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

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 215 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (213)
Fishing with Bobby
Fishing with Bobby
Fishing with Bobby
+210
Angler rating
200
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
93%
Sort by:
Featured  
Showing:
5 of 215 reviews
Richard D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Bobby

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on March 2, 2026
Had a great time on the water today with Capt Bobby and Travis, they couldnโ€™t have treated us any nicer!
Richard D. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Richard D. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

Jay D.
Excellent
4.7 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Very good
4.0 / 5
Overall

Tough time on the water but caught fish

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on February 12, 2026
Had an awesome time, caught some barricades and a rainbow flyer, water was rough and weather wasnโ€™t ideal but had a great...
Jay D. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Jay D. recommends Happy Day Charters
Mark review as helpful
You 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
Mark review as helpful
You found this review helpful
Cody T. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

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
Mark review as helpful
You found this review helpful
Derek L. recommends Happy Day Charters
Mark review as helpful
You 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   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
Mark review as helpful
You found this review helpful
Ryan M. recommends Happy Day Charters
Mark review as helpful
You found this review helpful