Lost Sailor Guide Service LLC 

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

Lost Sailor Guide Service LLC 

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

10/8 Fish are here, Time to get in on some fun rockfish topwater bites in the back bays. Lets catch some fish!

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!

10/8 Fish are here, Time to get in on some fun rockfish topwater bites in the back bays. Lets catch some fish!

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!

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Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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4 hour Striped Bass "2ppl only"
FREE Cancellation 3 days notice
4 hour trip starts at 7:00 AM
Seasonal trip
Sep 15 - Nov 30
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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
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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
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US $450
Entire boat: up to 4 people

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

Reviews (73)

  • 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, 2026 • 2 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.

  • Colleen Grine
    Colleen Grine
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    GREAT day on the bay.

    4 Hour Trip – Bay Fishing on August 9, 2026 • 2 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!!!

  • Daniel West
    Daniel West
    us
    Maryland, US
    Member since 2026
    5.0
    Verified

    really enjoyed with 5 yr old to 60 year old

    4 Hour Trip – Bay Fishing on August 5, 2026 • 4 adults • 1 child

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

  • Peter Rhee
    Peter Rhee
    Repeat angler
    us
    Washington D.C., US
    Member since 2024
    2 trips
    5.0
    Verified

    Awesome Captain!

    4 hour Striped Bass "2ppl only" on April 1, 2026 • 2 adults • 1 child

    My son and I really enjoyed our outing today and we especially liked Captain Skip! He was genuinely excited for us when we caught our first fish and was a joy to talk to throughout the trip. Will book again!

  • Susan Kelly
    Susan Kelly
    us
    Delaware, US
    Member since 2025
    5.0
    Verified

    5-Star Review for Captain Skip– A Perfect Day on the Water!

    4 Hour Trip – Bay Fishing on July 21, 2025 • 3 adults • 2 children

    We had an absolutely incredible day out on the water with Captain Skip! From start to finish, everything was smooth, professional, and a whole lot of fun. He put us right on the fish—we caught over 40! (While other boats around us weren’t having as much luck!) He really knows his stuff and worked nonstop to make sure we had lines in the water constantly. He even helped us fillet a big flounder that was over the size limit—now that’s a dinner the boys won’t forget! He handled my two energetic 12-year-old boys like a pro. Patient, encouraging, and funny—he kept them engaged the whole trip. If you’re looking for a memorable charter with someone who knows the water, keeps things safe, and makes it fun for the whole family—Captain Skip is your guy. We’ll definitely be booking again!

  • Brad Schrock
    Brad Schrock
    us
    Indiana, US
    Member since 2025
    5.0
    Verified

    Highly recommend

    4 Hour Trip – Bay Fishing on July 8, 2025 • 4 adults

    Captain Skip was awesome. Great communication before, and lots of fun on the water. He definitely knows his way around the area, taking us to many spots. Nothing was biting for anyone on the water, but it wasn’t for lack of trying. Captain Skip still made sure we had a great time. Will definitely go with Lost Sailor again next time.

  • Brinton Warren
    Brinton Warren
    us
    Virginia, US
    Member since 2024
    5.0
    Verified

    Great Guy, Great Fisherman, Great Local Knowledge

    4 Hour Trip – Bay Fishing on August 14, 2024 • 3 adults

    Loved our morning with Skip! He is totally laid back, but great to talk to. I love his boat and it was perfect for our group, Skip has great local knowledge— he knew where to find the fish,and he was super skilled at keeping our lines in the water. On the way back he gave us a tour of the marinas, including the boat of a famous American billionaire— I won’t name names. Such a cool experience for my sons. We will be going out with Skip again—I highly recommend him.

  • Tony Zaslav
    Tony Zaslav
    Repeat angler
    us
    Maryland, US
    Member since 2021
    8 trips
    5.0
    Verified

    We had the best time

    4 Hour Trip – Bay Fishing on July 15, 2025 • 3 adults

    I have taken a lot of charters with my boys and we agreed that Lost Sailor was our favorite so far. The Captain was great and super helpful and we caught a whole bunch of fish. I highly recommend ! 5 stars ⭐️ we will hopefully be back in August for round 2

  • Tammi Reid
    Tammi Reid
    us
    Pennsylvania, US
    Member since 2024
    5.0
    Verified

    An Amazing Trip!!

    4 Hour Trip – Bay Fishing on September 11, 2024 • 1 adult

    I highly recommend!! I can’t wait to get my next trip booked! Captain Skip is a great guy and is very knowledgeable of the waters and where the fish could be. We moved to a couple areas then he got us in to a great spot where I caught lots of blues.I had the best time I didn’t want the day to end I could fish with him all day. What a blast!

  • Kyle Arsenault
    Kyle Arsenault
    Repeat angler
    us
    California, US
    Member since 2024
    2 trips
    5.0
    Verified

    Felt like Fishing with a Friend

    4 Hour Trip – Bay Fishing on June 12, 2025 • 2 adults • 1 child

    Cpt. Skip was a great guy that catered to me and my son for a half day of flounder fishing. Reeled in 18, largest at about 15". Great guy who knows his craft. Would highly recommend!

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 1 – 5 of 73 reviews
Chris Guest
Chris Guest
us
Virginia, US
Member since 2026
5.0
Verified
great trip
4 Hour Trip – Bay Fishing on August 7, 2026 • 1 adult • 1 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
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, 2026 • 2 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
Adam Brown
Adam Brown
Repeat angler
us
New York, US
Member since 2024
2 trips
5.0
Verified
Great trip and time!
4 Hour Trip – Bay Fishing on August 12, 2026 • 4 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
Colleen Grine
Colleen Grine
us
Pennsylvania, US
Member since 2026
5.0
Verified
GREAT day on the bay.
4 Hour Trip – Bay Fishing on August 9, 2026 • 2 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!!!

Andrew Shingle
Andrew Shingle
us
Pennsylvania, US
Member since 2026
5.0
Verified
Great Day with Captain Skip!
4 Hour Trip – Bay Fishing on July 23, 2026 • 3 adults

Had a great day fishing with Captain Skip. He worked really hard to put us over fish and knew the area really well. Would definitely book with him again and recommend him to others.

Reported catch:
Flounder

FAQs about Lost Sailor Guide Service LLC

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The fish you can target

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Real catches by this captain

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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
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