Osprey Sportfishing 

4.9/5 (49 reviews)
 46 Anchor Drive, Orleans, MA 02653, United States

Osprey Sportfishing 

4.9/5 (49 reviews)
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46 Anchor Drive
Orleans, MA, United States
You may qualify for a Loyalty Program discount with Osprey Sportfishing. To check if you can use a Loyalty Program discount for your selected dates, please sign in.

Embark on an adventure with Osprey Sportfishing! The team has had many happy fishermen over the past 33 years and the new season is no different! Capt. Don Viprino loves teaching novices to fish, especially children, so do not let the lack of experience stop you from having a great time!

Capt. Don invites you to join him on The Osprey, a 35’ Bruno and Stillman boat. She’s powered by a strong 375 HP Caterpillar engine and accommodates up to 6 guests. You will catch fish in comfort and style with the Osprey’s fully enclosed cabin for those early and late season trips. She also features a private toilet, a bed, and a flybridge.

If it’s fillets for the dinner table you seek, go out in late April or early May for Haddock. Head out a bit later in the season to enjoy some light tackle action for Striped Bass and Bluefish. Jigging and trolling for Striped Bass is Capt. Don’s specialty and these trips are bound to be successful. For those diehard anglers who are up for a challenge, join later in the season chasing Bluefin Tuna! You’ll go up to 40 miles offshore for this “top shelf” fish.

Your trip will include everything you need to make a great catch possible, from rods and reels to bait, lures, and even a complimentary fish cleaning service at the end of the trip. You only need to bring your snacks and drinks.

Rock Harbor is a tidal harbor. This means that the exact time of departure needs to be scheduled according to the tides. Contact Capt. Don to schedule your exact trip time.

Osprey Sportfishing is looking forward to a new year of bent rods and great catches. Book your charters now for best availability out of one of the Cape’s most beautiful destinations, Rock Harbor in Orleans!

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Customer reviews

Rating summary

4.9/5
out of 5 stars from 49 reviews
Boat
4.8/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (64)

Fun afternoon!
Fun afternoon!
Fun afternoon!
+61

Angler rating

41
3
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

94%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

90%

Caught fish

100%

Showing 1 - 5 of 49 reviews
Showing: 5 of 49 reviews
Adrian Z.
Adrian Z.
5.0/5

Sep 4, 2025

Half Day Trip

Fun afternoon!

VERIFIED

Don and Cam were excellent. They took us out into the bay and found several really great spots for us to catch. We caught over 20 fish! They were both really supportive to both more experienced fishermen and total beginners. Would recommend, hope to book them again the next time we’re on the Cape!

Don and Cam were excellent. They took us out into the bay and found several really great spots for us to catch. We caught over...  

Review media 0
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 Adrian Z. recommends Osprey Sportfishing
 Adrian Z. recommends Osprey Sportfishing

Amber R.
Amber R.
5.0/5

Aug 6, 2025

Full Day Trip

Best Day Ever!

VERIFIED

We had an amazing experience and never stopped smiling and laughing. Great fishing. Don and Nick made us feel like pros even my 2 year old granddaughter!

We had an amazing experience and never stopped smiling and laughing. Great fishing. Don and Nick made us feel like pros even my...  

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 Amber R. recommends Osprey Sportfishing
 Amber R. recommends Osprey Sportfishing

Justin E.
Justin E.
5.0/5

Jun 26, 2025

Full Day Trip

Don and his son Landon were great

VERIFIED

Don and his son work hard to get us on fish. We limited out and I will be coming back in September for a tuna trip

Don and his son work hard to get us on fish. We limited out and I will be coming back in September for a tuna trip  

Review media 0
 Justin E. recommends Osprey Sportfishing
 Justin E. recommends Osprey Sportfishing

Kelsey S.
Kelsey S.
5.0/5

Jul 9, 2025

Full Day Trip

Awesome trip

VERIFIED

Caught tons of stripers and they were great with my young nephews

Caught tons of stripers and they were great with my young nephews  

Review media 0
Review media 0
Review media 1
 Kelsey S. recommends Osprey Sportfishing
 Kelsey S. recommends Osprey Sportfishing

Jimmy W.
Jimmy W.
5.0/5

Jul 7, 2025

Full Day Trip

Fun for everyone !!

VERIFIED

Everything was as good as it gets!

Everything was as good as it gets!  

Review media 0
Review media 1
Review media 2
 Jimmy W. recommends Osprey Sportfishing
 Jimmy W. recommends Osprey Sportfishing

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
October 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip
FREE Cancellation 7 days notice
4 Hour Trip, starts at 7:00 AM
Seasonal trip Apr 20 - Nov 15
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US $945 
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 Hour Trip, starts at 7:00 AM
Seasonal trip Apr 20 - Nov 15
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US $1,325 
Entire boat: up to 6 people
There are 2 people looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 49 reviews
Boat
4.8/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (64)

Fun afternoon!
Fun afternoon!
Fun afternoon!
+61

Angler rating

41
3
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

94%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

90%

Caught fish

100%

Showing 1 - 5 of 49 reviews
Showing: 5 of 49 reviews
Adrian Z.
Adrian Z.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Fun afternoon!

VERIFIED

Half Day Trip on September 4, 2025

Don and Cam were excellent. They took us out into the bay and found several really great spots for us to catch. We caught over 20 fish! They were both really supportive to both more experienced fishermen and total beginners. Would recommend, hope to book them again the next time we’re on the Cape!

Don and Cam were excellent. They took us out into the bay and found several really great spots for us to catch. We caught over 20 fish! They were both really supportive to both more experienced fishermen and total beginners. Would recommend, hope to book them again the next time we’re on the Cape!  

Review media 0
Review media 1
Review media 2
 Adrian Z. recommends Osprey Sportfishing

Amber R.
Amber R.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Best Day Ever!

VERIFIED

Full Day Trip on August 6, 2025

We had an amazing experience and never stopped smiling and laughing. Great fishing. Don and Nick made us feel like pros even my 2 year old granddaughter!

We had an amazing experience and never stopped smiling and laughing. Great fishing. Don and Nick made us feel like pros even my 2 year old granddaughter!  

Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
 Amber R. recommends Osprey Sportfishing

Justin E.
Justin E.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Don and his son Landon were great

VERIFIED

Full Day Trip on June 26, 2025

Don and his son work hard to get us on fish. We limited out and I will be coming back in September for a tuna trip

Don and his son work hard to get us on fish. We limited out and I will be coming back in September for a tuna trip  

Review media 0
 Justin E. recommends Osprey Sportfishing

Kelsey S.
Kelsey S.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Awesome trip

VERIFIED

Full Day Trip on July 9, 2025

Caught tons of stripers and they were great with my young nephews

Caught tons of stripers and they were great with my young nephews  

Review media 0
Review media 0
Review media 1
 Kelsey S. recommends Osprey Sportfishing

Jimmy W.
Jimmy W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Fun for everyone !!

VERIFIED

Full Day Trip on July 7, 2025

Everything was as good as it gets!

Everything was as good as it gets!  

Review media 0
Review media 1
Review media 2
 Jimmy W. recommends Osprey Sportfishing

FAQs about Osprey Sportfishing

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
35 ft
Year built
1981
Restored in
2020
Boat manufacturer
Bruno and Stillman
Boat type
Sportfishing

Engine model
Cummins QSB
Powered by
1 x 380HP
Max cruising speed
20 knots
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