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!



Select date to see available trips and rates:

  • Private trip
    Full Day Trip – Deep Sea
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    $1,200
    price breakdown
    $1,200
    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!
  • Private trip
    Full Day Trip – Reef Fishing
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    $1,000
    price breakdown
    $1,000
    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
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    $950
    price breakdown
    $950
    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
    Half Day Trip – Deep Sea (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    $700
    price breakdown
    $700
    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
    $700
    price breakdown
    $700
    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
    Half Day Trip – Reef Fishing (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    $600
    price breakdown
    $600
    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
    $600
    price breakdown
    $600
    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 (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    $550
    price breakdown
    $550
    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 Trip (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    $550
    price breakdown
    $550
    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!

About the Captain

Bobby Rose
West Bay, Cayman Islands
6 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) Barracuda (Great)
Bonefish Bonefish
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Marlin (Blue) Marlin (Blue)

Snapper (Mangrove) Snapper (Mangrove)
Snapper (Mutton) Snapper (Mutton)
Snapper (Yellowtail) Snapper (Yellowtail)
Tarpon Tarpon

Triggerfish (Gray) Triggerfish (Gray)
Tuna (Blackfin) Tuna (Blackfin)
Tuna (Yellowfin) Tuna (Yellowfin)
Wahoo Wahoo

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
Fighting Chair
GPS
Life Jackets
Fishfinder
Snorkeling Equipment
Multimedia System
Ice Box
Toilet
Fighting Chair
GPS
Life Jackets
Fishfinder
Snorkeling Equipment

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Snacks
Drinks
First Mate
Fishing License
Lunch

Cancellation Policy

Free cancellation up to 3 days prior to trip

Customers can cancel or modify their booking up to 3 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Crew Keeps Catch
Catch and Release Allowed
Catch and Release Mandatory

Payment

Book with 25% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 25% deposit to guarantee your reservation.
Pay remaining balance to captain
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

West Bay Fishing Calendar

Loading Fish Calendar!
Please Wait...

Customer Reviews

Rating Summary
Photos by reviewers (2)
4.61
out of 5 stars from 6 reviews
Boat
Crew
Experience
Half day with captain Bobby
Half day with captain Bobby
Angler Rating
5
0
1
0
0
Anglers Claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
83%
Appropriate for children
100%
Satisfied with the boat
100%
Catch intended fish
100%
Sort By:
Featured  
Showing:
5 of 6 reviews
Thomas C.
George Town
 5.00
Experience:
Boat
Crew
Overall

Capt Bobby was AWESOME!

VERIFIED   Half Day Trip – Reef Fishing (AM) on December 31, 2019
We booked a 1/2 day reef fishing for a group of six…to include 3 boys ages 9-11. My son had such a great time he asked...
Thomas C. recommends Happy Day Charters
Mark as helpful
You found this helpful
  Bobby Rose Captain replied

Christopher C.
George Town
 5.00
Experience:
Boat
Crew
Overall

Half day reef fishing. Happy Day Charter

VERIFIED   Half Day Trip – Deep Sea (AM) on January 8, 2020
My friend and I have never fish anything other ponds and small lakes back home. So we were very unsure about how this charter...
Christopher C. recommends Happy Day Charters
Mark as helpful
You found this helpful
Christopher C. recommends Happy Day Charters
Mark as helpful
You found this helpful

Rj C.
Beatrice, NE
 4.67
Experience:
Boat
Crew
Overall

Great day with Happy Day Charters and Capt Bobby

VERIFIED   Half Day Trip – Reef Fishing (AM) on January 30, 2020
We reef fished and Capt Bobby worked hard to put us on fish. Equipment and boat were great, fishing was fair. It was a slow...
Rj C. recommends Happy Day Charters
Mark as helpful
You found this helpful
Rj C. recommends Happy Day Charters
Mark as helpful
You found this helpful

Gary P.
Spring, TX
 5.00
Experience:
Boat
Crew
Overall

Half day with captain Bobby

VERIFIED   Half Day Trip – Deep Sea (AM) on January 1, 2020
We caught wahoo and barracuda which is what we wanted! We thoroughly enjoyed our conversation with the captain! Highly recommend...
Gary P. recommends Happy Day Charters
Mark as helpful
You found this helpful
Gary P. recommends Happy Day Charters
Mark as helpful
You found this helpful

Jeffrey W.
UPR MAKEFIELD, PA
 4.67
Experience:
Boat
Crew
Overall

Half day trip with Captain Peter.

VERIFIED   Half Day Trip – Reef Fishing (AM) on March 10, 2020
Peter did an amazing job locating great spots to fish off the reef.  Total catches were 16 with 9 keepers!!!  Could...
Jeffrey W. recommends Happy Day Charters
Mark as helpful
You found this helpful
Jeffrey W. recommends Happy Day Charters
Mark as helpful
You found this helpful