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
(201 reviews)
West Bay
 Last booking: 3 hours ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 201 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
186
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 201 reviews
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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Kurt B.
Excellent
4.7 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Very good
4.0 / 5
Overall

4.5 out of 5!

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on March 31, 2025
Captain Bobby and Travis were awesome. Very friendly, knowledgeable and hospitable. My 10-year old son and I did a half day...
Kurt B. recommends Happy Day Charters
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Kurt B. recommends Happy Day Charters
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Amy M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Snorkeling

VERIFIED   Half Day Snorkel/Stingray AM on November 29, 2025
had a great time, my kids are very introverted and bobby and his first mate were able to show them a great time. would do this...
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Amy M. recommends Happy Day Charters
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Marie B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic experience!

VERIFIED   Half Day Trip โ€“ Deep Sea (AM) on July 25, 2025
Captain and crew were very attentive and caring, my family and i had a wonderful day on the water and caught delicious fish!
Marie B. recommends Happy Day Charters
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Marie B. recommends Happy Day Charters
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Joseph U.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fun Day!

VERIFIED   Half Day Trip โ€“ Reef Fishing (AM) on June 25, 2025
Capt Bobby made the experience special. From explaining the Cayman waters to finding the fish, Capt was spot on!ย  Also, we...
Joseph U. recommends Happy Day Charters
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Joseph U. recommends Happy Day Charters
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