Happy Day Charters

Name: Happy Day Charters
Address: West Bay
Price range: trips from US $750 to US $1,600
Rating: 4.9

4.9/5 (200 reviews)

Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right, West Bay, Cayman Islands–

Meet the Captain

Happy Day Charters

4.9/5 (200 reviews)

Meet the Captain

Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right

West Bay, Cayman Islands

Trips & prices Targeted species Boat info What's biting What's included Contact captain

Trips & prices What's included Targeted species Boat info Reviews Contact captain

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

4.9/5

out of 5 stars from 200 reviews

See details

Boat

4.9/5

Crew

5.0/5

Experience

4.9/5

Photos & videos by reviewers (199)

+196

Anglers claimed

Good experience

96%

Appropriate for children

99%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

94%

Caught fish

92%

Showing 1 - 5 of 200 reviews

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Showing: 5 of 200 reviews

Joseph Petersen

5.0

Verified

Stop scrolling! You found him…

Half Day Snorkel/Stingray AM on July 30, 2025 • 4 adults

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.

Reported catch:

Response from Captain

July 31, 2025

Thank you so much for the kind review! We enjoyed having you and the kids today!

Liam Meyer

5.0

Verified

New

November fishing trip

Half Day Trip – Deep Sea (PM) on November 23, 2025 • 6 adults

Booked last minute and was hoping to find someone reliable and Bobby and the Mate Travis were just that. Was a tough day for fishing however they made sure to put us on a few! Caught a small tuna that was delicious dinner. All in all was a great trip and would highly recommend. They were both extremely friendly knowledgeable and took great pride in there careers as fishermen. Will definitely come back and fish with them next year!

Reported catch:

Patrick Strodtman

5.0

Verified

Fishing dream comes true!

Full Day Trip – Deep Sea on June 11, 2025 • 3 adults

We checked off a bucket list goal today and caught a blue marlin! Without Captain Bobby's maneuvering of the boat and the coaching from Travis, I don't believe we would have landed this beautiful fish. My nephew boated a skipjack tuna and we wrapped up the day with some blackfin tuna. Per Bobby's recommendation, we took the fresh tuna over to Morgan's where they prepared a masterpiece for my family! Thank you, Captain Bobby and Travis!

Jeffrey Whitacre

5.0

Verified

April fishing trip

Half Day Trip – Reef Fishing (AM) on April 29, 2025 • 2 adults • 3 children

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.

Reported catch:

James Studer

5.0

Verified

Wouldn't fish with anyone else.

Half Day Trip – Deep Sea (PM) on April 16, 2025 • 4 adults

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.

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December 2025

Su	Mo	Tu	We	Th	Fr	Sa

Number of days

Group Size

2 adults • 0 children

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Half Day Snorkel/Stingray AM

FREE Cancellation 3 days notice

4 Hour Trip

starts at 8:00 AM

US $750