Private Key West Deep Sea Fishing Charters

Experience the thrill of Key West deep sea fishing to the fullest on a hunt for trophy game fish in the open sea with your own private boat, captain, and crew.


  • Fully-equipped modern sport fishing boat reserved solely for you and your party.
  • Full-time professional captains ensure safety, comfort, and productive fishing.
  • Top-of-the-line fishing equipment, bait, tackle, and ice all included free.
  • Clean restrooms, comfortable seating, and plenty of cooler space for your snacks and beverages.
  • Classic Key West deep sea fishing for multiple species year-round.
  • Authorized reseller of™ Charters.


Imagine the docks of Key West’s historic charter boat row in the early morning. The air is cool, the water calmly laps the pilings, and small fish flip for food on the surface. Few fishermen are on the scene yet; most of the activity consists of captains and mates preparing vessels and gear for another day of Key West deep sea fishing. Marine engines burble, ice crunches into coolers, live-well pumps hum, scattered radio transmissions crackle. Reading the information in the email on your phone, you walk along the dock to your boat. The mate is on deck rigging various terminal setups to the numerous rods lined up in the holders. After a quick “Good Morning”, you hand him your group’s packs and duffels and he invites you to step onboard. You decide to linger on the dock for a few minutes and finish your coffee before getting aboard your fishing boat and settling in for the run out. The few scattered clouds are still pink with dawn, and it looks to be a great day to head offshore and fight big fish in the deep water.

Fishing Calendar

Does this sound like a dream to you? Maybe it’s a fishing show on one of the cable channels? It could easily be a reality, because with a couple of clicks and a few emails and phone calls you could have a Cool Key West Private Key West deep sea fishing charter set up for the sole enjoyment of yourself and whoever you would like to include in your party. Bring the family, invite friends, make a business networking impression, throw a bachelor party, bond with a new son- or daughter-in-law, put on your own fishing tournament, or go out and catch all the fish yourself. It is up to you, because, with a private charter, it is all for you.

Because Cool Key West is Key West’s number 1 online concierge service, with a solid history of bringing reasonably priced fun and adventure to thousands of satisfied island visitors, we have now been selected as an authorized reseller of the legendary charters offered by™. This means we can offer full access to private deep sea fishing charter trips out on the open Atlantic Ocean waters to the east of Key West. These are the Gulf Stream and deepwater offshore sites that have been internationally renowned for trophy big game fishing from the early 1900s onward, with the exploits of celebrity deep sea anglers like Zane Grey, Ernest Hemingway, Bing Cosby, Lee Marvin, and many others propelling dreams of Key West deep sea fishing adventure into the imaginations of fishermen everywhere.

Today, these waters are still home to the mighty, 1000 lb. plus Atlantic Blue Marlin, the most famous of all offshore billfish. Fast, high-jumping Sailfish are abundant as well, and when they move in to savage the huge schools of baitfish along the reef edges and weed lines in the late fall and spring, a fisherman might hook 20 sailfish in a day. Colorful Mahi-Mahi provide fast action and good eating throughout late spring and summer. High-speed, hard hitting predators like Barracuda, Blackfin Tuna, Kingfish, and Wahoo will strip your reel bare and challenge you to stop their runs. Deep-water bait fishing over wrecks and reefs will have you winching up Amberjack, Cobia, Grouper, Yellowtail Snapper, and Sharks including the awesome Hammerhead. When you send the bait deep on a Key West offshore fishing trip, you never know what is going to hit next.

The™ Charter Captains are masters of these waters, and the legendary fishing reported by Hemingway continues as Cool Key West teams with™ to hook fishermen up with the best of Key West Deep Sea Fishing. Our Key West deep sea fishing captains are on the water nearly every day. They are experts in bringing together time, location, technology, and technique to help you catch fish. They use the latest fishing electronics, their own well-honed fishing instincts, and natural indicators like changing water color, diving birds, flowing currents, and floating debris lines to put you on the fish. You might be trolling with lures or cut bait, casting or drop-fishing with live bait, surface-casting artificial plugs and lures, or kite fishing; whatever is going to bring fish over the side of the boat. And on your private deep sea fishing charter, it is all for you. No waiting for a chance in the fighting chair, no taking turns at the best spot on the rail, no struggling to get the mate’s attention when you need a re-bait, a new rig, or have a fish on.

All of our Key West deep sea fishing boats are fully-equipped for your comfort with clean restrooms, comfortable seating, and plenty of cooler space for all the cold drinks, snacks, and lunchtime treats that you want to bring. All necessary bait and tackle will be provided free, with top quality, well-maintained, professional-level fishing equipment standard on every boat. Try out gear built by manufacturers like Abaco, Blackfin, Crowder, Diawa, Ilander, Penn International, and Shimano, and set up by pros who have been hauling fish out of Key West waters for decades. Watch the color displays on the Garmin and Raymarine navigation and fish finding electronics. Check the Loran radar as it sweeps the area for signs of feeding birds. Play your favorite tunes on the sound system or use a variety of ship-to-shore communication facilities. It is all there to make your private Key West deep sea fishing charter a high-end angling adventure you will never forget.

If you are ready to enjoy a premium Key West deep sea fishing experience, you have come to the right place. If you have a particular trophy in mind, check out the FAQ section to see what is biting when. Or just come on down and rely on your captain, because these waters offer up high quality multi-species fishing action all year round. Contact Cool Key West to book your private Key West deep sea fishing charter now. When you book, you will be put in direct touch with your charter captain, and you can work out the details of your private trip in person. Experience the ultimate in offshore fishing with a Cool Key West private Key West deep sea fishing charter trip.


  • Duration: 4, 6, or 8 hours
  • Check-in time: Please be at the dock 15 minutes before the charter start time.
  • Departure point: Detailed check-in instructions - including address, Google map, and parking information - will be included in your final confirmation email.


  • Charter for up to 6
  • All Licenses
  • Bait and Tackle
  • Ice
  • Everything Except Food & Drinks


  • Gratuities (optional)

What To Bring

  • Confirmation Voucher
  • Sunscreen
  • Sunglasses
  • Camera
  • Comfortable Shoes
  • Food and Drinks


  • Authorized reseller of™ Charters.
  • Advance Purchase Recommended
  • Upon booking you will receive an instant receipt with Voucher Confirmation to follow
  • Capacity: 6

Booking Info

Voucher Confirmation Info

This tour accepts both printed and electronic vouchers (e-vouchers). You can either print the voucher and present a paper copy on the day of travel. Or, if you travel with a mobile device, simply show your Photo ID and present your voucher on your Smartphone or tablet on the day of travel.

Local Operator Information

Complete operator information, including local telephone number, will be included on your Confirmation Voucher.

Do I need to buy a fishing license?

No you do not. We have the required Florida Wildlife Commission charter licenses that cover all anglers fishing on our boats.

How long are the Fishing Charter Trips?

1/2 Day Trips = 4 Hours 3/4 Day Trips = 6 Hours Full Day Trips = 8 Hours

What experience level is necessary?

Our Key West Charter Guides and Captains can provide fun fishing for every angler from first-timer to expert. Whether you are a veteran sport fisherman looking to fine tune your game to Key West waters or a beginner just learning how to use a rod and reel, our Key West Guides are ready with friendly, patient advice and support.

How many people can go fishing on a charter?

Ultra Grand Slam can handle parties of up to 6 anglers.

Are alcoholic beverages allowed on board?

Yes, mild alcoholic beverages like Beer, Cider, Hard Lemonade, Wine, and Wine Coolers are allowed. However, for everyone’s safety, NO GLASS CONTAINERS are allowed on board - metal or plastic containers only please.

What kind of shoes should I wear?

Any footwear with closed-toes and non-marking soles will be fine.

What is the customary gratuity?

If you had a great trip and are happy with the service provided by our Key West Charter Captain and Crew, a tip of 15-20% of the total trip cost would be very much appreciated. And remember to recommend us to your friends!

Are food and refreshments included?

No, but you can bring your favorite foods and beverages and we will provide cooler space and ice to keep them fresh and cold.

Is fishing gear provided?

Yes, we provide the latest top-of-the-line fishing tackle available. In fact, our charters offer experienced fishermen a great chance to try out some top-notch gear. All fishing equipment is well-maintained, with line changed on a regular basis and terminal set-ups expertly chosen and tied on. Our gear is the best, but experienced fishermen are welcome to bring their favorite rod and reel if they like.

Is bait provided?

Yes. Whatever the fishing calls for: live bait, frozen bait, cut bait, or chum, our Charter Captains will have plentiful supplies on hand. The same thing goes for artificial bait such as lures, flies, or plugs.

What kind of clothing should I bring?

For protection from the hot sun of Key West, it is always best to cover yourself as much as possible. Caps or sun hats, bandanas, sun glasses, and of course sun screen are all necessities. In the winter, it can be quite cool and breezy offshore, so a light weight jacket may be useful. For winter season early morning trips, a pair of light gloves can also add comfort. Bring a small day pack or duffel bag for your extra clothing, cameras, binoculars, and other necessities.

DAILY LIMIT per person per day unless otherwise noted
28 in. fork
1 Monroe County Only
Black Drum
14-24 in.
12 in. fork
18 in.
33 in. fork
12 in. fork
Grouper - Nassau
Protected Species
Grouper - Warsaw
1 per vessel per day
Grouper - Speckled Hind
1 per vessel per day
12 in. fork
5 species aggregate
Protected Species
Mackerel - King
20 in. fork
Mackerel - Spanish
12 in.
Marlin - Blue
86 in.
Marlin - White
62 in.
Not less than 10 in. or more than 20 in.
10 per person per day of Permit and Pompano 10 aggregate may possess 1 over 20 in.
Not less than 10 in.
10 per person per day of Permit and Pompano 10 aggregate may possess 1 over 20 in.
Pompano - African
Not less than 24 in.
2 per person per day or per vessel whichever is less
Red Drum (Redfish)
Not less than 18 in. or more than 27 in.
57 in.
8 in.
1 per person or 2 per vessel whichever is less
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$ 800
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Please note: After your purchase is confirmed you will receive a complete tour itinerary with check-in time, location and what to bring.

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