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!



Select date to see available trips and rates:

  • Private trip
    Half Day Snorkel/Stingray AM
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    US $700
    Get ready for a fun adventure through some of the island's hottest locations! You'll be able to choose from numerous attractions, including Starfish Point, Rum Point, Stingray City, and Kaibo. You can customize your trip the way you'd like with snorkeling, sight-seeing, and some optional light fishing. Your captain will provide all necessary equipment and bait, as well as your fishing license. Snacks and cold beverages are available as well.
  • Private trip
    Half Day Snorkel/Stingray PM
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    US $700
    Enjoy some of the island's best attractions and get ready to catch amazing fish with Happy Day Charters! Choose from Stingray City, Starfish Point, Kaibo, and Rum Point and combine your trip with a bit of snorkeling, site-seeing, and if you want, some light fishing. You'll be provided with snacks and drinks as well as top-notch gear, and your fishing license. Get ready for a fun adventure and start planning your trip today!
  • Private trip
    Half Day Trip – Reef Fishing (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    US $700
    Fish some of Cayman's most beautiful reefs and get ready to catch a range of species, including Mangrove, Mutton, and Yellowtail Snapper, as well as Triggerfish, Barracuda, and Wahoo. All fishing gear and licenses are included in the price. The captain will also provide snacks and drinks to make sure your energy levels stay up!
  • Private trip
    Half Day Trip – Reef Fishing (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    US $700
    Bottom fish above productive reefs and target different species including Barracuda, Wahoo, Triggerfish, and Snapper. Everything you need is included, such as your rods, reels, bait, tackle and fishing license. Snacks and drinks will also be provided on board, so just bring some sunscreen, a hat, and sunglasses, and the rest will be covered.
  • Private trip
    Half Day Trip – Deep Sea (AM)
    In demand! Last booked: 1 day ago
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    US $750
    Join Happy Day Charters and get ready the ultimate offshore adventure! You'll fish top spots, such as South Sound and North and West Walls. Your main target species are Sailfish, Blue Marlin, Mahi Mahi, Blackfin and Yellowfin Tuna, Wahoo, and many more. Capt. Bobby will supply the gear and fishing licenses. Cold beverages and snacks are provided on board as well. Just be sure to pack some sunscreen, sunglasses, and a hat and you're all set.
  • Private trip
    Half Day Trip – Deep Sea (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    US $750
    Fish North Wall, South Sound or West Wall on this exclusive adventure. On this trip, Blue Marlin, Sailfish, Blackfin and Yellowfin Tuna, Mahi Mahi, Wahoo, and many other species. The captain will provide the fishing tackle, as well as your license. He'll also make sure you're hydrated and energized with cold drinks and snacks. Just bring sunblock, a hat, and sunglasses and the rest will be taken care of.
  • Private trip
    Full Day Snorkel/Stingray
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    US $1,400
    Customize your charter and enjoy a full day of some of the island's best fishing spots. The fishing grounds include Stingray City, Starfish Point, Rum Point, and Kaibo. On this trip, you'll be able to combine a bit of snorkeling, sight-seeing, cruising, and some light fishing. Tackle, licenses, snacks, and drinks are included. Just come ready to have a good time and the rest will be taken care of.
  • Private trip
    Full Day Trip – Reef Fishing
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    US $1,400
    Come experience some of the Cayman Island's most beautiful reefs. These waters are brimming with amazing bottom-dwelling species, including various types of Snapper, Triggerfish, Barracuda, Wahoo, and many more. All the necessary fishing gear and licenses are included. Just bring sunscreen, a hat, sunglasses, and any other personal items you may need and get ready for a fun day of fishing.
  • Private trip
    Full Day Trip – Deep Sea
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    US $1,500
    Choose from a number of top locations, including 12 Mile Bank (weather permitting), North and West Wall, South Side, and East End. Capt. Bobby will consult with you beforehand and discuss options, trends, and weather. Target species include Blackfin and Yellowfin Tuna, Marlin, Sailfish, Mahi Mahi, Wahoo, and many more. Tackle, bait, and licenses are included. Snacks and cold drinks will also be provided. Just come ready to have an amazing time and create lasting memories with Happy Day Charters!
There are 18 people looking at this charter.

FAQs about Happy Day Charters

Happy Day Charters offers the following trips to customers:
  • US $700 per group - Half Day Snorkel/Stingray AM (4 hours)
  • US $700 per group - Half Day Snorkel/Stingray PM (4 hours)
  • US $700 per group - Half Day Trip – Reef Fishing (AM) (4 hours)
  • US $700 per group - Half Day Trip – Reef Fishing (PM) (4 hours)
  • US $750 per group - Half Day Trip – Deep Sea (AM) (4 hours)
  • US $750 per group - Half Day Trip – Deep Sea (PM) (4 hours)
  • US $1,400 per group - Full Day Snorkel/Stingray (8 hours)
  • US $1,400 per group - Full Day Trip – Reef Fishing (8 hours)
  • US $1,500 per group - Full Day Trip – Deep Sea (8 hours)

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

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 )

Happy Day Charters offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing

Happy Day Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Deep Sea Fishing

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 the Captain

Bobby Rose
West Bay, Cayman Islands
ID & license verified
69 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!

About this listing

Targeted species

Barracuda (Great) Great Barracuda
Bonefish Bonefish
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Marlin (Blue) Blue Marlin

Boat specs

Pursuit (Center console) originally built in 1998, and restored in 2019. Powered by a 315HP Yanmar engine, with a maximum cruising speed of 25 knots.

Length
26 ft
Capacity
6 persons

Types of fishing

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing

Fishing techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Deep Sea Fishing

Amenities

Toilet
Private head
Fighting Chair
GPS
Fishfinder
Snorkeling Equipment
Available on all trips!
Multimedia System

Trip includes

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

Cancellation policy

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

Payment

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

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