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Marriage Proposal Engagement Cruise

Engagement romantics pick Sail Selina II for a totally unforgettable nautical wedding proposal on a private yacht.

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

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

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

Make your engagement unforgettable with a surprise nautical wedding proposal on a private yacht. Our Engagement Package offers a unique and creative way to pop the question, perfect for couples looking for an unforgettable and personalized experience. Book now for an unforgettable moment that you and your partner will treasure forever.

Afternoon Marriage Proposal
10-12, 12:30-2:30, 3:00-5:00
Evening Marriage Proposal
5:30-7:30, 7:30-9:30
+10% tax

♥Make Your Engagement Unforgettable♥

Get engaged in a picture-perfect setting with Sail Selina's romantic St Michaels engagement cruise on the picturesque Chesapeake Ba

Sail Selina II’s Private Charters

Thrill the love of your life with a surprise engagement on a boat, and make the moment you pop the question truly unforgettable. If you’re looking for the perfect wedding proposal that’s unique, private, and oh so romantic, look no further than Sail Selina II’s private yacht charters.

Experience the Magic of a Private Yacht Charter

Experience the ultimate in luxury and personalized service with Sail Selina II’s private yacht charters. Our beautiful yacht offers a unique and private experience perfect for couples looking to create unforgettable moments. Say “I do” to falling in love all over again against the stunning backdrop of the Chesapeake Bay.

She Said Yes! Celebrate your love and life together with a dreamy and private engagement cruise with Sail Selina in St Michaels, MD.

A Proposal to Remember

For the most memorable proposal, book a sail on our private yacht where you can get down on one knee and ask the biggest question of your life. We’ll help you set the perfect romantic tone with any special touches you request.

Engagement Photos

You can hire a professional photographer to capture the moment (call and ask Capt Iris how she’ll never suspect a thing) or our crew is happy to assist by taking tons of photos for your sailboat proposal memories that will last a lifetime. Our staff will work closely with you to ensure that your proposal is everything that you’ve ever imagined, from setting you up at the bow of the boat to playing a specific song during your private sail. Let us help make your engagement unforgettable and stress-free.

Experience an intimate engagement cruise with breathtaking sunset views and a bottle of bubbly celebratory champagne on our romantic sailboat Sail Selina in St Michaels. Private charter only

Celebrate in Style

After the big proposal moment, celebrate in style with a bottle of champagne. Bubbly is always a sure way to make your special event even more memorable.

When you book a private yacht charter with Sail Selina II, you can rest assured that your engagement will be a unique and magical experience that you and your partner will treasure forever. Don’t wait to start planning your unforgettable engagement – book your Sail Selina II private yacht charter today.

The two hour marriage proposal package includes a skippered yacht charter with a mini harbor tour, raising a historic gaff rigged classic sail and sailing the Miles River. Congratulations on your nautical engagement!

Have a professional Photographer Capture the magic of your special engagement day on a boat on the Chesapeake Bay with a unique and exclusive engagement sailboat tour in St Michaels, MD. Let Sail Selina custom design your special day

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 Reviews:

“Perfect Engagement on Sail Selina” by Ron L. – “I proposed to my girlfriend on Sail Selina and it was perfect. The crew helped me with everything and made sure everything was flawless. The experience, views, and champagne made it unforgettable. I can’t thank Sail Selina enough!”

“Magical Marriage Proposal” by Sarah S. – “My fiance and I sailed with Sail Selina and my fiancé proposed to me on board. It was a magical experience to say the least. The captain and crew went above and beyond to make it special and we will never forget it!”

“Sail Selina is the Perfect Proposal Spot” by Rami K. – “Sail Selina is the perfect proposal spot! I proposed to my fiancé on board with the help of the captain and crew. They made it a special and unforgettable experience. Highly recommend Sail Selina for an engagement or any special occasion.”


  • 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 engagement cruise!
  • 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.
  • 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 us more than 72 hours before departure to cancel at
  • 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.