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
(192 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 192 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (188)
We had a great time!
We had a great time!
Excellent!
+185
Angler rating
177
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 192 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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2 persons find this review helpful
You and 2 people found this review helpful
Shawn A. recommends Happy Day Charters
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2 persons find this review helpful
You and 2 people found this review helpful

Valorie D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

We had a great time!

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on September 18, 2025
Bobby and Travis were the BEST!ย  We caught a lot of fish. They have a great set up and cleaned our fish to take back home...
Valorie D. recommends Happy Day Charters
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Valorie D. recommends Happy Day Charters
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Tami H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Excellent!

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (PM) on September 15, 2025
Captain Bobby and Travis were a perfect fit for us!ย  They were knowledgeable,ย  friendly and very accommodating!ย  This is...
Tami H. recommends Happy Day Charters
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Tami H. recommends Happy Day Charters
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Michael G.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great family fishing trip

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on June 23, 2025
We enjoyed our morning fishing trip with Captain Bobby. We caught several trigger fish and barracuda. It was a laid back and...
Michael G. recommends Happy Day Charters
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Michael G. recommends Happy Day Charters
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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   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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