We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Lady Patty Sail Charters

Office - 21426 Wharf Rd, Boat - 6176 Tilghman Island Rd, Tilghman, MD 21671
Save
Review Highlights
Best chartered sail EVER

We've done chartered sails in Annapolis, Cambridge, St. Michaels and Newport RI. We did a morning... read more

Reviewed August 13, 2017
L9823HTkerenf
,
Pittsburgh, United States
Sunset sail...so nice!!

We are so glad we decided to take this sail. Such a beautiful and relaxing trip. The crew made it... read more

Reviewed July 7, 2017
Chmel325
,
Blue Ridge Summit, Pennsylvania
Read all 90 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
The classic yacht Lady Patty departs three times daily for the beautiful Chesapeake Bay from Tilghman Island, MD, just twelve scenic miles past St Michaels, MD from April 1 through October 31. Lady Patty is a 45' sailing yacht built in 1935 for offshore racing. She carries over 1000 square feet of sail and is USCG inspected for 16 passengers. During charters beer, wine and drink service is offered. We specialize in Champagne Sunset Sails. Don't settle for sailing in the rivers and harbors. Join us aboard the only sailing vessel in the area that sails on the open Chesapeake Bay. Come sail away aboard the classic yacht Lady Patty.
  • Excellent98%
  • Very good2%
  • Average0%
  • Poor0%
  • Terrible0%
Travelers talk about
“mate emma” (8 reviews)
“relaxing trip” (3 reviews)
“a lot of fun” (2 reviews)
Opens in 8 min
Hours
Hours Today: 10:00 AM - 8:30 PM
LOCATION
Office - 21426 Wharf Rd, Boat - 6176 Tilghman Island Rd, Tilghman, MD 21671
Write a ReviewReviews (90)
Traveler rating
Traveler type
Time of year
Language
All reviews
"mate emma"
in 8 reviews
"relaxing trip"
in 3 reviews
"a lot of fun"
in 2 reviews
"margaritas"
in 13 reviews
"sail"
in 41 reviews
"crew"
in 17 reviews
"weather"
in 12 reviews
"st"
in 10 reviews
"board"
in 8 reviews
"chesapeake"
in 11 reviews
"boat"
in 33 reviews
"michaels"
in 7 reviews
Filter

1 - 10 of 90 reviews

Reviewed August 13, 2017

We've done chartered sails in Annapolis, Cambridge, St. Michaels and Newport RI. We did a morning sail on July 15th and had the most enjoyable sail ever! The Captain and crew were informative and so gracious as we asked for picture after picture. The Chesapeake...More

Thank L9823HTkerenf
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded August 14, 2017

That is great news! I'm so glad you enjoyed yourselves. Thanks for the kind words and we look forward to sailing with you again in the future. Cheers! Jeff

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed July 7, 2017

We are so glad we decided to take this sail. Such a beautiful and relaxing trip. The crew made it so enjoyable. And the margaritas were soooo good.

Thank Chmel325
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed July 3, 2017 via mobile

We went sailing with Captain Jake and First Mate Emma over Fourth of July weekend and had an amazing time. 10 people total, 6 adults and 4 kids ranging from 1.5 to 9 years old. The kids had a blast and were allowed to steer...More

Thank E W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded July 5, 2017

Thanks so much for the kind words! I'm glad you enjoyed yourselves. I will definitely pass this on to Jake and Emma. Cheers! Jeff

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
See more reviews
Reviewed June 25, 2017

The crew is great! Emma and Joe took care of everyone very well. We got to sit back and enjoy the sights and glide along the water. Even though the evening was cloudy, we were able to see about 50 dolphins frolicking in the water...More

Thank Nurps
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed September 27, 2016

We opted for the Sunset Champagne Cruise. It was a perfect evening.More than enough wind to be able to sail. Captain Jeff and the first mate(his young son) were very knowledgeable and hospitable. Margaritas and champagne made the evening that much more relaxing! The sunset...More

1  Thank Charles L
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed September 16, 2016 via mobile

Had a beautiful sail boat trip to watch the sunset. Throughly enjoyed visiting with the captain and Sarah did a great job taking care of the passengers. Throughly enjoyed and would highly recommend sailing with this crew! Thank you for a great evening!!

1  Thank Deanna B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed September 7, 2016

We took the "Sunset Champagne Cruise" provided by Captain Jeff and his crew aboard the Lady Patty during our visit from Seattle. To say it was romantic was an understatement! Jeff and Sara, his first mate could not have been more accommodating. Serving up drinks...More

1  Thank Carl H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 23, 2016

We went on a beautiful sunset sail and had a realy nice sailing experience. The boat is beautiful and the captain very hospitable. And the sunset was outstanding

1  Thank F6980BTpaul
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 6, 2016

What an amazing way to experience the countless colors of the sunset over the Chesapeake Bay- on a historic sailboat with good friends, delicious drinks and a friendly captain and crew. Can't wait to return to the Lady Patty for another perfect sail!

1  Thank marymac1969
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed July 26, 2016

Captain Jeff and his first mate Emma were so accomplished and at ease with the sailboat that I felt as if I were floating on a cloud at times. Prone to seasickness, I always approach any smaller sized boat with a bit of trepidation-- so...More

Thank M H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Nearby
Nearby HotelsSee all Tilghman Hotels
Wylder Hotel Tilghman Island
7 reviews
1.22 km away
Lowes Wharf Marina Inn
48 reviews
4.98 km away
St. Michaels Harbour Inn, Marina & Spa
558 reviews
12.19 km away
St. Michaels Inn
522 reviews
12.21 km away
Nearby Restaurants
Tilghman Island Country Store
154 reviews
.81 km away
Two If By Sea
264 reviews
1.38 km away
Marker Five Restaurant
142 reviews
.17 km away
Characters Bridge Restaurant
155 reviews
.29 km away
Nearby Attractions
Skipjack -Rebecca T. Ruark Charter
100 reviews
1.39 km away
Tilghman Island Marina
35 reviews
.46 km away
Phillips Wharf Environmental Center
29 reviews
.29 km away
Ask a question
Questions & Answers
pat m
April 19, 2015|
Answer
Response from duskyjeff | Property representative |
Hello Pattir, Thanks for your inquiry about the Lady Patty! I'm glad you enjoyed sailing with us, We do sail in Annapolis on occasion but normally as a Private Charter. In the event of being there already we will offer... More
0
Votes