Fishing Charters
Fishing Charters in Chatham, Cape Cod
Enjoy a professionally guided fishing charter departing from Chatham Harbor with quick access to some of Cape Cod's most productive inshore and offshore waters.
Whether you are an experienced angler or heading out for your first trip, our private charters are designed to deliver a safe, comfortable, and memorable day on the water.
Private Charters
Each trip is private and tailored to your group, your experience level, and the type of fishing you want to do.
Departing from Chatham
Our marina location offers fast access to Chatham Harbor, Monomoy, Nantucket Sound, and offshore grounds.
Seasonal Opportunities
Depending on the season and conditions, trips may target striped bass, bluefish, bluefin tuna, shark, fluke, and more.
Why Fish With Outermost Harbor?
We combine experienced local captains, versatile charter options, and a premium Chatham departure point to create trips that are enjoyable for beginners and rewarding for serious anglers.
Local Knowledge Matters
Our captains know these waters and adjust each trip around weather, tides, current conditions, and where the best fishing is happening that day.
Built Around Your Group
From relaxed family outings to serious offshore runs, we can tailor the trip to your goals, comfort level, and experience.
Fast Access to Productive Water
Chatham provides access to a wide range of fishing opportunities, from protected local waters to some of the best offshore grounds in the region.
More Than Just Fishing
In addition to the fishing, many trips include incredible scenery, wildlife sightings, and the unforgettable experience of being out on Cape Cod waters.
Your Day on the Water
Professionally guided trips, experienced captains, and a versatile charter fleet built for Chatham waters and beyond.
USCG Master Captain Drew Downing and Outermost Harbor's Master Captain Devin Kahn help ensure a safe, enjoyable, and memorable day on the water.
Down East Charters, in cooperation with Outermost Harbor Marine, offers four fully customized boats designed for local waters, from the flats of Monomoy to offshore grounds.
Charter Boat Details
Our fleet includes a range of charter boats suited for offshore fishing, light tackle trips, shark and whale excursions, and shallow-water opportunities.
F/V Rainmaker
Our 33' Grady White Canyon, the F/V Rainmaker, is a beautiful platform for Chatham's fisheries and beyond. Raymarine has sponsored the boat with top-of-the-line electronics. This boat has a marine toilet, ample seating, and one of the most comfortable rides you will find.
F/V Isla Grace
The Isla Grace is our go-anywhere fishing machine with an open layout, commercial electronics, and twin Yamaha power. Built for offshore performance, this is the boat you want when heading out for bluefin tuna or striped bass.
Light-Tackle Flagship
Wide open deck space and top-tier Simrad electronics make this the perfect platform for fly and spin fishing, while still capable offshore.
Skinny Water Specialist
Built for the flats and backwater fishing around Monomoy, this skiff allows anglers to access shallow areas and even wade prime spots.
Charter Rates
Current pricing for our Chatham fishing charters.
Why Fish With Us?
Experienced Local Captains
We are in our 15th year of full-time charter fishing out of Chatham. Our focus is creating safe, well-planned trips with great communication and an enjoyable experience for every guest.
Prime Location
A short ride from the dock brings us to some of the most productive waters on Cape Cod, including Monomoy, Nantucket Sound, and offshore grounds.
All Skill Levels Welcome
We cater to first-time anglers and experienced fishermen alike, adjusting techniques and trip style to fit your group.
Wildlife & Full Experience
Many trips include sightings of seals, whales, dolphins, and even great white sharks — making your day on the water unforgettable.
What to Bring
Recommended Items
- Non-marking shoes or boots
- Extra layer or windbreaker
- Sunglasses & sunscreen
- Food & drinks
- Camera or phone
Important Notes
- No flip flops or bare feet
- No spray sunscreen
- Beer/wine allowed in moderation
- No drugs allowed
- Kids under 12 must wear life jackets
Payment & FAQ
Payment
Cash, credit cards, checks, and PayPal accepted.
Do I Need Experience?
No — great for beginners and experienced anglers.
What Can We Catch?
Striped bass, bluefish, bluefin tuna, fluke, shark, and more depending on season.
Private Charters?
Yes — all trips are private for your group.
Departure Location
Outermost Harbor Marina in Chatham.
How to Book
Contact us to plan your trip and check availability.
Fishing Charter Gallery
A look at some of the fishing experiences our guests enjoy on Cape Cod waters.
Chatham Fishing Charter FAQ
What kinds of fishing charters do you offer?Coastal trips for striped bass in 4, 6, and 8-hour lengths, and offshore bluefin tuna charters — all private for your group, up to 6 guests.
Where do trips leave from?Right from Outermost Harbor Marine in Chatham — minutes from some of Cape Cod’s most productive inshore and offshore water, without a long steam to the grounds.
Do I need experience?No — trips are tailored to your group and experience level, from first-timers and families to seasoned anglers.
How far in advance should I book?Summer dates fill quickly — book as early as you can. Pick your preferred dates online and we’ll confirm with the captain.
How do I book a fishing charter?Request your trip at book.outermostharbor.com/charters — choose striped bass or tuna, pick dates, and place a deposit hold to lock in your request.