Next AvailableJun 30

Book with Shawn Bessex

Playtime sportfishing

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Kailua-Kona HI

Shawn Bessex, Captain at Playtime sportfishing

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Looking for an unforgettable Hawaii fishing experience? Step aboard with Playtime Sportfishing and discover why Kailua Kona fishing charters are some of the best in the world. Led by Captain Shawn—a seasoned angler who grew up fishing the waters of Hawaii and Alaska—you’ll benefit from decades of hands-on experience. His passion for fishing started young and continues to fuel every trip he leads out of Kailua-Kona.

The waters off the Big Island are home to some of the most sought-after game fish in the Pacific. Depending on the season, you might reel in Blue Marlin, Striped Marlin, Shortbill Spearfish, Yellowfin Tuna (Ahi), Mahi Mahi, or Wahoo (Ono). Captain Shawn uses proven techniques like light tackle, trolling, jigging, and more to help you hook your target species. If fly fishing is your game, let him know—just be sure to bring your own gear.

Families, friends, and first-timers are all welcome aboard. If you're planning to bring little ones, child-sized life vests may be available—just ask ahead. Pack your favorite snacks and settle in for an exciting day of deep sea fishing in Kailua Kona. Playtime Sportfishing trips are designed to be comfortable, fun, and productive for anglers of all skill levels.

Your fishing adventure begins on a 26’ Shamrock sportfishing boat, built for both comfort and performance. The vessel is outfitted with outriggers, downriggers, a fighting chair, and top-tier fishing gear. There's even a private toilet on board, making it an ideal choice for longer outings. Rods, reels, tackle, and lures are included, so you can focus on the fun.

To help you land that dream catch, a skilled First Mate will be on hand throughout the trip. Mates typically work for tips, and it’s customary to offer 10–20% based on your experience. Their expertise and support can make all the difference when the big one hits.

Don’t forget your sun protection—bring a hat, sunglasses, and reef-safe sunscreen (no sprays, please). Bottled water will be on board, and moderate alcohol is allowed (no glass or hard liquor). Whether you're chasing a trophy Marlin or simply soaking in the beauty of Hawaii’s coastline, deep sea fishing Kailua Kona with Playtime Sportfishing is a trip to remember.

Upcoming Availability

June 2025

July 2025

Expertise & Attributes

fishing

Deep Sea Fishing

Good with Families

Good with Kids

Good with Large Groups

Good with New Anglers

Live Bait

Master Guide

Nature / Wildlife Views

Saltwater Fishing

Fishing Techniques

JiggingTrolling FishingFly FishingHeavy TackleLight TackleDeep Sea / Bottom Fishing

What's Included

Good to Knows

Your Guide has some important details about your trip with them.

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

What's Included

Good to Knows

Your Guide has some important details about your trip with them.

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Trips Available with Playtime sportfishing

Fishing

Starting At $575

Private Half Day Multi-Species Fishing

Fishing: Offshore

Fishing Boat:

Playtime • 26' Shamrock • Max 5 guests (base trip price includes 5 guests)

Description:

Enjoy a half-day deep sea fishing Kailua Kona adventure with this mid-morning, four-hour trip focused on targeting a variety of Hawaii’s top pelagic species. Bottom fishing may also be an option upon request, depending on weather and sea conditions. This seasonal charter is available Mondays and Tuesdays and is ideal for both beginners and experienced anglers. Families are welcome, and children can join the fun—just check ahead for youth life vests if you don’t have your own. Your First Mate will assist throughout the trip and typically works for tips (10–20% is customary). Don’t forget your hat, sunglasses, reef-safe sunscreen (non-spray), and some snacks.

Fishing

Starting At $600

Private Half Day Multi-Species Fishing (AM)

Fishing: Offshore

Fishing Boat:

Playtime • 26' Shamrock • Max 5 guests (base trip price includes 5 guests)

Description:

Start your morning with a four-hour Kailua Kona fishing charter designed to target a variety of pelagic species found in Hawaiian waters. This deep sea fishing Kailua Kona experience can also be tailored for bottom fishing upon request, depending on ocean conditions. Perfect for individuals, groups, or families—children are welcome on board. Be sure to ask in advance about child-sized life vests if needed. A professional First Mate will be there to assist with gear and techniques; a 10–20% tip is customary. Bring a hat, sunglasses, reef-safe sunscreen (non-spray), and a few snacks. Bottled water is provided, and moderate alcohol is allowed (no glass containers or hard liquor).

Fishing

Starting At $700

Private 6-Hour Morning Fishing Trip

Fishing: Offshore

Fishing Boat:

Playtime • 26' Shamrock • Max 5 guests (base trip price includes 5 guests)

Description:

Kick off your day at 6:00 AM with a 6-hour Kailua Kona fishing charter along Hawaii’s world-famous Kona coast. This deep sea fishing Kailua Kona trip is ideal for targeting a variety of pelagic species, with options to customize based on seasonal fish activity. Bottom fishing is available with advance notice and favorable conditions. An experienced First Mate will be on board to assist throughout your trip—tips of 10–20% are customary for their service. Pack your hat, polarized sunglasses, reef-safe non-spray sunscreen, and a few snacks. Bottled water is provided for your comfort. Moderate alcohol is permitted, but please avoid glass bottles and hard liquor while onboard.

Fishing

Starting At $800

Private 8-Hour Pelagic Fishing Trip

Fishing: Offshore

Fishing Boat:

Playtime • 26' Shamrock • Max 5 guests (base trip price includes 5 guests)

Description:

Spend a full 8 hours on the water with this Kailua Kona fishing charter, targeting a variety of pelagic species found in Hawaiian waters. Your deep sea fishing Kailua Kona experience includes a range of techniques, such as trolling, live bait, and stand-up tackle—adjusted based on the conditions and what’s biting. Trips can also be tailored for bottom fishing with advance notice. An experienced First Mate will be on board to assist throughout the day; a 10–20% tip is customary for their service. Bring a hat, polarized sunglasses, reef-safe (non-spray) sunscreen, and your favorite snacks. Bottled water is included. Moderate alcohol is allowed, but please no glass containers or hard liquor.

Fishing

Starting At $600

Private Half Day Multi-Species Fishing (PM)

Fishing: Offshore

Fishing Boat:

Playtime • 26' Shamrock • Max 5 guests (base trip price includes 5 guests)

Description:

Spend your afternoon on a 4-hour Kailua Kona fishing charter designed to target a wide variety of pelagic species. This deep sea fishing Kailua Kona trip launches in the late morning and offers opportunities to catch Blue Marlin, Striped Marlin, Shortbill Spearfish, Yellowfin Tuna, Wahoo, and Mahi Mahi—depending on the season. You'll be guided by an experienced crew, with a skilled First Mate ready to assist throughout the trip. Mates typically work for tips, and it’s customary to offer 10–20%. Be sure to bring a hat, sunglasses, and non-spray reef-safe sunscreen. Bottled water is provided. Moderate alcohol is welcome, but please avoid glass containers and hard liquor for safety.

Vehicle

Playtime

Boat Type:

Boat Guest Capacity:

Boat Length:

26 ft

Manufacturer Name:

Shamrock

Model Year:

1995

Engine Manufacturer Name:

Ford

# of Engines:

Horsepower Per Engine:

260

Maximum Cruising Speed:

Features: Fighting Chair First Mate Bait Tank Outriggers Tuna Tubes Toilet Ice-Box Refrigerator Fish Finder GPS Radar

Your trip starts on a 26’ Shamrock sportfishing boat built for comfort and performance. Outriggers, downriggers, a fighting chair, private toilet, and premium gear are all on board—just bring the fun!