On The Side Charters 

5.0
(24 reviews)
 Sally Snyder Way, Newburyport, MA 01950, United States–

On The Side Charters 

Newburyport, MA, United States
–
29 ft
6
5.0
(24 reviews)

On The Side Charters operates out of the historic town of Newburyport, MA, offering a variety of fishing trips from 3 to 10 hours. The waters around Newburyport are teeming with a wide range of species, and On The Side Charters makes the most of this fact, by offering trips targeting anything from Mackerel and Flounder in the shallows, to huge Sharks and monster Bluefin Tuna way out into the ocean.

The boat you will be spending the day on is a 29' Webbers Coast downeast with room aboard for up to 6 guests. She's powered by an impressive 280 HP General Motors engine, meaning you will waste no time getting to the best fishing grounds offshore, and comes equipped with everything you will need for some awesome fishing.

The vessel features all-new Simrad electronics, with CHIRP sonar to allow the best possible view of what lurks beneath you. Once you're locked in on your catch, a choice of realistic lures and live bait fresh from the tank will be too tempting for any fish to ignore, and the vessel's tournament grade tackle will give you the best chance of landing whatever you sink your hook into.

Captain Jonathan Carey takes pride in offering one of the best selections of trips around, welcoming clients aboard for anything from 3-hour stints after work catching tasty Striped Bass for dinner, to 10-hour offshore adventures doing battle with giant Bluefin Tuna. In order to be productive targeting so many species, he offers a choice of light and heavy tackle, with the option to troll, spin, jig, and pop, as well as to drift, fly, and kite fish.

Even if fishing is not your thing, On The Side Charters have the perfect trip for you, taking in the Newburyport waterfront on a 2-hour sunset cruise. No matter what trip you choose, Captain John will work with you to make sure it is exactly what you are looking for. On offshore trips, all large Bluefin are kept by the boat, but Captain John will give you a 10% discount on your next trip.

On The Side Charters operates out of the historic town of Newburyport, MA, offering a variety of fishing trips from 3 to 10 hours. The waters around Newburyport are teeming with a wide range of species, and On The Side Charters makes the most of this fact, by offering trips targeting anything from Mackerel and Flounder in the shallows, to huge Sharks and monster Bluefin Tuna way out into the ocean.

The boat you will be spending the day on is a 29' Webbers Coast downeast with room aboard for up to 6 guests. She's powered by an impressive 280 HP General Motors engine, meaning you will waste no time getting to the best fishing grounds offshore, and comes equipped with everything you will need for some awesome fishing.

The vessel features all-new Simrad electronics, with CHIRP sonar to allow the best possible view of what lurks beneath you. Once you're locked in on your catch, a choice of realistic lures and live bait fresh from the tank will be too tempting for any fish to ignore, and the vessel's tournament grade tackle will give you the best chance of landing whatever you sink your hook into.

Captain Jonathan Carey takes pride in offering one of the best selections of trips around, welcoming clients aboard for anything from 3-hour stints after work catching tasty Striped Bass for dinner, to 10-hour offshore adventures doing battle with giant Bluefin Tuna. In order to be productive targeting so many species, he offers a choice of light and heavy tackle, with the option to troll, spin, jig, and pop, as well as to drift, fly, and kite fish.

Even if fishing is not your thing, On The Side Charters have the perfect trip for you, taking in the Newburyport waterfront on a 2-hour sunset cruise. No matter what trip you choose, Captain John will work with you to make sure it is exactly what you are looking for. On offshore trips, all large Bluefin are kept by the boat, but Captain John will give you a 10% discount on your next trip.

Jonathan Carey
Captain
Jonathan Carey
15 years of experience
ID & credentials verified

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
Change
3 Hour Trip – Evening Bass Fishing
Non-refundable
3 hour trip starts at 4:00 PM
Seasonal trip
May 15 - Oct 15 (Mon, Tue, Wed, Thu, Fri)
US $525
Entire boat: up to 4 people
4 Hour Trip – Bass (Morning)
Non-refundable
4 hour trip starts at 7:00 AM
Seasonal trip
May 15 - Oct 15 (Sat, Sun)
US $800
Entire boat: up to 6 people
4 Hour Trip – Bass (Afternoon)
Non-refundable
4 hour trip starts at 3:30 PM
Seasonal trip
May 15 - Oct 15 (Sat, Sun)
US $800
Entire boat: up to 6 people
8 Hour Trip – Sharks
Non-refundable
8 hour trip starts at 7:00 AM
Seasonal trip
Jul 1 - Oct 15
US $1,500
Entire boat: up to 6 people
10 Hour Trip – Bluefin & Sharks
Non-refundable
10 hour trip starts at 6:00 AM
Seasonal trip
Jun 1 - Oct 15
US $1,650
Entire boat: up to 6 people

Customer reviews

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Rating

5.0
24 reviews
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (12)

Reviews (24)

  • Ken Lafferty
    Ken Lafferty
    us
    Massachusetts, US
    Member since 2023
    5.0
    Verified

    Three Hour Weekly

    3 Hour Trip – Evening Bass Fishing on August 2, 2023 • 4 adults • 2 children

    Very good experience. Capt Jonathan accommodated us in a short notice booking. We managed to get on the fish and had a great time. Local and knowledgeable Capt from the immediate area. I would recommend this booking.

  • Aaron  Lazenby
    Aaron Lazenby
    Repeat angler
    us
    New York, US
    Member since 2020
    2 trips
    5.0
    Verified

    An afternoon with Capt. Jon

    3 Hour Trip – Evening Bass Fishing on August 24, 2022 • 3 adults • 1 child

    We had a wonderful afternoon with Captain Jon aboard the Stand Sure. He literally put us on fish within seconds of dropping the lure in the water. I would highly recommend On The Side Charters and Capt Jon. We look forward to our next visit and booking with him again. Thanks Capt Jon!

  • David Adams
    David Adams
    us
    New Hampshire, US
    Member since 2022
    5.0
    Verified

    Halfday AM trip with Capt Jon

    4 Hour Trip – Bass (Morning) on July 29, 2023 • 6 adults

    Great time and A great way to start the day. Will be back soon. Thank you for all of us.

  • Tom Nordhougen
    Tom Nordhougen
    us
    Massachusetts, US
    Member since 2022
    5.0
    Verified

    Evening blue cruise

    3 Hour Trip – Evening Bass Fishing on August 22, 2022 • 3 adults

    Overall we had a great time out. Capt. Jonathan was on top of everything, and provided some great tips on fishing the area. I would definitely recommend On The Side Charters.

  • Robert Grzela
    Robert Grzela
    Repeat angler
    us
    Massachusetts, US
    Member since 2022
    6 trips
    5.0
    Verified

    First time fishing together

    4 Hour Trip – Bass (Afternoon) on July 16, 2022 • 2 adults • 1 child

    We had a great experience. Thank you Jonathan.

  • Jason Niederkorn
    Jason Niederkorn
    us
    Massachusetts, US
    Member since 2026
    4.7
    Verified

    August fishing trip

    3 Hour Trip – Evening Bass Fishing on August 24, 2026 • 6 adults • 2 children
  • Kyle Mckenna
    Kyle Mckenna
    us
    Michigan, US
    Member since 2025
    5.0
    Verified

    August fishing trip

    4 Hour Trip – Bass (Morning) on August 16, 2025 • 3 adults
  • Robert Brewer
    Robert Brewer
    us
    New York, US
    Member since 2022
    5.0
    Verified

    3 hour trip with Captain Jon

    3 Hour Trip – Evening Bass Fishing on August 3, 2022 • 4 adults • 2 children

    Jon was a great guide and his knowledge of the local waters was greatly appreciated. My son in law, grandsons and I had a great time. Landed several good size fish in a short period of time. When a captain enjoys his Chosen profession as much as Jon does, it’s easy to please his party. Nice guy with a good boat. Happy sailing my friend, keep up the great work. I highly recommend a charter with On the side charters. 👍🏻😎🤙 Mr. Brewer

  • Caleb Porter
    Caleb Porter
    us
    Ohio, US
    Member since 2023
    5.0
    Verified

    Great time even without luck

    4 Hour Trip – Bass (Afternoon) on September 30, 2023 • 6 adults

    My group and I had an amazing time even though we had no luck at all. The Captain tried everything he could to get us at least something but even without catching anything my group just enjoyed the time with the Captain.

  • Roger Scandura
    Roger Scandura
    us
    Massachusetts, US
    Member since 2023
    5.0
    Verified

    Fishing trip

    4 Hour Trip – Bass (Morning) on July 9, 2023 • 4 adults

    We had an outstanding trip with Jon. A true professional. My cousins had never fished in the ocean before this trip however Jon made sure that they caught fish ! A memorable day Thanks Jon !!!

FAQs about On The Side Charters

On The Side Charters offers the following trips to customers:
  • US $525 per group, additional US $50 per person after 4 guests - 3 Hour Trip – Evening Bass Fishing (3 hours)
  • US $800 per group - 4 Hour Trip – Bass (Afternoon) (4 hours)
  • US $800 per group - 4 Hour Trip – Bass (Morning) (4 hours)
  • US $1,500 per group - 8 Hour Trip – Sharks (8 hours)
  • US $1,650 per group - 10 Hour Trip – Bluefin & Sharks (10 hours)
When you book a trip with On The Side Charters, you can expect the following amenities onboard:
  • Toilet Full Marine Head with Holding Tank
  • GPS New Simrad NSS 9
  • Fishfinder CHIRP Sonar 1Kw
  • Bed Full VBerth
  • Live bait well
  • Kitchen
  • Outriggers
  • Ice box
  • Radar 24 mile Furuno
Trips booked with On The Side Charters include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • Catch cleaning & filleting
  • First mate
  • Fishing license
On The Side Charters offers the following types of fishing:
  • River fishing
  • Inshore fishing
  • Nearshore fishing
  • Offshore fishing
On The Side Charters offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Trolling
  • Spinning
  • Jigging
  • Popping
  • Fly fishing
  • Drift fishing
  • Kite fishing
  • Deep sea fishing
Top targeted fish species with On The Side Charters include:
  • Bass (Striped)
  • Bluefish (Tailor)
  • Dogfish
  • Flounder
  • Mackerel (Atlantic)
  • Shark (Blue)
  • Shark (Mako)
  • Shark (Porbeagle)
  • Shark (Thresher)
  • Skate
  • Tuna (Bluefin)

Your captain

Jonathan Carey
Jonathan Carey
Newburyport, Massachusetts, United States
29 Fishing Reports
ID & license verified
24 Customer reviews
Typical response within 6 hours
Member since June 2017
In addition to being an experienced captain in my own right, I have mated for and learned from some of the best old time captains in the area. I bring to the table over 20 years experience fishing from Provincetown Cape Cod to the Gulf of Maine out to Georges Bank chasing Striped Bass to Bluefin Tuna and everything in between. For the last ten years, I have been a commercial Tuna and Bass fisherman. My experience covers commercial, charter, and head boat fishing. As a lifetime angler, I enjoy both fresh and saltwater fishing. My passion, however, is definitely saltwater. This transition occurred after my first experience catching a Bluefin Tuna....I can still hear that drag screaming!!! If you are a life long angler like myself or a begginer, let me share my love of the ocean and fishing with you and your group. I guarantee you will not only leave with a memorable experience but also new knowledge, and most likely some dinner! We are now offerong corporate charters on our 37' Duffy.
Jonathan Carey
Jonathan Carey
Fully verified
29
reports
24
reviews
2017
member since
~6h
response
In addition to being an experienced captain in my own right, I have mated for and learned from some of the best old time captains in the area. I bring to the table over 20 years experience fishing from Provincetown Cape Cod to the Gulf of Maine out to Georges Bank chasing Striped Bass to Bluefin Tuna and everything in between. For the last ten years, I have been a commercial Tuna and Bass fisherman. My experience covers commercial, charter, and head boat fishing. As a lifetime angler, I enjoy both fresh and saltwater fishing. My passion, however, is definitely saltwater. This transition occurred after my first experience catching a Bluefin Tuna....I can still hear that drag screaming!!! If you are a life long angler like myself or a begginer, let me share my love of the ocean and fishing with you and your group. I guarantee you will not only leave with a memorable experience but also new knowledge, and most likely some dinner! We are now offerong corporate charters on our 37' Duffy.

The fish you can target

Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Dogfish
Dogfish
Flounder
Flounder
Atlantic Mackerel
Atlantic Mackerel
Blue Shark
Blue Shark
Mako Shark
Mako Shark
Porbeagle Shark
Porbeagle Shark
Thresher Shark
Thresher Shark
Skate
Skate
Bluefin Tuna
Bluefin Tuna
Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Dogfish
Dogfish
Flounder
Flounder
Atlantic Mackerel
Atlantic Mackerel

Real catches by this captain

  • Two anglers proudly displaying a large Striped Bass while fishing on a sunny day in open waters.
    Fish 1
    Striped Bass
    Kyle M.
    Kyle M.
  • A young angler proudly displaying a large Striped Bass while fishing on a boat, with a clear blue sky in the background.
    Fish 1
    Striped Bass
    Some nice bass around in and above the slot likit size with some keepers in the mix.
  • An angler proudly displaying a striped bass while fishing from a boat, showcasing a successful catch in a coastal environment.
    Fish 1
    Striped Bass
    Greta morning with the Smiths. Loaded up on macks and hammered on the bass.
  • Group of anglers proudly displaying their catch of striped bass while out on the water.
    Fish 1
    Striped Bass
    Couple nice ones for a group photo capitolized on a double hook up on live bait and artificial, they couldnt resist. Dates still available, the weather isnt the only thing heating up!!
  • Young angler holding two large fish aboard a boat with a marina and open water in the background.
    Fish 1
    Bluefish (Tailor)
    Ken L.
    Ken L.
    Very good experience. Capt Jonathan accommodated us in a short notice booking. We managed to get on the fish and had a great time. Local and knowledgeable Capt from the immediate area. I would recommend this booking.
  • Group of adult anglers proudly displaying a large striped bass aboard a fishing boat, enjoying a day on the water.
    Fish 1
    Striped Bass
    David A.
    David A.
    Great time and A great way to start the day. Will be back soon. Thank you for all of us.
  • Safety examination sticker for a commercial fishing vessel, detailing compliance with USCG regulations.
    Dockside examination with a US Coast guard complete and we are ready to rock and roll!
  • A well-maintained fishing boat displayed on land, showcasing its sleek design and vibrant colors.
    Captain John has been hard at work paint is done systems are checked and we are a few days away from starting the 2023 season! Book early to reserve your preferred date!
  • A family proudly displaying their catch of Bluefish while enjoying a fishing trip on the water.
    Aaron  .
    Aaron .
    We had a wonderful afternoon with Captain Jon aboard the Stand Sure. He literally put us on fish within seconds of dropping the lure in the water. I would highly recommend On The Side Charters and Capt Jon. We look forward to our next visit and booking with him again. Thanks Capt Jon!
  • A young angler proudly displaying a large fish while fishing offshore, accompanied by an adult in a bright rain jacket.
    Tom N.
    Tom N.
    Overall we had a great time out. Capt. Jonathan was on top of everything, and provided some great tips on fishing the area. I would definitely recommend On The Side Charters.

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
6 persons
Boat length
29 ft
Year built
1994
Restored in
2018
Boat manufacturer
Webbers Cove
Boat type
Downeast
Engine model
GM 350
Powered by
1 x 280HP

What kind of fishing will you do?

River Fishing
Inshore Fishing
Nearshore Fishing
Offshore Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Trolling
Spinning
Jigging
Popping
Fly Fishing
Drift Fishing
Kite Fishing
Deep Sea Fishing

Which amenities are available onboard

Toilet
Full Marine Head with Holding Tank
GPS
New Simrad NSS 9
Fishfinder
CHIRP Sonar 1Kw
Bed
Full VBerth
Live bait well
Kitchen
Outriggers
Ice box
Radar
24 mile Furuno
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
First mate
Fishing license

How cancellations work

Deposit non-refundable
If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
Like jackets available for children 12 and under
You keep catch
Crew keeps catch
Boat keeps Giant Tuna from offshore trips.
Catch and release allowed

How you can pay

Book with 10% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
 Cash
 Checks

What’s biting in Newburyport right now

Bass (Striped)Bass (Striped)
Bluefish (Tailor)Bluefish (Tailor)
FlounderFlounder
Mackerel (Atlantic)Mackerel (Atlantic)
Shark (Blue)Shark (Blue)
Shark (Mako)Shark (Mako)
Tuna (Bluefin)Tuna (Bluefin)

Compare similar fishing charters

Current
On The Side Charters
On The Side Charters
5.0
(24)
29 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+9
4 hour trip • 6 persons
US $800