St. Michaels Sailing Charters, St Michaels MD

Sailing daily April-Nov. Choose between two sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern catamaran.

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Lady Patty’s next chapter is taking shape. ⚓️
From sanding and restoring original details to fresh paint and finishing touches, every step is about honoring her history while preparing her for new sails on the Chesapeake Bay.
Stay tuned for the final reveal!
#LadyPatty

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Your Chesapeake escape begins April 17th!✨⛵️

We’re getting the sails ready, the water is calling, and a new season on the Chesapeake Bay awaits.

Book your spring sail and start the tradition!
https://t.co/BoQX1isnaL

#stmichaelsmd #chesapeakebay #easternshoremd #visitmaryland

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Lady Patty is home in St. Michaels! After an incredible journey, the real work begins: getting her ready for the season ahead. She’ll be open for charter in 2026, and we’re excited to share every step of her restoration!

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Meet Lady Patty — a stunning 1935 wooden ketch with nearly a century of stories in her sails. From offshore racing victories to Transpacific adventures and decades as a beloved Bay charter, this historic beauty is officially back where she belongs, right here in St. Michaels!

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

https://t.co/AADMwwIHwn

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Special Wine Tasting Cruise Aboard Sail Selina II – A Chesapeake Bay Delight https://t.co/x2k9CQzZ3K

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

@LaurasFocus cute!

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Sail Selina II 25th Anniversary Celebration: A 1920s Flapper Gala

Join us on May 3, 2025, for an unforgettable evening

More info & Tickets https://t.co/LPpKkyqXjx
410-726-9400

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Check out our new review on WeddingWire! https://t.co/mtsWZB59z3

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Our season starts April 19. Lets go sailing! 410-726-9400 https://t.co/oFhRKc5SaT

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Check out our new review on WeddingWire! https://t.co/wWnzMgHc2i

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Remeber this video? Where were you when you first saw it?
#Video #sailselina #stmichaels #summer #boattour

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Surprise engagment despite having a photographer aboard!
#photoshoot #engagement #proposal #sailselina #stmichaelsmd

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

New crew Collin & Rob working on the mast boot
#crew #sailselina #stmichaels #newseason #boattour

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

First Mate of 15 years Gazebo Jon models our baseball cap & polo in white. Dashing dont you think? #swag #poloshirt #ballcap #sailselina #stmichaels

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Highly polished brass hardware. Gotta love an old wooden boat! #sailselina #stmichaels #brasshardware #boattour #historicboat

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Mother of the Bride looking pretty! #blue #boatwedding #sailselina #stmichaelswedding #BouquetOfRoses #motherofthebride

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

Who's ready to pop the question in a breathtaking setting, surrounded by the serene beauty of the waters and the Chesapeake Bay on Sail Selina? Share your thoughts using #romanticcruise #proposalplanning #engagementatsea #luxuryyacht #perfectsetting"

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

What do you think will be your favorite wine tasting memory aboard Sail Selina's luxury yacht, where you'll sip fine wine, enjoy beautiful views, & immerse yourself in a rich sensory experience? Share using #winelovers #winetasting #sensoryjourney #relaxationmode #SailSelina"

[St. Michaels Sailing Charters, St Michaels MD @SailStMichaels]

"Rain or shine, what a stunning and intimate setting for your wedding day, where moments like these, under the awning in the rain, become unforgettable memories that will last a lifetime - #intimatewedding #oceansetting #rainorshine #unforgettablemoments #weddingmemories"