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
(203 reviews)
West Bay
 Last booking: 6 days ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 203 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (199)
reef fishing
reef fishing
Happy Day Charter
+196
Angler rating
188
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 203 reviews
Nathan S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Fishing Trip

VERIFIED   NEW  Half Day Trip โ€“ Reef Fishing (AM) on January 2, 2026
This was the first guided fishing trip I took my kids on. Bobby and Travis were great. They had all the patience, while my...
Nathan S. recommends Happy Day Charters
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Nathan S. recommends Happy Day Charters
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Laura A.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Day

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on June 4, 2025
We took our two young kids on a 4 hr reef fishing trip with Bobby and Travis. Both were really great with our kids. We went...
Laura A. recommends Happy Day Charters
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Laura A. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

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

Fishing dream comes true!

VERIFIED   Full Day Trip โ€“ Deep Sea on June 11, 2025
We checked off a bucket list goal today and caught a blue marlin! Without Captain Bobbyโ€™s maneuvering of the boat and the...
Patrick S. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Patrick S. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

Cody T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

An Amazing Day on the Work and Play!

VERIFIED   Half Day Snorkel/Stingray PM on November 27, 2025
Bobby and his crew, Travis were great! They were kind, personable and very accommodatingโ€ฆmaking our trip to suit. Bobbyโ€™s...
Cody T. recommends Happy Day Charters
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Derek L.
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 โ€“ Deep Sea (AM) on November 13, 2025
Only caught a small Tuna but it was a quiet day for everyone. Had a great time trolling around and learning from Captain Bobby...
Derek L. recommends Happy Day Charters
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Derek L. recommends Happy Day Charters
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