Lost Sailor Guide Service LLC
Lost Sailor Guide Service LLC
The 2 person rockfish trips will begin when the fish show up in the back bays. I will update this post as soon as we have some fish to play with. Looking forward to this fall season. Hold fast!
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!
The 2 person rockfish trips will begin when the fish show up in the back bays. I will update this post as soon as we have some fish to play with. Looking forward to this fall season. Hold fast!
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 availability and prices
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Customer reviews
Rating
Anglers' gallery (79)
What anglers say
Reviews (73)
Johnny SwordsRepeat angler5.0VerifiedTop notch Captain, Great Experience!
4 hour Striped Bass "2ppl only" on April 7, 2026 • 2 adultsMy 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 Grine5.0VerifiedGREAT day on the bay.
4 Hour Trip – Bay Fishing on August 9, 2026 • 2 adultsCaptain 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 West5.0Verifiedreally enjoyed with 5 yr old to 60 year old
4 Hour Trip – Bay Fishing on August 5, 2026 • 4 adults • 1 childCaptain Skip was great. Got us on the fish. Was prompt and fun to hang out with.
Peter RheeRepeat angler5.0VerifiedAwesome Captain!
4 hour Striped Bass "2ppl only" on April 1, 2026 • 2 adults • 1 childMy 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 Kelly5.0Verified5-Star Review for Captain Skip– A Perfect Day on the Water!
4 Hour Trip – Bay Fishing on July 21, 2025 • 3 adults • 2 childrenWe 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 Schrock5.0VerifiedHighly recommend
4 Hour Trip – Bay Fishing on July 8, 2025 • 4 adultsCaptain 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 Warren5.0VerifiedGreat Guy, Great Fisherman, Great Local Knowledge
4 Hour Trip – Bay Fishing on August 14, 2024 • 3 adultsLoved 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 ZaslavRepeat angler5.0VerifiedWe had the best time
4 Hour Trip – Bay Fishing on July 15, 2025 • 3 adultsI 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 Reid5.0VerifiedAn Amazing Trip!!
4 Hour Trip – Bay Fishing on September 11, 2024 • 1 adultI 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 ArsenaultRepeat angler5.0VerifiedFelt like Fishing with a Friend
4 Hour Trip – Bay Fishing on June 12, 2025 • 2 adults • 1 childCpt. 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
Anglers' gallery (79)
What anglers say
All reviews (73)
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.
Thanks for the review Chris. Glad we could switch the time up to match the tide. We found a few. Good fun.
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.
Thanks for the review. Fun morning chasing those things around.
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.
Thanks Adam, was a fun morning for sure. Glad we got past 4. 🤪
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!!!
Thank you, Seeing Jake holding that 1st flounder he's ever caught made my day!
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.
Thanks Andrew, Was a pleasure having you guys out. A 1st for me even with that flounder size. lol. Hope to see you guys again. Really the smallest one ever caught on my boat.
FAQs about Lost Sailor Guide Service LLC
- 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)
- GPS
- Fishfinder
- Live bait well
- Wireless trolling motor
- Ice box
- 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.)
- Inshore fishing
- Flats fishing
- Backcountry fishing
- Light tackle
- Spinning
- Jigging
- Popping
- Bass (Striped)
Your captain
Bishopville, Maryland, United States
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.
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
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.
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.
How you can pay
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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