Bachelorette Bachelor Party Cruise

Your Party Experience

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing bay breeze and scenic water views as you mingle with your group.

During your 2-hour cruise, a complimentary bottle of champagne is included for your celebration. Wine, beer, and non-alcoholic beverages are available for purchase by the glass onboard. Guests also have the option to upgrade to an open bar per person during checkout for a seamless, all-inclusive experience. Whether you’re toasting an engagement, counting down to the big day, or simply enjoying time with friends, this cruise pairs great drinks with unforgettable scenery.

Sip, celebrate, and take in beautiful waterfront vistas, historic harbor views, and the peaceful openness of the bay. Our friendly, experienced crew keeps the festive atmosphere going while ensuring your comfort and safety from start to finish. 🥂

Choose Your Vessel

⛵ Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

⛵ Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay.

What Guests Love

• Flexible Drink Options: One complimentary bottle of champagne is provided for your cruise — perfectly chilled and ready to celebrate. Wine, beer, and non-alcoholic beverages are available for purchase by the glass, with an optional open-bar upgrade available during checkout.

• Celebration-Ready Vibe: Perfect for bachelorette and bachelor parties, birthdays, girls’ trips, or any festive gathering.

• Relaxing Sailing Experience: Smooth sails, refreshing breezes, and beautiful water views set the tone.

• Friendly Crew: Attentive captains and crew keep the good times going while ensuring comfort and safety.

• Stunning Scenery: Enjoy waterfront views of historic St. Michaels and the Chesapeake Bay.

Location

Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland, a charming Eastern Shore town celebrated for its fresh seafood, historic streets, and welcoming small-town atmosphere.

Whether you’re planning a day trip to St. Michaels or a sailing charter on the Eastern Shore of the Chesapeake Bay, our excursions are conveniently located:

• 90 minutes from Philadelphia, Baltimore, and Washington, D.C.

• 1 hour from Annapolis

Arrive early to explore the quaint town, enjoy local restaurants, or stroll along the waterfront before your relaxing sail.

Good to Know Before You Go

Arrival:
Please arrive 15 minutes prior to departure at the dock behind the Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.

Restrooms:
Lady Patty has a small marine head for emergency use, and Epiphany features a private, spacious marine head. Both are located down a short set of steps. For all guests, we recommend using the Harbour Inn lobby restrooms before boarding.

Parking:
Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.

Shoes & Attire:
Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Ladies, please avoid high heels. Light jackets or layers are recommended on cooler days.

Sunscreen & Hats:
If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.

Weather:
Safety and comfort are our priority. The captain may cancel due to weather, with the final decision made about 15 minutes before departure. There is no charge if a sail is cancelled due to weather, and we will do our best to rebook you, issue a gift card, or provide a refund.

Beverages & Food:
During your 2-hour cruise, a complimentary bottle of champagne is included — perfectly chilled and ready for your celebration. Wine, beer, additional champagne, and non-alcoholic beverages are available for purchase by the glass, with an optional open-bar upgrade available during checkout — giving your group the flexibility to celebrate your way. We also partner with local businesses to offer pre-ordered, charter-friendly food options ready upon arrival. For full details on onboard food and beverage options, please see our policies.

Ready to Set Sail?

Raise a glass and soak in sweeping Chesapeake Bay views during an unforgettable bachelor or bachelorette party cruise. Perfect for celebrating the bride- or groom-to-be, this festive sail blends beautiful scenery, great drinks, and unforgettable memories with friends.

Book your 2-Hour Bachelorette or Bachelor Cruise now! Dates fill quickly — especially on weekends — so reserve your spot and get the party started today! 🎉