Day On The Bay Charters 

4.9
(181 reviews)
 Somerset Street 205, Ocean City, MD 21842, United States–

Day On The Bay Charters 

Ocean City, MD, United States
–
30 ft
6
4.9
(181 reviews)

Excited to cast a line in Ocean City? That's what Day On The Bay Charters is here for! Captain Josh will be your guide, giving you access to years of knowledge and experience.

Depending on the season, you might hook into Clam, Sheepshead, Crab, Flounder, Spotted Seatrout, Skate, Speckled Trout, Weakfish, and plenty more. Depending on the species you're after, you may find yourself spinning, jigging, or maybe something more specialized in this area. For the more adventurous among you, there's bowfishing.

If you're traveling with the family, you will be glad to know that kids are welcome aboard! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. And, you can't go wrong with snacks!

You'll be casting lines from a 30' Lowe pontoon boat with a capacity for 6 passengers. Its very stable, safe and comfortable, and comes with all the essentials. Capt. Josh has rods and reels for you, along with lures. Live bait is on offer, but you should ask the captain whether you'll be catching it yourself.

The fishing license is provided, that covers the entire boat. Some species might be protected or require a tag to keep them, so make sure you know what to expect.

You can't go wrong when you bring bottled water, sunglasses, and sunblock (non-spray). Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.

Now and then the fish might get away, but a day on the water never should. So make it happen, with Day On The Bay Charters!

Excited to cast a line in Ocean City? That's what Day On The Bay Charters is here for! Captain Josh will be your guide, giving you access to years of knowledge and experience.

Depending on the season, you might hook into Clam, Sheepshead, Crab, Flounder, Spotted Seatrout, Skate, Speckled Trout, Weakfish, and plenty more. Depending on the species you're after, you may find yourself spinning, jigging, or maybe something more specialized in this area. For the more adventurous among you, there's bowfishing.

If you're traveling with the family, you will be glad to know that kids are welcome aboard! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. And, you can't go wrong with snacks!

You'll be casting lines from a 30' Lowe pontoon boat with a capacity for 6 passengers. Its very stable, safe and comfortable, and comes with all the essentials. Capt. Josh has rods and reels for you, along with lures. Live bait is on offer, but you should ask the captain whether you'll be catching it yourself.

The fishing license is provided, that covers the entire boat. Some species might be protected or require a tag to keep them, so make sure you know what to expect.

You can't go wrong when you bring bottled water, sunglasses, and sunblock (non-spray). Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.

Now and then the fish might get away, but a day on the water never should. So make it happen, with Day On The Bay Charters!

Josh A Wentling
Captain
Josh A Wentling
38 years of experience
responds within an hour

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
Group Size
2 adults • 0 children
Change
2hr early bird special.
FREE Cancellation 30 days notice
2 hour trip starts at 7:00 AM
Seasonal trip
May 1 - Oct 1
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people
2hr fishing/cruise -brunch special
FREE Cancellation 30 days notice
2 hour trip starts at 9:15 AM
Seasonal trip
May 1 - Oct 1
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people
2hr kids special
FREE Cancellation 30 days notice
2 hour trip starts at 11:30 AM
Seasonal trip
May 1 - Oct 1
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people
2hr afternoon delight
FREE Cancellation 30 days notice
2 hour trip starts at 1:45 PM
Seasonal trip
May 1 - Oct 1
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people
2 hr happy hour
FREE Cancellation 30 days notice
2 hour trip starts at 4:00 PM
Seasonal trip
May 1 - Oct 1
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people
Sun set special
FREE Cancellation 30 days notice
2 hour trip starts at 6:15 PM
Seasonal trip
May 1 - Sep 10 (Mon, Tue, Wed, Thu, Fri, Sun)
Flounder
Sheepshead
Speckled Trout
Weakfish
+3
US $275
Entire boat: up to 6 people

Customer reviews

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Rating

4.9
181 reviews
4.9
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (137)

What anglers say

94%
Great experience
99%
Family friendly
98%
Friendly captain
98%
Good boat
97%
Recommended
79%
Caught fish

Reviews (181)

  • Caitlyn Magee
    Caitlyn Magee
    us
    New York, US
    Member since 2026
    5.0
    Verified

    Awesome Time

    2hr fishing/cruise -brunch special on July 14, 2026 • 4 adults

    We had an awesome time on this fishing trip! The whole experience was relaxed, fun, and exactly what we were hoping for. The captain was fantastic—friendly, knowledgeable, patient, and made everyone feel comfortable, He kept the atmosphere light and enjoyable while making sure we had every opportunity to catch fish. We never felt rushed, and it was clear he genuinely wanted everyone to have a great time. We made some great memories and would absolutely book another trip. Highly recommend if you’re looking for a laid-back day on the water with a great captain!

  • Jaime Schlegel
    Jaime Schlegel
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    so much fun!!

    2 hr happy hour on August 7, 2026 • 5 adults

    Captin Josh was awesome! My 4 kids and I had a very nice cruise out to some great fishing spots. The water was extremely busy due to the White Marlin boating contest and Captin Josh navigating us through the traffic was flawless. He educated us on homes, history and taught kids how to fish in the bay. My one daughter caught a pregnant blue crab and he took time to teach us all and show us her “sponge” like egg sack. Thank you for a wonderful trip Captin Josh!! We will definitely reach back out for future rides when OCMD.

  • Tammy Bullied
    Tammy Bullied
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    Captain Josh was great!

    2hr kids special on September 1, 2026 • 4 adults • 2 children

    Captain Josh was very knowledgeable, patient and generous with his bait. Only complaint with my husband was that the women got all the fish (Me) LOL. He took us in the areas that were good spots. My catch for the 2hr trip was 3 Flounder, a Seabass and 2 crabs. I had one Flounder that was 18” that Josh quickly and professionally cleaned for us, bagged it up for us to take home. We will definitely look up Josh nexf year when we return. We all enjoyed our trip!

  • Matthew Hayes
    Matthew Hayes
    us
    Ohio, US
    Member since 2026
    5.0
    Verified

    Best trip ever!

    2hr fishing/cruise -brunch special on September 5, 2026 • 6 adults • 2 children

    The Captain was AMAZING! My wife and I took our daughter, her husband and two children, and the captain was great with the kids, a two year-old and a seven-year-old. We even got to do a little sightseeing! We got his business card so the next time we’re back in the area we can make sure we book with him. Great memories were made today. If you’re thinking about going, this is the guy to book. He is fantastic!

  • Gina Shade
    Gina Shade
    us
    Pennsylvania, US
    Member since 2026
    4.7
    Verified

    Good time and relaxing

    2hr early bird special. on June 30, 2026 • 4 adults • 2 children

    Captain Josh made it easy. We asked questions. We learned. All four of us fished. We only caught two sea bass and lots of little crabs. Nothing large enough to keep unfortunately. But it was a good time. We did the 7 am two hour tour on the bay. We would do it again. All the equipment was in good working order. The captain had lots of knowledge of the craft and the area. Thanks again.

  • Susan Anders
    Susan Anders
    us
    Maryland, US
    Member since 2026
    5.0
    Verified

    Always fun with Capt Josh!

    2hr afternoon delight on September 12, 2026 • 6 adults

    Capt Josh takes you wherever you want to go, will stop on the beach so you can swim, or stop at the bar to grab drinks or food or what we did, which was just float around the bay for 2 hours with good stories and drinks in the cooler.

  • Gregory Young
    Gregory Young
    us
    Ohio, US
    Member since 2026
    5.0
    Verified

    What a great time!

    2hr fishing/cruise -brunch special on June 30, 2026 • 6 adults • 2 children

    Not everyone caught a fish but thats why they call it fishing and not catching. The captain was a great guy and worked hard for us. He had good knowledge and stories. If we're ever in tbe area again, we'll definitely book another trip.

  • Kaitlin Cribbs
    Kaitlin Cribbs
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    Highlight of our trip!

    2hr afternoon delight on August 16, 2026 • 6 adults

    We had an amazing time fishing! The captain was incredibly helpful and great to chat with throughout the trip. We had such a fun experience and will absolutely be back next year with the family. Thank you so much!!

  • Kristin Dare
    Kristin Dare
    us
    Maryland, US
    Member since 2026
    5.0
    Verified

    Great family evening!

    Sun set special on August 5, 2026 • 4 adults

    We did the sunset trip. The captain was very nice and knowledgable. We had a ton of bites but we reeled in some crabs. Even had bites from a stingray and shark! Will definitely book with him again.

  • Josh Hartman
    Josh Hartman
    Repeat angler
    us
    Pennsylvania, US
    Member since 2024
    2 trips
    5.0
    Verified

    2 hour kid friendly trip.

    2hr kids special on June 10, 2026 • 4 adults • 2 children

    Took our 8 and 4 year old out for their first time. Captain Josh did an awesome job. Very knowledgeable and very hospitable. Already looking forward to booking our next trip with him!

FAQs about Day On The Bay Charters

Day On The Bay Charters offers the following trips to customers:
  • US $275 per group - 2 hr happy hour (2 hours)
  • US $275 per group - 2hr afternoon delight (2 hours)
  • US $275 per group - 2hr early bird special. (2 hours)
  • US $275 per group - 2hr fishing/cruise -brunch special (2 hours)
  • US $275 per group - 2hr kids special (2 hours)
  • US $275 per group - Sun set special (2 hours)
When you book a trip with Day On The Bay Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
Trips booked with Day On The Bay Charters include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • First mate (20% of the trips fare is standard tip.)
  • Fishing license
Day On The Bay Charters offers the following type of fishing:
  • Inshore fishing
Day On The Bay Charters offers the following fishing techniques:
  • Light tackle
  • Spinning
Top targeted fish species with Day On The Bay Charters include:
  • Bluefish (Tailor)
  • Flounder
  • Speckled Trout
  • Weakfish

Your captain

Josh A Wentling
Josh A Wentling
Ocean City, Maryland, United States
181 Customer reviews
Typical response within an hour
Member since May 2024
Capt. Josh has spent 35+ years on the water. He is third generation hunting and fishing guide. He has Comercial fished and charter fished from NJ to Mexico. He's won and placed in numerous offshore fishing tournaments. He has guided for waterfowl, upland birds and big game in Nebraska, Iowa, Illinois and Maryland for over 30 years. He truly is an outdoors man. He'll do everything in his power to ensure you have a enjoyable day on the water.
Josh A Wentling
Josh A Wentling
181
reviews
2024
member since
~1h
response
Capt. Josh has spent 35+ years on the water. He is third generation hunting and fishing guide. He has Comercial fished and charter fished from NJ to Mexico. He's won and placed in numerous offshore fishing tournaments. He has guided for waterfowl, upland birds and big game in Nebraska, Iowa, Illinois and Maryland for over 30 years. He truly is an outdoors man. He'll do everything in his power to ensure you have a enjoyable day on the water.

The fish you can target

Bluefish (Tailor)
Bluefish (Tailor)
Flounder
Flounder
Speckled Trout
Speckled Trout
Weakfish
Weakfish
Bluefish (Tailor)
Bluefish (Tailor)
Flounder
Flounder
Speckled Trout
Speckled Trout
Weakfish
Weakfish

Real catches by this captain

  • A smiling captain at the helm of a fishing boat, ready for a day on the water.
    Susan A.
    Susan A.
    Capt Josh takes you wherever you want to go, will stop on the beach so you can swim, or stop at the bar to grab drinks or food or what we did, which was just float around the bay for 2 hours with good stories and drinks in the cooler.
  • Family fishing from a small open boat in calm coastal waters, with an adult angler holding a rod and two young anglers aboard.
    Matthew H.
    Matthew H.
    The Captain was AMAZING! My wife and I took our daughter, her husband and two children, and the captain was great with the kids, a two year-old and a seven-year-old. We even got to do a little sightseeing! We got his business card so the next time we’re back in the area we can make sure we book with him. Great memories were made today. If you’re thinking about going, this is the guy to book. He is fantastic!
  • An angler is filleting a flatfish on a boat while a young companion observes, showcasing a hands-on fishing experience.
    Fish 1
    Fish 2
    Flounder
    Tammy B.
    Tammy B.
    Captain Josh was very knowledgeable, patient and generous with his bait. Only complaint with my husband was that the women got all the fish (Me) LOL. He took us in the areas that were good spots. My catch for the 2hr trip was 3 Flounder, a Seabass and 2 crabs. I had one Flounder that was 18” that Josh quickly and professionally cleaned for us, bagged it up for us to take home. We will definitely look up Josh nexf year when we return. We all enjoyed our trip!
  • Angler displaying a flatfish in a landing net aboard a covered fishing boat near a sandy shoreline, with fellow passengers in the background.
    Fish 1
    Flounder
    Kaitlin C.
    Kaitlin C.
    We had an amazing time fishing! The captain was incredibly helpful and great to chat with throughout the trip. We had such a fun experience and will absolutely be back next year with the family. Thank you so much!!
  • Young angler and an adult display a small fish aboard a fishing boat during an inshore fishing trip.
    Fish 1
    Sheepshead
    Rachel G.
    Rachel G.
    Thank you Captains Josh and Casey for a fun day fishing. My kids had a great time and want to come back soon!
  • A flounder caught in a net while fishing on a boat, showcasing the excitement of the catch.
    Fish 1
    Flounder
    Jaime S.
    Jaime S.
    Captin Josh was awesome! My 4 kids and I had a very nice cruise out to some great fishing spots. The water was extremely busy due to the White Marlin boating contest and Captin Josh navigating us through the traffic was flawless. He educated us on homes, history and taught kids how to fish in the bay. My one daughter caught a pregnant blue crab and he took time to teach us all and show us her “sponge” like egg sack. Thank you for a wonderful trip Captin Josh!! We will definitely reach back out for future rides when OCMD.
  • A group of anglers on a boat, with one young man actively reeling in a fish while receiving guidance from an experienced fisherman.
    Kristin D.
    Kristin D.
    We did the sunset trip. The captain was very nice and knowledgable. We had a ton of bites but we reeled in some crabs. Even had bites from a stingray and shark! Will definitely book with him again.
  • A young angler smiles while holding a small fish, with an adult companion nearby, aboard a fishing boat in a coastal setting.
    Michael P.
    Michael P.
    We had an awesome time. The captain is a great guy and knows his stuff. We will be back.
  • A smiling angler holds a flounder in a net while fishing on a boat during a sunny day.
    Fish 1
    Flounder
    Mathew H.
    Mathew H.
    We went out on the sunset trip didnt catch alot but thats fishing.Captain was supe nice we loved the trip and would definitely go again.
  • A scenic sunset view over calm waters, taken from a boat, showcasing the tranquil fishing environment.
    Christopher O.
    Christopher O.
    It really was the perfect trip. A beautiful cruise on the bay as the sun was setting. And everyone caught multiple fish! Definitely recommend it 👌

What is the boat like?

Boat image
Boat category
Other
Capacity
6 persons
Boat length
30 ft
Year built
1995
Restored in
2024
Boat manufacturer
Lowe
Boat type
Pontoon
Engine model
Suzuki
Powered by
1 x 115HP
Max cruising speed
25 knots

What kind of fishing will you do?

Inshore Fishing

Which fishing techniques you can try

Light Tackle
Spinning

Which amenities are available onboard

GPS
Fishfinder
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
First mate
20% of the trips fare is standard tip.
Fishing license

How cancellations work

Free cancellation up to 30 days prior to trip
You can cancel or modify your booking up to 30 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
More details

What the listing policies are

Pickup agreed upon reservation
Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.
Child friendly
You keep catch
Catch and release allowed

How you can pay

Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% 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
 Visa
 Mastercard
 PayPal
 Checks
When paying the remaining balance with a credit card, an additional 5% charge will apply.

What’s biting in Ocean City right now

Bluefish (Tailor)Bluefish (Tailor)
FlounderFlounder
Speckled TroutSpeckled Trout
WeakfishWeakfish

Compare similar fishing charters

Current
Day On The Bay Charters
Day On The Bay Charters
4.9
(181)
30 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+2
2 hour trip • 6 persons
US $275