facebook pixel

Windermere Fishing Guides

Check real-time availability on 23 Windermere fishing trips. Online booking | 5 / 5 stars | Guides from $340

Choose a Date
5/5 Average Rating

Experts Available 24/7

Licensed & Insured Guides

100% Weather Guarantee

Recently Booked Fishing Guides Near Windermere, Fl

Fishing in Windermere

Lake, River Fishing Trip in Windermere

Orlando Bass Fishing Charter

NEW
20 ft 1 - 4 People From $350
Fishing in Windermere

Lake Fishing Trip in Windermere

South Florida Bass Fishing

NEW
20 ft 1 - 3 People From $350
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Night Bowfishing (4 Hours)

100% (1)
18 ft 1 - 2 People From $200
Fishing, Hunting in Clermont

Alligator Fishing, Hunting Trip in Clermont

Trophy Gator

NEW
1 - 4 People From $4,000
Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Key West

Deep Sea, Inshore, Nearshore Fishing Charter in Key West

Offshore Fishing,Reef & Wreck And Sunset

NEW
35 ft 1 - 6 People From $900
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Kissimmee Bass Fishing Charter

NEW
20 ft 1 - 4 People From $350

Most Popular Types of Trips in Windermere

“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

Lake Fishing Guides Near Windermere, Fl

Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Largemouth Hookfest

NEW
20 ft 1 - 4 People From $400
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Night Bowfishing (4 Hours)

100% (1)
18 ft 1 - 2 People From $200
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Sunset Bass & Night Gator Eco-Tour

100% (1)
18 ft 1 - 2 People From $250
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Lake Toho Largemouth Bass Run

100% (3)
20 ft 1 - 4 People From $300
Fishing in Kissimmee

Lake, River Fishing Trip in Kissimmee

Pontoon Fishing Charter

100% (3)
25 ft 1 - 6 People From $550
Fishing in Kissimmee

Lake Fishing Trip in Kissimmee

Kissimmee Bass Fishing Charter

NEW
20 ft 1 - 4 People From $350

Inshore Fishing Guides Near Windermere, Fl

Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Key West

Deep Sea, Inshore, Nearshore Fishing Charter in Key West

Offshore Fishing,Reef & Wreck And Sunset

NEW
35 ft 1 - 6 People From $900
Fishing in Sebastian

Flats, Inshore Fishing Charter in Sebastian

Orlando Bowfishing

NEW
23 ft 1 - 6 People From $650
Fishing in Kissimmee

Inshore Fishing Charter in Kissimmee

Indian River Saltwater Trip

NEW
20 ft 1 - 4 People From $600

More Fishing Guides Near Windermere, Fl

Fishing in Kissimmee
Fishing in Kissimmee
Fishing in Kissimmee
trip description for Largemouth Hookfest in Kissimmee

Are you ready to hammer some incredible Largemouth in some of America's most productive bassfishing territory? Look no further—this trip with Captain David has everything you need for a great day, and is open to everyone, regardless of your experience level. Captain David is a highly successful tournament angler with several years of experience fishing this area, so you can be confident that you're in capable hands. You'll chase fish from the deck of Captain David's 20' Ranger bay boat, a perfect craft for fishing calm lakes and rivers. Cast out with a wide variety of artificial lures and bait, and get ready for the fight of your life! Bass here love to go after a huge variety of gear, from classic Ned and Texas rigs to mouse lures, live bait, and more. Captain David will provide everything you need for a great trip, including high-quality, rods, reels, and tackle. All you need to bring is sunscreen, sun protection, and a smile! Read More

Lake Fishing Trip in Kissimmee

Largemouth Hookfest

NEW
20 ft 1 - 4 People From $400
Fishing in Kissimmee
Fishing in Kissimmee
Fishing in Kissimmee
trip description for Sunset Bass & Night Gator Eco-Tour in Kissimmee

Hop on board with Captain Randy for an exciting sunset cruise on the Kissimmee Chain of Lakes, headwaters to the Florida Everglades! On this trip, Captain Randy will help you catch a plethora of Florida Largemouth Bass and take you to some incredible wildlife views along the way. No matter if you're a beginner trying to land your first bass or an expert angler looking to set a new personal record, this trip is for you. The Kissimmee Chain of Lakes is one of the top lakes in the country for trophy bass fishing. Captain Randy also loves teaching beginners the tips and tricks of bass fishing. On the night tours, you will see a variety of reptiles, insects, fish and amphibians. Alligators are very active at night. Captain Randy is a highly seasoned gator hunter and is very skilled at finding alligators in the darkness of night. Using lights to see the eyes of the alligator glowing at night, Captain Randy will get you up close to some of these prehistoric monsters. It’s not uncommon to see one to 100 gators on a tour! The temperatures are much cooler at night, a good way to beat the summer heat, and not bake in the sun. On this trip, Captain Randy will take you out on his 18' airboat equipped with a 500 HP engine and an array of generator-powered lights to show where the fish are swimming. Captain Randy can accommodate up to 3 people on this 2-hour adventure. You’ll want to bring food and drinks of your choice (no glass), an ice chest for your day’s catch, and, of course, some great company! Enjoy your day on the water with Captain Randy! Read More

Lake Fishing Trip in Kissimmee

Sunset Bass & Night Gator Eco-Tour

100% (1)
18 ft 1 - 2 People From $250
Fishing in Kissimmee
Fishing in Kissimmee
Fishing in Kissimmee
trip description for Lake Toho Largemouth Bass Run in Kissimmee

If you've been wanting to hook some massive Largemouth Bass on one of America's great fishing lakes, look no further—this trip with Captain Jeanine has everything you need for a blue-ribbon day on the water. Lake Tohopekaliga—affectionately known as Lake Toho—is an ideal habitat for Bass, with warm temperatures, lots of food, and plenty of cover. It's also a great place for anglers, with miles of shoreline and plenty of structure to cast towards. Whether you're an experienced angler or just looking to try something fun on your vacation, this is a perfect trip to hook a new personal best! Captain Jeanine runs these trips aboard her 20' Javelin bass boat, which is an ideal vessel for this water. Cast out with live shiner or an artificial lure, and get ready for the fight of your life! These big Bass love to eat, but hate to get caught. Captain Jeanine will provide everything you need for a great trip, including top-dollar rods and reels. All you need to bring is sunscreen, sun protection, and a smile! You can purchase a Florida fishing license before leaving the dock. Read More

Lake Fishing Trip in Kissimmee

Lake Toho Largemouth Bass Run

100% (3)
20 ft 1 - 4 People From $300
Fishing in Kissimmee
Fishing in Kissimmee
Fishing in Kissimmee
trip description for Bass Fishing the Kissimmee in Kissimmee

Hop on board with Captain Randy for an exciting day on the Kissimmee Chain of Lakes, headwaters to the Florida Everglades! On this trip, Captain Randy will help you catch a plethora of Florida Largemouth Bass that call this lake home. No matter if you're a beginner trying to land your first bass or an expert angler looking to set a new personal record, this trip is for you. The Kissimmee Chain of Lakes is one of the top lakes in the country for trophy bass fishing. Captain Randy also loves teaching beginners the tips and tricks of bass fishing. On this trip, Captain Randy will take you out on his 18' airboat equipped with a 500 HP engine and an array of generator-powered lights to show where the fish are swimming. Captain Randy can accommodate up to 3 people on this 2-hour adventure. You’ll want to bring food and drinks of your choice (no glass), an ice chest for your day’s catch, and, of course, some great company! Enjoy your day on the water with Captain Randy! Read More

Lake Fishing Trip in Kissimmee

Bass Fishing The Kissimmee

NEW
18 ft 1 - 3 People From $300
Fishing in Sebastian
Fishing in Sebastian
Fishing in Sebastian
trip description for Orlando Bowfishing in Sebastian

What is bowfishing? Bowfishing in a nutshell is an adventure like no other. Amazing amounts of wildlife with incredible views from sunsets to the cypress swamps that have been here long before we were. Combining fishing and hunting into one for you to test your skills as an archer! That’s just what bowfishing is in a nut shell…. Come see for yourself everything that bowfishing has to offer. Give us a call to book a fully guided bowfishing trip for you and your friends or family. Bowfishing is also great for company outings No group of people too big! (6 guests per boat). Around here it’s common to harvest Sheepshead, Black Drum, Garfish, Bowfin, Tilapia, Flounder, and more All bows, and equipment are included in the price. There’s no need to buy a fishing license, just show up ready for some fishing! Be mindful that some species may have special rules or limited seasons. Your captain will help you follow regulations while you fish. Thinking of bringing the whole family? Kids are absolutely welcome! If you don’t have a child-sized life vest of your own, be sure to ask if there’s one on board. Also, remember to bring snacks so that nobody gets cranky on an empty belly! Read More

Flats, Inshore Fishing Charter in Sebastian

Orlando Bowfishing

NEW
23 ft 1 - 6 People From $650
Fishing in Kissimmee
Fishing in Kissimmee
Fishing in Kissimmee
trip description for Pontoon Fishing Charter in Kissimmee

Enjoy the beautiful waters of Lake Toho in Kissimmee Florida aboard our, join Captain Steve on his pontoon boat. If you’re looking to cast a few lines, take in the sights, and have an all-around fun day, this is the Lake Toho charter for you. Families will have a great time with the captain. He knows these waterways in and out and makes sure you have everything you need for a memorable day onboard. There’s something for everyone aboard this pontoon boat. Youngsters, and the young at heart, can’t get enough of the fishing while the others sit back in the shade under the cover top. Those looking to relax can chill out on the comfortable couches with a beverage, take in the views, and take pictures of the catches. Captain Steve also has a cooler onboard so you don’t have to bring your own, and ample ice storage for food and drinks. Bass fishing on Lake Toho offers plenty of opportunities in a relaxed atmosphere. Hook trophy Bass, Crappie, Bluegill, and Florida Gar in these calm waters. Trips aboard the pontoon boat is mostly catch and release but he’s happy to bag the fish up for you. In Florida it is illegal for captains to clean and fillet your catch as it attracts alligators. So no cleaning at the docks like saltwater. There’s fishing equipment for every angler to use onboard, no matter how many. What you’ll want to bring is sunglasses, hats, drinks, food! Bottled water is provided and you’re free to bring any other drinks including alcohol. Please try to avoid refreshments in glass packaging. If you’re looking for a little more than just casting a line, may take in the sights, and have an all-around fun day, this is the charter for you. It’s also considered a fantastic wildlife tour because we see Bald Eagles and many other birds. The local Florida Alligator is a favorite and usually visits a trip. Read More

Lake, River Fishing Trip in Kissimmee

Pontoon Fishing Charter

100% (3)
25 ft 1 - 6 People From $550
See All Trips in Windermere

Everything to Know About Booking a Fishing Guide in Windermere

What are the best fishing trips in Windermere?

Our Damn Good Guides currently offer 23 trips in Windermere, and the most popular trips in the area are Orlando Bass Fishing Charter guided by Steve and South Florida Bass Fishing guided by Justin.

Our guides in Windermere are rated a 5 out of 5 based on 2681 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 charter include Kissimmee and Clermont.

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

What types of fishing trips are common in Windermere?

Deep Sea fishing is the most popular in Windermere as well as lake fishing, inshore fishing, and river fishing.

The most commonly sought after species in Windermere are: 1. largemouth bass, 2. crappie, 3. tilapia, and 4. alligator gar.

The most common fishing techniques in Windermere are light tackle fishing, trolling, and artificial lure fishing but jigging and live bait fishing are popular as well.

How much does a Windermere fishing trip cost?

in Windermere prices can range anywhere from about $340 to $2,510, but the average price for a half day trip in Windermere is $1,052. The average price for a full day trip in Windermere is $974.

What month is best for fishing in Windermere?

The most popular season for fishing in Windermere is spring, and most anglers book their trips 17 days in advance.

Do I need a Windermere fishing license and what are the bag limits in Windermere?

If you’re thinking about a saltwater trip, you’re in luck! Our saltwater fishing tours in Windermere don’t require you to purchase a fishing license – your group is covered by your boat’s captain. For freshwater trips, you’ll still need to purchase a license. See here for more information on fishing licenses, bag limits, and fishing season regulations in Windermere. When in doubt, your fishing guide will always know the right rules and regulations.

Popular Types of Fishing In Windermere

The most common types of fishing charters in Windermere, Florida are bass fishing charters and fly fishing charters. Bass fishing charters are perfect for those looking to catch largemouth bass, which is the most common fish found in the area. Fly fishing charters are great for those looking for a more challenging and adventurous experience.

Other types of fish that can be caught in Windermere include bluegill, crappie, and catfish. Depending on the type of fishing charter you choose, you may also have the opportunity to catch other species such as tilapia and sunshine bass.

When booking a Windermere fishing charter, be sure to ask about the landmarks you may visit during your trip. Some popular landmarks include Lake Butler, Lake Down, and the Butler Chain of Lakes. These areas are known for their beautiful scenery and abundant fish populations, making them the perfect spots for a day of fishing.

The Best Places To Fish In Windermere

Windermere, Florida is a great destination for fishing enthusiasts. With its numerous lakes and waterways, there are plenty of opportunities to catch a variety of fish. Here are some of the best places to fish in Windermere, Florida:

1. Lake Butler - This lake is known for its largemouth bass and is a popular spot for fishing charters.

2. Lake Down - Another great spot for largemouth bass, Lake Down is also home to bluegill, crappie, and catfish.

3. Lake Bessie - This lake is known for its trophy-sized bass and is a popular spot for fishing charters.

4. Lake Tibet - With its clear waters, Lake Tibet is a great spot for catching bass, crappie, and bluegill.

5. Lake Sheen - This lake is known for its largemouth bass and is a popular spot for fishing charters.

6. Lake Chase - This lake is home to a variety of fish, including largemouth bass, bluegill, and catfish.

7. Lake Louise - This lake is known for its trophy-sized bass and is a popular spot for fishing charters.

8. Lake Isleworth - With its clear waters, Lake Isleworth is a great spot for catching bass, crappie, and bluegill.

9. Lake Cypress - This lake is known for its largemouth bass and is a popular spot for fishing charters.

10. Lake Blanche - This lake is home to a variety of fish, including largemouth bass, bluegill, and catfish.

Other Things To Do In Windermere

While Windermere fishing charters are a popular attraction, there are plenty of other things to do in this charming Florida city. Take a stroll through the beautiful gardens at the Harry P. Leu Gardens or explore the local history at the Winter Garden Heritage Museum. For a fun day out with the family, head to the nearby Walt Disney World Resort or Universal Studios Orlando. If you're looking for a more relaxing activity, take a scenic boat tour on the Butler Chain of Lakes or enjoy a round of golf at one of the many world-class courses in the area. And don't forget to indulge in some delicious local cuisine at one of Windermere's many restaurants and cafes.

Recent Reviews of Captain Experiences

  • ★★★★★
    We were able to schedule a bow fishing trip with captain Bobby. We had an absolutely amazing experience with him. Ended up shooting a ton of fish and saw them constantly. Bobby was knowledgeable and very personable. I would recommend booking with Bobby, we will next time we’re in the area.

    Taylor A. with Randy D. of Kissimmee, Florida

  • ★★★★★
    Capt. Steve did an awesome job keeping our crew of six old salts on fish while battling the wind and unseasonably cold weather. We landed fish and were happy with our day out. Capt. Steve was professional and personable.

    Joseph G. with Steve N. of Kissimmee, Florida

  • ★★★★★
    Very knowledgeable captain and we caught lots of fish even though it wasn’t the best fishing day. Had an excellent time and would recommend to any level fisherman!

    Anthony L. with Jeanine P. of Kissimmee, Florida

  • ★★★★★
    5star fishing with Randy. My daughter & I had a wonderful time.

    Judith J. with Randy D. of Kissimmee, Florida

  • ★★★★★
    Great trip, way beyond expectations. Caught a great selection of large mouth. Thanks for the excellent time.

    Todd A. with Jeanine P. of Kissimmee, Florida

  • ★★★★★
    Great time, caught a bunch of fish. Patrick was very knowledgeable and knew the spots to go. Will go again.

    Todd A. with Jeanine P. of Kissimmee, Florida

  • ★★★★★
    Very nice man, a true professional! Great knowledge and work ethic. Handled the ages from 85-3 with grace and class! Thank you Steve!

    Douglas C. with Steve N. of Kissimmee, Florida

  • ★★★★★
    Had the best time. Captain worked hard to keep all 6 of us fishing. Can’t wait to go again!

    William S. with Steve N. of Kissimmee, Florida

Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re licensed, insured and vetted by our team of outdoor experts who know them on a first-name basis. We hand pick our Damn Good Guides, and our network spans all across the country 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 Trips in Windermere