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
(181 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 181 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
166
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 181 reviews
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
Mark review as helpful
You found this review helpful
Kurt B. recommends Happy Day Charters
Mark review as helpful
You found this review helpful

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 โ€“ 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 โ€“ 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