Your Day on the Water

USCG Master Captain Drew Downing and Outermost Harbor's Captain Devin Kahn ensure you a safe, fun-filled day on the water. Down East Charters, in cooperation with Outermost Harbor Marina, offers (4) fully customized boats designed for local waters.

Our 33’ Grady White Canyon, the F/V Rainmaker, is a beautiful platform for Chatham's fisheries and beyond. Raymarine has sponsored the boat and has us under way with top of the line electronics. This boat has a marine toilet and ample seating forward and aft. The Rainmaker will bring you to the fishing grounds quickly and in style with one of the most comfortable rides you are going to find. Great platform for our Shark tours and Whale watching trips as well. This boat is USCG commercially inspected and compliant.

Our 26' (29' LOA) Regulator Marine Classic, F/V Isla Grace. This is one of the safest and most rugged boats of all-time. This is our go-anywhere, do-anything fishing machine. It has an open deck layout ready for casting and jigging with tons of storage. Redundant commercial grade electronics package including auto pilot and full offshore safety. Two 2025 F200 Yamaha four strokes that are whisper quiet with a 400mi range. This is a boat you want to be on when we start the daily hunt offshore for Tuna or Bass. The Isla Grace is USCG commercially inspected and compliant.

Our light-tackle flagship, a 2013 Jones Brothers Cape Fisherman 26 with Yamaha power, 9'4'' beam, and wide open deck space for fly and spin fishing. Top-notch Simrad electronics suite with twin 16'' displays and open array HALO radar. The epitome of elegance in simplicity--this is an ideal boat for fly fisherman and rips trips but has the chops to fish offshore as well.

We also have a 20' Carolina skiff with a Yamaha 115 and jack plate for skinny water. This boat is at home in the shallows and flats of Monomoy, and the back reaches of harbors for spring bass. Low freeboard and a ladder allow anglers to hop out and wade sandbars in prime spots. Please check our FLY FISHING tab for more info on light tackle/fly trips on the Carolina.

Tackle: Down East Charters fishes high quality equipment from North Chatham Outfitters. We carry light action vertical jig, live bait, and casting spinning rods with braided line from Daiwa USA and casting and rip fly rods from Orvis and Far Bank. We primarily fish cast and jig style with multiple anglers in the water at the same time and a great fight from hooked fish. We only fish live bait when its most effective. Outfitting the boat with different combos means multiple approaches throughout the day and tide.

Fly Fishermen: We love to fly fish and are passionate about it! Please let us build a trip for you. Please look at our Fly Fishing Page for details/trip options.

Multi-Boat Trips: Have a large group and want to do something fun? We can coordinate. We have 3 boats capable of taking up to 6 people each. We would fish multiple boats in the same areas and tag-team the fishing grounds. Don't go on a party boat--have the party on our boats! We have availability and are scheduling out in advance. Inquire today.

Great White Shark Trips: We have our three charter boats available to provide the best Great White Shark tour available. Our launch location at the marina is 5 min from the sharking grounds! Our location for departure means more time with the sharks. Guided by a spotter plane above, finding and spending time with our local resident Great White Sharks has never been better. Visitors and locals alike can participate in ‘Citizen Science’ as they add white shark sightings to the Sharktivity App. Although shark sightings are not guaranteed, we have had a 99% success rate historically on seeing sharks when the conditions permit. Please contact us for availability and pricing. Bucket-List material if you are visiting Chatham.

Whale Watching: We love these trips and they depart on our offshore boats and can take up to 6 people. We hope to find whales close to shore but often have to go 10-20mi from our harbor. Up close viewing of Humpbacks, Minke, Finbacks, Pilot Whales, and occasional rarities such as Beaked Whales and Orcas! Atlantic White-Sided dolphin and Harbor Porpoise are also seen with regularity. Molas, sea turtles, and Basking Sharks also have been spotted out there. Our 3.5 hour window gives us plenty of time on-site to follow groups of surfacing mammals and explore. Bring a camera!

Seasonal Calendar and Trip Options

May 15-Jun 1: (1) Jumbo Sea Bass with light tackle and jigs in Nantucket Sound. Great fun and delicious table-fare. Tautog also available. (2)Light tackle and fly fishing for early run bass in the harbors and Pleasant Bay.

Jun 1-Jul 1: (1) Best sight-fishing of the year in Chatham for migratory Stripers. Difficult and rewarding, fisherman have a chance to see and cast to bass on the flats of Monomoy and south cape beaches. (2) Squid run for bigger Stripers begins 1st week and the rips open up. (3) Early run Tuna most years at middle to end of the month. Great chance at Bluefin Tuna to the east of Chatham on the bait/troll and with top water stick baits/jigs. The king of gamefish in the northeast. This fishery remains steady throughout the summer. Please contact us for offshore conditions and reports.

Jun 15-Oct 15: World-Class Striped Bass and Bluefish fishing locally up and down the beach and at the Monomoy Rips on all tackle. Great Whale Watching all summer and fall typically.

July 15th-Oct 15th: Best Great White Shark Viewing Window.

Aug 15-Nov 15: (1) Fall push of warm water Albies, Bonito, and Spanish Macs to the west and off Chatham. Truly a test on light tackle and so much fun! (2) Tuna fall migration. Great chance at inshore and offshore tuna all along the outer cape on a variety of tackle. Typically the best time for cast and jig for these critters.

Your Captains

Son of a native Cape Codder, Captain Drew Downing has grown up spending a lot of time on the sand bar and developed a passion for boating and fishing at a very young age. After several seasons commercial fishing with a rod and reel, Drew transitioned to the charter side of the industry. These days on board the Isla Grace, we thoroughly enjoy fishing with experienced anglers and novices alike, and showcasing everything that is awesome about our local waters. We also pride ourselves on only keeping what is going to be eaten fresh, as guide and captain efforts really drive sound fish handling and conservation practices. We want you to catch them on the NEXT trip as well! Lastly, there is always something new to learn and experience when you leave the harbor--there are no two days alike--and it's all about having fun out there!

Drew has had the opportunity to live/study in Vermont, Florida, Wyoming, New Zealand, and Hawaii. Founded in river fishing for trout and steelhead with the flyrod, Capt. Drew has been extremely fortunate to be able to chase all kinds of fish all over the world. Experience in different styles of fishing helps Down East Charters' anglers learn new tactics and patterns to take to their own home waters. We relish the opportunity to get you onboard and start telling fish tales!

Capt. Drew is a Yamaha national fishing team pro guide, a Daiwa pro team member, an Orvis and Far Bank endorsed pro, and locally a charter partner with North Chatham Outfitters.

Capt. Drew splits his time between Chatham and northern Vermont with his wife Erika, daughter Isla Grace, sons Zane and Reid, and mutts Riggs and Charlie.

We are pleased to welcome Captain Tom D'amato back to our captain's position again this season. Tom brings eight years of experience navigating Chatham and surrounding waters. On board, you'll find a consummate professional who blends a deep passion for fishing with a daily commitment to safety, conservation, and fun. Tom is also a recent father and is GREAT with young anglers and family trips. So whether you're a first-time angler or a seasoned pro, Captain Tom’s approach is positive, patient, and skillful and we think you will really enjoy your time onboard with him!

Why Fish With Us?

We are in our 15th year of full-time charter fishing out of Chatham and there are a couple things that we really prioritize in our business--first and foremost, we are friendly local captains and pride ourselves on developing lasting friendships with our guests forged on the water. This starts with a good trip plan, sound forecasting/communications, and a captain and vessel prepared for a safe day on the open ocean. Underway, we have always been about showcasing our world-class fishery on the outer Cape and getting our anglers tight to fish with tackle and methods that make it fun! With these goals in mind, most of our trips are returning guests at this point. We aim to be patient and accommodating with first-time anglers as well as provide unique and challenging fishing opportunities when we have seasoned pro's on board. We take charters out on multiple boats everyday of the summer and fall so we have a great idea of where the bite is and what's going on. Additionally, we are unique in that we do everything from fly and light tackle to big game and offshore at a high level, and our boat options are great platforms for this wide brush stroke approach.

Location is really important and Outermost Harbor is our homeport. A very short boat ride leads to the most diverse waterways and fishing grounds on Cape Cod. Cool ocean water during the heat of summer leads to a consistent summer fishery. We also have Nantucket Sound's warm water for great early and late season fishing. A lot of years, we have fish when others do not.

Truly great trips catch fish, have fun, AND get to experience the local inhabitants. We are fortunate to have a ton of sea life on Chatham's doorstep and Monomoy national wildlife sanctuary as a backdrop. Up close viewing of seal colonies, sea birds, whales, dolphins, sunfish, and sharks. We see Great Whites in the surf line almost daily now and can put you right next to them in safety.

There are a bunch of charter outfits locally that do a great job--in fact, a lot of us are friends and work together to ensure we are putting our guests on top of fish trip after trip. As you weigh your options, we hope that you give us a try, we'd love to have you on board and I'm sure you'll have a day to remember. Thanks- Capt. Drew

What to Bring

-Sneakers/Rubber Boots/Flip-Flops/Non-Marking (No Bare Feet for Safety)

-Extra Layer or Windbreaker (Usually few degrees cooler out there)

-Camera/Phone

-Small Cooler/Bag for Drinks/Snacks

-Sunscreen (NON-SPRAY PLEASE/Stains Gel Coat) and Sunglasses

-Few Beers or Wine Permitted (No Drugs allowed)

-A Great Attitude--It's Going to be a Blast!

(Children under 12 years of age are required to wear U.S. Coast Guard approved life jackets in Massachusetts above deck on any vessel that is underway)