Happy Day Charters
4.9/5 (229 reviews)
Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right, West Bay, Cayman Islands–
Happy Day Charters
4.9/5 (229 reviews)
Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right
West Bay, Cayman Islands
Happy Day Charters offers a number of excursions that cater to all levels of anglers. Whether you're a deep-sea 'finatic' or a beginner, each trip can be customized based on your preferences.
Captain Bobby Rose has been fishing the crystal waters of the Cayman Islands since 2005. Over the past years, he's gained a reputation as being one of the top choices for offshore fishing. With his charisma, passion, and knowledge, you and your family are guaranteed to have an amazing day on the water!
Your journey will take place on a 26' Pursuit center console, equipped with top-of-the-line navigational electronics, safety gear, and custom fishing tackle. You'll have a cover over you're head for shade and a multimedia system so you can bump your favorite tunes while you fish.
The boat also comes with a fighting chair, a private toilet, a cooler, and a comfortable deck that accommodates up to 6 guests. Children of all ages are welcome aboard and Capt. Bobby provides kids' size life jackets for them.
On full-day trips, you'll have the opportunity to explore a number of the hottest fishing spots of the Caribbean Sea. Some of these locations include 12 Mile Bank, North and South Wall, East End, and other deep trenches where lots of different types of fish congregate.
You'll target a plethora of species, including Marlin, Sailfish, Tuna, Mahi, Snapper, Wahoo, Barracuda, and more. On shorter trips, you'll be able to stay closer to shore and catch Tarpon, Bonefish, Triggerfish, Jack Crevalle, and other inshore species.
Top-quality custom tackle is provided, including snorkeling gear in case you'd like to take a dip. Capt. Bobby also provides biscuits, chips, and other quick snacks, as well as cold water and soda.
Happy Day Charters already has everything taken care of for you, including your fishing license. So just bring sunscreen, a hat, sunglasses, and a camera and get ready for an exciting adventure off the coast of the Cayman Islands!
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Drinks
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Drinks
Rating
4.9
229 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience
Anglers' gallery (217)
What anglers say
97%
Great experience
99%
Family friendly
100%
Friendly captain
100%
Good boat
95%
Recommended
93%
Caught fish
All reviews (229)
Filter
Sort by: Featured
Showing 1 – 5 of 229 reviews
Jillian Scott
Manitoba, Canada
•
Member since 2026
5.0
Verified
Absolutely Incredible Charter
Half Day Trip – Reef Fishing (PM) on April 2, 2026 • 2 adults • 2 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:
1
Stephanie Stecz
Chicago, IL, US
•
Member since 2024
5.0
Verified
Perfect afternoon!
Half Day Trip – Deep Sea (PM) on January 3, 2026 • 6 adults
Our family of 6 had a great afternoon deep sea fishing with Captain Bobby and Travis. It took awhile for the fish to start biting, but it was worth the wait! We caught a huge wahoo, a nice tuna, and a barracuda. Capt Bobby cut the fish for us and walked us over to Morgan's, where they prepared the most amazing dinner for us with our catch.
This was our first deep sea fishing experience, and we'll definitely do it again. We were lucky with perfect weather. The boat is comfortable, and Bobby and Travis were perfect guides - teaching us about the island and answering the many questions we asked.
I would highly recommend Happy Day Charters!
0
Blake Koen
Texas, US
•
Member since 2026
5.0
Verified
Amazing day with Captain Bobby
Half Day Trip – Reef Fishing (AM) on March 11, 2026 • 2 adults
What a fantastic experience. Boat was fantastic and comfortable and snacks and drinks were provided and the reef fishing was spectacular. Captain Bobby was punctual, super friendly, full of great conversation and most importantly defintelty knew where to put us on the fish! Very helpful with my son and even heped him reel in a shark (which was released once we realized what was reeled in). I will definitely hire him again when we return to the island and recommend him if anyone is looking for a great time. We caught a ton of fish and had a blast. 5 stars. Total pro!
Reported catch:
0
Andrew Culross
Michigan, US
•
Member since 2026
5.0
Verified
New
Captain Bobby was above and beyond.
Half Day Trip – Reef Fishing (PM) on May 6, 2026 • 2 adults • 1 child
Myself, my wife and our 5 year old went our with Captain Bobby reef fishing. it was just the 4 of us. He educated us, loaded our bait each time we needed, and helped our son have a blast. He was fantastic and genuinely fun. We caught a huge barracuda, Snapper, and lots of other smaller fish. He did a 5 star job and a pleasure to be with. The boat was clean and the experience was memorable.
Reported catch:
0
Christopher Hicks
Greenville, SC, US
•
Member since 2025
5.0
Verified
dont book anyone else ! Bobby is the real deal
Half Day Trip – Reef Fishing (AM) on April 10, 2026 • 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:
0
Trip availability and prices
Trip Date:
Days:
Group Size:
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May 2026
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Half Day Snorkel/Stingray AM
4 hour trip starts at 8:00 AM
US $750
Entire boat: up to 6 people
US $750
Entire boat: up to 6 people
Half Day Trip – Reef Fishing (AM)
4 hour trip starts at 8:00 AM
US $750
Entire boat: up to 6 people
US $750
Entire boat: up to 6 people
Half Day Snorkel/Stingray PM
4 hour trip starts at 1:00 PM
US $750
Entire boat: up to 6 people
US $750
Entire boat: up to 6 people
Half Day Trip – Reef Fishing (PM)
4 hour trip starts at 1:00 PM
US $750
Entire boat: up to 6 people
US $750
Entire boat: up to 6 people
Half Day Trip – Deep Sea (AM)
4 hour trip starts at 8:00 AM
US $800
Entire boat: up to 6 people
US $800
Entire boat: up to 6 people
Half Day Trip – Deep Sea (PM)
4 hour trip starts at 1:00 PM
US $800
Entire boat: up to 6 people
US $800
Entire boat: up to 6 people
Full Day Snorkel/Stingray
8 hour trip starts at 8:00 AM
US $1,500
Entire boat: up to 6 people
US $1,500
Entire boat: up to 6 people
Full Day Trip – Reef Fishing
8 hour trip starts at 8:00 AM
US $1,500
Entire boat: up to 6 people
US $1,500
Entire boat: up to 6 people
Full Day Trip – Deep Sea
8 hour trip starts at 8:00 AM
US $1,600
Entire boat: up to 6 people
US $1,600
Entire boat: up to 6 people
There are 24 people looking at this charter.
Rating
4.9
229 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience
Anglers' gallery (217)
What anglers say
97%
Great experience
99%
Family friendly
100%
Friendly captain
100%
Good boat
95%
Recommended
93%
Caught fish
All reviews (229)
Filter
Sort by: Featured
Showing 1 – 5 of 229 reviews
Jillian Scott
Manitoba, Canada
Member since 2026
5.0
Verified
Absolutely Incredible Charter
Half Day Trip – Reef Fishing (PM) on April 2, 2026 • 2 adults • 2 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:
1
Stephanie Stecz
Chicago, IL, US
Member since 2024
5.0
Verified
Perfect afternoon!
Half Day Trip – Deep Sea (PM) on January 3, 2026 • 6 adults
Our family of 6 had a great afternoon deep sea fishing with Captain Bobby and Travis. It took awhile for the fish to start biting, but it was worth the wait! We caught a huge wahoo, a nice tuna, and a barracuda. Capt Bobby cut the fish for us and walked us over to Morgan's, where they prepared the most amazing dinner for us with our catch.
This was our first deep sea fishing experience, and we'll definitely do it again. We were lucky with perfect weather. The boat is comfortable, and Bobby and Travis were perfect guides - teaching us about the island and answering the many questions we asked.
I would highly recommend Happy Day Charters!
0
Blake Koen
Texas, US
Member since 2026
5.0
Verified
Amazing day with Captain Bobby
Half Day Trip – Reef Fishing (AM) on March 11, 2026 • 2 adults
What a fantastic experience. Boat was fantastic and comfortable and snacks and drinks were provided and the reef fishing was spectacular. Captain Bobby was punctual, super friendly, full of great conversation and most importantly defintelty knew where to put us on the fish! Very helpful with my son and even heped him reel in a shark (which was released once we realized what was reeled in). I will definitely hire him again when we return to the island and recommend him if anyone is looking for a great time. We caught a ton of fish and had a blast. 5 stars. Total pro!
Reported catch:
0
Andrew Culross
Michigan, US
Member since 2026
5.0
Verified
New
Captain Bobby was above and beyond.
Half Day Trip – Reef Fishing (PM) on May 6, 2026 • 2 adults • 1 child
Myself, my wife and our 5 year old went our with Captain Bobby reef fishing. it was just the 4 of us. He educated us, loaded our bait each time we needed, and helped our son have a blast. He was fantastic and genuinely fun. We caught a huge barracuda, Snapper, and lots of other smaller fish. He did a 5 star job and a pleasure to be with. The boat was clean and the experience was memorable.
Reported catch:
0
Christopher Hicks
Greenville, SC, US
Member since 2025
5.0
Verified
dont book anyone else ! Bobby is the real deal
Half Day Trip – Reef Fishing (AM) on April 10, 2026 • 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:
0
FAQs about Happy Day Charters
The fish you can target
What is the boat like?
Boat category
Center console boats
Capacity
6 persons
Boat length
26 ft
Year built
1998
Restored in
2019
Boat manufacturer
Pursuit
Boat type
Center console
Engine model
Yanmar
Powered by
1 x 315HP
Max cruising speed
25 knots