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
(186 reviews)
West Bay
 Last booking: 4 days ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 186 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (175)
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+172
Angler rating
171
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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5 of 186 reviews
Joseph P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Stop scrolling! You found himโ€ฆ

VERIFIED   NEW  Half Day Snorkel/Stingray AM on July 30, 2025
Bobby Rose and crew are simply the best. We had an amazing charter and Bobby is one of the most kind, thoughtful and customer-focused...
Joseph P. recommends Happy Day Charters
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Jeffrey W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

April fishing trip

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on April 29, 2025
ย  ย  We booked a reef fishing tour for four hours. My wife and children (all < 10 years old) had a great time. The larger...
Jeffrey W. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Jeffrey W. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

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

Wouldn't fish with anyone else.

VERIFIED   Half Day Trip โ€“ Deep Sea (PM) on April 16, 2025
Capt. Bobby and his First Mate Travis were spectacular!! Ocean was rough needed to stay within the bay and do reef fishing....
James S. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
James S. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

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
You and 1 other person found this review helpful
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

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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1 person finds this review helpful
You and 1 other person found this review helpful
Laura A. recommends Happy Day Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful