Selina II Sailing Charters
Categories
Activities, Rentals, & MoreRecreation
Hours:
The Selina II operates 7 days a week April-Nov. Reservations are required. Limited to 6-guests
Driving Directions:
For detailed driving directions to Sail Selina II, please visit our Directions/Parking page.
Address: 101 N Harbor Road, St Michaels MD
Free Parking
About Us
Sail Selina II – An Exclusive & Intimate Chesapeake Bay Sailing Experience
Step aboard the Sail Selina II, a beautifully restored 1926 catboat, for a truly upscale and exclusive sailing experience in St. Michaels, MD. With a strictly limited capacity of just 6 guests, relax, unwind, and let go: every cruise offers an intimate, personalized journey through maritime history, blending classic elegance with modern comfort.
Relax as we glide through St. Michaels Harbor, then set sail on the scenic Miles River, where polished bronze, gleaming mahogany, and billowing white sails set the tone for an unforgettable adventure. Whether you're seeking a peaceful two-hour day sail, a romantic sunset champagne cruise, or an elevated wine-tasting experience, every voyage aboard Sail Selina II is designed to be as timeless as the Chesapeake itself.
Your captain, Iris Robertson, carries on a cherished family tradition as the granddaughter of Selina II’s original owners, offering stories, sailing insights, and warm hospitality that make every trip truly special.
?? Location: Harbour Inn, 101 N Harbor Rd, St. Michaels, MD 21663. Directions
? Now booking for our FINAL 2025 SEASON! Secure your spot before this legendary vessel sets sail one last time.
?? Call 410-726-9400 to reserve your cruise today!
Video Media
Images
Events
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday Apr 28, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Apr 29, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Apr 29, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Apr 30, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Apr 30, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 1, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 1, 2025
Sail Selina II 25th Anniversary Celebration: A 1920s Flapper Gala
- Sail Selina II 25th Anniversary Celebration: A 1920s Flapper Gala
- Saturday May 3, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday May 5, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 6, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 6, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 7, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 7, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 8, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 8, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday May 12, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 13, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 13, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 14, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 14, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 15, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 15, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday May 19, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 20, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 20, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 21, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 21, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 22, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 22, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday May 26, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 27, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday May 27, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 28, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday May 28, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 29, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday May 29, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday Jun 2, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 3, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 3, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 4, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 4, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 5, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 5, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday Jun 9, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 10, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 10, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 11, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 11, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 12, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 12, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday Jun 16, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 17, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 17, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 18, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 18, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 19, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Thursday Jun 19, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Monday Jun 23, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 24, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Tuesday Jun 24, 2025
Brews & Cruise: A Craft Beer Tasting Under Sail
- Beer tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Sample craft beers while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 25, 2025
Savor the Sea: Wine Tasting Sailing Adventures!
- Wine tasting cruise aboard the historic Sail Selina II in St. Michaels, MD! Enjoy a flight of while sailing the Chesapeake Bay on an intimate six-guest tour.
- Wednesday Jun 25, 2025
