Happy Day Charters
Happy Day Charters
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
Rating
Anglers' gallery (236)
What anglers say
Reviews (259)
Stephanie Stecz5.0VerifiedPerfect afternoon!
Half Day Trip – Deep Sea (PM) on January 3, 2026 • 6 adultsOur 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!
Clint DorsettRepeat angler5.0VerifiedNewGreat Fiahing Trip
Full Day Trip – Deep Sea on October 13, 2026 • 3 adultsWe did a full day of fishing with a mixture of deep sea and reef fishing. Caught 15 or so black fin tuna since nothing else biting today and caught several fish on the reef
Elvin BeachRepeat angler5.0Verified2025 & 2026 Trips
Half Day Snorkel/Stingray PM on June 28, 2026 • 5 adults • 1 childTook my family of 5 (me and 4 girls) out fishing, snorkeling, and to stingray city with Bobby & Travis in 2025 and then again on 2026. They are awesome and made all of the trips fun and comfortable for my family. Hoping to head back again next year and someday go during conch season to try our luck with them.
Amanda Novak5.0VerifiedThe crew really made the experience.
Half Day Trip – Deep Sea (AM) on June 5, 2026 • 2 adultsCaptain Bobby was amazing! He made sure we were comfortable at all times. They had booze, soda, gatorade, and water for us. Let us connect to the speaker. After the trip he filleted the fish for us to take home. Overall awesome experience will be making it a tradition everytime we come back to Cayman.
Luis Esquivel5.0VerifiedExcellent experience!
Half Day Trip – Deep Sea (PM) on June 22, 2026 • 4 adults • 2 childrenCaptain Bobby and Travis where top notch. Will definitely use them next trip. Our friends are coming in July and definitely will get them hooked up with captain Bobby. Thanks again for great trip.
Tennille Lisell5.0VerifiedFantastic!
Half Day Trip – Reef Fishing (AM) on April 17, 2026 • 3 adults • 2 childrenWe had a great trip. Boat was clean, comfortable he had cold drinks and snacks. We went reef fishing, caught quite a few fish. My girls (10 & 12) wanted to go snorkeling, that fun and beautiful! When we are in Cayman Islands again, we will be booking a deep sea and another reef fishing experience with Captain Bobby and First mate Travis again. What a team!!
Jeremy Nelson5.0VerifiedCapt. Bobby and Travis were great!
Half Day Trip – Reef Fishing (AM) on June 8, 2026 • 5 adults • 1 childCrew was great and very accommodating. We had to take a member back to the dock who wasnt feeling great and there was no fuss about that. Tons of fun!
Kyle Schmillen5.0VerifiedGreat time!
Half Day Trip – Deep Sea (AM) on May 8, 2026 • 5 adultsHad a great outing with Capt Bobby and Travis today. I would highly recommend them for your next charter experience.
Cody Turner5.0VerifiedAn Amazing Day on the Work and Play!
Half Day Snorkel/Stingray PM on November 27, 2025 • 4 adultsBobby and his crew, Travis were great! They were kind, personable and very accommodating…making our trip to suit. Bobby’s fresh conch dip was amazing! They definitely delivered a memorable Cayman experience for our family!! Thank you, Bobby and Travis! :)
Derek Lin5.0VerifiedGreat Time
Half Day Trip – Deep Sea (AM) on November 13, 2025 • 3 adultsOnly caught a small Tuna but it was a quiet day for everyone. Had a great time trolling around and learning from Captain Bobby Rose and the Mate Travis. They had everything ready to go. Would have been nice to get a quick intro brief for the general procedures and safety things.
Rating
Anglers' gallery (236)
What anglers say
All reviews (259)
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! ⭐⭐⭐⭐⭐
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.
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!
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!
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!
FAQs about Happy Day Charters
- US $750 per group - Half Day Snorkel/Stingray AM (4 hours)
- US $750 per group - Half Day Snorkel/Stingray PM (4 hours)
- US $750 per group - Half Day Trip – Reef Fishing (AM) (4 hours)
- US $750 per group - Half Day Trip – Reef Fishing (PM) (4 hours)
- US $800 per group - Half Day Trip – Deep Sea (AM) (4 hours)
- US $800 per group - Half Day Trip – Deep Sea (PM) (4 hours)
- US $1,500 per group - Full Day Snorkel/Stingray (8 hours)
- US $1,500 per group - Full Day Trip – Reef Fishing (8 hours)
- US $1,600 per group - Full Day Trip – Deep Sea (8 hours)
- Toilet Private head
- Fighting chair
- GPS
- Fishfinder
- Snorkeling equipment Available on all trips!
- Multimedia system
- Ice box Cooler filled with ice
- Rods, reels & tackle (Custom )
- Live bait
- Lures
- Catch cleaning & filleting
- Snacks
- Drinks
- First mate (Tips are always appreciated! )
- Fishing license
- Lunch (Happy to stop for lunch at customer's expense/time )
- Inshore fishing
- Nearshore fishing
- Offshore fishing
- Reef fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Deep sea fishing
- Barracuda (Great)
- Bonefish
- Dolphin (Mahi Mahi)
- Marlin (Blue)
- Snapper (Mangrove)
- Snapper (Mutton)
- Snapper (Yellowtail)
- Tarpon
- Triggerfish (Gray)
- Tuna (Blackfin)
- Tuna (Yellowfin)
- Wahoo
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Barracuda (Great)
Bonefish
Dolphin (Mahi Mahi)
Marlin (Blue)
Snapper (Mutton)
Snapper (Yellowtail)
Tarpon
Tuna (Blackfin)
Tuna (Yellowfin)
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