Live Bait Sailfishing

Starting at $1000 | 8 Hour | Deep Sea | 3 People

About Your Trip

Hop on board with Captain Jeff and prepare for an action-packed day of Sail Fishing! Islamorada is a renowned fishing hotspot with some of the best inshore and backcountry fisheries in the world, home to dozens of exciting species. You also have easy access to the offshore waters if you want to go after some bigger fish! From October to April, you can even target some Sailfish as they travel up and down the reef's edge.

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About Your Boat

Boat Type
Center Console
Boat Manufacturer
Boat Length

About Your Guide

Captain Jeff has spent his life fishing, and has fished all over the world throughout the years. From the British and US Virgin Islands, Mexico, Belize, Bahamas, and up and down the East Coast - but for him there’s no place like the Florida Keys. Captain Jeff has yet to find a place where he can go that has the variety that Islamorada has to offer.

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Start Location

96 Madeira Road, Islamorada, FL 33036, United States

Amenities and Information

Water Type

Deep Sea

Skill Levels

Advanced, Beginner, Intermediate


All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.


Feel free to enjoy responsibly, but please no glass.

Live Bait

Yes, Included


You will get a refund if the trip is canceled due to weather.

Boat Restroom

No, this boat does not have a bathroom on board.


No meal provided.


Amberjack, Blackfin Tuna, Cobia, Mahi Mahi, Sailfish


Bottom Fishing, Heavy Tackle Fishing, Light Tackle Fishing

Gear & Packing

Rods, reels & tackle
At an Additional Rate
No added costs.
Recommended Packing
Nothing required, we always recommend sunglasses, sunscreen, water, and weather-appropriate clothing.
Required Items
Nothing additional needed.

Things To Keep In Mind

Payment & Tipping
After paying the deposit, a QR Code will be emailed to you. On the day of the trip, your guide will scan your QR code to automatically transfer the remaining balance. The only cash needed is for a customary tip (we recommend 20%).
Cancellation/Refund Policy
The deposit for this trip is non-refundable.

Where to Buy a Fishing License

No license needed for this trip.

Pricing & Availability

To check pricing, please select a trip date, duration, group size and start time.

100% Weather Protection

Receive a full refund in the event of inclement weather.


Ken E.


December 30, 2022

My son and I had a fantastic morning catching all kinds of fish. You can’t find a more knowledgeable fisherman in the area. Thanks for a great day!

Donald S.


December 22, 2022

Clean and well equipped boat with knowledgeable captain. New the spots and how to catch them. Will book again on our next trip down.

Robert C.


June 24, 2022

We had a great fun time out with Captain Jeff. He had us on Mahi in no time and we chased them for the duration of a half day 4 hour trip. We caught a few and have Mahi lunch and dinner scheduled for days! Jeff was an easy going ...Read More

Eric H.


March 9, 2022

We did not having any luck targeting Tarpon, but we knew it was going to be hit or miss since our only window was in early March and it was windy. We spent almost all our time with bait in the water, so we did not waste time driving ...Read More

First Time Booking with Us?

Captain Experiences is the home of over 1000 Damn Good fishing and hunting guides. Our mission is to unlock the outdoors for everyone, and we want to help you get out there through our no-hassle online booking experience and our team of outdoors experts.
We vet our guides to make sure they are the best of the best. We want guides who not only put you on 'em, but show you a great time, keep you safe, and give you a memorable experience with your group.
Once you've paid your deposit at checkout, we'll send you a QR code (like a mobile boarding pass). Just show your guide your QR code on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the case of inclement weather, our guides will make the call and we'll work with you to reschedule your trip or issue a full refund. Your safety is our top concern.
Once you book the trip, we will connect you directly with the guide to go over any additional details. In the meantime, our location specialists are always available to answer your questions via email, text, chat, or call!