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Guides > Captain Stephen Roland

Professional Cryer Fishing Charters

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Montauk NY

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Guides > Captain Stephen Roland

Professional Cryer Fishing Charters

locationMontauk NY

Guidesly Guarantee

Your Captain

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Stephen Roland

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Stephen Roland, Captain at Professional Cryer Fishing Charters

Captain Stephen operates fishing trips out of Montauk aboard a 36' Osmond Beal Downeast vessel. Anglers can explore these waters, which are rich in Thresher Shark, Black Seabass, and Bluefin Tuna, under Stephen’s expert guidance. The best way to learn about fishing is to join him on the water. Montauk is waiting for you with a fish that has your name on it, and Professional Cryer Fishing Charters is ready to assist you in catching it. With years of professional experience, Captain Stephen serves as an invaluable guide for the day.


Depending on the season, a variety of fish can be caught, including Striped Bass, Black Seabass, Scup (Porgy), Mako Shark, Thresher Shark, Blue Shark, Bigeye Tuna, Bluefin Tuna, Yellowfin Tuna, Tautog, Flounder, and more. Guests may engage in various fishing techniques during the trip, such as trolling, jigging, or bottom fishing, or even more specialized methods suited for the area.


Professional Cryer Fishing Charters is a family-friendly service, allowing the whole family to unplug and enjoy the day together. Children must wear life vests, so it’s important to check if the appropriate sizes are available on board. Guests are encouraged to bring snacks for an energy boost during the trip.


The 36’ Downeast Osmond Beal accommodates up to six passengers, providing a spacious cockpit that ensures comfort while fishing. Equipped with modern safety gear and electronics, the boat also has a first mate on board to assist with fishing needs, including cleaning and filleting the catch. A customary 20% tip for the mate is appreciated, and crushed ice is included with the charter.


Quality rods, reels, tackle, and lures are provided, with live bait available upon request. There's no need to worry about purchasing a fishing license, allowing guests to come aboard without hassle. However, it's important to be aware that certain species may have specific regulations or limited seasons, so asking the captain about what to expect is always a good idea.


For a successful outing, it’s advisable to bring non-spray sunblock, a hat, rubber boots, and sunglasses. Water is complimentary, and while alcohol is permitted in moderation, the captain prefers to avoid hard liquor and glass bottles. A toilet is also available on board for convenience.


Get ready to hit the water with Professional Cryer Fishing Charters!

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Upcoming Availability

July 2025
August 2025

Fishing Techniques

JiggingTrolling FishingDeep Sea / Bottom Fishing

What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Show More

Trips Available with Professional Cryer Fishing Charters

Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip Top-Rated
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip Instant Booking
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip Fishing - Wrecks
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip

Set out on a 7-hour private fishing adventure starting at 6:00 AM, available seasonally from May 15 to November 30 on weekdays (Mon-Fri). Priced at $1,150 for up to 6 guests, this trip is perfect for targeting a variety of species, including Striped Bass, Black Sea Bass, Fluke, Cod, Tautog, and Porgies. Enjoy inshore, reef, and wreck fishing using techniques like bottom fishing and jigging aboard a comfortable vessel with a spacious cockpit. A 20% gratuity for the first mate is customary for their assistance throughout the trip. Book today and get ready for an exciting day exploring Montauk’s

Trip

Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip Maximum 6 persons allowed
(base trip price includes 6 guests)
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip 7 Hours
Fishing Charter Montauk | 7 HR Private Wreck or Reef FishingTrip 6:00 AM
$1,150

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Charter Fishing Montauk | 5 HR Private Trip
Best Price Guarantee
Charter Fishing Montauk | 5 HR Private TripTop-Rated
Charter Fishing Montauk | 5 HR Private TripInstant Booking
Charter Fishing Montauk | 5 HR Private TripFishing - Inshore
Charter Fishing Montauk | 5 HR Private Trip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Charter Fishing Montauk | 5 HR Private Trip

Experience a 5-hour fishing adventure starting at 6:00 AM aboard a spacious and comfortable vessel, perfect for targeting Striped Bass, Fluke, Black Sea Bass, and Porgies. Priced at $850 for up to 6 people, this trip runs seasonally from May 15 to November 30 on weekdays (Mon-Fri). Enjoy fishing with bottom fishing, jigging, and trolling techniques as you explore prime inshore waters. A 20% gratuity for the first mate is appreciated for their help throughout the trip. With free cancellation up to 14 days in advance, book your outing today and prepare for a productive and fun day on the water!

Morning Trip

Charter Fishing Montauk | 5 HR Private TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Charter Fishing Montauk | 5 HR Private Trip5 Hours
Charter Fishing Montauk | 5 HR Private Trip6:00 AM
$850

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Fishing Charters in Montauk | 10 HR Private Charter Trip
Fishing Charters in Montauk | 10 HR Private Charter TripTop-Rated
Fishing Charters in Montauk | 10 HR Private Charter TripInstant Booking
Fishing Charters in Montauk | 10 HR Private Charter TripFishing - Inshore
Fishing Charters in Montauk | 10 HR Private Charter Trip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Fishing Charters in Montauk | 10 HR Private Charter Trip

Enjoy a 10-hour private fishing adventure starting at 6:00 AM, available seasonally from May 15 to November 30 on weekdays (Mon-Fri). Priced at $1,500 for up to 6 guests, this trip offers a full day of fishing targeting Striped Bass, Black Sea Bass, Fluke, Cod, Tautog, and Porgies. Experience inshore, reef, and wreck fishing using techniques like bottom fishing, jigging, and drift fishing aboard a spacious and comfortable vessel. A 20% gratuity for the first mate is appreciated for their assistance throughout the day. Book now to secure your spot and enjoy a memorable day of fishing in Montauk

Full Day Trip

Fishing Charters in Montauk | 10 HR Private Charter TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Fishing Charters in Montauk | 10 HR Private Charter Trip10 Hours
Fishing Charters in Montauk | 10 HR Private Charter Trip6:00 AM
$1,500

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Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing Trip
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing TripTop-Rated
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing TripInstant Booking
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing TripFishing - Inshore
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing Trip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Montauk NY Fishing Charters | 10 HR Private Block Island Fishing Trip

Experience an unforgettable full day of fishing on a spacious and comfortable vessel designed for maximum enjoyment. This 10-hour trip starts at 6:00 AM and runs seasonally from May 15 to November 30, available Monday through Friday. Priced at $1,600 for up to six guests, this adventure offers an excellent opportunity to target popular species such as Striped Bass, Fluke, Blackfish, Cod, Sea Bass, and Porgies! Your fishing adventure will involve various techniques, including bottom fishing, jigging, and drift fishing, ensuring a dynamic experience tailored to the day's conditions.

Full Day Trip

Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing Trip10 Hours
Montauk NY Fishing Charters | 10 HR  Private Block Island Fishing Trip6:00 AM
$1,600

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Fishing Charters in Montauk NY | 10 HR Private Shark Charter Trip
Fishing Charters in Montauk NY | 10 HR Private Shark Charter TripTop-Rated
Fishing Charters in Montauk NY | 10 HR Private Shark Charter TripInstant Booking
Fishing Charters in Montauk NY | 10 HR Private Shark Charter TripFishing - Offshore
Fishing Charters in Montauk NY | 10 HR Private Shark Charter Trip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Fishing Charters in Montauk NY | 10 HR Private Shark Charter Trip

Set on an unforgettable full-day fishing adventure targeting some of the ocean's most formidable predators! This 10-hour trip starts at 6:00 AM and operates seasonally from May 15 to November 30, available Monday through Friday. Priced at $1,750 for up to six guests, this experience is perfect for shark enthusiasts eager to catch Thresher, Mako, Blue, Hammerhead, and other regional sharks. You'll be fishing from a comfortable vessel featuring a spacious cockpit, allowing everyone ample room to engage in the action. The experienced crew will equip you with quality tackle, ensuring a success!

Full Day Trip

Fishing Charters in Montauk NY | 10 HR Private Shark Charter TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Fishing Charters in Montauk NY | 10 HR Private Shark Charter Trip10 Hours
Fishing Charters in Montauk NY | 10 HR Private Shark Charter Trip6:00 AM
$1,750

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Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing Trip
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing TripTop-Rated
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing TripInstant Booking
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing TripFishing - Offshore
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing Trip

Professional Cryer Fishing 36'Osmond Beal Max 6 guests (base trip price includes 6 guests)

Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing Trip

Experience the excitement of tuna fishing with our Extended Day Trip, featuring a 12-hour adventure starting at 3:00 AM. This seasonal trip runs from May 15 to November 30, available Monday through Friday, and is designed for up to six passengers at a price of $2,600. Set out on a comfortable vessel with a spacious cockpit, perfect for targeting Bluefin, Yellowfin, and Albacore tuna up to 30 miles offshore. You’ll be accompanied by an experienced crew equipped with top-quality tackle, ensuring an exceptional fishing experience. Please note that a 20% gratuity for the first mate is customary.

Full Day Trip

Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing Trip12 Hours
Fishing Charters in Montauk NY | 12 HR Private Tuna Fishing Trip3:00 AM
$2,600

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Vehicle

Professional Cryer Fishing

Boat Type:

Boat Guest Capacity:

6

Boat Length:

36 ft

Manufacturer Name:

Osmond Beal

Model Year:

2003

Engine Manufacturer Name:

Scania

# of Engines:

1

Horsepower Per Engine:

450

Maximum Cruising Speed:

16

Features: Bait Tank Toilet Fish Finder GPS Radar

Professional Cryer Fishing Charters Osmond Beal Boat

The 36' Osmond Beal Cabin Cruiser is a 2003 Downeast-style boat with a 450HP Scania engine and a top speed of 16 knots. It comfortably seats 6 passengers, making it perfect for fishing trips or cruising in style.

Boat

Professional Cryer Fishing Charters Osmond Beal Boat image 0

Professional Cryer Fishing

Boat Type:

Boat Guest Capacity:

6

Boat Length:

36 ft

Vehicle Details

FAQs about Professional Cryer Fishing Charters

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