St. Michaels Wine Tasting Cruise

Discover Wine Tasting Cruises on our Sailing Yachts!

Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with St. Michaels Sailing Charters. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in the basics of wine tasting while taking in breathtaking views of one of the most picturesque waterfronts in America. With limited availability for just 6-13 guests per excursion, our wine cruises are perfect for a special girls night out or with your sweetheart.

Experience the rich aromas and flavors of 3 reds and 3 whites, including a stunning Italian Pinot Grigio that will transport your senses to the breathtaking vineyards of Italy. We lovingly handpick a constantly changing selection of global wines, ensuring that each excursion with us is a unique, personalized adventure that you’ll remember for years to come.

Sip on your favorite wine while taking in the gentle breeze and tranquility of the Chesapeake Bay. Unwind and relax on our classic or modern sailboats, with exceptional service from our friendly and experienced crew. Feel the warmth of the sun on your skin as you explore the beauty of St. Michaels, MD from the water.

Our wine tours are available throughout the week at 12:30-2:30 pm and 3:00-5:00 pm, so there’s no excuse not to join us for a once-in-a-lifetime experience. Book a private charter for an even more intimate and customized experience for up to 13 guests for the ultimate indulgence.

Please note that there is a $115 per person charge for the wine tour, with a minimum of 2 guests plus applicable tax and tip to the crew. We also have a 10% amusement tax in St. Michaels harbor, and a 20% crew’s tip.

Available with prior reservations, St. Michaels Sailing Charters 2 hour St Michaels, MD wine tasting cruises include:

• An introduction to the basics of wine tasting
• Sampling 3 reds and 3 whites
• We finish by enjoying a full glass of your favorite wine

We serve wines from around the world with a constantly changing selection based on the most recent of our favorites.

• $115 per person, minimum 2 guests (+tax/tip)
• Private charter up to 13 guests (+tax/tip)

Plus there is a 10% amusement tax in St. Michaels harbor, and a customary 20% tip for the crew.

Wine Cruises are available Sun-Sat 12:30-2:30pm and 3:00-5:00pm.

St. Michaels Sailing Charter wine cruises are located in St Michels MD, just an hour from Annapolis, making it the perfect day trip to share with loved ones or make it a special girls night out.

Limited to just 6-13 guests for a truly personal experience.

Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 44-foot Leopard catamaran.

Epiphany, our 44-foot Leopard catamaran, is the ideal setting for a relaxing day on the water with up to 6 of your family members and friends. Epiphany is also available for private bareboat charters to hold up to 13 guests. Designed for comfort, she features both forward and aft cockpit areas covered by a continuous hardtop, offering excellent protection from the elements. The aft cockpit’s spacious dining table is the perfect spot to enjoy a charcuterie board along with a selection of wine, beer, and soft drinks available for purchase. Up front, the trampoline area offers a relaxing place to sunbathe or simply soak in the sweeping Chesapeake Bay views as we sail. Epiphany is the perfect setting for a family reunion, anniversary celebration, or any special gathering on the water!

What to expect:

Immaculate Sailboats: Our beautifully kept sailing boats offer a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of our sailboats, making it the perfect setting for a memorable trip on the water.

Friendly and Experienced Crew: Our knowledgeable and engaging crew will enhance your sailing experience by providing valuable insights about the area and sailing. Guests have raved about the crew’s friendliness and expertise, making them feel welcome and comfortable throughout the trip.

Tranquil Sailing Trip: Take a break from the hustle and bustle of daily life with our peaceful and serene sailing experience. Guests have consistently praised the calming and rejuvenating experience of being on the water, creating the perfect escape from the stresses of everyday life.

Amenities:

• Weather: We want to ensure your safety and comfort, hence the captain may decide to cancel due to bad weather, and this decision is made 15 minutes prior to departure. Rest assured there is no charge if the sail gets cancelled. We’re often asked whether we sail in rainy weather. We do sail even if it’s lightly misting, but not in heavy rain as we want you to have the best experience possible. It’s no fun sitting on the pouring rain! Epiphany has several covered options as well to get out of the elements if needed.
• Swag: Our ships store includes custom St. Michaels Sailing Charters embroidered shirts, baseball caps, zip hoodies, tote bags, beach towels, stemless wine glasses, and more.  You can pre-order at checkout or let our crew know you are interested in shopping for a souvenir.
• Comfortable Seating: Lady Patty offers seating along each side of the wooden cabin top as well as cushioned seating in the rear cockpit area with the captain. Epiphany has numerous cushioned seating options in covered front and rear cockpit areas with two dining tables. Guests can also lounge on comfy beanbag chairs or captains reclining chairs on the bow for a front row view of the sail. All seating offers great visibility of the journey.
• Attire: Be sure to bring comfortable shoes, cameras, sunhats, and a light jacket in spring and fall. It’s about 10 degrees cooler on the water so plan accordingly.
• Max 13 passengers: Children of all ages are welcome aboard our yachts. We love kids! We have infant, toddler, and youth life jackets to fit all sizes and ages. The U.S. Coast Guard considers all children (regardless of how small they are or what age they are) to be passengers, and as such, you need to count them in, too. For example, mom, dad, and their six-month-old are three guests, not two.
• Safety: Our yachts are exceptionally clean and well-maintained, with all modern safety features (life jackets, VHF etc). Foul weather gear is available in the event of unexpected bad weather.
• Cancellation 24/72 hrs: Reservations made on a per person basis can be cancelled up to 24 hrs before departure for a full refund.  72 cancellation for private charters.
• Toilet: Epiphany features a modern marine bathroom (head) located down a short set of steps. Lady Patty also has a more rustic head, accessed in the same way. We recommend using the lobby restroom at the Harbour Inn before boarding for added convenience.
• Accessibility: Getting aboard is easy most of the time unless we have an extremely high or extremely low tide in which case there is a step up or a step down to get aboard. Most of the time the deck is just about the same height as the dock so its a simple to walk aboard.  Once on deck there are 2 steps down into the cockpit.  Our Captain and first mate are there to assist any one who needs a hand while on the stairs.  So far we’ve been able to get everyone on and off regardless of capability, yea!
• Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663.  If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.
• Beer: Sometimes there is someone in your group who would just rather drink beer.  That’s okay too, just let us know and we will be happy to give them a beer tasting tour while you sip your wine.