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!
Customer reviews
Rating summary
Photos & videos by reviewers (180)
+177Angler rating
Anglers claimed
Good experience
96%
Appropriate for children
99%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
94%
Caught fish
92%
Jul 30, 2025
Half Day Snorkel/Stingray AM
Stop scrolling! You found him…
Bobby Rose and crew are simply the best. We had an amazing charter and Bobby is one of the most kind, thoughtful and customer-focused captains we’ve ever experienced. We are not an easy charter. I’m a sole parent of three smalls (7, 9 and 19 - two girls and a boy). They each have different wants, capabilities and attention spans. Bobby asked all the right questions when we originally set-up the charter and, two months later on charter day, he remembered and executed every request perfectly. He scheduled our day to avoid crowds and to give us the opportunity to anchor and explore in the exact right space. All of the sting rays know and love Bobby. We then moved to the reef and Bobby introduced us to his two best friend sea turtles. We wrapped up the day with fishing and our bait was in the water in seconds and we were pulling fish up in just minutes. How does this even happen? Easy. Bobby Rose. Stop scrolling and book with Bobby before his calendar is full. He’s you personal guide, captain and local friend.
Bobby Rose and crew are simply the best. We had an amazing charter and Bobby is one of the most kind, thoughtful and customer-focused...
Captain replied
Apr 29, 2025
Half Day Trip – Reef Fishing (AM)
April fishing trip
We booked a reef fishing tour for four hours. My wife and children (all < 10 years old) had a great time. The larger fish weren’t biting, but we caught several smaller fish in the bay. When they stopped biting, we moved on to stingray city to keeps the kids occupied. Bobby and Travis jumped in the water as soon as we were anchored and immediately were showing my kids the stingrays. Each of my three children had an up close experience thanks to the two of them. This was way better than the larger tour groups that had one guide for 25+ people. They then took us to an area for snorkeling that was incredible. My kids felt like they were watching a seen from Finding Nemo as soon as their masks were underwater. They had life jackets for all the kids. They had appropriately sized masks and snorkels. They even used a tethered lifering for my kids to hang onto while snorkeling to keep everyone safe. When my kids were done snorkeling, Bobby simply reeled them back in. I highly recommend these two. I’ve been on several other fishing adventures and these guys were the best! Enjoy and don’t hesitate to book an experience with them.
We booked a reef fishing tour for four hours. My wife and children (all < 10 years old) had a great time. The larger fish...
Apr 16, 2025
Half Day Trip – Deep Sea (PM)
Wouldn't fish with anyone else.
Capt. Bobby and his First Mate Travis were spectacular!! Ocean was rough needed to stay within the bay and do reef fishing. Wasn't a problem for me or my family. We just want to fish. Was a slow day for sure but Captain Bobby and Travis are very personable friendly guys. Past the time by getting to know the island and them. We caught a lot of fish, two were keepers. Travis actually dove in when my daughter's fish managed to rap themselves around rock on the sea floor. He was able to untangle the line and my daughter reeled in a nice 10 lb Snapper! Not sure I've ever seen the first mate do that before! We were doing another trip on another boat for something else shortly after this one finished. I wasn't sure what I was going to do with the fish that we caught.George pointed out that we can bring the filleted fish to the restaurant near the dock. Morgan's. Was a great idea! Dinner was fantastic. Knowing them now, when I come back they will be my go-to for fishing. Thanks again for a great day.
Capt. Bobby and his First Mate Travis were spectacular!! Ocean was rough needed to stay within the bay and do reef fishing. Wasn't...
Mar 7, 2025
Half Day Trip – Deep Sea (AM)
Awesome trip!
Captain Bobby and 1st mate Mark were unbelievably awesome! We caught a couple of tuna! Both Bobby and Mark were knowledgeable about the fishing grounds, knew exactly where to go, and how to rig up to catch fish. Professionalism and kindness were off the charts great, and gave myself and my 11 year old son one hell of a trip. We both would highly recommend to look up Captain Bobby for your fishing trip. His boat and equipment are top notch. We will definitely go out with him again when we travel back to Grand Cayman!
Captain Bobby and 1st mate Mark were unbelievably awesome! We caught a couple of tuna! Both Bobby and Mark were knowledgeable...
Jun 4, 2025
Half Day Trip – Reef Fishing (AM)
Great Day
We took our two young kids on a 4 hr reef fishing trip with Bobby and Travis. Both were really great with our kids. We went out deeper and caught plenty of fish for lunch, then he took us to a shallower reef spot so my 5 year old could reel some in and ended on a high note for her. Boat was clean and comfortable. Crew was knowledgeable and felt very safe. We took our catch to Morgan's after Bobby cleaned them and had a truly spectacular lunch (highly recommend).
We took our two young kids on a 4 hr reef fishing trip with Bobby and Travis. Both were really great with our kids. We went out...
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (180)
+177Angler rating
Anglers claimed
Good experience
96%
Appropriate for children
99%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
94%
Caught fish
92%
Experience:
Boat
Crew
Overall
Stop scrolling! You found him…
Half Day Snorkel/Stingray AM on July 30, 2025
Bobby Rose and crew are simply the best. We had an amazing charter and Bobby is one of the most kind, thoughtful and customer-focused captains we’ve ever experienced. We are not an easy charter. I’m a sole parent of three smalls (7, 9 and 19 - two girls and a boy). They each have different wants, capabilities and attention spans. Bobby asked all the right questions when we originally set-up the charter and, two months later on charter day, he remembered and executed every request perfectly. He scheduled our day to avoid crowds and to give us the opportunity to anchor and explore in the exact right space. All of the sting rays know and love Bobby. We then moved to the reef and Bobby introduced us to his two best friend sea turtles. We wrapped up the day with fishing and our bait was in the water in seconds and we were pulling fish up in just minutes. How does this even happen? Easy. Bobby Rose. Stop scrolling and book with Bobby before his calendar is full. He’s you personal guide, captain and local friend.
Bobby Rose and crew are simply the best. We had an amazing charter and Bobby is one of the most kind, thoughtful and customer-focused captains we’ve ever experienced. We are not an easy charter. I’m a sole parent of three smalls (7, 9 and 19 - two girls and a boy). They each have different wants, capabilities and attention spans. Bobby asked all the right questions when we originally set-up the charter and, two months later on charter day, he remembered and executed every request perfectly....
Experience:
Boat
Crew
Overall
April fishing trip
Half Day Trip – Reef Fishing (AM) on April 29, 2025
We booked a reef fishing tour for four hours. My wife and children (all < 10 years old) had a great time. The larger fish weren’t biting, but we caught several smaller fish in the bay. When they stopped biting, we moved on to stingray city to keeps the kids occupied. Bobby and Travis jumped in the water as soon as we were anchored and immediately were showing my kids the stingrays. Each of my three children had an up close experience thanks to the two of them. This was way better than the larger tour groups that had one guide for 25+ people. They then took us to an area for snorkeling that was incredible. My kids felt like they were watching a seen from Finding Nemo as soon as their masks were underwater. They had life jackets for all the kids. They had appropriately sized masks and snorkels. They even used a tethered lifering for my kids to hang onto while snorkeling to keep everyone safe. When my kids were done snorkeling, Bobby simply reeled them back in. I highly recommend these two. I’ve been on several other fishing adventures and these guys were the best! Enjoy and don’t hesitate to book an experience with them.
We booked a reef fishing tour for four hours. My wife and children (all < 10 years old) had a great time. The larger fish weren’t biting, but we caught several smaller fish in the bay. When they stopped biting, we moved on to stingray city to keeps the kids occupied. Bobby and Travis jumped in the water as soon as we were anchored and immediately were showing my kids the stingrays. Each of my three children had an up close experience thanks to the two of them. This was way better than the...
Experience:
Boat
Crew
Overall
Wouldn't fish with anyone else.
Half Day Trip – Deep Sea (PM) on April 16, 2025
Capt. Bobby and his First Mate Travis were spectacular!! Ocean was rough needed to stay within the bay and do reef fishing. Wasn't a problem for me or my family. We just want to fish. Was a slow day for sure but Captain Bobby and Travis are very personable friendly guys. Past the time by getting to know the island and them. We caught a lot of fish, two were keepers. Travis actually dove in when my daughter's fish managed to rap themselves around rock on the sea floor. He was able to untangle the line and my daughter reeled in a nice 10 lb Snapper! Not sure I've ever seen the first mate do that before! We were doing another trip on another boat for something else shortly after this one finished. I wasn't sure what I was going to do with the fish that we caught.George pointed out that we can bring the filleted fish to the restaurant near the dock. Morgan's. Was a great idea! Dinner was fantastic. Knowing them now, when I come back they will be my go-to for fishing. Thanks again for a great day.
Capt. Bobby and his First Mate Travis were spectacular!! Ocean was rough needed to stay within the bay and do reef fishing. Wasn't a problem for me or my family. We just want to fish. Was a slow day for sure but Captain Bobby and Travis are very personable friendly guys. Past the time by getting to know the island and them. We caught a lot of fish, two were keepers. Travis actually dove in when my daughter's fish managed to rap themselves around rock on the sea floor. He was able to untangle...
Experience:
Boat
Crew
Overall
Awesome trip!
Half Day Trip – Deep Sea (AM) on March 7, 2025
Captain Bobby and 1st mate Mark were unbelievably awesome! We caught a couple of tuna! Both Bobby and Mark were knowledgeable about the fishing grounds, knew exactly where to go, and how to rig up to catch fish. Professionalism and kindness were off the charts great, and gave myself and my 11 year old son one hell of a trip. We both would highly recommend to look up Captain Bobby for your fishing trip. His boat and equipment are top notch. We will definitely go out with him again when we travel back to Grand Cayman!
Captain Bobby and 1st mate Mark were unbelievably awesome! We caught a couple of tuna! Both Bobby and Mark were knowledgeable about the fishing grounds, knew exactly where to go, and how to rig up to catch fish. Professionalism and kindness were off the charts great, and gave myself and my 11 year old son one hell of a trip. We both would highly recommend to look up Captain Bobby for your fishing trip. His boat and equipment are top notch. We will definitely go out with him again when...
Experience:
Boat
Crew
Overall
Great Day
Half Day Trip – Reef Fishing (AM) on June 4, 2025
We took our two young kids on a 4 hr reef fishing trip with Bobby and Travis. Both were really great with our kids. We went out deeper and caught plenty of fish for lunch, then he took us to a shallower reef spot so my 5 year old could reel some in and ended on a high note for her. Boat was clean and comfortable. Crew was knowledgeable and felt very safe. We took our catch to Morgan's after Bobby cleaned them and had a truly spectacular lunch (highly recommend).
We took our two young kids on a 4 hr reef fishing trip with Bobby and Travis. Both were really great with our kids. We went out deeper and caught plenty of fish for lunch, then he took us to a shallower reef spot so my 5 year old could reel some in and ended on a high note for her. Boat was clean and comfortable. Crew was knowledgeable and felt very safe. We took our catch to Morgan's after Bobby cleaned them and had a truly spectacular lunch (highly recommend).
FAQs about Happy Day Charters
The fish you can target
What is the boat like?
