Windward Fishing Charters

Windward Fishing Charters is located in Sarasota and offers to show you a memorable time out of Siesta Key and the surrounding areas. Whether you are an experienced fisherman or a first-timer, Capt. Timothy will ensure that everyone has a great time. Also, kids are more than welcome to come aboard, just make sure to let the captain know ahead of time to make sure he has child life jackets on board.

Capt. Timothy will do his best to make sure you have a fun day full of fishing. This involves many different trip options. On these trips, you can expect to use techniques such as light tackle, heavy tackle, bottom fishing, and trolling.

Your fishing adventure starts on a 22’ Pathfinder boat fully restored in 2022. It’s equipped with a tower for shade and sighting fish, power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. She can safely take up to 5 anglers and also comes with an ice box to put the keeper fish in.

All rods, reels, terminal tackle, live bait, lures, bottled water, and ice are included in the price so you can focus on what really matters, fishing. Your trip will include all the necessary fishing licenses for the day. At the end of the trip, Capt. Tim will clean and bag the keepers that you want to take home.

Book your trip now and hit the water with Windward Fishing Charters!



Select date to see available trips and rates:

  • Private trip
    4 Hour Trip (AM)
    Just booked! Last booked: 8 hours ago
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 8:00 AM
    US $600
    This trip is a great way to spend the morning. The boat will depart at 8:00 a.m. and will go for a variety of species, also depending on what bite has been hot lately. Just bring some snacks and any drinks and the rest is taken care of!
  • Private trip
    4 Hour Trip (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 1:00 PM
    Seasonal trip Oct 1 - Jun 1
    US $600
    This trip is a great way to spend the afternoon. The boat will depart at 1:00 pm and will go for a variety of species, depending on what bite has been the best lately. Just bring some snacks and drinks, and the rest is taken care of!
  • Private trip
    6 Hour Trip
    In demand! Last booked: 14 hours ago
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 8:00 AM
    US $850
    If 4 hours are not enough, this 6-hour charter will give more time to fish longer and run farther. It's recommended to bring a lunch for this trip, or you can stop at a local restaurant on the water per request. You'll target many species and also have time to do different techniques.
  • Private trip
    6 Hour Trip – Tarpon
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 8:00 AM
    Seasonal trip May 1 - Jun 30
    US $900
    This trip is for the avid angler looking to target tarpon. The time of the trip will vary due to tides.
    Targeted fish
    Tarpon
    Tarpon
There are 12 people looking at this charter.

FAQs about Windward Fishing Charters

Windward Fishing Charters offers the following trips to customers:
  • US $600 per group - 4 Hour Trip (AM) (4 hours)
  • US $600 per group - 4 Hour Trip (PM) (4 hours)
  • US $850 per group - 6 Hour Trip (6 hours)
  • US $900 per group, additional US $50 per person after 3 guests - 6 Hour Trip – Tarpon (6 hours)

When you book a trip with Windward Fishing Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live Bait Well
  • Wireless Trolling Motor
  • Ice Box

Trips booked with Windward Fishing Charters include:
  • Rods, reels & tackle
  • Live Bait (Bait is on the boat ready to go before the trip starts and is included in the price. )
  • Lures
  • Catch cleaning & filleting
  • Drinks
  • Fishing License (Fishing licenses are included and cover all guests. )

Windward Fishing Charters offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Flats Fishing
  • Backcountry Fishing

Windward Fishing Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Jigging

Top targeted fish species with Windward Fishing Charters include:
  • Black Drum
  • Cobia
  • King Mackerel (Kingfish)
  • Pompano
  • Redfish
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Spotted Seatrout
  • Tripletail

Meet the Captain

Timothy Crowley
Sarasota, Florida, United States
1 Fishing Report
ID & license verified
137 Customer reviews
Response time within an hour
Member since March 2022
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
Captain Tim grew up fishing these waters that he will take you fishing on. He dreamed of becoming a fishing charter captain since he was a child, and will always go the extra mile to make sure everyone on the boat has a great time. Captain Tim also loves to be able to teach his guests new fishing techniques and takes great pride in his work.

About this listing

Targeted species

Black Drum Black Drum
Cobia Cobia
King Mackerel (Kingfish) King Mackerel (Kingfish)
Pompano Pompano

Boat specs

Pathfinder (Center console) originally built in 2000, and restored in 2022. Powered by a 175HP Yamaha engine, with a maximum cruising speed of 43 knots.

Length
22 ft
Capacity
5 persons

Types of fishing

Inshore Fishing
Nearshore Fishing
Flats Fishing
Backcountry Fishing

Fishing techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging

Amenities

GPS
Fishfinder
Live Bait Well
Wireless Trolling Motor
Ice Box

Trip includes

Rods, reels & tackle
Live Bait
Bait is on the boat ready to go before the trip starts and is included in the price.
Lures
Catch cleaning & filleting
Drinks
Fishing License
Fishing licenses are included and cover all guests.

Cancellation policy

Free cancellation up to 7 days prior to trip

You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

Listing policies

Pickup included in price
Transfer from hotels or jetties in Sarasota to departure site is available and included in trip rates.
Child Friendly
You Keep Catch

Payment

Book with 15% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
When paying the remaining balance with a credit card, an additional 3% charge will apply.

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