Marriage Proposal Engagement Cruise

♥Make Your Engagement Unforgettable♥

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.

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.

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!

What to expect:

Immaculate Sailboat:

Step aboard the Sail Selina II, where timeless elegance and meticulous care create an intimate and luxurious setting for your engagement. As you take your first step onto the polished teak deck, feel the history beneath your feet—this 1926 vintage catboat is more than just a sailboat; it’s a piece of maritime art, preserved in immaculate condition. Every detail, from the gleaming brass fittings to the pristine white sails, reflects the dedication to maintaining its classic beauty.

The ambiance is undeniably romantic—perfect for a private moment when you drop to one knee, the shimmering waters of Chesapeake Bay reflecting your love story. Guests consistently describe the Sail Selina II as the most beautiful and well-kept sailboat they’ve ever seen, making it the ideal backdrop for an unforgettable proposal.

Friendly and Experienced Crew:

From the moment you arrive, you’ll feel the warmth and genuine hospitality of Captain Iris and her crew. With a welcoming smile and a personable approach, they create an atmosphere that puts you instantly at ease. As you sail, their engaging stories of local legends and Chesapeake Bay history add a layer of magic to your special day.

But they do more than just navigate the boat—they craft an experience, attending to every detail to make your proposal seamless and memorable. Whether it’s capturing the perfect photo as you pop the question or toasting to your future with a glass of champagne, the crew’s passion and expertise ensure every moment is special. Guests frequently rave about their friendliness and professionalism, calling the crew a key part of their unforgettable engagement experience.

Tranquil Sailing Trip: Escape into a world of serenity and romance on Chesapeake Bay. The gentle sway of the vintage catboat, the whisper of the wind in the sails, and the sun’s golden glow on the water create a peaceful, intimate atmosphere. As you sail along the tranquil Miles River, the stress of everyday life melts away, leaving only the present moment and the person beside you.

This is more than just a sailing trip—it’s a sanctuary of love and tranquility, the perfect setting for an unforgettable proposal. With just the two of you (and a few osprey) as witnesses, the world fades away, leaving only the echo of your vows on the open water. Guests consistently praise the calming, rejuvenating experience of sailing aboard the Selina II, describing it as the most romantic and peaceful escape they’ve ever known.

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.”

Amenities:

• 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 sailselina1926@gmail.com.
• 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.