A nice day spent on the charter, Captain and first mate were awesome. A little windy, but they kept the Miss Patty very enjoyable!

Sunset cruise on 31 May 2026 was spectacular. Great crew, knowledgeable, hospitable and friendly. Always eager to explain all that is going on. Captain GM was excellent. Book this cruise!!! read more

Thoroughly enjoyed the 5/1/26 first sunset sail on the Lady Patty, and had been looking forward to it since the 9/2/25 last sunset sail on Selina II! Wonderful people -- Captain GM, Laura Bell and the entire crew provided a truly memorable experience and we're looking forward to soon returning for an encore. Last-minute clouds muted the sunset, but we returned to harbor/marina by the light of a beautiful full moon. Can't visit St. Michaels without such sailing! read more

I needed to get away, and saw this excursion via Eric Oranges' wine happenings. Wine tasting and sailing! Right up my alley. I booked and made reservation at Harbour Inn- I love that I stayed at before. Approached by a spry lady, I was asked my name - she turned out to be the granddaughter of this 1926 New England Charter, Capt Iris. Very personable and knowledgable as she pointed out things along St Michaels banks e.g., The Perry Inn and the focal point filming of The wedding crashers. The name Selina, itself had family virtue and significance-pronounced different ways, the one I remember is as in Selena Gomez. We were also quizzed on how many tons the vessel weighed. My guess way low-16 tons!!. We marveled at the woodwork and upkeep of the ship and hours to maintain- not to mention gas cost. We were offered our choice of beverage- I had a tasty Chardonnay, although I'm not sure the brand. The first mate. Was agile at that point coasting in a nice spot to put up the sail, beautiful as the sky was starting to cast its evening glow with the sunset. It was truly relaxing as we made small talk about catfish and enjoyed the ambiance. I then had a second Pinot Noir however the water being a little choppy declined a third- we were Rockin ! a little with wind picking up. It was a very enjoyable outing and I would do it again in a heartbeat! Next time I want to be at the helm lol, if only for a photo shot. Speaking of photos...a picture paints a thousand words...btw the name means 'moonlight' read more

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We had a lovely afternoon sail on the Selina. The weather was not great most of the day but Capt Iris took us out safely and we were rewarded with a gorgeous sunset. The boat is lovely and we greatly enjoyed hearing about its history, as well as learning about the area. Highly recommend! read more

St. Michaels Sailing Charters - Boat Charters Near Me - St Michaels, Maryland

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great trip on Selina. Capt iris was awesome Had to cancel my trip last minute and she was able to let me switch for a later date read more

Beautiful cruise. Captain Iris was great. She told of the history of the area which was nice. She was very interesting to talk with. First mate was also very personable. The sailboat was a vintage treasure to experience! Extremely clean and well maintained. We would do this cruise again & again. read more

Captain Iris provided us with a wonderful bit of history and local lore. Selina II is a well maintained boat and you can tell how much the captain cares about it. We were one of 3 couples on the boat and it felt like having our own private tour. I highly recommend this experience! read more

St. Michaels Sailing Charters - Deck of the boat Selina II - Boat Charters Near Me - St Michaels, Maryland

Sailing with the Selina II is a great adventure when visiting St. Michaels. The captain's extensive knowledge of sailing and the area are unmatched. It's educational and fun; the best 2 hours of the day. read more

St. Michaels Sailing Charters - Tour the St. Michaels waterfront and harbor in the Selina II, a classical and beautiful sailboat - Boat Charters Near Me - St Michaels, Maryland

We had a great trip with Captain Iris on Salina II. She has great stories about the area and made it a fun trip for everyone.

If you are looking for a relaxing quintessential Eastern shore/ chesapeake bay experience; this is it and so much more! The Captin and her First mate are so knowledgeable. The Selina II has a special story and she is in her final season in St. Michaels before relocating to the New York area. Don't miss out! read more

Sailing with Captain Iris was one of the best parts of our trip to Saint Michaels. She is so knowledgeable and her knowledge of the history of the beautiful homes we sailed by was amazing. And to add to our adventure, Captain Iris saw a smaller sailboat in distress and with her expertise, Captain Iris was able to rescue the boater and tow him and his sailboat safely into the harbor. What an amazing adventure and Captain Iris is one in 1 million. You would definitely enjoy a sale with her. read more

We first sailed with Captain Iris 10 years ago with our children. This year we chose to return for a Monday night for a moonlight cruise. Captain Matt and first mate Mike were top notch. Informative and attentive. Weather was perfect in our eyes, clear with almost full moon. Wasn't much wind, but the Salina II sailed beautifully. Plenty of beverages, great history of a beautiful vessel, and a photograph worthy sunset. Thank you so much for a wonderful night! read more

St. Michaels Sailing Charters - Boat Charters Near Me - St Michaels, Maryland

Sunset Sail was perfect! Captain and First mate Collin did a fantastic job. Beverage and food selection was great!! read more

St. Michaels Sailing Charters - On the boat! - Boat Charters Near Me - St Michaels, Maryland

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The captain was very knowledgeable and shared a lot of information pertaining to the history of the boat and the area. The first mate was efficient, attentive and friendly. The sail boat itself was very beautiful. read more

This was our second time sailing with Captain Iris and, as before, it's an experience that never disappoints! We were blessed with perfect weather and there is something extraordinary about moving silently on the beautiful waters on a gorgeous and lovingly maintained and gleaming sailboat that is just plain good for the soul. Everything about the experience was just lovely. I honestly thing this is one of those MUST-DO activities for anyone visiting the Maryland Eastern Shore. read more

Wonderful experience - we did the Moonlight cruise from 7:30-9:30PM. The boat is a beautifully maintained craft with such a rich history. Captain Iris is an amazing woman. Her knowledge and skills of sailing the Selina II was just a delight to watch. She seemed to sail by a Zen-like intuition. I can understand why the crew - Captain Tim and Captain-in-training Dan wanted to be there to learn from her. The wine, IPA beer and champagne were great. Captain Iris was charming and the crew so friendly and interesting. A wonderful way to spend an evening, out on the open waters with the quiet calm of sailing and enjoying great conversation. read more

Sail Selina II is a MUST if you are ever in Saint Michaels, Maryland. The professionalism of the staff is outstanding. They were very friendly and I felt as though they were not even part of the staff during our sail. We booked the 2-hour Sunset Champagne Cruise, which we will do OVER and OVER again. The views, the tranquility, the peace, the breeze, what more can you ask for? The champagne was also very good and we were served hors d'oeuvres: carrots, hummus and crackers. I excepted better hors d'oeuvres but I am still giving Sail Selina II five stars because we were beyond pleased with this activity. As you all know, everyone is worried about COVD right now. The sail only allows 6 guests per sail and has designated areas for guests to stay within their area/section. We wore masks to board the boat but we were able to take them off while sailing. We had to put them back on while docking. We were also offered some sanitizer before boarding. Don't think about it, BOOK THE CRUISE! read more

St. Michaels Sailing Charters - Boat Charters Near Me - St Michaels, Maryland

The Captain was well informed and did a great job informing us on St. Michaels history and landmarks. First mate was attentive and helpful! The wine tasting was excellent from semi sweet Pinot Grigio to the Merlow! Peaceful, fun, informative and worth the trip! read more

We had a lovely afternoon sail (with the wine tasting)! We were in town for our first anniversary, and the wine tasting sail was the perfect outing. We were with another few couples and the crew of 2. Our captain was genial and welcoming, and my husband even got to help hoist the sails! We also lucked out to have a beautiful day perfect for sailing, and there was a historic sailboat race in progress! Our captain used the opportunity to tell us all about the historic types of sailboats, it was very interesting and he was extremely knowledgeable. read more

I've gone out on Sail Selina II with Captain Iris multiple times and on several different cruises (Sunset, wine tasting, and afternoon), and every experience was fantastic! I highly recommend that you put this on your list of things to do in St. Michaels. Captain Iris talks about the history of the town and also about her sailing vessel. Selina II has been in her family for three generations! The boat is beautiful and Captain Iris is the best! read more

Captain Iris was incredible to work with for our surprise engagement cruise and even came up with a cover story for the photographer aboard. I cannot say enough about how pleasant the planning process was and then the trip exceeded our expectations. The boat is beautiful along with the views on the water. I would 10/10 recommend this unforgettable experience to anyone else. read more

Great weather. The boat is in perfect condition And as close to original as could be. Captain Iris is a pro and dedicated to the boat. The wind was perfect for our sail. I recommend this trip when in town. read more

Thank you for a wonderful sail Captain Iris. I truly enjoyed the smooth sail! Anyone looking for a relaxing few hours try a sail on the Selina II. read more

St. Michaels Sailing Charters - Boat Charters Near Me - St Michaels, Maryland

Great way to celebrate our 50th anniversary! in addition to a "smooth sailing" outing we learned the history of the Selina II and a lot about the crabs and oysters in the Chesapeake Bay. Captain Iris is a wealth of information. I highly recommend the sunset cruise that we took. read more

Great 2 hour sailing ride! We were on board with 2 other couples, along with Capt Matt and 1st Mate Mike, who were both skilled sailors and both were Eagle Scouts!! We received a nice history of the 3rd generation tall ship sail boat. There was a toilet available on board. Water was free and soft drinks, beer, and wine were available for purchase on board. We learned a bit about some of the landmarks along the Miles River as well as the names of the birds we saw. Just a super pleasant way to pass a few hours during the afternoon. read more

St. Michaels Sailing Charters - Aboard Celina II - Boat Charters Near Me - St Michaels, Maryland

What a perfect excursion in a town built around its sailing heritage. Captain Iris was wonderful as both our skipper and tour guide. The crew was very hospitable as well. I also recommend doing the wine/beer tasting package so that you can try various local spirits. read more

We went on the Selena 11 While staying in Saint Michaels. It was a windy cooler day but the crew was so nice and kept us from being in the bumpy waters and out of the wind . we had a very nice time. I highly recommend it. Make reservations far in advance , only 6 allowed onboard read more

For our 42 wedding anniversary we decided to sail on the Selina II. What a great day. Tim our captain was very informative and as a windsurfer he explained how to sail a CATBoat, very cool. Mike our 1st mate was very friendly and eager to make our trip wonderful. We also found that one couple was also celebrating their wedding anniversary and the other was celebrating theirs in 2 days. The boat is beautiful , well maintained and the crew is very experienced and fun to sail with. A 10 star day!! read more

Wonderful early evening cruise. Relaxing and beautiful scenery and Captain Iris is a skilled and knowledgeable guide. Highly recommend

The Selina is beautiful! My friend and I had an amazing time. The Captain and first mate were knowledgeable and attentive. I would definitely recommend this to others and will sign up again the next time that I am in St. Michaels. read more

Lovely experience on a classic wooden sailboat. Top flight captain, 6 passenger capacity. 2 hours out and about st michael's environs. recommend highly. Pristine boat condition, nice amenities. Thanks. Hal read more

The Selina is absolutely beautiful! The care and love poured into her is apparent. The crew is knowledgeable, friendly, and allows anyone interested to assist and sail. The included beverages are a nice touch as well. We had a wonderful time celebrating my partner's birthday with the moonlight cruise. Catching the end of the sunset and all the stars was an experience I won't forget. I highly recommend the Selina! You won't be disappointed! read more

We sailed with Captain Iris today to celebrate our 45 wedding anniversary and it was wonderful. The sailboat is clean and beautiful! The two hour trip was just us and the captain and 1st mate. We wish we would have gone longer. Captain Iris was incredible and very knowledgeable of the Chesapeake Bay! We totally recommend this sailing company! We will be back to ride with Captain Iris!! read more

Enjoyed a morning sail on Selina II. Capt. and mate made the trip very enjoyable. We heard a lot about the boat and the St. Michael's area. Once out of the harbor, they raised the main sail and enjoyed a time of true sailing in a light breeze. The trip was very pleasant and we highly recommend it. read more

What a treat spending a couple hours on the Selina II! Captain Iris was friendly, welcoming, and so knowledgeable on a wide variety of topics. The conversation never lagged between us, the crew, and the family from Allentown sailing with us. This was a perfect way to honor our fifth anniversary, which is traditionally the "wood" year -- the Salina II's wooden beauty was beyond stunning. Book a trip -- you won't be disappointed. read more

Highly recommend!! Beautiful boat with an awesome captain and first mate who are both knowledgeable about the area and its rich history. They do a great job catering to the guest's needs. If you have a question they have an answer. If you want to relax they let you relax. Just an overall fun experience that we will definitely be doing again!! read more

We had a wonderful champagne cruise on the Sail Selina ll with Michael and Mike! They provided some interesting history of the area, but more importantly were extremely personable and professional! We were told before boarding that they might need to shorten the cruise because of an impending storm, and unfortunately that did happen, but it was still worth the money. A very memorable evening!! Also, the woman who booked the cruise for us was extremely knowledgeable and helpful, patiently answering all my questions and providing restaurant suggestions. Great overall experience! read more

The moonlight cruise on Selina II was a fantastic experience. Captain Iris and her crew were very hospitable and the boat is beautiful.

It was well worth the sailing experience with a knowledgeable , attentive crew. Everyone treated you like family. It was a great chance to spend time with two other new couples. Spend the time and enjoy the trip! read more