Happy Day Charters 

4.9/5 (178 reviews)
 Cayman Islands Yacht Club, Yacht Drive, Dock B, First slip on right, West Bay, 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!

Bobby Rose

Captain

Bobby Rose

20 years of experience
 responds within an hour

Highlights

 Fishing License
 Live Bait
 You Keep Catch
 Catch cleaning & filleting
 Drinks
 Toilet
 Child Friendly
 Snorkeling Equipment
 Ice Box
 Rods, reels & tackle
 Fighting Chair
 Food (Snacks & Lunch)

Plan your trip

Trip Date:
Days:
Group Size:
Almost there...
Half Day Snorkel/Stingray AM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $750 
Half Day Trip – Reef Fishing (AM)

 In demand! Last booked: 3 days ago

FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $750 
Half Day Snorkel/Stingray PM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Price for up to 6 people
US $750 
Half Day Trip – Reef Fishing (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Price for up to 6 people
US $750 
Half Day Trip – Deep Sea (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $800 
Half Day Trip – Deep Sea (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Price for up to 6 people
US $800 
Full Day Snorkel/Stingray
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,500 
Full Day Trip – Reef Fishing
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,500 
Full Day Trip – Deep Sea
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,600 
There are 11 people looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 178 reviews
Boat
4.9/5
Crew
5.0/5
Experience
4.9/5

Photos & videos by reviewers (155)

Great family fishing trip
Great family fishing trip
Great family fishing trip
+152

Angler rating

164
5
4
0
0

Anglers claimed

Good experience

96%

Appropriate for children

99%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

93%

Caught fish

92%

Showing 1 - 5 of 178 reviews
Jeffrey W.
Jeffrey W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

April fishing trip

VERIFIED

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...  

 Jeffrey W. recommends Happy Day Charters
1 person finds this review helpful

James S.
James S.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Wouldn't fish with anyone else.

VERIFIED

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...  

Review media 0
Review media 1
 James S. recommends Happy Day Charters
1 person finds this review helpful

Seneca T.
Seneca T.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great afternoon at Stingray City and reef fishing

VERIFIED
NEW

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.  

 Seneca T. recommends Happy Day Charters

William W.
William W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

The best on the island!

VERIFIED
NEW

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!  

Review media 0
 William W. recommends Happy Day Charters

Shawn A.
Shawn A.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Awesome trip!

VERIFIED

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...  

 Shawn A. recommends Happy Day Charters
1 person finds this review helpful

...

FAQs about Happy Day Charters

What are the trip rates for Happy Day Charters?

Happy Day Charters offers the following trips to customers:

  • 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)
Which amenities are available onboard with Happy Day Charters?

When you book a trip with Happy Day Charters, you can expect the following amenities onboard:

  • Toilet Private head
  • Fighting Chair
  • GPS
  • Fishfinder
  • Snorkeling Equipment Available on all trips!
  • Multimedia System
  • Ice Box Cooler filled with ice
What's included in the trip price with Happy Day Charters?

Trips booked with Happy Day Charters include:

  • 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 )
What types of fishing does Happy Day Charters offer?

Happy Day Charters offers the following types of fishing:

  • Inshore Fishing
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing
What fishing techniques does Happy Day Charters offer?

Happy Day Charters offers the following fishing techniques:

  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Deep Sea Fishing
Which fish species can I catch with Happy Day Charters?

Top targeted fish species with Happy Day Charters include:

  • Barracuda (Great)
  • Bonefish
  • Dolphin (Mahi Mahi)
  • Marlin (Blue)
  • Snapper (Mangrove)
  • Snapper (Mutton)
  • Snapper (Yellowtail)
  • Tarpon
  • Triggerfish (Gray)
  • Tuna (Blackfin)
  • Tuna (Yellowfin)
  • Wahoo

Meet your captain

Bobby Rose

West Bay, Cayman Islands

178 Customer reviews
Response time within an hour
Member since August 2019

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!

Fish you can target

Great Barracuda
Great Barracuda
Bonefish
Bonefish
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Blue Marlin
Blue Marlin
Mangrove Snapper
Mangrove Snapper
Mutton Snapper
Mutton Snapper
Yellowtail Snapper
Yellowtail Snapper
Tarpon
Tarpon
Gray Triggerfish
Gray Triggerfish
Blackfin Tuna
Blackfin Tuna
Yellowfin Tuna
Yellowfin Tuna
Wahoo
Wahoo

Your boat

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

Where you can fish

Inshore Fishing

Nearshore Fishing

Offshore Fishing

Reef Fishing

How you can fish

Light Tackle

Heavy Tackle

Bottom Fishing

Deep Sea Fishing

What's on board

Toilet

Private head

Fighting Chair

GPS

Fishfinder

Snorkeling Equipment

Available on all trips!

Multimedia System

Ice Box

Cooler filled with ice

Included in the price

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

How cancellations work

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.

Listing policies

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

How to pay

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

What’s biting in West Bay right now

Barracuda (Great)Barracuda (Great)
BonefishBonefish
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Marlin (Blue)Marlin (Blue)
Snapper (Mutton)Snapper (Mutton)
Snapper (Yellowtail)Snapper (Yellowtail)
TarponTarpon
Tuna (Yellowfin)Tuna (Yellowfin)
WahooWahoo
11 people are looking at this charter.