Key West Sailfish Fishing Charters

77 Fishing Charters

The best out of 77 charter fishing deals in Key West - enter dates to check availability

Top Sailfish Fishing in Key West

Showing top 10 charters
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Angler's Choice
Listing image
Meet the Captain

34 ft

up to 6

Wild Bill Sport Fishing

 
State licensed
 
Key West
3/4 Day Trip
This 6-hour trip gives you a bit more time for fishing, and you can still get back in time to run some errands. Target species include Shark (many species including Blacktip, Hammerhead, Lemon, Tiger, Blacknose). Grouper, Snapper, King, Spanish, Cero mackerel. The crew will supply the fishing gear, license, bait if available, bottled water, and will clean your catch. Bring a camera, sunblock, a cap, non-marking shoes, food and beverages.
Instant Confirmation
Price for up to 6 people
US $1,250
Angler's Choice
Listing image

36 ft

up to 6

Hooked Up Charters

 
Federally permitted
 
Key West
Full Day
fish
fish
fish
fish
+6
These trips are ideal for winter months. The weather might be a bit colder, but the fishing is definitely hot! Check the morning bite and go after Yellowtail Snapper, Mutton Snapper, Mangrove Snapper, Grouper, King Mackerel, and many more.
Instant Confirmation
Price for up to 6 people
US $1,400
Angler's Choice
Listing image

39 ft

up to 6

Jolly Roger II

 
Federally permitted
 
Key West
Half Day Trip
Spend your exploring Key West by land, and then join your captain for a 4-hour trip out to the hottest fishing grounds! Your captain mostly takes guests trolling – he calls it 'reef to bluewater trolling, ' as these are the areas you'll be targeting. You'll have the opportunity to hook anything from King Mackerel, Wahoo, Barracuda, and maybe even a Mahi Mahi or two. Your captain loves tailoring trips to suit your needs, so let him know what you want to catch. Rods, reels, bait, and tackle included. This 4
Instant Confirmation
Price for up to 6 people
US $950
Angler's Choice
Listing image

42 ft

up to 6

My Ohana Sport Fishing

 
Federally permitted
 
Key West
Full Day Trip
fish
fish
fish
fish
You and the captain will target the species that are best for the month. Sailfish, Wahoo, Tuna, Mahi and possibly Blue Marlin
Instant Confirmation
Price for up to 6 people
US $1,800
Angler's Choice
Listing image

50 ft

up to 6

Corsair Sportfishing Key West

 
Federally permitted
 
Key West
Half Day Trip
fish
fish
fish
fish
+5
4 hours in the will give you a chance to battle some of the biggest A-listers in the area. You'll be going up to 7–12 miles from the coast in pursuit of Mahi Mahi, Sailfish. Tuna, King Mackerel, Wahoo, Snapper, Grouper, and everything else that takes the bait. If you're a person, this is the trip for you! You'll be going after Mahi Mahi, Wahoo, Sailfish, Tuna, King Mackerel Snapper, and Grouper, just to name a few. This trip will take you anywhere from 7–12 miles from shore.
Price for up to 6 people
US $1,000
Angler's Choice
Listing image

40 ft

up to 6

Linda D IV

 
Federally permitted
 
Key West
Half Day Trip
This trip is perfect for anyone looking to avoid the rush hour. Expect to target species like Mahi Mahi, Amberjack, Grouper, and Snapper. Rods, reels, and terminal tackle are included in the price, so all you need to do is bring some food and drinks for a day to remember. Even a shorter trip can be very lucrative in Key West. You'll have the chance to go after the likes of Mahi Mahi, Amberjack, Grouper, and Snapper.
Instant Confirmation
Price for up to 6 people
US $1,100
Angler's Choice
Listing image
Meet the Captain

27 ft

up to 4

ScreamingLines Center Console – 27'

 
Key West
Inshore/Offshore Half Day Trip (PM)
fish
fish
fish
fish
+6
This afternoon adventure is a great way to get the freshest fish meat for your dinner. Target Snapper, Grouper, Mahi, Tuna and many more. They go above and beyond to satisfy customers helping them in anyway possible to ensure you have a great time on his boat. This young man has his own family so he has tons of patience for kids and beginners. The born and raised conch captain/owner will show you everything you need to know and fill your bucket with a tasty catch.
Instant Confirmation
Price for up to 4 people
US $750
Angler's Choice
Listing image
Meet the Captain

33 ft

up to 6

Kilo Whiskey Charters

 
Federally permitted
 
Key West
Half Day Trip (4hr )
fish
fish
fish
fish
+13
Enjoy a four-hour half-day trip tailored to your preferred fishing style, whether it's offshore or nearshore. Captain Anthony will provide expert suggestions based on what's currently biting, but the final choice is always yours. Try various techniques like trolling, bottom fishing, deep dropping, or live baiting, and experience the thrill of fishing with a seasoned professional. This flexible adventure ensures a memorable and exciting outing on the vibrant waters of Key West.
Instant Confirmation
Price for up to 6 people
US $1,000
Angler's Choice
Listing image
Meet the Captain

30 ft

up to 6

RideOut Charters

 
Federally permitted
 
Key West
4 Hour Trip
fish
fish
fish
fish
+7
This trip is perfect for anyone who wants to get out and catch some fish! On this charter we could be You'll be targeting snapper, grouper, jacks, mahi mahi, wahoo, sailfish, and tarpon. Everything you need is included in this charter. Things you may need are sunglasses, the proper cloths for the conditions, and whatever food and drink you want.
Price for up to 6 people
US $900
Angler's Choice
Listing image

26 ft

up to 4

Conch Queen Charters

 
Stock Island
4 Hour Inshore/Reef
fish
fish
fish
fish
+7
4 hour fishing trip. Gear, license, bait, tackle, bottled water, and ice provided. Can target inshore, reef, wreck, or offshore species, weather dependant!
Instant Confirmation
Price for up to 2 people
US $750
Angler's Choice
Listing image
Meet the Captain

34 ft

up to 6

Wild Bill Sport Fishing

 
State licensed
 
Key West
3/4 Day Trip
This 6-hour trip gives you a bit more time for fishing, and you can still get back in time to run some errands. Target species include Shark (many species including Blacktip, Hammerhead, Lemon, Tiger, Blacknose). Grouper, Snapper, King, Spanish, Cero mackerel. The crew will supply the fishing gear, license, bait if available, bottled water, and will clean your catch. Bring a camera, sunblock, a cap, non-marking shoes, food and beverages.
Instant Confirmation
Price for up to 6 people
US $1,250
Angler's Choice
Listing image

36 ft

up to 6

Hooked Up Charters

 
Federally permitted
 
Key West
Full Day
fish
fish
fish
fish
+6
These trips are ideal for winter months. The weather might be a bit colder, but the fishing is definitely hot! Check the morning bite and go after Yellowtail Snapper, Mutton Snapper, Mangrove Snapper, Grouper, King Mackerel, and many more.
Instant Confirmation
Price for up to 6 people
US $1,400
Angler's Choice
Listing image

39 ft

up to 6

Jolly Roger II

 
Federally permitted
 
Key West
Half Day Trip
Spend your exploring Key West by land, and then join your captain for a 4-hour trip out to the hottest fishing grounds! Your captain mostly takes guests trolling – he calls it 'reef to bluewater trolling, ' as these are the areas you'll be targeting. You'll have the opportunity to hook anything from King Mackerel, Wahoo, Barracuda, and maybe even a Mahi Mahi or two. Your captain loves tailoring trips to suit your needs, so let him know what you want to catch. Rods, reels, bait, and tackle included. This 4
Instant Confirmation
Price for up to 6 people
US $950
Angler's Choice
Listing image

42 ft

up to 6

My Ohana Sport Fishing

 
Federally permitted
 
Key West
Full Day Trip
fish
fish
fish
fish
You and the captain will target the species that are best for the month. Sailfish, Wahoo, Tuna, Mahi and possibly Blue Marlin
Instant Confirmation
Price for up to 6 people
US $1,800
Angler's Choice
Listing image

50 ft

up to 6

Corsair Sportfishing Key West

 
Federally permitted
 
Key West
Half Day Trip
fish
fish
fish
fish
+5
4 hours in the will give you a chance to battle some of the biggest A-listers in the area. You'll be going up to 7–12 miles from the coast in pursuit of Mahi Mahi, Sailfish. Tuna, King Mackerel, Wahoo, Snapper, Grouper, and everything else that takes the bait. If you're a person, this is the trip for you! You'll be going after Mahi Mahi, Wahoo, Sailfish, Tuna, King Mackerel Snapper, and Grouper, just to name a few. This trip will take you anywhere from 7–12 miles from shore.
Price for up to 6 people
US $1,000
Angler's Choice
Listing image

40 ft

up to 6

Linda D IV

 
Federally permitted
 
Key West
Half Day Trip
This trip is perfect for anyone looking to avoid the rush hour. Expect to target species like Mahi Mahi, Amberjack, Grouper, and Snapper. Rods, reels, and terminal tackle are included in the price, so all you need to do is bring some food and drinks for a day to remember. Even a shorter trip can be very lucrative in Key West. You'll have the chance to go after the likes of Mahi Mahi, Amberjack, Grouper, and Snapper.
Instant Confirmation
Price for up to 6 people
US $1,100
Angler's Choice
Listing image
Meet the Captain

27 ft

up to 4

ScreamingLines Center Console – 27'

 
Key West
Inshore/Offshore Half Day Trip (PM)
fish
fish
fish
fish
+6
This afternoon adventure is a great way to get the freshest fish meat for your dinner. Target Snapper, Grouper, Mahi, Tuna and many more. They go above and beyond to satisfy customers helping them in anyway possible to ensure you have a great time on his boat. This young man has his own family so he has tons of patience for kids and beginners. The born and raised conch captain/owner will show you everything you need to know and fill your bucket with a tasty catch.
Instant Confirmation
Price for up to 4 people
US $750
Angler's Choice
Listing image
Meet the Captain

33 ft

up to 6

Kilo Whiskey Charters

 
Federally permitted
 
Key West
Half Day Trip (4hr )
fish
fish
fish
fish
+13
Enjoy a four-hour half-day trip tailored to your preferred fishing style, whether it's offshore or nearshore. Captain Anthony will provide expert suggestions based on what's currently biting, but the final choice is always yours. Try various techniques like trolling, bottom fishing, deep dropping, or live baiting, and experience the thrill of fishing with a seasoned professional. This flexible adventure ensures a memorable and exciting outing on the vibrant waters of Key West.
Instant Confirmation
Price for up to 6 people
US $1,000
Angler's Choice
Listing image
Meet the Captain

30 ft

up to 6

RideOut Charters

 
Federally permitted
 
Key West
4 Hour Trip
fish
fish
fish
fish
+7
This trip is perfect for anyone who wants to get out and catch some fish! On this charter we could be You'll be targeting snapper, grouper, jacks, mahi mahi, wahoo, sailfish, and tarpon. Everything you need is included in this charter. Things you may need are sunglasses, the proper cloths for the conditions, and whatever food and drink you want.
Price for up to 6 people
US $900
Angler's Choice
Listing image

26 ft

up to 4

Conch Queen Charters

 
Stock Island
4 Hour Inshore/Reef
fish
fish
fish
fish
+7
4 hour fishing trip. Gear, license, bait, tackle, bottled water, and ice provided. Can target inshore, reef, wreck, or offshore species, weather dependant!
Instant Confirmation
Price for up to 2 people
US $750

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Sailfish Fishing in Key West

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Key West

4.8
/5
Based on 30,498 reviews by FishingBooker anglers

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