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Day on the Bay Charters 

4.5/5 (13 reviews)
 205 Somerset Street, Ocean City, MD 21842, United States–

Day on the Bay Charters 

Ocean City, MD, United States
–
30 feet
6
4.5/5 (13 reviews)
Trips & prices Boat info What's included Contact captain Activities
Trips & prices What's included Boat info Reviews Contact captain Activities

You may qualify for a Loyalty discount with Day on the Bay Charters. To check if the Loyalty discount is available for your selected dates, please sign in.

Join us for an unforgettable day on the water, where every moment is designed to create lasting memories. Whether you’re in the mood for a lively daytime booze cruise, a serene sunset sail, or a festive evening tour of Christmas lights on the bay, we have the perfect cruise for you. In the fall, our leaf-peeping cruises are a favorite, offering a front-row seat to the vibrant autumn colors reflected in the water.

Each cruise is a blend of relaxation and fun, with the freedom to enjoy the bay your way. Our vessels are spacious and comfortable, making it easy to unwind as you take in the stunning views, sip on your favorite drink, or capture the perfect photo of the season’s beauty.

As a family-run, family-oriented operation, we pride ourselves on creating a warm and welcoming atmosphere. Whether you’re planning a laid-back day with friends or a special family outing, we go the extra mile to ensure you have a fantastic time. Let us know what you’d like to experience, and we’ll tailor the trip to make it everything you imagined and more.

So come aboard, relax, and enjoy the beauty of the bay—your perfect day on the water awaits

Join us for an unforgettable day on the water, where every moment is designed to create lasting memories. Whether you’re in the mood for a lively daytime booze cruise, a serene sunset sail, or a festive evening tour of Christmas lights on the bay, we have the perfect cruise for you. In the fall, our leaf-peeping cruises are a favorite, offering a front-row seat to the vibrant autumn colors reflected in the water.

Each cruise is a blend of relaxation and fun, with the freedom to enjoy the bay your way. Our vessels are spacious and comfortable, making it easy to unwind as you take in the stunning views, sip on your favorite drink, or capture the perfect photo of the season’s beauty.

As a family-run, family-oriented operation, we pride ourselves on creating a warm and welcoming atmosphere. Whether you’re planning a laid-back day with friends or a special family outing, we go the extra mile to ensure you have a fantastic time. Let us know what you’d like to experience, and we’ll tailor the trip to make it everything you imagined and more.

So come aboard, relax, and enjoy the beauty of the bay—your perfect day on the water awaits

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Customer reviews

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Rating

4.5
(13 reviews)
4.4
Boat & equipment
4.5
Captain & crew
4.5
Experience

All reviews (13)

Showing 1 – 5 of 13 reviews
Kennedi Dawson
Kennedi Dawson
us
Pennsylvania, US
•
Member since 2026
5.0
Verified
A Perfect Sunset Cruise with Captain Josh
2 Hour Trip – Sunset Special on June 14, 2026 • 4 adults
I normally don’t leave reviews unless an experience is either exceptionally good or exceptionally bad, and thankfully this one falls into the first category. Our sunset cruise with Day on the Bay Charters was absolutely wonderful. Captain Josh Wentling was professional, friendly, and communicative from the very beginning. Before the cruise, he kept me informed and answered any questions I had, which made the entire process stress-free. The boat was clean, comfortable, and very well maintained. What really stood out was that Captain Josh took the time to ask what we wanted to see rather than simply following a standard route. We mentioned that we wanted to view Assateague Island from the water, and he happily accommodated our request without hesitation. Throughout the cruise, he was personable, knowledgeable, and great to talk with, making the experience feel both relaxing and memorable. We also had our elderly grandmother with us, who uses a walker, and Captain Josh went above and beyond to ensure she boarded and exited the boat safely and comfortably. The entire experience exceeded our expectations, and it was one of the highlights of our trip to Ocean City. I highly recommend Day on the Bay Charters and Captain Josh to anyone looking for a private, personalized, and enjoyable cruise experience. We will definitely book again the next time we’re in Ocean City!
Response from Captain
June 15, 2026
Thank you so much for the kind words. I enjoyed meeting you and your family. I look forward to seeing yall soon. Sincerely, Jw
Johnny Puylara
Johnny Puylara
us
New York, US
•
Member since 2026
5.0
Verified
New
Best experience on the pontoon boat!!
2 Hour Trip – Afternoon Special on July 9, 2026 • 5 adults
Our day with Captain Josh was awesome! We spent time exploring the bay, seeing all the wild horses, and even took us on a tour through the different marinas where the tourisrs and locals all go. Hands down one of the best experiences here, ever!! Thank you, Captain Josh for a fun filled “Day on the bay” with you. We will definitely be back to sail again!! The Puylara Family
Mallory Moynihan
Mallory Moynihan
us
New York, US
•
Member since 2026
5.0
Verified
New
Great Memories!
2 Hour Trip – Sunset Special on June 20, 2026 • 4 adults
Captain Josh was very accomodating, laid back, and fun! He made our trip a blast and would highly recommend. Will definitely be back to book again with him.
Response from Captain
June 26, 2026
thank you. hope to see yall again
China Ross
China Ross
us
Pennsylvania, US
•
Member since 2026
5.0
Verified
Amazing!
2 Hour Trip – Afternoon Special on May 29, 2026 • 6 adults
Josh was attentive to our needs, great conversationalist and very accommodating
Response from Captain
June 14, 2026
thank you so much
ANDREW HOFFMAN
ANDREW HOFFMAN
Member since 2025
5.0
Verified
A great time on the water!
2 Hour Trip – Sunset Special on July 24, 2025 • 5 adults • 1 child
Josh is a great captain and knows everything you could possibly want to know about the area and its history! Highly recommended!!

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour Trip – Sunrise Special
FREE Cancellation 7 days notice
2 hour trip starts at 7:00 AM
Seasonal trip
May 1 - Oct 1
US $275
Private tour: up to 6 people
2 Hour Trip – Brunch Special
FREE Cancellation 7 days notice
2 hour trip starts at 9:15 AM
Seasonal trip
May 1 - Oct 1
US $275
Private tour: up to 6 people
2 Hour Trip – Lunch special
FREE Cancellation 7 days notice
2 hour trip starts at 11:30 AM
Seasonal trip
May 1 - Oct 1
US $275
Private tour: up to 6 people
2 Hour Trip – Afternoon Special
FREE Cancellation 7 days notice
2 hour trip starts at 1:45 PM
Seasonal trip
May 1 - Oct 1
US $275
Private tour: up to 6 people
2 Hour Trip – Happy Hour
FREE Cancellation 7 days notice
2 hour trip starts at 4:00 PM
Seasonal trip
May 1 - Oct 1
US $275
Private tour: up to 6 people
2 Hour Trip – Sunset Special
FREE Cancellation 7 days notice
2 hour trip starts at 6:15 PM
Seasonal trip
May 1 - Oct 1 (Mon, Tue, Wed, Thu, Fri, Sun)
US $275
Private tour: up to 6 people
2 Hour Trip – Christmas Lights
FREE Cancellation 7 days notice
2 hour trip starts at 5:00 PM
Seasonal trip
Nov 10 - Dec 23
US $300
Private tour: up to 6 people
There are 5 people looking at this charter.

Customer reviews

Loading...

Rating

4.5
(13 reviews)
4.4
Boat & equipment
4.5
Captain & crew
4.5
Experience

All reviews (13)

Showing 1 – 5 of 13 reviews
Kennedi Dawson
Kennedi Dawson
us
Pennsylvania, US
Member since 2026
5.0
Verified
A Perfect Sunset Cruise with Captain Josh
2 Hour Trip – Sunset Special on June 14, 2026 • 4 adults
I normally don’t leave reviews unless an experience is either exceptionally good or exceptionally bad, and thankfully this one falls into the first category. Our sunset cruise with Day on the Bay Charters was absolutely wonderful. Captain Josh Wentling was professional, friendly, and communicative from the very beginning. Before the cruise, he kept me informed and answered any questions I had, which made the entire process stress-free. The boat was clean, comfortable, and very well maintained. What really stood out was that Captain Josh took the time to ask what we wanted to see rather than simply following a standard route. We mentioned that we wanted to view Assateague Island from the water, and he happily accommodated our request without hesitation. Throughout the cruise, he was personable, knowledgeable, and great to talk with, making the experience feel both relaxing and memorable. We also had our elderly grandmother with us, who uses a walker, and Captain Josh went above and beyond to ensure she boarded and exited the boat safely and comfortably. The entire experience exceeded our expectations, and it was one of the highlights of our trip to Ocean City. I highly recommend Day on the Bay Charters and Captain Josh to anyone looking for a private, personalized, and enjoyable cruise experience. We will definitely book again the next time we’re in Ocean City!
Response from Captain
June 15, 2026
Thank you so much for the kind words. I enjoyed meeting you and your family. I look forward to seeing yall soon. Sincerely, Jw
Johnny Puylara
Johnny Puylara
us
New York, US
Member since 2026
5.0
Verified
New
Best experience on the pontoon boat!!
2 Hour Trip – Afternoon Special on July 9, 2026 • 5 adults
Our day with Captain Josh was awesome! We spent time exploring the bay, seeing all the wild horses, and even took us on a tour through the different marinas where the tourisrs and locals all go. Hands down one of the best experiences here, ever!! Thank you, Captain Josh for a fun filled “Day on the bay” with you. We will definitely be back to sail again!! The Puylara Family
Mallory Moynihan
Mallory Moynihan
us
New York, US
Member since 2026
5.0
Verified
New
Great Memories!
2 Hour Trip – Sunset Special on June 20, 2026 • 4 adults
Captain Josh was very accomodating, laid back, and fun! He made our trip a blast and would highly recommend. Will definitely be back to book again with him.
Response from Captain
June 26, 2026
thank you. hope to see yall again
China Ross
China Ross
us
Pennsylvania, US
Member since 2026
5.0
Verified
Amazing!
2 Hour Trip – Afternoon Special on May 29, 2026 • 6 adults
Josh was attentive to our needs, great conversationalist and very accommodating
Response from Captain
June 14, 2026
thank you so much
ANDREW HOFFMAN
ANDREW HOFFMAN
Member since 2025
5.0
Verified
A great time on the water!
2 Hour Trip – Sunset Special on July 24, 2025 • 5 adults • 1 child
Josh is a great captain and knows everything you could possibly want to know about the area and its history! Highly recommended!!

FAQs about Day on the Bay Charters

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What the boat is like

Boat category
Other
Boat type
Pontoon
Boat manufacturer
Lowe
Boat Model
30
Year built
1995
Boat length
30 ft
Capacity
6 persons
Engine model
Suzuki
Max crusing speed
25 knots
Powered by
1 x 115HP
Engine Type
Outboard
Fuel Type
Gas
Boat category
Other
Boat type
Pontoon
Boat manufacturer
Lowe
Boat Model
30
Year built
1995
Boat length
30 ft
Capacity
6 persons
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