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!
Captain
Bobby Rose
Highlights
In demand! Last booked: 3 days ago
Rating summary
Photos & videos by reviewers (155)
Angler rating
Anglers claimed
Good experience
96%
Appropriate for children
99%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
93%
Caught fish
92%
Experience:
Boat
Crew
Overall
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
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
Half Day Snorkel/Stingray PM on June 26, 2025
Captain Bobby and Travis were great! We went to Stingray city and Captain Bobby and Travis got us up close and personal with some stingrays. The fishing was a little slow, but they got us on some fish and my kids had a great time. The weather wasn’t perfect, but the crew made our time with them amazing and have already recommended them to friends headed to Grand Cayman.
Captain Bobby and Travis were great! We went to Stingray city and Captain Bobby and Travis got us up close and personal with some stingrays. The fishing was a little slow, but they got us on some fish and my kids had a great time. The weather wasn’t perfect, but the crew made our time with them amazing and have already recommended them to friends headed to Grand Cayman.
Experience:
Boat
Crew
Overall
Half Day Trip – Deep Sea (AM) on June 19, 2025
These guys are amazing! Very knowledgeable and ran the spread correctly. We fish the OC MD tournaments every year (White Marlin Open, Big Fish Classic, Tuna Tournament and the Mid Atlantic) and we have fished with the best. I’m always skeptical when I travel and fish because I want to make sure we’re fishing with professionals. These guys are very professional. Guy Harvey fishes with these guys!
These guys are amazing! Very knowledgeable and ran the spread correctly. We fish the OC MD tournaments every year (White Marlin Open, Big Fish Classic, Tuna Tournament and the Mid Atlantic) and we have fished with the best. I’m always skeptical when I travel and fish because I want to make sure we’re fishing with professionals. These guys are very professional. Guy Harvey fishes with these guys!
Experience:
Boat
Crew
Overall
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...
Happy Day Charters offers the following trips to customers:
When you book a trip with Happy Day Charters, you can expect the following amenities onboard:
Trips booked with Happy Day Charters include:
Happy Day Charters offers the following types of fishing:
Happy Day Charters offers the following fishing techniques:
Top targeted fish species with Happy Day Charters include:
West Bay, Cayman Islands
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!
Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Light Tackle
Heavy Tackle
Bottom Fishing
Deep Sea Fishing
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
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
No minimum age
You Keep Catch
Except for Billfish & small species
Crew Keeps Catch
Only if the guest doesn't want to keep it
Catch and Release Allowed
Catch and Release Mandatory
All Billfish & small species
Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express