Selina II Sailing Charters

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!