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
(180 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 180 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (157)
Wonderful day on the water!
Wonderful day on the water!
Great family fishing trip
+154
Angler rating
165
6
4
0
0
Anglers claimed
Good experience
96%
Friendly captain
100%
Recommend this charter
93%
Appropriate for children
99%
Satisfied with the boat
100%
Caught fish
91%
Sort by:
Featured  
Showing:
5 of 180 reviews
Donald C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Excellent Trip

VERIFIED   Half Day Trip – Deep Sea (AM) on March 26, 2025
Did a half day with Captain Bobby. It was excellent. Caught fish, he and his first mate (Travis maybe his name escapes me and...
Donald C. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Donald C. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

John L.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Bobby and mate Travis are AWESOME!

VERIFIED   Half Day Snorkel/Stingray PM on March 25, 2025
Such a super trip for my wife and I!!! Awesome day on the water. Great snorkeling spots and Stingray City! For a small group/couple...
John L. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
John L. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

Norman E. F.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic Trip and Great Crew

VERIFIED   Half Day Trip – Reef Fishing (AM) on June 16, 2025
Bobby and Travis were a lot of fun. They took us to several different spots while reef fishing. We were not able to take any...
Norman E. F. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Norman E. F. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

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

Stingray City, Starfish Point and snorkeling.

VERIFIED   Half Day Snorkel/Stingray AM on June 10, 2025
Bobby and Travis are great. Took us to some great spots for snorkeling, stingray city and starfish point. We have a family...
Jared D. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Jared D. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

Matt M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Very enjoyable fishing trip

VERIFIED   Half Day Trip – Deep Sea (PM) on August 1, 2024
Capt. Bobby Rose and his mate Travis were great guides. They were engaging and friendly and made the trip very enjoyable overall....
Matt M. recommends Happy Day Charters
Mark review as helpful
You found this review helpful
Matt M. recommends Happy Day Charters
Mark review as helpful
You found this review helpful