Damn Good Fly Fishing Charters In Chatham

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

Choose a Date

Recently Booked Fly Fishing Charters In Chatham, Ma

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

Inshore, Flats Fishing in Chatham

Early Season Cape Cod Flyfishing

100% (4)
20 ft 1 - 3 People From $706
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Chatham

Midsummer-Fall Cape Cod Flyfishing

100% (4)
20 ft 1 - 4 People From $942
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Brewster

Nantucket Sound Half Or Full Day

NEW
20 ft 1 - 2 People From $575
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Brewster

Brewster / Monomoy Flats Skiff Trip

NEW
22 ft 1 - 2 People From $575
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Brewster

Saltwater - Flats Wading

NEW
1 - 3 People From $300
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Flats in Dennis

Trophy Striped Bass

100% (5)
27 ft 1 - 12 People From $800

Top Types of Fly Fishing Trips in Chatham

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

All Target Species in Chatham

  • 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 Fly Fishing Charters In Chatham, Ma

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

Deep Sea, Nearshore, Flats in Yarmouth

Cape Cod Striped Bass Fishing

100% (1)
25 ft 1 - 8 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Nantucket

Nantucket Inshore Trip

NEW
21 ft 1 - 3 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Nantucket

Nantucket Half-Day Run

NEW
23 ft 1 - 3 People From $1,030
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Westport

Buzzards Bay Inshore - Seacraft

100% (1)
20 ft 1 - 2 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Westport

Buzzards Bay Inshore

100% (1)
25 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hingham

Boston Harbor Striped Bass

NEW
28 ft 1 - 6 People From $800

Other Captain Experiences Trips in Chatham

Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Early Season Striper 33’

100% (4)
33 ft 1 - 6 People From $1,177
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Chatham

Tuna Trip - 26' Regulator

100% (4)
26 ft 1 - 4 People From $1,530
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Chatham

Chatham Fishing Trip

NEW
30 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Fall Striper Trip - 26' Regulator

100% (4)
26 ft 1 - 6 People From $824
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Falmouth

Albies, Bonito, Spanish Mackerel

100% (1)
28 ft 1 - 6 People From $660
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Midsummer Striper - 33’ Grady White

100% (4)
33 ft 1 - 6 People From $1,177
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Early Season Striper - 26’

100% (4)
26 ft 1 - 6 People From $942
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Orleans

Rock Harbor Classic Sportfish

100% (2)
43 ft 1 - 6 People From $800
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Dennis

Cape Cod Bay Bass And Bluefish

100% (12)
26 ft 1 - 6 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Chatham

Tuna Trip - 33' Grady White

100% (4)
33 ft 1 - 6 People From $1,883
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Fall Striper - 33’ Grady White

100% (4)
33 ft 1 - 6 People From $1,177
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Chatham

Midsummer Striper - 26’ Regulator

100% (4)
26 ft 1 - 6 People From $942

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 Chatham fly fishing charter

What are the best fly fishing charters in Chatham?

The best fly fishing charters in Chatham are:

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

Our Damn Good Guides currently offer 12 fly fishing trips in Chatham, and the most popular trips in the area are Early Season Cape Cod Flyfishing guided by Drew, Midsummer-Fall Cape Cod Flyfishing guided by Drew, and Nantucket Sound Half Or Full Day guided by George.

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 fly fishing guides / fishing lessons in Chatham? Check out our beginner and family friendly fly fishing guides in Chatham.

What types of fly fishing charters are common in Chatham?

Inshore fishing is the most popular type of fishing for fly fishing in Chatham as well as flats fishing.

The most commonly sought after species for fly fishing in Chatham are: 1. bonito and 2. striped bass.

How much do Chatham fly fishing charters cost?

Prices for fly fishing in Chatham can range anywhere from about $573 to $1,820, but the average price for a half day trip for fly fishing in Chatham is $982. The average price for a full day trip for fly fishing in Chatham is $1,280.

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 on a fly fishing charter in Chatham?

The most popular season to go on a fly fishing charter in Chatham is summer, and most anglers book their trips 32 days in advance.

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

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

Last updated: June 12, 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 Fly Fishing Trips in Chatham