Bobby Rose
Captain

Bobby Rose

West Bay, Cayman Islands
250+ reviews
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!

Charter

Rating

4.9
258 reviews
4.9
Boat & Equipment
5.0
Captain & Crew
4.9
Fishing Experience

What anglers say

96%
Good experience
100%
Friendly captain
96%
Recommend this charter
98%
Appropriate for children
100%
Satisfied with the boat
93%
Caught fish

All reviews (258)

Showing 15 of 258 reviews
  • David Noble
    David Noble
    us
    Florida, US
    Member since 2026
    5.0
    Verified

    Captain Bobby and Travis Were Stellar!

    Half Day Trip – Deep Sea (AM)3 adults

    We had an outstanding day on the water with Captain Bobby and Travis from Happy Days Charters. From the moment we stepped aboard, they were professional, friendly, knowledgeable, and made sure everyone had a fantastic time. They worked hard to put us on fish, and their passion for what they do really showed. The highlight of the trip came after we returned to the dock. Captain Bobby filleted the fish we caught and personally walked us over to Morgan’s Seafood Restaurant, where they prepared our fresh catch for us. Enjoying fish we had just caught only hours earlier was such a memorable experience and truly made the day extra special. If you’re looking for a first-class fishing charter in Grand Cayman with a crew that genuinely cares about providing an exceptional experience, look no further than Happy Days Charters. Captain Bobby and Travis exceeded our expectations in every way. Thank you both for an unforgettable day… we can’t wait to come back! ⭐⭐⭐⭐⭐

    Reported catch:
    Gray Triggerfish
    Mutton Snapper
  • Jillian Scott
    Jillian Scott
    ca
    Manitoba, Canada
    Member since 2026
    5.0
    Verified

    Absolutely Incredible Charter

    Half Day Trip – Reef Fishing (PM)4 adults2 children

    We had an absolutely incredible day out on the water with Captain Bobby and his first mate Travis! From start to finish, they were attentive, professional, and genuinely passionate about making sure we had the best experience possible. As a family of four, we were able to pack so much into our trip! Fishing, feeding turtles right from the boat (such a cool experience!), and even kissing stingrays at Stingray City. Bobby and Travis made everything easy and fun, taking the time to explain what we were seeing, identifying fish, and sharing great stories and local knowledge about the Cayman Islands. At Stingray City, they went above and beyond to make sure each of us felt comfortable and got the most out of the experience. Their energy, patience, and expertise really stood out. We have done charter trips before, but this was hands down the best one we have ever had. We can’t recommend Captain Bobby and Travis highly enough! If you’re thinking about booking, do it. You won’t regret it!

    Reported catch:
    Great Barracuda
  • Christopher Hicks
    Christopher Hicks
    us
    Greenville, SC, US
    Member since 2025
    5.0
    Verified

    dont book anyone else ! Bobby is the real deal

    Half Day Trip – Reef Fishing (AM)4 adults

    everything was perfect from the start to finish - fishing , deckhand’s experience, best captain in Cayman - you cant go wrong - family friends and very well organized- knowledgeable of the entire area and everyone was super happy at the end of the day - everything we caught was brought to morgans to hook em and cook em - couldn’t of been a better day - we will be back many times to go out with happy day / Bobby again , being from Tennessee we are very glad we chose this charter. thanks again Bobby and Carmen

    Reported catch:
    Gray Triggerfish
  • John Lynch
    John Lynch
    us
    New Jersey, US
    Member since 2026
    5.0
    Verified
    NEW

    Outstanding Day!

    Half Day Trip – Deep Sea (AM)2 adults

    Captain Bobby and VJ were fantastic. Extremely experienced, accomodating and friendly. We ended up catching Mackerel and several tuna which Bobby prepared for us. We had so much extra time that we stopped to snorkel at a shipwreck. I went with my wife but could easily make this a family outing or boys day fishing.

    Reported catch:
    Blackfin Tuna
  • Nicole Houser
    Nicole Houser
    us
    Illinois, US
    Member since 2026
    5.0
    Verified

    Great Time

    Half Day Trip – Deep Sea (AM)6 adults2 children

    We had a great time fishing. The fish weren’t really biting, but Captain Bobby and his First Mate Travis were amazing. We ended up getting at least one fish which made the kids day. They reached out to other boats to find out where the fish may be, but everyone struck out that day. Overall great experience and if we were to do it again, it would be with this charter. Super friendly, nice and knowledgeable not only about fishing but the islands as well.

    Reported catch:
    Great Barracuda

Real catches shared by our community

  • Happy Day Charters
    Happy Day ChartersWest Bay
    Fishing with Bobby
    Cece I.
    Cece I.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    2025 & 2026 Trips
    Elvin B.
    Elvin B.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Fishing with Bobby
    David W.
    David W.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Excellent experience!
    Luis E.
    Luis E.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Great Time
    Chad G.
    Chad G.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Capt. Bobby and Travis were great!
    Jeremy N.
    Jeremy N.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    The crew really made the experience.
    Amanda N.
    Amanda N.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Great time!
    Kyle S.
    Kyle S.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Fantastic!
    Tennille L.
    Tennille L.
  • Happy Day Charters
    Happy Day ChartersWest Bay
    Fishing with Bobby
    Richard D.
    Richard D.

What's biting with Happy Day Charters in West Bay

Top catches for September