Damn Good Winthrop Fishing Charters

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

Choose a Date
5/5 Average Rating

Recently Booked Fishing Charters In Winthrop, Ma

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Winthrop

8 Hour-Spring Cape Cod Combo Trip

NEW
27 ft 1 - 5 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Winthrop

Boston Harbor - Striper & Blues

NEW
27 ft 1 - 5 People From $900
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Boston

Boston Inshore Fishing

100% (1)
31 ft 1 - 12 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Boston

8 Hours Bottom Fishing MA & RI

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

Inshore, Nearshore Fishing in Boston

Cape False Albacore & Bonito

NEW
26 ft 1 - 8 People From $1,300
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Boston

Full Day Trip – Offshore

NEW
29 ft 1 - 4 People From $1,400

Top Types of Trips in Winthrop

What makes Captain Experiences Damn Good?

Damn Good Guides

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

Damn Good Guides

Experts Available 24/7

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

Experts Available 24/7

100% Weather Guarantee

We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“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

Top Species for Fishing in Winthrop

All Target Species in Winthrop

  • 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 Fishing Charters In Winthrop, Ma

Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Boston

Light Tackle Bass & Bluefish

NEW
29 ft 1 - 4 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Boston

Boston Harbor Stripers & Blues

100% (2)
31 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Boston

Afternoon Boston Striped Bass Trip

NEW
26 ft 1 - 10 People From $900
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Boston

Luxury Offshore Tuna/Shark Trip

100% (2)
31 ft 1 - 6 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Boston

Boston Bass

100% (2)
33 ft 1 - 12 People From $950
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Quincy

4-6 Hour Trip – Striped Bass

100% (4)
25 ft 1 - 4 People From $575

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:

Everything to Know About Booking a Fishing Charter in Winthrop

What are the best fishing charters in Winthrop?

The best fishing charters in Winthrop are:

Why should I book a fishing charter in Winthrop with Captain Experiences?

Our Damn Good Guides currently offer 32 trips in Winthrop, and the most popular trips in the area are 8 Hour-Spring Cape Cod Combo Trip guided by Vinny, Boston Harbor - Striper & Blues guided by Vinny, and Boston Inshore Fishing guided by Joe.

Our guides in Winthrop are rated a 5 out of 5 based on 8235 verified reviews on Captain Experiences.

All guides on Captain Experiences are 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.

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

What types of fishing charters are common in Winthrop?

Inshore fishing is the most popular type of fishing in Winthrop.

The most commonly sought after species in Winthrop are: 1. bluefish, 2. striped bass, 3. black seabass, and 4. scup.

The most common fishing techniques in Winthrop are light tackle fishing, artificial lure fishing, and bottom fishing but drift fishing and jigging are popular as well.

How much do Winthrop fishing charters cost?

Prices in Winthrop can range anywhere from about $750 to $2,600, but the average price for a half day trip in Winthrop is $1,084. The average price for a full day trip in Winthrop is $2,048.

Is booking a fishing guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a fishing guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced fishing guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is on the water every day and knows the area like the back of their hand is going to give you the best chances of success.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for fishing in Winthrop?

The most popular season for fishing in Winthrop is summer, and most anglers book their trips 16 days in advance.

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

See here for more information on fishing licenses in Winthrop, bag limits for target species, and fishing season regulations in Winthrop. When in doubt, your guide will always know all the relevant rules and regulations in Winthrop.

Recent Reviews

  • ★★★★★
    Joe and Arty put us on the fish and kept moving us to them We caught more and better strippers than I ever have. And they were great guys!

    Jonathan K. | July 18, 2025

    Trip: Boston Inshore Fishing

Narrow Down Your Search

Top Targeted Fishing Species in Winthrop

Top Types of Fishing in Winthrop

Last updated: July 13, 2026

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions

See All Trips in Winthrop