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

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

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

What an amazing experience, Captain Kisses was a wonderful host with lots of amazing stories of the area. Definitely the highlight of our trip! read more

I booked a sailing tour with Saul Selina II for my wife's birthday. We're the type that prefer experiences over things, and boy did this deliver! The boat was gorgeous and intimate while still being roomy. Captain Matt and his mate Mike were awesome. This is something we definitely plan to do again! read more

We took our kids on an afternoon sail and they had a fun time. It was a scenic sail and First mate Mike basically babysat our kids. Thanks Mike! Capt Tim was fun and informative. Overall, we enjoyed ourselves and it was nice to not be behind a desk for a day! read more

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

See all

Sail Selina provided an excellent tour of St Michaels and the Miles River. Once we motored out of the harbor, sails went up and the peaceful, relaxation began. My husband and I added beer tasting for our mid-day cruise. The beer was ice cold and the selections tasty. We would definitely do this again. BTW, book early if you want the champagne cruise. We booked 3 weeks out and nothing was available surrounding the day we wanted. read more

My husband and I did a Moonlight Cruise with Captain Iris, her staff, and two other couples. The experience was first class, top notch! I highly recommend to any couple who is in St. Michaels! We had beautiful weather, wonderful company, and a phenomenal experience. We were so grateful to make it off the wait list -- word to the wise -- get on the wait list, even if you don't think you'll get in! Will definitely do again when we return to the area! Thanks for a fantastic experience!!! read more

Michael and Skip entertained us with the rich history of the boat Selina II and also the history of St. Michaels. We had an awesome time and a very peaceful sail. We'll be back for more sailing soon. Jerome J. read more

Sailing on Selina II is great! Well maintained ship, professional captain and crew, and a fun time out on the Bay!

If you want the serenity and relaxing feel of a sail boat cruise, Selina II in St. Michaels is your choice! Friendly captain and first mate make this trip worthy of a visit. I recommend the beer sample, you get the local craft beer extravaganza! We had a beautiful day for our trip. Book early as there is only room for 6. I get the sense that families are welcome but adults must be in attendance! read more

Had a delightful sunset cruise on this beautiful boat. Captain Matt and his first mate, Mike were super hospitable and courteous. The ride on the sail boat was super smooth. My fiancé and I had a blast and highly recommend Sail Selina to those who are looking to get away to a quiet and tranquil place on the water. read more

In this summer of COVID pandemic fear it was great to find a safe water experience with a fabulous crew and just two other couples. I can't wait to do this again with grandkids. btw- This is a great boating experience even for small children and toddlers! No one is going overboard on this boat! If you think you'll get sick... this is a very smooth sailing vessel. Not to worry! read more

This sailing charter was professional, clean and informative on local lore. The captain was fun and easy going. Both my wife and I felt at home. We couldn't have asked for better weather. read more

We went for a restful sail in the early afternoon. We were fortunate that the weather was perfect. There were 2 other couples but the boat is quite wide so we could easily practice social distancing. Our captain was Iris, the owner of Selina II. During our 2-hour sail she shared the history of the boat which has been in her family since 1926. She also talked a lot about the environmental issues facing the Chesapeake. Would recommend for all visitors to St. Michaels. read more

Great day, great boat, great crew, great tour. Highlight of our trip to St. Michael's. read more

My wife and I went sailing yesterday and it was awesome. Captain Iris and Chris were a great staff. I'm planning on going back with my family. Go for it, you won't be disappointed. Best moment will be when you'll be in the middle of the waters and the engine will be turned off! Don't forget your sunscreen!!! read more

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

See all

My husband had a wonderful afternoon cruise on the Selina ll on April 23, 2021. The boat is in pristine condition, and the crew were knowledgeable about local history, and very professional sailers. Highly recommend a sail on the Selina ll. read more

Great sailing. Fun crew. Lucky with the weather. Beautiful way to spend an afternoon. Will certainly recommend the Selina. read more

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

See all

The moonlight cruise we went on yesterday was an excellent way to see the sunset. Charlie and Captain Matt made my family of 5 feel at ease during our calm evening sail. Booking was extremely easy; when I called, Bonnie was super helpful in answering my questions and finding the perfect time for my family to sail. read more

Had a wonderful afternoon aboard the Selina. Only 6 people max so it felt so private and relaxing. Captain (owners) so knowledgeable about area with just the right amount of history and current tidbits. Would definitely recommend. read more

Whatever your reason for going for a cruise on the Selina, they have you covered. Nostalgia, check. Selina is a beautiful craft, with rich history, almost 100 years old, restored to perfection. The crew, knowledgeable and dedicated, explaining all the details about sailing, down to the science of how the wind moves. Romance, who can resist a perfect evening cruise, with a wonderful selection of beverages and snacks. The best activity in St. Michaels read more

My husband and I had a nice sail and met two other couples. The captain was very pleasant and added some interesting facts about St. Michael's along the way, but seemed a little to focused on getting her boat ready for a photo shoot that evening, so the two mates were busy polishing brass during the sail and the captain had to keep answering her phone because her receptionist was off for the day. One of the couples brought a dog, which didn't thrill me, but I will say the dog was very well behaved and Captain Iris was very gracious about the dog coming along and provided booties for it so the varnish of the boat wouldn't get scratched. We didn't do the wine or beer tastings. One of the couples did and I would add that had we decided to do them, I would have been disappointed since the couple in question only tried two beers, which to me, is not much of a tasting. The booking added a 20% gratuity at the time of payment, so for two people at $150, that was an extra $30. I probably wouldn't have tipped that much given we weren't doing either wine or beer tastings, but it was a smooth sail and nice company. read more

I'm very disappointed in my experience with Sail Selina. We had a wedding package booked with Sail Selina. After experiencing a nightmare medical emergency and pleading our situation with Iris and Bonnie, I was informed that they were keeping over $500 of my payment for a service they did not provide claiming they lost revenue on our Monday morning charter. I did not receive a call or email explaining this prior to them executing a meager refund on my credit card statement. Bonnie's words were "we are a business how do you expect us to get by" or something to that effect. I was presented with a façade of kind, understanding ladies operating a family business but once they had my money this changed. I would not recommend this business due to lack of compassion. Think twice about booking with them if you think you or a loved one may become ill. read more

Absolutely L-O-V-E-D this sailing trip!! I booked this excursion for my husband's birthday & was really hoping he would enjoy it. Luckily, the weather held out and it was the highlight of our visit to St. Michael's. Captain Iris is very friendly and welcoming, while also extremely knowledgeable of the surrounding area's history and tremendously skilled on the sea. The boat is 90 years old and absolutely gorgeous which sets the tone for a very intimate and memorable experience. We opted for wine tasting which was super fun and had lovely conversation with the other people on board. It was the perfect balance between great weather, fantastic company, delicious wine and a captain that makes sailing look easy and effortless. I would highly recommend this trip!!! read more

We had a lovely time on this boat. The crew was personable, engaging, knowledgeable and kind. They did everything to ensure we had a great sail and that it was. We enjoyed ourselves so much that we plan to sail again in the fall. The boat is beautiful too and it is kept in fine condition! The champagne choice was very good too! read more

See all

Would give them 6 stars if I could. Super nice boat. Almost 100 year old cat boat that looks almost like new its so well cared for. Captain is 3rd generation only owners with plenty of stories about the history of the boat and St. Michaels. Well worth the money and its less than the sail out of Perry. Got a extra bonus as a small pod of dolphins greeted the boat on the way back. read more

A beautiful sailing excursion! Captain Iris was wonderful. She is knowledgeable about the history of the St. Michael's and shared fun facts as we sailed on the bay. She let us choose the type of sail we wanted and we opted for the smooth one, where we follow the wind for a nice ride. She went above and beyond for us, as my hat flew overboard and she orchestrated the hat "rescue" with a couple she knew sailing by! Also, we had a dog with us and she gave us little booties for her to wear on her paws so she could come aboard; a huge plus. Beer and water available to buy. Overall, a picturesque and peaceful sail. read more

One of the main activities my friends and I wanted to partake in on our trip to St. Michael's was a sailing venture, which we ended up thoroughly enjoying thanks to Captain Iris and Frank. The Selina II sailboat can hold up to 6 passengers. I sailed/cruised with two friends and two additional passengers who were on their honeymoon. Captain Iris made the trip sociable, interesting, and entertaining. We thought she was such a riot! My friend scrapbooked our trip and many "Captain Iris-isms" made it into her St. Michael's scrapbook page, and we still find ourselves quoting Captain Iris regularly. Captain Iris is a wonderful host and is passionate about sailing the Selina II, which is her Grandfather's boat, and the oldest surviving boat of its kind. Captain Iris has a nice rapport with her crewmember Frank. Frank was very attentive to our needs. He allowed two of us to assist him in hoisting the sails. And he also graciously served us several refills of wine/beer/champagne and also provided hummus, veggies and crackers. We were offered a plethora of drinks options since they apparently hosted a wine tasting the day before. Btw, Captain Iris also offers wine tastings, dinners, and overnight ventures. Any of these would likely be amazing! Additionally, Captain Iris officiates weddings on the Selina II. Of course, it would need to be intimate because only 6 people can fit on the boat. I was most interested in the Moonlight Cruise but there was no full moon due that weekend. Our second choice was the 2-hr Sunset Cruise. The weather was overcast and we were a bit concerned that we would not be able to sail prior to our arrival. Typically the decision is made at the dock as to whether it's safe to depart. Luckily for us the weather held out for the most part and even provided additional enjoyment since we were basically the only people on the water - how relaxing! It turns out that we we did have to come into the harbor approximately 20 minutes early since there was a lighting storm brewing in the distance. Captain Iris invested in some high tech weather equipment and was able to track the storm and get us safely into the harbor in time for us to get to our car and subsequently to our dinner reservations before the storm hit. We appreciated her dedication to safety. And even though the trip was cut short a bit, we saw plenty and enjoyed ourselves immensely. My friends and I found the sailing trip to be exactly what we needed! My friend mentioned a month later that the only thing she has done this year that has turned out to actually be relaxing was the sailing trip and our trip to St. Michael's. You know how you sometimes need a vacation from your vacation? This was not one of those circumstances. If you want some downtime, this is the ticket. The cost is worth it - $93 for the cruise, tax, tip and this includes a $5 discount for paying with cash. There is a 72 hour cancellation policy. I booked one month in advance, but I am a major pre-planner. I think the couple on the boat with us booked that day. I would book in advance though. read more

See all

So very-very honored, Captain Iris... Thank you! Looking forward to the new, celebratory season... Happy-Happy Birthday Selina II!! You know me, I must get my annual fill... SOON. Fair winds. read more

If you're bored with shopping, drinking, and eating, and you're looking for something different to do in the StM area, then give Captain Iris a call. If you're fortunate enough to have the perfect weather that we did, this is an extremely enjoyable trip. The Captain obviously loves her boat, it is flawless and beautiful. Capt Iris has painstakingly stained, polished, and stained again until the almost 100 yr old vessel comes alive again. The Captain will give you the history of the area but she is flexible and allows her passengers to dictate the flow of the conversation. It is a most enjoyable event to set sail and breathe the air in the 2 hour tour, a 2 hour tour. read more

Enjoyable morning sail, with excellent, knowledgable experienced captain Tim and first mate Mike. Highly recommend.

What a beautiful boat and amazing experiences with Capt Iris. We went on a private charter and had a blast, even got to drive and learn a few things. Thanks for a great time Capt Iris! read more

A EASY 5 star review!!! What a way to help celebrate our 40th Wedding Anniversary. The Most amazing time sailing this spectacular vessel with the best crew tag team Capt Iris and her First Mate Frank made it the most enjoyable time. So informative and at the same time respectful of our time just sailing and enjoying the beautiful time on water! I had the opportunity to assist Frank in raising the sail !!! Amazing. My advise is book a cruise for your stay in St Michaels you will be soooooo glad you did! read more

St. Michaels Sailing Charters - Celebrating our40th Anniversary ....Amazing! - Boat Charters Near Me - St Michaels, Maryland

A MUST DO in St Michaels. Wonderful memory for our Honeymoon. The sunset cruise included sipping great wine, and star gazing. As other reviewers have mentioned, Capt Iris and Chris were engaging, knowledgeable and made the trip fantastic! The maximum of six passengers keeps it wonderfully personal. I'll go again, and recommend it for anyone! Far exceeded all expectations! read more

To celebrate our second Babymoon, I had scheduled a week in St. Michaels with my wife & two year old son. Our time spent on the Selina II with Captain Chris & his First Mate, Paul, was by far the best part of our vacation. Not only were they knowledgeable & experienced in their craft, they were such well rounded people. We plan on making St. Michaels an annual occurrence- Sail Selina II will certainly be a part of the tradition. All the best to the Sail Selina II family. Your friends, John, Kim & Captain LJ read more

I booked a beer tasting cruise for my husband's 40th birthday and we had a blast! Wonderful crew and a gorgeous boat! I would highly recommend it! read more

Our sunset cruise was so great with Captain Chris and Trevor aboard the Selina II. We had two other couples with us and it was fun. I would say for the two hours, there was about an hour of sailing and about an hour of lazing along in the river. The boat is absolutely gorgeous and in excellent condition for being such an old historic boat! Captain Chris gave us some history of the boat and St. Michaels in the beginning of our journey. Most of the time was spent drinking and mingling with our fellow participants and the crew. It was a nice evening with beautiful scenery and new friends aboard a beautiful boat. read more

Captain Iris is the best. We did the beer tasting along with our sail and it was great. The beer we had was from a local brewery, Eastern Shore Brewing. We had 3 beers to try and heard about the brewery and the making of the beer. Captain Iris did a great job. The Selina II was a beautiful vessel and it was great to hear the history of the ship and how Captain Iris came about running it. This is definitely a must if you are heading to the Chesapeake Bay area. read more