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
(250 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 250 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (235)
Fishing with Bobby
Fishing with Bobby
Fishing with Bobby
+232
Angler rating
232
8
4
1
0
Anglers claimed
Good experience
96%
Friendly captain
100%
Recommend this charter
95%
Appropriate for children
98%
Satisfied with the boat
100%
Caught fish
93%
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Showing:
5 of 250 reviews
David N.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Bobby and Travis Were Stellar!

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on July 5, 2026
We had an outstanding day on the water with Captain Bobby and Travis from Happy Days Charters. From the moment we stepped aboard,...
David N. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
David N. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

Jillian S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Absolutely Incredible Charter

VERIFIED   Half Day Trip โ€“ Reef Fishing (PM) on April 2, 2026
We had an absolutely incredible day out on the water with Captain Bobby and his first mate Travis! From start to finish, they...
Jillian S. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Jillian S. recommends Happy Day Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful

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

Amazing day with Captain Bobby

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on March 11, 2026
What a fantastic experience.ย  Boat was fantastic and comfortable and snacks and drinks were provided and the reef fishing...
Blake K. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Blake K. recommends Happy Day Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful

Christopher H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Dont book anyone else ! Bobby is the real deal

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on April 10, 2026
everything was perfect from the start to finish - fishing , deckhandโ€™s experience, best captain in Cayman - you cant go wrong...
Christopher H. recommends Happy Day Charters
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Christopher H. recommends Happy Day Charters
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Nathaniel P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Father-Daughter fishing

VERIFIED   Half Day Trip โ€“ Reef Fishing (PM) on March 16, 2026
My husband and daughter spent the afternoon fishing with Captain Bobby Rose and his crew and had an awesome experience. ๐Ÿคฉ๐Ÿฅธ๐ŸŽฃThey...
Nathaniel P. recommends Happy Day Charters
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Nathaniel P. recommends Happy Day Charters
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