (143)
Best fishing trip ever !
Best fishing trip ever !
Best fishing trip ever !
+140
Angler rating
153
4
4
0
0
Anglers claimed
Good experience
97%
Friendly captain
100%
Recommend this charter
93%
Appropriate for children
99%
Satisfied with the boat
100%
Caught fish
93%
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Showing:
5 of 166 reviews
Shawn A.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Awesome trip!

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on March 7, 2025
Captain Bobby and 1st mate Mark were unbelievably awesome!ย  We caught a couple of tuna!ย  Both Bobby and Mark were knowledgeable...
Shawn A. recommends Happy Day Charters
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1 person finds this review helpful
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Shawn A. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

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   NEW  Half Day Trip โ€“ 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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Brian S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great family experience

VERIFIED   Half Day Trip โ€“ Deep Sea (PM) on July 25, 2024
We recently had the pleasure of going on a deep-sea fishing charter with Captain Bobbie in the beautiful waters of the Cayman...
Brian S. recommends Happy Day Charters
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2 persons find this review helpful
You and 2 people found this review helpful
Brian S. recommends Happy Day Charters
Mark review as helpful
2 persons find this review helpful
You and 2 people found this review helpful

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   NEW  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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Norm W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Good Fun!

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on July 21, 2024
Captain Bobby and asst CJ were on top of things constantly making sure hooks were sufficiently baited and locating fish that...
Norm W. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Norm W. recommends Happy Day Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful