About Your Guide

Chris Freed

Independent Guide
Born and raised on Oahu, Captain Chris brings over 40 years of local fishing experience to the table—and he’s all about putting fish in the box.

Unlike boats that troll lures all day, Captain Chris keeps it dynamic. You’ll fish live bait, dead bait, vertical jig, downrig, or drop for bottom species—whatever it takes to stay on the bite.

With a commercial fishing mindset, he runs a fully outfitted operation: pro-grade fish boxes, ice machines, bait, tackle—you name it. When the fish are firing, you’re locked and loaded to capitalize.

The boat is family-friendly and super comfortable, with a full-size couch, bunk beds, and a private bathroom. Patient, experienced deckhands are on board to coach anglers of all skill levels.

About Your Guide

Chris Freed

Independent Guide
Born and raised on Oahu, Captain Chris brings over 40 years of local fishing experience to the table—and he’s all about putting fish in the box.

Unlike boats that troll lures all day, Captain Chris keeps it dynamic. You’ll fish live bait, dead bait, vertical jig, downrig, or drop for bottom species—whatever it takes to stay on the bite.

With a commercial fishing mindset, he runs a fully outfitted operation: pro-grade fish boxes, ice machines, bait, tackle—you name it. When the fish are firing, you’re locked and loaded to capitalize.

The boat is family-friendly and super comfortable, with a full-size couch, bunk beds, and a private bathroom. Patient, experienced deckhands are on board to coach anglers of all skill levels.
Scroll for more

Multi Day Fishing Trip

NEW 1 - 4 People 48 - 96 Hours From $3,800
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip
Multi Day Fishing Trip

About Your Trip

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

Get ready to experience Hawaii’s wild side on an unforgettable multi-day fishing adventure with Captain Chris. Born and raised on Oahu, Captain Chris brings over 40 years of experience fishing these waters and a lifetime of local knowledge to every trip. Whether you're a seasoned angler or brand new to offshore fishing, this is your chance to discover Hawaii’s most remote and productive fishing grounds—far beyond the reach of standard day trips.

These multi-day trips...

About Your Trip

Get ready to experience Hawaii’s wild side on an unforgettable multi-day fishing adventure with Captain Chris. Born and raised on Oahu, Captain Chris brings over 40 years of experience fishing these waters and a lifetime of local knowledge to every trip. Whether you're a seasoned angler or brand new to offshore fishing, this is your chance to discover Hawaii’s most remote and productive fishing grounds—far beyond the reach of standard day trips.

These multi-day trips
are built for those who want more than just a few hours on the water. Staying aboard Captain Chris’s 35’ Bertram flybridge vessel, you’ll have everything you need for a comfortable and action-packed few days at sea. The boat is fully outfitted with top-tier electronics and fishing gear, as well as bunk beds, a fold-out couch, a spacious private bathroom, and a full-size couch to relax between bites. With sleeping accommodations for up to four passengers and room for six to fish at once, the setup is ideal for families or groups looking to share a true Hawaiian fishing adventure.

From the moment you leave the dock, Captain Chris and his experienced mate will be focused on putting you on fish. As commercial fishermen running recreational charters, their goal is to make every moment count. You won’t be dragging lures all day long—instead, you’ll use a full range of techniques including live bait, dead bait, bottom fishing, downrigging, and vertical jigging. During daylight hours, you’ll chase a wide mix of prized Hawaiian species like Blue and Striped Marlin, Yellowfin and Bigeye Tuna, Mahi Mahi, Wahoo, Giant Trevally, Spearfish, and a variety of reef and bottom species. When the sun goes down, the action continues with light tackle night fishing for a whole different lineup of nocturnal predators.

These trips offer more than just world-class fishing—they’re a chance to explore parts of Hawaii few visitors ever get to see. Multi-day options include island-hopping adventures, weather buoy runs to chase pelagics in open water, and shoreline explorations along remote coasts only accessible by boat. Along the way, you may drop anchor to step ashore on deserted beaches, hike to hidden waterfalls, or simply relax in some of the most pristine settings in the Pacific. Whether you're focused purely on the fishing or want a mix of angling and exploration, Captain Chris will customize the itinerary to fit your goals.

These trips typically wrap up around 4pm on the final day, giving you plenty of time for one last bite before heading back to the dock. Fish over 80 lbs will stay with the boat due to storage and quality control needs, but if you’d like to take home more than 50 lbs of fish, Captain Chris is happy to work with you if you let him know in advance.

If you’re ready to take your Hawaiian fishing experience to the next level, there’s no better way than spending multiple days at sea with Captain Chris. From serious offshore fishing to unforgettable island exploration, this is more than a trip—it’s an adventure you'll never forget.
Amenities

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Air Conditioning

This boat has air conditioning.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Federal Permit

This boat is federally permitted to go deep offshore.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Live Bait

Live bait is not used on this trip.

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Scroll for more

About Your Boat

Boat photo for Multi Day Fishing Trip
Boat photo for Multi Day Fishing Trip
Boat photo for Multi Day Fishing Trip
Boat Type
Sportfisher
Boat Manufacturer
Bertram
Year Built
2018
Boat Length
35'

About Your Boat

Boat Type
Sportfisher
Boat Manufacturer
Bertram
Year Built
2018
Boat Length
35'
Boat Restroom
Yes
Scroll for more

Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Heavy Tackle Fishing
Trolling

Type of Fishing

Need a Place to Stay?

Pearl Fishing Oahu Photo Gallery

Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Multi Day Fishing Trip
October 8th, 2025
Haleiwa, Hawaii
Book Now

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions