Damn Good Sailfish Fishing Charters In Islamorada

Check real-time availability and compare rates on Islamorada sailfish fishing trips. Confidently book your next day on the water.

Choose a Date
4.83/5 Average Rating

Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns

100% Weather Guarantee

We want to keep everyone safe, so in the case of inclement weather we'll work with you to reschedule at no cost

Recently Booked Sailfish Fishing Charters In Islamorada, Fl

Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Reef Thrill

99% (69)
40 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Live Bait Sailfishing

NEW
23 ft 1 - 3 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Half Day Deep Sea

NEW
39 ft 1 - 12 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Offshore Fishing Experience

100% (1)
36 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Islamorada Deep Sea Trophy Hunt

100% (2)
45 ft 1 - 6 People From $950
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Full Day Islamorada Trip

100% (19)
44 ft 1 - 12 People From $1,800

Top Types of Sailfish Trips in Islamorada

“Our Damn Good Guides go above and beyond, and we’ve handpicked every single one. We’re passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

All Target Species in Islamorada

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)

More Sailfish Fishing Charters In Islamorada, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

3/4 Day Deep Sea

NEW
39 ft 1 - 12 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Offshore Islamorada Trip

94% (17)
48 ft 1 - 6 People From $1,200
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Hot Pursuit In The Gulf Stream

100% (17)
37 ft 1 - 6 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Islamorada Full Spectrum Trip

100% (10)
25 ft 1 - 4 People From $1,350
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Full Day Deep Sea

NEW
39 ft 1 - 12 People From $1,600
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Morning Half

100% (19)
44 ft 1 - 12 People From $1,100
See All Sailfish Trips in Islamorada

Need a Place to Stay?

Everything to Know About Booking an Islamorada sailfish fishing charter

What are the best sailfish fishing charters in Islamorada?

What is sailfish fishing in Islamorada all about?

In Islamorada, sailfish are among the most sought-after game fish, drawing anglers from around the world to the renowned waters of the Florida Keys. Sailfish are known for their remarkable size, speed, and acrobatic displays, making them a thrilling catch for both novice and experienced anglers alike. These majestic fish migrate through the offshore waters of Islamorada during the winter months, offering anglers prime opportunities for unforgettable fishing experiences. Sailfish are prized for their challenging fights, often testing anglers' skills and equipment to the limit.

Anglers targeting sailfish in Islamorada typically employ trolling techniques, using rigged baits or artificial lures trailed behind the boat to entice strikes. Anglers cruise along the edge of the Gulf Stream and offshore reefs, covering a large area of water in search of feeding sailfish. Once a sailfish is hooked, it puts on a spectacular display of leaps, tail walks, and high-speed runs, thrilling anglers with its acrobatics. Sailfish are highly prized among sport fishermen for their challenging fights and are considered one of the most prestigious game fish to catch in Islamorada.

In addition to trolling, live bait fishing is another effective technique for targeting sailfish in Islamorada. Anglers deploy live baits such as pilchards, ballyhoo, or threadfin herring near surface-feeding fish or structure-rich areas where sailfish are known to congregate. This method allows anglers to present natural baits in a way that mimics the behavior of natural prey, increasing the chances of enticing strikes from sailfish. With their impressive size, speed, and aerial displays, sailfish offer anglers in Islamorada thrilling opportunities for memorable fishing adventures in the beautiful waters of the Florida Keys.

What are the most popular months to fish for sailfish fishing in Islamorada?

In Islamorada, the sailfish season typically aligns with their migration patterns, which coincide with the winter months in the Florida Keys. Sailfish begin their annual migration southward from late fall to early winter, following the warm waters of the Gulf Stream. During this time, anglers in Islamorada have prime opportunities to target sailfish as they pass through the offshore waters of the Florida Keys. The sailfish season in Islamorada is characterized by consistent action, with peak fishing occurring from December to February when sailfish numbers are at their highest.

Winter marks the peak of the sailfish season in Islamorada, offering anglers the best chances for successful outings targeting these majestic game fish. As sailfish migrate southward along the edge of the Gulf Stream, they pass through the offshore waters of Islamorada, providing anglers with thrilling opportunities for catch-and-release fishing. Anglers can expect frequent encounters with sailfish during this time, with multiple hookups possible in a single day of fishing. The sailfish season in Islamorada coincides with favorable weather conditions, with calm seas and mild temperatures enhancing the overall fishing experience.

While the winter months are prime for sailfish fishing in Islamorada, sailfish can also be caught during other times of the year, particularly during transitional periods when water temperatures are moderate. In addition to the winter season, spring and early summer can also offer productive fishing for sailfish in Islamorada. During these months, anglers may encounter sailfish feeding in shallower waters closer to shore, providing opportunities for exciting nearshore fishing experiences. Overall, the sailfish season in Islamorada spans from late fall to early summer, offering anglers a wide window of opportunity to target these prized game fish in the beautiful waters of the Florida Keys.

What techniques are popular for catching sailfish in Islamorada?

In Islamorada, anglers employ various effective techniques to target sailfish, capitalizing on their migratory patterns and feeding behavior in the offshore waters of the Florida Keys. One of the most common methods for sailfish fishing in Islamorada is trolling. Anglers troll with rigged baits or artificial lures behind their boats, covering a large area of water along the edge of the Gulf Stream and offshore reefs where sailfish are known to congregate. Trolling allows anglers to present baits or lures at varying depths and speeds, increasing the likelihood of enticing strikes from sailfish. This method is particularly effective during the winter months when sailfish migrate through the waters of Islamorada in search of prey.

Live bait fishing is another popular technique for targeting sailfish in Islamorada. Anglers deploy live baits such as pilchards, ballyhoo, or threadfin herring near surface-feeding fish or structure-rich areas where sailfish are known to hunt. This method allows anglers to present natural baits in a way that mimics the behavior of natural prey, increasing the chances of enticing strikes from sailfish. Live bait fishing can be highly productive, especially when targeting sailfish that are actively feeding near the surface or in shallower waters.

Another effective technique for targeting sailfish in Islamorada is kite fishing. Anglers deploy a kite from their boat, suspending live baits from the kite lines to simulate the behavior of struggling baitfish near the surface. This method allows anglers to present baits in a natural and enticing manner, enticing strikes from sailfish that are cruising near the surface or hunting in the vicinity. Kite fishing is particularly effective in calm conditions and allows anglers to cover a large area of water while keeping baits in the strike zone for extended periods. With their impressive size, speed, and acrobatic displays, sailfish offer anglers in Islamorada thrilling opportunities for memorable fishing adventures throughout the year.

What other species are popular in Islamorada?

In addition to targeting sailfish, anglers visiting Islamorada have an abundance of other species to pursue, ensuring a diverse and exciting fishing experience. One popular species among anglers is the mahi-mahi, also known as dolphin or dorado. These colorful and acrobatic fish inhabit the offshore waters surrounding Islamorada, particularly near weed lines, floating debris, and offshore structures. Mahi-mahi are prized for their delicious flesh and are known for their aggressive strikes and aerial displays, making them a favorite among anglers. Anglers can target mahi-mahi using a variety of techniques, including trolling with artificial lures or natural baits, as well as casting to schools of fish found around floating objects.

Another sought-after species in Islamorada is the yellowtail snapper, prized for its delicate flavor and challenging fights. Yellowtail snapper inhabit the shallow reefs and wrecks surrounding Islamorada, where they can be targeted using light tackle and live or cut bait. These colorful fish are known for their stealthy behavior and keen eyesight, providing anglers with a rewarding challenge. Yellowtail snapper fishing in Islamorada is particularly productive during the spring and summer months when these fish are abundant in the warm waters of the Florida Keys.

In addition to mahi-mahi and yellowtail snapper, anglers in Islamorada can pursue a variety of other species, including wahoo, tuna, marlin, grouper, snapper, and tarpon, among others. Wahoo are fast-swimming predators found in the offshore waters of Islamorada, offering anglers exciting opportunities for high-speed trolling. Tuna are also abundant in the offshore waters, with blackfin and yellowfin tuna being the most commonly targeted species. Marlin, including blue marlin and white marlin, are prized game fish known for their size and strength, providing anglers with thrilling battles offshore. Inshore, anglers can target species such as tarpon, snook, bonefish, permit, and mangrove snapper, offering a diverse range of fishing experiences in the rich and bountiful waters of Islamorada.

Recent Reviews

  • ★★★★★
    Paul and first mate Gary worked hard all day on our 8 hour trip offshore. Targeting Blackfin Tuna, Mackerel and Sailfish all day and keeping us over the fish with consistent bites. Would definitely recommend to anybody who wants a good experience offshore and will hopefully be back again in the future.

    Adam T. | October 13, 2025

    Trip: Ultimate Offshore Thrills

  • ★★★★★
    My wife and I had the pleasure of taking a trip with Captain George. He and his mate Kyle picked us up on time and took us out for a great day of fishing. Weather was definitely sporty but his boat handled it comfortably. They were very well prepared to for everything. Having a boat myself I asked a lot of questions on techniques and such. Captain George was very help and wasn't hesitant to share his knowledge. We had a great time. They were upbeat and personable. We ended up will a cooler full of yellow tail snapper, a nice mutton snapper, a nice fight on a good-sized bonito. They recommended a good place to cook it up for us. I would highly recommend taking a trip with Captain George.

    Andy T. | August 15, 2025

    Trip: Layton Fishing Adventure

  • ★★★★★
    My son and I went out with captain Larry and we had an amazing time. He is extremely knowledgeable and has great experience. We caught a lot of big fish and had the time of our lives. I recommend this to all looking for a great fishing trip experience.

    Ronen S. | August 12, 2025

    Trip: Hot Pursuit In The Gulf Stream

  • ★★★★★
    It is always the right thing to trust professionals. Captain Pete and his mate Chuck are such. The day started kind of slow, but they were able to adjust in time and turn it into a success. We caught a variety of tasty fish which Chuck skillfully filleted. 👍👍👍👍👍

    Oksana T. | August 7, 2025

    Trip: Key Largo Offshore

  • ★★★★★
    We had an awesome day with Captain Aaron. He dialed up the perfect weather. We caught a bunch of fish, including this 25 pound bull.

    Todd H. | July 14, 2025

    Trip: Offshore Fishing

Other Featured Cities

What's biting in Islamorada?

View Sailfish Fishing Reports from our damn good guides.

Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

See All Sailfish Trips in Islamorada