Lost Sailor Guide Service LLC 

4.9/5 (73 reviews)
 Shell Mill Road, Bishopville, MD 21813, United States

Lost Sailor Guide Service LLC 

Bishopville, MD, United States
25 ft
4
4.9/5 (73 reviews)

Welcome to Lost Sailor Guide Service LLC, your gateway to unforgettable fishing adventures in Ocean City! Join Captain Skip Maisel for an exciting day on the water, where you'll chase prized fish and take in the stunning beauty of Maryland’s coast. Whether you’re looking to fish inshore, nearshore, flats. Captain Skip knows exactly how to make your trip both productive and enjoyable.

Aboard a 25’ Privateer pilothouse boat, you'll have all the amenities you need for a smooth and safe adventure. With room for up to 4 anglers, this boat is powered by a new 300HP Suzuki engine. You’ll also have an ice-box and livewell to keep your catch fresh throughout the day.

On your trip, you’ll have the chance to reel in a variety of exciting fish, including Bluefish, Striped Bass, Flounder, and Weakfish. Whether you prefer light tackle, bottom fishing, drift fishing, jigging, or popping, Captain Skip will guide you to the best spots using the most effective techniques. Families are welcome, and kids over 6 can join the adventure too. Please contact the Capt. when kids are fishing. Whether you choose to keep or release your catch, the choice is yours!

Captain Skip takes care of everything — from fishing rods and reels to tackle, licenses, and even drinks. All you need to bring are your favorite snacks and a sense of adventure! Adult beverages are allowed.

Book your trip with Lost Sailor Guide Service LLC today, and get ready for a fantastic fishing experience that you’ll remember for years to come!

Welcome to Lost Sailor Guide Service LLC, your gateway to unforgettable fishing adventures in Ocean City! Join Captain Skip Maisel for an exciting day on the water, where you'll chase prized fish and take in the stunning beauty of Maryland’s coast. Whether you’re looking to fish inshore, nearshore, flats. Captain Skip knows exactly how to make your trip both productive and enjoyable.

Aboard a 25’ Privateer pilothouse boat, you'll have all the amenities you need for a smooth and safe adventure. With room for up to 4 anglers, this boat is powered by a new 300HP Suzuki engine. You’ll also have an ice-box and livewell to keep your catch fresh throughout the day.

On your trip, you’ll have the chance to reel in a variety of exciting fish, including Bluefish, Striped Bass, Flounder, and Weakfish. Whether you prefer light tackle, bottom fishing, drift fishing, jigging, or popping, Captain Skip will guide you to the best spots using the most effective techniques. Families are welcome, and kids over 6 can join the adventure too. Please contact the Capt. when kids are fishing. Whether you choose to keep or release your catch, the choice is yours!

Captain Skip takes care of everything — from fishing rods and reels to tackle, licenses, and even drinks. All you need to bring are your favorite snacks and a sense of adventure! Adult beverages are allowed.

Book your trip with Lost Sailor Guide Service LLC today, and get ready for a fantastic fishing experience that you’ll remember for years to come!

Skip Maisel
Captain
Skip Maisel
20 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip availability and prices

Trip Date:
Group Size:
August 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Almost there...
4 hour Striped Bass "2ppl only"
FREE Cancellation 3 days notice
4 hour trip starts at 7:00 AM
Seasonal trip
Apr 1 - May 31
Bass (Striped)
US $350
Entire boat: up to 4 people
4 Hour Trip – Bay Fishing
FREE Cancellation 3 days notice
4 hour trip starts at 7:00 AM
Seasonal trip
Apr 1 - Oct 15
Bass (Striped)
Flounder
Weakfish
US $450
Entire boat: up to 4 people
4 Hour Trip – Bay Fishing
FREE Cancellation 3 days notice
4 hour trip starts at 12:00 PM
Seasonal trip
Apr 1 - Sep 30
Bass (Striped)
Bluefish (Tailor)
Flounder
US $450
Entire boat: up to 4 people
There are 7 people looking at this charter.

Customer reviews

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Rating

4.9
73 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (79)

What anglers say

98%
Great experience
90%
Family friendly
100%
Friendly captain
100%
Good boat
99%
Recommended
90%
Caught fish

All reviews (73)

Frequently mentioned
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Showing 15 of 73 reviews
Chris Guest
Chris Guest
us
Virginia, US
Member since 2026
5.0
Verified
New
great trip
4 Hour Trip – Bay Fishing on August 7, 20261 adult1 child

first, we messaged back amd forth with Cap. skip regarding moving out fishing time back to work better with tides and fishing. then, we had a small sanfu (my fault entwrily) as to where we wefe meeting for pick up. Cap Skip went out of his way to pick us up at a differrnet location. then we had great day of fishing and he did an awesoem job of working with us to catch fish. Coulding recommend someone better.

Reported catch:
Flounder
Skip Maisel
Response from Captain

Thanks for the review Chris. Glad we could switch the time up to match the tide. We found a few. Good fun.

Johnny Swords
Johnny Swords
Repeat angler
us
New Jersey, US
Member since 2025
3 trips
5.0
Verified
Top notch Captain, Great Experience!
4 hour Striped Bass "2ppl only" on April 7, 20262 adults

My son and I had such a great time. The captain was super friendly and knowledgeable of the fishing grounds. He put us on the fish quickly. The boat was very clean, and the gear used was in excellent working condition. He kept us out a little longer than the 4 hours we paid for, hitting all his honey holes looking for fish. It was a great time for sure. You won’t go wrong if you book this boat for a fishing trip.

Reported catch:
Striped Bass
Skip Maisel
Response from Captain

Thanks for the review. Fun morning chasing those things around.

Adam Brown
Adam Brown
Repeat angler
us
New York, US
Member since 2024
2 trips
5.0
Verified
New
Great trip and time!
4 Hour Trip – Bay Fishing on August 12, 20264 adults

Trip was great we caught about 30 flounders. We had great weather an the Captain was great and friendly. True personalized service. One of the best fishng boat experiences in 22 years and definitely the most catches in single outing.

Reported catch:
Flounder
Skip Maisel
Response from Captain

Thanks Adam, was a fun morning for sure. Glad we got past 4. 🤪

Colleen Grine
Colleen Grine
us
Pennsylvania, US
Member since 2026
5.0
Verified
New
GREAT day on the bay.
4 Hour Trip – Bay Fishing on August 9, 20262 adults

Captain Skip gave us the best day on the bay. So kind, so knowledgable and friendly. he helped us with everything and made sure we were comfortable and having fun. Our son caught his first fish. Smiles all around. Highly recommend!!!

Skip Maisel
Response from Captain

Thank you, Seeing Jake holding that 1st flounder he's ever caught made my day!

DANIEL WEST
DANIEL WEST
us
Maryland, US
Member since 2026
5.0
Verified
New
really enjoyed with 5 yr old to 60 year old
4 Hour Trip – Bay Fishing on August 5, 20263 adults1 child

Captain Skip was great. Got us on the fish. Was prompt and fun to hang out with.

Skip Maisel
Response from Captain

Thanks for the review. i had a great time with you guys. Always enjoy having the young kids on my boat and catching them a few fish.

FAQs about Lost Sailor Guide Service LLC

Lost Sailor Guide Service LLC offers the following trips to customers:
  • US $350 per group - 4 hour Striped Bass "2ppl only" (4 hours)
  • US $450 per group - 4 Hour Trip – Bay Fishing (4 hours)
  • US $450 per group - 4 Hour Trip – Bay Fishing (4 hours)
When you book a trip with Lost Sailor Guide Service LLC, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live bait well
  • Wireless trolling motor
  • Ice box
Trips booked with Lost Sailor Guide Service LLC include:
  • Rods, reels & tackle
  • Lures
  • Catch cleaning & filleting (We do not charge for cleaning fish.)
  • Drinks (I have Gatorades and water on the boat. Included.)
  • First mate (Some days we have a 1st mate along for the trip. )
  • Fishing license (We cover anyone that's on the boat.)
Lost Sailor Guide Service LLC offers the following types of fishing:
  • Inshore fishing
  • Flats fishing
  • Backcountry fishing
Lost Sailor Guide Service LLC offers the following fishing techniques:
  • Light tackle
  • Spinning
  • Jigging
  • Popping
Top targeted fish species with Lost Sailor Guide Service LLC include:
  • Bass (Striped)

Your captain

Skip Maisel
Skip Maisel
Skip Maisel

Bishopville, Maryland, United States

6 Fishing Reports
ID & license verified
73 Customer reviews
Typical response within an hour
Member since October 2021
Angler's Choice

The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.

Lost Sailor Guide Service LLC is owned and operated by Capt. Skip Maisel who has been fishing on the Eastern Shore his entire life. Capt. Skip has experience in the back bays and off the Ocean City coast, along with tournament experience and over a decade of commercial crabbing knowledge. When fishing with Capt. Skip, you can be sure that you are with one of the most experienced captains in town! Your charter can be for either a half or full day inshore adventure fishing out of Ocean City, Maryland. Depending on conditions, you'll find yourself fishing the bay, water close to the shoreline, or a close-by wreck. After growing up on the water, Capt. Skip knows all the hot spots to make your trip one of the best. All tackle and fishing equipment will be provided for your charter as well as necessary fishing licenses. The captain provides sodas and water, beer is on you. You will work out where he will pick you up in the OC area for most trips. Capt. Skip thanks you for checking out his charter and looks forward to seeing you.

6 Fishing Reports
ID & license verified
73 Customer reviews
Typical response within an hour
Member since October 2021
Angler's Choice

The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.

Lost Sailor Guide Service LLC is owned and operated by Capt. Skip Maisel who has been fishing on the Eastern Shore his entire life. Capt. Skip has experience in the back bays and off the Ocean City coast, along with tournament experience and over a decade of commercial crabbing knowledge. When fishing with Capt. Skip, you can be sure that you are with one of the most experienced captains in town! Your charter can be for either a half or full day inshore adventure fishing out of Ocean City, Maryland. Depending on conditions, you'll find yourself fishing the bay, water close to the shoreline, or a close-by wreck. After growing up on the water, Capt. Skip knows all the hot spots to make your trip one of the best. All tackle and fishing equipment will be provided for your charter as well as necessary fishing licenses. The captain provides sodas and water, beer is on you. You will work out where he will pick you up in the OC area for most trips. Capt. Skip thanks you for checking out his charter and looks forward to seeing you.

The fish you can target

Striped Bass
Striped Bass
Striped Bass
Striped Bass

Real catches by this captain

  • great trip
    Chris G.
    Chris G.
  • really enjoyed with 5 yr old to 60 year old
    Daniel W.
    Daniel W.
  • Great Day with Captain Skip!
    Andrew S.
    Andrew S.
  • Top notch Captain, Great Experience!
    Johnny S.
    Johnny S.
  • Awesome Captain!
    Peter R.
    Peter R.
  • Skip is a great captain and host!
    Lawrence M.
    Lawrence M.
  • The best !
    Jenny M.
    Jenny M.
  • 5-Star Review for Captain Skip– A Perfect Day on the Water!
    Susan K.
    Susan K.
  • We had the best time
    Tony Z.
    Tony Z.
  • Highly recommend
    Brad S.
    Brad S.

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
4 persons
Boat length
25 ft
Year built
2006
Boat manufacturer
Privateer
Boat type
Pilothouse
Engine model
Suzuki
Powered by
1 x 300HP
Max cruising speed
35 knots

What kind of fishing will you do?

Inshore Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Spinning
Jigging
Popping

Which amenities are available onboard

GPS
Fishfinder
Live bait well
Wireless trolling motor
Ice box
What's included in the trip price
Rods, reels & tackle
Lures
Catch cleaning & filleting
We do not charge for cleaning fish.
Drinks
I have Gatorades and water on the boat. Included.
First mate
Some days we have a 1st mate along for the trip.
Fishing license
We cover anyone that's on the boat.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 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
12 and up. Message us for younger kids please.
You keep catch
We follow MD regulations.
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

 PayPal

 Bank transfer

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Current
Lost Sailor Guide Service LLC
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4.9
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US $450