Sail Selina II

Tourist attraction · St. Michaels

Sail Selina II

Tourist attraction · St. Michaels

1

101 N Harbor Rd, St Michaels, MD 21663

Photos

Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null
Sail Selina II by null

Highlights

Sail historic yacht with wine, beer, and stargazing tours  

Placeholder
Placeholder

101 N Harbor Rd, St Michaels, MD 21663 Get directions

sailselina.com

Menu

Information

Static Map

101 N Harbor Rd, St Michaels, MD 21663 Get directions

+1 410 726 9400
sailselina.com
sailselinaII

Menu

Features

payment credit card

Last updated

Sep 1, 2025

Powered By

You might also like

Terms of Use • Privacy Policy • Cookie Policy
 © 2025 Postcard Technologies, Inc.
@travelleisure

St. Michaels, Maryland, Travel Guide

"A docked sailboat offering cruises on the Miles River and greater Chesapeake Bay; visitors are encouraged to take a sunrise or sunset sail. Brian Ball recommends boarding for a scenic harbor experience, and Emily Wilhelm, curator of celebrations at the property, says, "A sunrise or sunset sail is the perfect way to unwind and is nothing short of magical, especially if bald eagles, blue herons, and dolphins make an appearance." - Lydia Mansel Lydia Mansel Lydia Mansel is a writer with more than eight years of experience editing and writing for both brands and online publications—with a particular focus on travel, fashion, and lifestyle. She’s also the founder of the travel site justpacked.com.  Travel + Leisure Editorial Guidelines

https://www.travelandleisure.com/st-michaels-maryland-travel-guide-8786805
View Postcard for Sail Selina II

John Winstead

Google
We are so grateful to have had the incredible opportunity to sail aboard Selina II with Captain Iris, crew, and other guests. This is an experience you don’t want to miss when visiting Saint Michael’s. This history of the vessel and family of stewards over the decades is nothing short of astounding. Make sure to take advantage of this opportunity before Selina II finds a new port of call. Captain Iris and her vessel are one of a kind. The experience will leave you with a smile every single time it crosses your mind.

Diane Pugliese

Google
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 experience and Captain Iris is one in 1 million. You would definitely enjoy a sale with her on the Selena II.

Marie Crenwelge Tilkens

Google
I went aboard the Sail Selina to photograph a family session, and not only was the sail absolutely beautiful, but Captain Iris was so informative and accommodating with our group. She guided us to the best spots for lighting and views on the beautiful Chesapeake Bay, and her crew member even caught my drone when it went rogue. I highly recommend the Sail Selina!

Tresa Howington

Google
We love Captain Iris and the Selina II! It is the best sailing experience imaginable! We have sailed on this vessel during the day and at sunset previously. For my birthday this year, we booked the moonlight cruise. Captain Iris is a delightful host! On top of her knowledge of everything nautical, historical, and geographical, she is an expert on the night skies! Stargazing with Captain Iris on the Selina II is the best! Thank you for providing such a beautiful experience. It made my birthday very special!

Scott Grosh

Google
We had a delightful experience on Selina this past Wednesday. This was our 4th outing going back more than a few years. Any time on the water is time well spent, especially on such an historic craft. Captain Rob Chichester was amazing. At the conclusion of our sail, we did have the chance to greet Captain Iris Robertson and wish her well. It is an experience not to be missed.

Chrissy Cottrill

Google
Our group of 4 had a blast on our sailing cruise in St.Michael's on The Selina II. The captain held Selina II close to her heart as it was her grandfathers. She had so much knowledge of the waters, boats, sailing and many other things. A very smart intellectual. She treated us as “guests on her families yacht” as she said. Though we didn’t get to sail into more waters or much around St. Michael’s, it was an absolutely gorgeous day and we learned some pretty cool things along with what nautical miles means. LOL. It was a relaxing time for us all.

Joanna Pearson

Google
We had the time of our lives! Capt. Iris and John were so great. The trip was relaxing and we loved hearing their stories and dancing with Capt. Iris. The boat was so beautiful, too. Truly a great trip and 100% would go again.

Marianne Green

Google
We celebrated our anniversary with a Champagne Sunset Cruise aboard the Selina II - what a beautiful night. The sailboat is gorgeous and Captain Iris and the crew made every moment interesting. Great info about St. Michael’s, wonderful views and a joy to be on this beautiful vessel.

Rich S.

Yelp
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

Dasey T.

Yelp
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.

Robert ..

Yelp
This was the best trip ever! So good in fact, me and my soon to be wife have decided to have our wedding on this vessle. The regalness of the boat is undeniable and the Captain is one of the most wonderful people I've ever met (and her first mate Matt aint shabby either). Thank you Capt Iris for providing a once in a lifetime adventure.

Mary K.

Yelp
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.

Valerie T.

Yelp
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!

Karen T.

Yelp
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!

Diane P.

Yelp
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.
google avatar

Mrs D.

Yelp
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.

Anne J.

Yelp
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.

Todd G.

Yelp
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.

Gerard D.

Yelp
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.
google avatar

R P.

Yelp
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!

Linda M.

Yelp
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!
google avatar

Marice K.

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

Tim M.

Yelp
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.

Gregg M.

Yelp
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.

Jeffrey C.

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

Kizi N.

Yelp
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!

Arlene G.

Yelp
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.
google avatar

Selena H.

Yelp
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.
google avatar

James K.

Yelp
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.
google avatar

Emily A.

Yelp
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.
google avatar

Hal H.

Yelp
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
google avatar

Chris M.

Yelp
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.

Lauren S.

Yelp
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!
google avatar

Lynn Z.

Yelp
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

Alaine G.

Yelp
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!!
google avatar

Bob V.

Yelp
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!!
google avatar

L O.

Yelp
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.

Doug R.

Yelp
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!!
google avatar

Shirley B.

Yelp
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.
google avatar

Andy B.

Yelp
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!

Lindsay L.

Yelp
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!!!

John F.

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

Jeanne H.

Yelp
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!
google avatar

Damon S.

Yelp
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!

Sandy R.

Yelp
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!
google avatar

Vc C.

Yelp
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.

Laura R.

Yelp
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.

M B.

Yelp
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.
google avatar

Wendy R.

Yelp
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!

Robb H.

Yelp
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.
google avatar

Regina C.

Yelp
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.

Robert P.

Yelp
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.

Dorothy K.

Yelp
Great sailing. Fun crew. Lucky with the weather. Beautiful way to spend an afternoon. Will certainly recommend the Selina.
google avatar

Andrea C.

Yelp
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.

Helene P.

Yelp
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.

Myra M.

Yelp
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!
google avatar

Elizabeth K.

Yelp
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!!!