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St. Michaels Wine Tasting Cruise

Sample some great wines and learn the basics of wine tasting aboard the fabulous Sail Selina II!

Quick Details

⏰  Check-in: 15 minutes prior to departure

📍  Location: Harbour Inn, 101 N Harbor Road, St Michaels MD

icon, arrow Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings

icon Trip Advisor’s #1 Boat Tour in St Michaels

⭐⭐⭐⭐⭐ Google Reviews: Over 1,040 5 star reviews!

Per Person
Private Charter

Discover Wine Tasting Cruises on a Classic Sail Boat!

Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. 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 six 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. Capt Iris lovingly handpicks 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 sail boat, 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.

Experience the perfect weekend getaway with our exclusive wine tasting cruise offering an intimate setting, fantastic wine, and breathtaking views of the Chesapeake Bay in St. Michaels

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 six 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, Sail Selina II’s 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 Capt Iris’ favorites.

  • $115 per person, minimum 2 guests (+tax/tip)
  • Private charter up to 6 guests $645 (+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.

Sail Selina wine cruise is 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 guests for a truly personal experience.

 Sip back and relax with Sail Selina's winetasting crew in St. Michaels, as our first mate serves a tray of crisp and chilled white wines - Book your experience today


“Fantastic Wine Tasting Cruise” by Christa M. – “The wine tasting cruise with Sail Selina was fantastic. The captain and crew were knowledgeable and friendly, and provided us with a great selection of wines to taste. The views of Chesapeake Bay were breathtaking, and we had an amazing time. Highly recommend!”

“Perfect Day on the Water” by Tea S. – “My husband and I went on a wine tasting cruise with Sail Selina and it was a perfect day on the water. The crew was welcoming and provided a great selection of wines to taste. The view of the bay and sunset were stunning. It was an unforgettable experience and we can’t wait to do it again!”

What to expect:

Immaculate Sailboat: Our beautifully kept sailing boat offers a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of the sailboat, 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.


  • Swag: Don’t forget to visit our ship’s store and grab some awesome swag! Exclusive Selina II embroidered polo shirts, stylish baseball caps, cozy zip hoodies, and can coozies – all yours to pre-order or purchase onboard. Shop now and take home the perfect souvenir from your unforgettable sailing adventure!
  • Comfortable Seating: Sturdy Double Settees on either side of the ship’s wheel offer seating on cushions for 2 big people. Or sit in our vintage captains chairs with cloth seats located on the cockpit sole for seats that offer back support.  All seating offers good visibility from the cockpit area where you will be sitting.  Occasionally guests ask to go forward and sit on the hard cabin top. You are welcome to do so if you have good balance, are sure footed, and can hold a hand rail.
  • Max 6 passengers: Must be 21 or older to participate in the beer tasting portion of this trip.
  • Safety: Sail Selina II is exceptionally clean and well-maintained, with all modern safety features (life jackets, VHF etc) tastefully concealed to honor her historic legacy. Foul weather gear is available in the event of unexpected bad weather.
  • Cancellation 24/72 hrs: Reservations made on a per person basis cancellation is 24 hrs. Private Charters are 72hrs.
  • 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. Its no fun sitting on the pouring rain!
  • Toilet: Yes, we have a very clean marine head onboard for your convenience; however, it is limited and located down four steps. To ensure your maximum comfort during your journey, we recommend you make use of the shore-side facilities inside the Harbour Inn before embarking.
  • 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 OK too, just let us know and we will be happy to give them a beer tasting tour while you sip your wine.  Info about our beer tasting cruises here:

Please note: If you are not booking a private charter, this sail requires two or more people. Amusement tax and crew gratuity added on.

Still have questions? ☎ 410-726-9400