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
(238 reviews)
West Bay
 Last booking: 8 hours ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 238 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (224)
Great Time
Great Time
Capt. Bobby and Travis were great!
+221
Angler rating
223
6
4
0
0
Anglers claimed
Good experience
97%
Friendly captain
100%
Recommend this charter
95%
Appropriate for children
99%
Satisfied with the boat
100%
Caught fish
94%
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Showing:
5 of 238 reviews
Nicole H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Time

VERIFIED   NEW  Half Day Trip โ€“ Deep Sea (AM) on May 29, 2026
We had a great time fishing. The fish werenโ€™t really biting, but Captain Bobby and his First Mate Travis were amazing. We...
Nicole H. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Nicole H. 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
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1 person finds this review helpful
You and 1 other person found this review helpful

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

Perfect afternoon!

VERIFIED   Half Day Trip โ€“ Deep Sea (PM) on January 3, 2026
Our family of 6 had a great afternoon deep sea fishing with Captain Bobby and Travis.ย  It took awhile for the fish to start...
Stephanie S. recommends Happy Day Charters
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Stephanie S. recommends Happy Day Charters
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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
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1 person finds this review helpful
You and 1 other person found this review helpful

Tim R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

SUPER FRIENDLY CREW!!

VERIFIED   NEW  Half Day Snorkel/Stingray PM on June 2, 2026
The crew on our trip were really friendly and extremely knowledgeable about the wildlife and the island.ย  We were a family...
Tim R. recommends Happy Day Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Tim R. recommends Happy Day Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful