Happy Day Charters 

4.9/5 (237 reviews)
 Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right, West Bay, Cayman Islands

Happy Day Charters 

West Bay, Cayman Islands
26 ft
6
4.9/5 (237 reviews)

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!

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!

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Customer reviews

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Rating

4.9
237 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (222)

What anglers say

97%
Great experience
99%
Family friendly
100%
Friendly captain
100%
Good boat
95%
Recommended
94%
Caught fish

All reviews (237)

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Frequently mentioned
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Showing 15 of 237 reviews
Nicole Houser
Nicole Houser
us
Illinois, US
Member since 2026
0
5.0
Verified
New
Great Time
Half Day Trip – Deep Sea (AM) on May 29, 20264 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
Jillian Scott
Jillian Scott
ca
Manitoba, Canada
Member since 2026
1
5.0
Verified
Absolutely Incredible Charter
Half Day Trip – Reef Fishing (PM) on April 2, 20262 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
Stephanie Stecz
Stephanie Stecz
us
Chicago, IL, US
Member since 2024
0
5.0
Verified
Perfect afternoon!
Half Day Trip – Deep Sea (PM) on January 3, 20266 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!
Blake Koen
Blake Koen
us
Texas, US
Member since 2026
1
5.0
Verified
Amazing day with Captain Bobby
Half Day Trip – Reef Fishing (AM) on March 11, 20262 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:
Great Barracuda
Yellowtail Snapper
Gray Triggerfish
Tim Reeves
Tim Reeves
us
Tennessee, US
Member since 2026
0
5.0
Verified
New
SUPER FRIENDLY CREW!!
Half Day Snorkel/Stingray PM on June 2, 20262 adults1 child
The crew on our trip were really friendly and extremely knowledgeable about the wildlife and the island. We were a family of three with an 11 year old daughter who was really nervous about the stingrays and they knew exactly how to make her comfortable and have a great time. If you are ever in need of a charter in the Grand Cayman, I would look no further!

Trip availability and prices

Trip Date:
Days:
Group Size:
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June 2026
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Number of days
1
Group Size
2 adults • 0 children
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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
Half Day Trip – Reef Fishing (AM)
4 hour trip starts at 8:00 AM
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
Half Day Trip – Reef Fishing (PM)
4 hour trip starts at 1:00 PM
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
Half Day Trip – Deep Sea (PM)
4 hour trip starts at 1:00 PM
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
Full Day Trip – Reef Fishing
8 hour trip starts at 8:00 AM
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
There are 18 people looking at this charter.

Customer reviews

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Rating

4.9
237 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (222)

What anglers say

97%
Great experience
99%
Family friendly
100%
Friendly captain
100%
Good boat
95%
Recommended
94%
Caught fish

All reviews (237)

Filter
Frequently mentioned
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Showing 15 of 237 reviews
Nicole Houser
Nicole Houser
us
Illinois, US
Member since 2026
0
5.0
Verified
New
Great Time
Half Day Trip – Deep Sea (AM) on May 29, 20264 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
Jillian Scott
Jillian Scott
ca
Manitoba, Canada
Member since 2026
1
5.0
Verified
Absolutely Incredible Charter
Half Day Trip – Reef Fishing (PM) on April 2, 20262 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
Stephanie Stecz
Stephanie Stecz
us
Chicago, IL, US
Member since 2024
0
5.0
Verified
Perfect afternoon!
Half Day Trip – Deep Sea (PM) on January 3, 20266 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!
Blake Koen
Blake Koen
us
Texas, US
Member since 2026
1
5.0
Verified
Amazing day with Captain Bobby
Half Day Trip – Reef Fishing (AM) on March 11, 20262 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:
Great Barracuda
Yellowtail Snapper
Gray Triggerfish
Tim Reeves
Tim Reeves
us
Tennessee, US
Member since 2026
0
5.0
Verified
New
SUPER FRIENDLY CREW!!
Half Day Snorkel/Stingray PM on June 2, 20262 adults1 child
The crew on our trip were really friendly and extremely knowledgeable about the wildlife and the island. We were a family of three with an 11 year old daughter who was really nervous about the stingrays and they knew exactly how to make her comfortable and have a great time. If you are ever in need of a charter in the Grand Cayman, I would look no further!

FAQs about Happy Day Charters

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The fish you can target

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What is the boat like?

Boat image
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
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