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Chesapeake Bay Champagne Sunset Sail

Take in a gorgeous sunset with a tasty glass of bubbly on this Chesapeake Bay cruise.

Quick Details

⏰ Check-in time: 15 minutes prior to departure

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

icon, arrow  Free Cancellation: Up to 72 hours before departure on SunsetSail

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

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

Private Charter

Enjoy Chesapeake Bay on a Champagne Sunset Cruise near Annapolis

Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you!

As the sun dips below the horizon, casting a golden glow over the tranquil waters of Saint Michaels on Chesapeake Bay, Sail Selina’s Sunset Champagne Sail invites you to indulge in a sensory experience like no other. Feel the gentle breeze caress your skin as you listen to the soothing melody of the waves lapping against the hull. Savor the aroma of champagne as it mingles with the salty sea air, enhancing the ambiance of the moment. With each sip of bubbly, you’ll be transported to a realm of serenity and luxury, where every sensation is a celebration of the beauty that surrounds you. From the stunning sunset views to the exquisite taste of champagne, every moment of our Sunset Champagne Cruise is a feast for the senses.

Escape for a relaxing 2-hour sailing adventure with us in St. Michaels, MD. Experience personalized tours led by our top-notch captains and crew, including our enchanting sunset champagne cruise. Sail aboard the luxurious Selina II, accommodating just 6 guests, for an intimate taste of the history of sail. Let the gleaming mahogany and brightly polished brass of our premier charter boat transport you to a bygone era.

Included in this sunset cruise near Annapolis is a brief harbor tour where Captain Iris (or her relief captain) talks about what you see along the picturesque waterfront including the floating boat collection at the Chesapeake Bay Maritime Museum, the history of the town of St. Michaels, MD and the story of her grandfather’s historic yacht, Sail Selina II. Learn the secret of how this classic 1926 yacht has survived so long.  Then we depart the harbor and go out onto the Miles River, put up the sails, and follow the wind! If we are lucky we might even get to see some wildlife like Osprey, Bald Eagles, and porpoise.

Refreshments: Immediately following the raising of the sails, we raise our glasses and toast the wind and sunset. Included is your choice of:

  • a really easy-to-drink champagne,
  • or white wine including an un-oaked chardonnay, pinot grigio, and sauvignon blanc
  • or red wine including a Merlot, Pinot Noir, or Cab Sav
  • or a selection of handcrafted icy cold beer from craft breweries all over Maryland
  • we also have sodas, coke, diet coke & sprite as well as water,
  • all accompanied by a complimentary tray of light hors-d’oeuvres, including carrots, crackers and a dip, typically hummus.

Guests often ask what they should wear on the champagne sunset cruise. We recommend you come ready to go to dinner. Wear comfortable shoes and don’t forget your camera. We also suggest a light jacket in spring and fall. And ladies: no heels, please!

If you enjoy the beauty and nostalgia of a by-gone era and the comfort and upscale ambiance of a 1926 family yacht, choose Sail Selina II for your sunset champagne charter. Reserve your romantic sunset sailing tour online today for a unique experience you will remember forever.

 Cherish the breathtaking Chesapeake Bay sunset aboard Sail Selina II's sailboat with a glass of bubbly on our St Michaels Maryland sunset champagne cruise

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.

Trip Advisor Testimonial:

“Unforgettable Sunset Champagne Cruise” by jennyg295 – “Our sunset champagne cruise with Sail Selina was simply unforgettable. The crew was fantastic, the boat was comfortable, and the views were stunning. Highly recommend for anyone looking for a unique and memorable experience in the Chesapeake Bay.”


  • 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 consume adult beverages.
  • Children: Please note that while this excursion is primarily an adult experience, well-behaved children are more than welcome to join in on the fun. We love children and have life jackets for all ages and all sizes of kids. The Coast Guard considers every kid no matter how young or how little to be a passenger, and as such require their own ticket.  For example, mom, dad, and their six-month-old are three guests, not two.
  • 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 72 hrs: Please email cancellations at least 72 hrs before departure to
  • 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.
  • Accessibility: It is easy to get aboard our sail boat most of the time, except during extremely high or low tides where there may be a step up or down to get aboard. Usually, the deck is about the same height as the dock, so it’s easy to walk aboard. Once aboard there are 2 steps down to get to the cockpit. But don’t worry – our Captain and first mate are always there to help anyone who needs assistance. We’re proud to say that we’ve been able to accommodate all guests, regardless of their physical abilities or limitations.
  • 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. Only an hour from Annapolis St Michaels Maryland is easy to find, and has lots of parking.

Please note: If you are not booking a private charter, this Chesapeake sunset champagne cruise sailboat tour requires at least two people to book in order to go out. Amusement tax and crew gratuity added on.

Sip Champagne and get lost in the mesmerizing sunset views of the Eastern Shore on Sail Selina II's exclusive sailboat excursion in St Michaels, MD