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Sailfish Fishing Charters In Islamorada

Check real-time availability on Islamorada sailfish fishing trips. Online booking | 4.76 / 5 stars | Guides from $900

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Recently Booked Sailfish Fishing Charters Near Islamorada, Fl

Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Offshore Thrills

100% (13)
40 ft 1 - 6 People From $1,100
Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Deep Water Adventure

100% (4)
32 ft 1 - 6 People From $1,500
Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Offshore Islamorada Trip

NEW
48 ft 1 - 6 People From $1,200
Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Ultimate Offshore Thrills

100% (1)
40 ft 1 - 6 People From $1,400
Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Reef Thrill

50% (2)
40 ft 1 - 6 People From $950
Fishing in Islamorada

Deep Sea Fishing Charter in Islamorada

Reef To Offshore: Fishing Frenzy

NEW
1 - 6 People From $1,400

Most Popular Types of Sailfish Trips in Islamorada

“Our Damn Good Guides go above and beyond to provide you an incredible trip, and we’ve handpicked every single one. We’re passionate about the outdoors and about empowering people to find the perfect-match guide for the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

More Sailfish Fishing Charters Near Islamorada, Fl

Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for 3/4 Day Trip in Islamorada

6 Hour 3/4 day trip for up to 6 people departs at 0630. You will be going out on a spacious 44' Express Marlago Jefferson Yacht. Twin 450 HP 3208 Caterpillar engines. Vessel is equipped with all the electronics needed. GPS, Sonar, Radar, VHF and more. You will be using top of the line tackle, rods and reels, Vessel is equipped with fighting chair, 2 large live wells, Outriggers, Center rigger, Downrigger and many other specific tools that we use to target all the different species that roam these Florida Keys waters. Summertime we may start on the reef then work offshore or we may run straight offshore. Depends what is happening each day. We will generally start by catching some live bait then either stop at the reef to target some snapper, Grouper etc or we may head straight offshore and target Blackfin Tuna, Mahi, Wahoo and many other species depending on the action each day. Wintertime we may stay close to the reef but target species such as Sailfish, Wahoo, Blackfin Tuna King Mackerel, and again can target the many Snapper species that thrive here. All you need to bring is whatever you would like to eat and drink and we have everything else ready for you to come aboard and enjoy a great day and create some unforgettable memories Please remember to thank your mate with a 20% tip. Read More

Deep Sea, Nearshore Fishing Charter in Islamorada

3/4 Day Trip

100% (1)
44 ft 1 - 6 People From $1,400
Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for BEST! Sport fishing Trips in Islamorada, Whale Harbor in Islamorada

Our friendly experienced crew will help you catch fish and have fun on a fully equipped air conditioned 43 foot Viking Sport Fishing Boat with a full Tower. We accommodate up to 6 anglers with plenty of seating. We are committed to making your Sport Fishing trip as productive as possible. We search area reefs and the Gulf Stream for the best fishing opportunities available each day. Sailfish, Mahi, Tuna, Wahoo, Snapper, Amberjack, Marlin, Sharks, Cobia, and other Sport Fish are real possibilities and can be caught. We are Sport fishing and it is possible you may catch only a few fish due to adverse weather. We are located in Whale Harbor Marina Islamorada Florida Keys, mile marker 83.5 next to the Sea Food Buffet. Whale Harbor is a fishing destination known as the Sport Fishing Capitol of the World. We welcome novice, and experienced anglers to have fun fishing with us. We encourage you to ask us questions about Sport fishing. Read More

Deep Sea, Nearshore Fishing Charter in Islamorada

BEST! Sport Fishing Trips In Islamorada, Whale Harbor

NEW
43 ft 1 - 6 People From $1,100
Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for Islamorada Offshore Experience in Islamorada

Join Captain Tony on this incredible offshore sportfishing trip here in Islamorada, Florida! Islamorada is known worldwide as a Mecca for sportfishing, and there's no better guide to the rich waters here than Captain Tony. On board his sleek and comfortable 32' SeaVee center console, you'll have a perfect opportunity to chase a variety of classic sportfish, including Blackfin Tuna, Mahi Mahi, and Wahoo towards the top of the water column, plus a bunch of Grouper and Snapper species that lurk down in the reefs and rocks. Whatever fish you want to go after or method you want to try, just let Captain Tony know, and he'll get you properly set up for success! He also has tons of expert pointers to improve your fish-fighting skills and put you in the best possible position to catch a new personal best. Captain Tony will also switch gears in order to give you a superior experience, whether that means switching to bottomfishing midway through, or letting out trolling lines, drift fishing, or otherwise. Captain Tony's 32' SeaVee is a beautiful boat, and sports twin 300-HP Yamaha engines and a Seakeeper system that prevents boat roll and seasickness! As a center console vessel, you'll be able to fish 360º around the boat, making it perfect for groups of up to six people. Plus, she features recently-updated electronics, side-scanning sonar, radar, multiple live wells, and an oversized box for your big fish. Captain Tony will provide all rods, reels and tackle. All you need to bring are good vibes and whatever you care to eat and drink. Enjoy your day out on the water! Read More

Deep Sea, Nearshore Fishing Charter in Islamorada

Islamorada Offshore Experience

NEW
32 ft 1 - 6 People From $1,000
Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for Hot Pursuit in the Gulf Stream in Islamorada

Launching from Whale Harbor with Captain Larry puts you a mere 30 minutes ride offshore to the Gulf Stream's premier hot spots. Captain Larry and crew won’t waste a moment taking you to the action either. On these trips, you will head out up to 30 miles offshore and to target Dolphin, Blackfin Tuna, Amberjack, Wahoo, Shark, Marlin, Sailfish, King Mackerel, and more! If your interest peaked at dolphin/mahi-mahi, you should book your trip from May to October when the population explodes! The charter boat trolls rigged baits and lures to locate schools of dolphin that range from 5 to 50 pounds. Once a school is found, their voracious appetites and abundant numbers result in a feeding frenzy you’ll never forget. And, since Mahi is excellent table fare, you’ll want to keep them for dinner. Your boat’s mate will gladly fillet them and you can arrange to have your catch prepared at any of the local restaurants. From November to April, Captain Larry primarily targets sailfish, using live bait on light tackle. Catching the baitfish (ballyhoo) on the way out to the deep water is a super fun way to start off your adventure (Especially given the prospect that those fish will turn into even bigger fish!) The ballyhoo are chummed up to the surface, where they are caught by cast net or by fishing for them using tiny hair hooks. Once the bait well is full, the boat runs to the outside edge of the reef and the action begins. If you’ve never hooked into a 7-foot-long tail-walking sailfish on light tackle, you’re in for a thrill of a lifetime! We practice catch and release for all bill fishing and ask about no-kill fish mounts. All you need to bring for your trip with Captain Larry are your favorite snacks, drinks, and lunch if you'd like. Captain Larry will provide everything else from a captain & crew that cares, all the licenses, rods, tackle & bait, a clean & spacious vessel, and a filleting and bagging service for your catch! Read More

Deep Sea Fishing Charter in Islamorada

Hot Pursuit In The Gulf Stream

NEW
1 - 6 People From $1,600
Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for Morning Half in Islamorada

4 Hour 1/2 day trip for up to 6 people departs at 0630. You will be going out on a spacious 44' Express Marlago Jefferson Yacht. Twin 450 HP 3208 Caterpillar engines. Vessel is equipped with all the electronics needed. GPS, Sonar, Radar, VHF and more. You will be using top of the line tackle, rods and reels, Vessel is equipped with fighting chair, 2 large live wells, Outriggers, Center rigger, Downrigger and many other specific tools that we use to target all the different species that roam these Florida Keys waters. Summertime - we will generally fish on the reef for various Snappers such as Yellowtail, Mutton, Mangrove and some others. More than often we will take some time to troll and target Wahoo, Blackfin Tuna, Mahi and a few others when they are close enough to go after in the allotted time. Wintertime - we again stay close to the reef but target species such as Sailfish, Wahoo, Blackfin Tuna King Mackerel, and again can target the many Snapper species that thrive here. All you need to bring is whatever you would like to eat and drink and we have everything else ready for you to come aboard and enjoy a great day and create some unforgettable memories Please remember to thank your mate with a 20% tip. Read More

Deep Sea, Nearshore Fishing Charter in Islamorada

Morning Half

100% (2)
44 ft 1 - 6 People From $1,000
Fishing in Islamorada
Fishing in Islamorada
Fishing in Islamorada
trip description for Afternoon Half in Islamorada

4 Hour half day trip for up to 6 people departs at 1:00pm. You will be going out on a spacious 44' Express Marlago Jefferson Yacht. Twin 450 HP 3208 Caterpillar engines. Vessel is equipped with all the electronics needed. GPS, Sonar, Radar, VHF and more. You will be using top of the line tackle, rods and reels, Vessel is equipped with fighting chair, 2 large live wells, Outriggers, Center rigger, Downrigger and many other specific tools that we use to target all the different species that roam these Florida Keys waters. Summertime - we will generally fish on the reef for various Snappers such as Yellowtail, Mutton, Mangrove and some others. More than often we will take some time to troll and target Wahoo, Blackfin Tuna, Mahi and a few others when they are close enough to go after in the allotted time. Wintertime - we again stay close to the reef but target species such as Sailfish, Wahoo, Blackfin Tuna King Mackerel, and again can target the many Snapper species that thrive here. All you need to bring is whatever you would like to eat and drink and we have everything else ready for you to come aboard and enjoy a great day and create some unforgettable memories Please remember to thank your mate with a 20% tip. Read More

Deep Sea, Nearshore Fishing Charter in Islamorada

Afternoon Half

100% (1)
44 ft 1 - 6 People From $1,000
See All Sailfish Trips in Islamorada

Everything to Know About Booking an Islamorada sailfish fishing charter

What are the best sailfish fishing charters in Islamorada?

Our Damn Good Guides currently offer 41 sailfish trips in Islamorada, and the most popular trips in the area are Offshore Thrills guided by Paul, Deep Water Adventure guided by Conan, and Offshore Islamorada Trip guided by Frank.

Our guides in Islamorada are rated a 4.76 out of 5 based on 2694 verified reviews on Captain Experiences.

All guides on Captain Experiences are licensed, insured, and vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Other popular cities nearby for booking a Sailfish charter include Marathon, Key Largo and Tavernier.

Looking for kid friendly sailfish guides / fishing lessons in Islamorada? Check out our beginner and family friendly sailfish guides in Islamorada.

What types of sailfish fishing charters are common in Islamorada?

Deep Sea fishing is the most popular for sailfish in Islamorada as well as nearshore fishing and inshore fishing.

The most common fishing techniques in Islamorada are trolling, heavy tackle fishing, and bottom fishing but live bait fishing and artificial lure fishing are popular as well.

How much do Islamorada sailfish fishing charters cost?

for sailfish in Islamorada prices can range anywhere from about $900 to $1,899, but the average price for a half day trip for sailfish in Islamorada is $1,044. The average price for a full day trip for sailfish in Islamorada is $1,562.

What month is best for sailfish fishing in Islamorada?

The most popular season for sailfish fishing in Islamorada is spring, and most anglers book their trips 34 days in advance.

Do I need a Islamorada fishing license for sailfish and what are the bag limits for sailfish in Islamorada?

You’re in luck! Our fishing tours in Islamorada don’t require you to purchase a fishing license – your group is covered by your boat’s captain. See here for more information on bag limits and fishing season regulations 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 of Captain Experiences

  • ★★★★★
    We had an amazing time on a tough fishing day, would definitely book again when I am in the area. Andrew is great with the kids, and super patient with the beginners. He did everything he could to put us on fish. He also pointed out the abundance of wildlife, including sea turtles, hammerhead sharks, and a manatee. Everything we could hope for with my son's first saltwater fishing adventure.

    William S. with Andrew A. of Key Largo, Florida

  • ★★★★★
    We booked a 3/4 day after speaking with the captain the (plan) was made to shoot out deep and if we were not hitting them we would come in on the 3/4 day booking rather than a full day. Captain troy and his first mate worked as hard as I have ever seen to get fish on the boat. Not sure but at one time I think he had a deep running plug in one marlin plug and 4 top water trolling plugs so it looked like they were shooting for many different depths. We finally got into the mahi-mahi it was on. The first mate and captain maneuvered through 4 men as quick as humanly possible pulling fish off the lines and baiting hooks and handing them back. The only true way to explain it would be controlled chaos. These guys are GREAT at what they do and both the first mate and the captain seem to be fantastic people in there own right. So if your looking for a hard working boat stop here at Miller Time....

    Vance T. with Troy W. of Islamorada, Florida

  • ★★★★★
    Great fishing. Captain Paul delivered and put us on plenty of Mahi-Mahi. 5 star experience.

    Gary A. with Paul J. of Islamorada, Florida

  • ★★★★★
    We had a rough weather day but Capt Joe Joe put us on a lot of Mahi off shore and Yellowtail closer in. Outstanding day for our group and great boat handling skills from our captain and first mate. Will definitely book with them again.

    Arthur D. with Joel B. of Marathon, Florida

  • ★★★★★
    Very good inshore trip - caught plenty of fish and numerous species. Planning to book again next year,

    David S. with Joel B. of Marathon, Florida

  • ★★★★★
    I have been fishing the keys for 10 years but learned a ton fishing with Captain Troy and first mate James. We caught a 2 man limit of nice sized yellow tail in 1.5 h. Very friendly folks made for a great day ! Highly recommend!

    Thomas J. with Troy W. of Islamorada, Florida

  • ★★★★★
    We had a blast fishing with Captain Troy and his crew! They did everything possible to provide us an exciting adventure during our vacation. We caught a variety of fish and enjoyed grilling them up that evening. We highly recommend Captain Troy for your Florida Keys fishing adventure.

    Patrick G. with Troy W. of Islamorada, Florida

  • ★★★★★
    Great charter. Awesome Captain and First Mate

    Robert P. with Joel B. of Marathon, Florida

  • ★★★★★
    Awesome day. Great Capt. and 1st mate.

    Thomas E. with Ben Z. of Marathon, Florida

  • ★★★★★
    We had a great time! Captain Paul was great and John worked his butt off to get is on fish. Highly recommend.

    Mike H. with Paul J. of Islamorada, Florida

  • ★★★★★
    I went on my 1st trip out of Islemorada with my son. The action was unbelievable! Capt Paul and his mate John put us on the fish early and often. It was our best fishing trip ever! It definitely won’t be our last. Thanks again Capt. Paul!

    Joe H. with Paul J. of Islamorada, Florida

  • ★★★★★
    Captain Paul and John were excellent today. We had so much fun and were treated very well. Highly recommend him to anyone.

    Robert S. with Paul J. of Islamorada, Florida

  • ★★★★★
    Had an amazing trip with Captain Paul and excellent deck hand John. We would recommend Paul, John, and Reef Runner to all looking to book an offshore trip.

    Scott B. with Paul J. of Islamorada, Florida

  • ★★★★★
    We had a great time with Joel & his crew. Caught a ton of fish, & enjoyed our time offshore :) We’ll be back to do it again!

    Casie B. with Joel B. of Marathon, Florida

  • ★★★★★
    Captain Paul and First Mate John were awesome. Captain Paul found fish quickly and after a school of Mahi would pass, he was able to find another quickly. John worked his butt off hooking up bait for the next school and changing lines as needed. Definitely a great time with knowledgeable fishermen. Wouldn’t hesitate to book another trip.

    Dan H. with Paul J. of Islamorada, Florida

  • ★★★★★
    Awesome fishing trip with captain Paul and John! Knowledgeable and very helpful! Got a lot of fish on and came back with some mahi! Cleaned out fish and filleted. Got recommendations on where to take our fish to eat and who to see to send our fish back home!

    Ashley B. with Paul J. of Islamorada, Florida

  • ★★★★★
    Our group of four had a great time!!! Will take a trip again with Joel the next time we are in Marathon FL.

    Russell O. with Joel B. of Marathon, Florida

  • ★★★★★
    Capt. Paul and his mate John make the perfect team. The expertise and knowledge in which they performed their job made for an extremely successful and pleasant experience. We will definitely book a trip with Capt. Paul and John the next time we are in the keys.

    Paul P. with Paul J. of Islamorada, Florida

  • ★★★★★
    Where do I start? I am a Florida native and this was the most AMAZING trip I’ve ever had. From the great time on the boat, excellent gear, the best captain and first mate I’ve been around in 30 years of fishing, and let’s not forget TONS OF FISH!!!! If you are planning a trip here look no further than Capt Joel!!!! AMAZING !!!!!

    Robert M. with Joel B. of Marathon, Florida

  • ★★★★★
    Wow what a great time we had. Captain Scott was awesome caught some fish, great conversation as well would recommend to anybody.

    Nickolas T. with Scott G. of Tavernier, Florida

What's biting in Islamorada?

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