Chesapeake Bay Sailing Trip

Enjoy a Relaxing Scenic Sailboat Ride on the Chesapeake Bay

5 stars rating 77 Reviews
participantsparticipants Price for 2 Participants
Chesapeake Bay Sailing Trip Unique Gift
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$90

Chesapeake Bay Sailing Trip

Enjoy a Relaxing Scenic Sailboat Ride on the Chesapeake Bay

5 stars rating 77 Reviews
participantsparticipants Price for 2 Participants

Enjoy the beauty of the Chesapeake Bay during an hour and a half sightseeing sailing trip aboard the Crab Royale, an Irwin 40 MKII. This five-star rated experience gift is one of the best things to do on Maryland's beautiful Eastern Shore!

The fun begins in Rock Hall, MD when you meet with the friendly Captain Mark and his first mate Suzanne at the dock. They will welcome you aboard the sailboat and fill you in on the details of this 90 minute sailing trip on the Bay. Once everyone has boarded the boat, it’s time to head out to the open waters. After the Captain has navigated the ship out of the marina into Chesapeake, you and the rest of the guests can take your turn at the helm, help raise the sails or simply sit back and relax and enjoy a complementary beverage. The sun sparkling off of the Bay, the fresh sea air and picturesque views are just a few of the things this popular experience has to offer.

So whether you are looking for the perfect unique gift or fun things to do on the Eastern Shore, this Chesapeake Bay Sailing Trip is the ticket!

Who Who
The Chesapeake Bay Sailing Trip Xperience Certificate® is for two participants. There will be up to four additional participants on the sail.

Guests Guests
This experience is not suitable for non-paying guests.

LocationLocation
Maryland, Rock Hall

When When
The Chesapeake Bay Sails are offered seven days a week April thru October, subject to availability. May through August sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset. April and September through October weekday sails are offered 1½ hour prior to sunset and weekend sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset.

duration Duration
The Eastern Shore Sail Boat Rides have a cruise length 1½ hours and a total duration of approximately 2 hours.

Weather Weather
The Chesapeake Bay Sailing Trips may be rescheduled by the Captain due to high winds, heavy rain, fog or other inclement weather.

What to wear What to wear
Dress comfortably, flat, non-marking rubber-soled shoes and layers are recommended for this sailing adventure.

Additional Information Additional Information
Sails take place on a an Irwin 40 MKII which is skippered by a USCG-licensed captain and crew. Participation is limited to individuals 3 years of age or older.

While motion sickness is possible, it is unlikely and can be reduced by avoiding heavy meal(s) prior to the scheduled sail. All passengers must sign a release form.

Gratuity for the Captain & Crew is not included and may be extended following your sail.

Additional InformationITEM/SKU NUMBER  XD-963-001

Cancellation Policy Cancellation Policy
All changes to reservations for the Chesapeake Bay Sailing Experience require seven (7) days advance notice.

Xperience Certificates® cannot be exchanged once a reservation for the experience has been made.

Price Price: $90


Who Who:
The Chesapeake Bay Sailing Trip Xperience Certificate® is for two participants. There will be up to four additional participants on the sail.


Guests Guests:
This experience is not suitable for non-paying guests.


When When:
The Chesapeake Bay Sails are offered seven days a week April thru October, subject to availability. May through August sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset. April and September through October weekday sails are offered 1½ hour prior to sunset and weekend sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset.


duration Duration:
The Eastern Shore Sail Boat Rides have a cruise length 1½ hours and a total duration of approximately 2 hours.


Weather Weather:
The Chesapeake Bay Sailing Trips may be rescheduled by the Captain due to high winds, heavy rain, fog or other inclement weather.


What to wear What to wear:
Dress comfortably, flat, non-marking rubber-soled shoes and layers are recommended for this sailing adventure.


Additional Information Additional Information:

Sails take place on a an Irwin 40 MKII which is skippered by a USCG-licensed captain and crew. Participation is limited to individuals 3 years of age or older.

While motion sickness is possible, it is unlikely and can be reduced by avoiding heavy meal(s) prior to the scheduled sail. All passengers must sign a release form.

Gratuity for the Captain & Crew is not included and may be extended following your sail.


Additional InformationITEM/SKU NUMBER  XD-963-001


Cancellation Policy Cancellation Policy:

All changes to reservations for the Chesapeake Bay Sailing Experience require seven (7) days advance notice.

Xperience Certificates® cannot be exchanged once a reservation for the experience has been made.


Review of Chesapeake Bay Sailing Trip 

5 stars

 My son gave us a gift certificate at Christmas for a sailing trip out of Rock Hall, MD. Our trip was on 9/19/15 and we had a wonderful time! The skipper & first mate were lots of fun and very friendly. They offered us complimentary margaritas, soft drinks & water. We were sorry when it was time to head back to the pier. It was a lovely little trip that we highly recommend. (And a great gift!) 

- - Maryland

A lovely afternoon with lovely people 

5 stars

 My great experience actually began before we even boarded, when someone from Blue Crab Chesapeake Charters called us to warn us about a car accident on the Bay Bridge that was causing gridlock. They offered to reschedule if we were not able to make our original sailing time, but we were fortunate to arrive just in time.

After battling through the terrible traffic to reach Rock Hall, my husband and I had a wonderful experience sailing on the Crab Royale with our friends and Captain Mark and Suzanne. The boat is clean, well-kept, and comfortable. The crew are friendly, and they helped us forget about the stress of the long drive with complimentary margaritas. It's also so nice to sail on a smaller vessel with few passengers - you get to really enjoy the quiet and beauty of the bay.

Many thanks to Blue Crab Chesapeake Charters for a very enjoyable experience! 

- - Laurel, MD

Rock hall sailing 

5 stars

 I purchased this as a Christmas gift for my husband. I wasn't sure what to expect. The experience was great. The captain was friendly and did a wonderful job of explaining everything as we went along. I would recommend this to anyone. The cost was more than affordable and I cannot wait to do this again. 

- - Lorton, virginia

Chesapeake Bay Sailing Trip 

4 stars

 To much wind but very well handled by the skipper. We never raised more than about 2/3 of the roller genoa. That was plenty of sail. I have been sailing since childhood and I was hoping to have a chance at the helm but under the conditions I didn't even consider asking. Note; I crewed on the boat that won class B in the Annap/Newport 1957 

- - Chestertown

Rockhall Sailing Trip 

5 stars

 We had a great time out on the water. We received this as a gift, and we're looking forward to making another trip back. 

- - McLean, VA

Sailing Trip 

5 stars

 We were treated very well by Captain Mike & Suzanne. My husband has to use crutches to walk from a back injury. They were extremely helpful & concerned about his comfort. It was one of the best experiences we've encountered! I recommend a Chesapeake Bay Sailing Trip to anyone! 

- - Rock Hall, MD

Sunset sailing trip 

5 stars

 My wife and I received this trip as a gift from our daughter and it was terrific. The evening had an Indian summer temperature, a beautiful sunset and smooth as silk sailing. Capt. Mark and his Mate Suzanne were a pleasant engaging couple who supplied some good background music and a nice margarita. The trip was very enjoyable and relaxing. We will sail with them again with some friends. 

- - Chesapeake Bay (Rock Hall, Maryland)

Sailing Adventure 

5 stars

 This was a gift from our children. It was a great adventure we loved it so much we will definitely book this again as a gift or for ourselves 

- - Rock Hall Maryland

Sailing for Two 

5 stars

 What a fantastic gift to give someone! This trip was given to me as a 50th bday gift. We could have not asked for a more beautiful evening to sail. The crew was extremely nice. The boat was just beautiful. The overall experience was one I will be taking about for a long time. 

- - Rock Hall, MD

Blue Crab Chesapeake Bay Charters 

5 stars

 We spent 2 wonderful hours in the company of Captain Mark and his First Mate on their beautiful boat they were delightful hosts. The weather was perfect and we were under sail all the way - what a lovely, relaxing experience it was! We would definitely recommend Blue Crab to all our friends and family. 

- - Rock Hall

Out of this world experience! 

5 stars

 Great sailing experience. The captain and crew were awesome: Attentive, knowledgeable and super fun! I have recommended them to my family! 

- - Rock Hall , MD

Chesapeake Sailing 

5 stars

 We had a wonderful trip. Captain Mark and his wife were very accommodating, putting us at ease and making sure we were comfortable. We thoroughly enjoyed our sailing trip and would recommend this trip to everyone. 

- - Rock Hall, Maryland

Great Time 

5 stars

 We had a wonderful time, the only thing that would have made it better, would have been a longer sail. 

- - Rock Hall MD

Sailing 

5 stars

 A very nice sailing experience with Capt. Mark. 

- - Chesapeake Bay

A Wonderful Afternoon 

5 stars

 My husband and I spent a wonderful afternoon with with Captain Mark on his beautiful sailboat. The margaritas were great and the views were spectacular! 

- - Falls Church, VA

Chesapeake Bay Cruise 

5 stars

 Great morning on the boat. Would highly recommend the trip to anyone. Very hard to beat Mark and Suzanne as crewmates. will definitely come back again. 

- - Frederick, MD

Chesapeake Bay Sailing 

5 stars

 Really nice experience, great crew. It was have been nice to go out to the Bay Bridge. 

- - Rockhall, MD

Chesapeake Bay Sailing 

5 stars

 Perfect evening for sailing, beautiful sunset, great boat, and Captain Mark was the best. 

- - Rockville, MD

Sunset Sail 

5 stars

 We has a wonderful time recently with Captain Mark and First (and only) Mate Suzanne. This was our second trip with them, after a gap of a few years, and it was as delightful as before. They were kind and helpful when our out-of-town friend's six-year-old got a little seasick and thought he would throw up (he didn't!). We plan another trip with Mark and Suzanne soon. Their service is one of the nicest features of a nice town. 

- - Rock Hall MD

Great trip 

5 stars

 My wife and I had a great time. The whole experience was very relaxing and a nice way to get out of the city for a while. 

- - Washington, D.C.

Sunset Sail 

5 stars

 We had a great time with Capt. Mark and his crew. The wind was great, and we had a perfect sunset sail. Would recommend this to any couple for a special evening. 

- - Gettysburg, PA

Chesapeake Bay Sailing 

5 stars

 Fantastic! I would do it again and again! Captain and crew were great! 

- - Rock Hall

Sailboat ride 

5 stars

 Fabulous. Definitely a 5. 

- - Aston, PA

Sailing 

5 stars

 We had a very nice day. Not a lot of wind, but Captain was a great host, very friendly and engaging. 

- - Chadds Ford, PA

Chesapeake Bay Sailing 

5 stars

 My husband and I had a great time sailing. Captain Mark and Suzanne were personable, and made it a fun experience. The complimentary margaritas were a nice surprise! I would definitely recommend this experience to other couples and families. 

- - Dover, DE

Excellent Evening 

5 stars

 My husband and I had a wonderful time with Captain Mark and Suzanne! They were personable, knowledgeable, and gave us a great tour of the Rock Hall area. We would definitely go again! 

- - Baltimore, MD

Bay Sailing Cruise 

5 stars

 A great sail. It was a very hot day, but very comfortable on the water. The captain and crew were very hospitable and enjoyed showing off their community. Rock Hall is a bit of a hike, but a nice little town. 

- - Washington

Sailing Trip 

5 stars

 Had a great time sailing with Captain Mark and Mate Suzanne. Everything was so perfect. 

- - Valley Lee

Chesapeake Bay Sailing 

5 stars

 My daughter and I had the most enjoyable sailing experience last Sunday with Captain Mark and his first mate Suzanne. It was a beautiful evening and the sunset was spectacular. Captain Mark timed the crescendo of Taichovsky perfectly as the last bit of sun descended over the water. The weather was perfect and Mark and Suzanne make it a most memorable experience with their pleasant, friendly demeanor. I highly recommend this experience to others. 

- - Washington, D.C.

Sailing on the Chesapeake 

4 stars

 Captain Mark runs a good show. We had a nice sail on a beautiful evening with well timed music to cap off the sunset. We would recommend this and plan on doing it again. 

- - Chesapeake Bay

Chesapeake Sailing 

5 stars

 We had a wonderful time on this sailing adventure. Captian Mark and Suzanne were amazing. This is definitely an amazing way to see the sunset over the Baltimore skyline, and a fun way to spend time with your loved one. I would definitely do this again. 

- - Carlisle, PA

Saiing Chesapeake 

5 stars

 I booked this as a gift for my then fiance as a christmas present. Unfortunately, we could not make the date last year because my father passed away. A year later we were still able to make the trip. Mark and Suzanne were very accomodating and friendly. It was a calming sailing experience. 

- - Gaithersburg, MD

Sailing Chesapeake Bay 

5 stars

 We had an awesome time sailing the Chesapeake Bay out of Rock Hall, Maryland. We often cruise the bay in our powerboat but not too often in a sailboat. The water was a little rough with the impending hurricane, but we had a wonderful time and lots of wind to fill the sails! Thank you for a great time. 

- - Rock Hall, MD

Sailing 

5 stars

 We had a wonderful experience with Captain Mark and his boat sailing out of Rock Hall, MD. 

- - Rock Hall

Amazing Time!! 

5 stars

 This was the best 2 hours spent unwinding and relaxing in Quiet!! Captain Mark and Susan were great..Thank You!! 

- - MARYLAND

Sailing Review 

5 stars

 Mark and Suzanne were perfect hosts! They know how to make their guests relax and have fun. We were able to bring champagne on the boat, take lots of photos, and enjoy a gorgeous sunset. They even let my boyfriend surprise me with a proposal on the boat! Thanks for a wonderful experience! 

- - Rock Hall, MD

Terrific Sail 

5 stars

 My kids bought me a sailing trip and gave me a trip filled with love. Just 2 hours on this boat is vacation. Thank you Captain Mark and the loyal first mate! 

- - Stafford, VA

Great Sailing Trip! 

5 stars

 I enjoyed it. 

- - Baltimore

The Perfect Outing 

5 stars

 Captain Mark and his wife were lovely hosts for our evening boat ride. They were both beyond friendly and warm, but still had a very professional demeanor. The night and weather were perfect, though I know that's really beyond anyone's control. We wish we had arranged to spend the night out in Rock Hill, but it was still a doable drive after having a late dinner at the restaurant where you board. Definitely a great experience! 

- - Washington, DC

Chesapeake Bay Sailing Review 

5 stars

 I absolutely loved this experience! It was such a wonderful romantic getaway that I would recommend for anyone! The captain was very friendly and made the experience very enjoyable! 

- - Rock hall

Great Trip 

5 stars

 We had a great time on this trip with Captain Mark. 

- - Virginia

Chesapeak Bay saling 

5 stars

 It was a beautiful sunset and our Captain and his wife were delightful...had lunch at Waterman's and dancing later with a live band. 

- - Pa.

Sailing Chesapeake Bay 

5 stars

 The sailing trip was very nice and the captain of the sail boat was very accommodating. We would definitely recommend the experience to anyone else interested. 

- - Washington, D.C.

Sailing Trip 

5 stars

 We had a wonderful time on our cruise. We were celebrating my husbands birthday, and were able to bring our bubbly to toast. Capt. Mark was a great host. 

- - Rock Hall

Sailing Trip 

5 stars

 What an awesome experience. The day was beautiful and the boat was awesome. The captain of the boat was incredible and made the experience one that will not soon be forgotten. 

- - Alexandria, Virginia

Got More Than I Bargained For! 

5 stars

 My family and I had a blast! More fun that I had expected. Capt. Mark and Suzanne made us feel comfortable and they shared stories with us so it was bit of learning experience. We had snacks and drinks onboard. Everything was perfect. I would definitely go back again. And I can't wait to try another experience with Experience Days! 

- - Frederick, Md

Sailing Experience 

5 stars

 Most excellent, despite a weather snafu! Captain Mark was very accommodating, pleasant and knowledgeable. With our originally scheduled trip postponed due to Mother Nature, Captain Mark worked with us to ensure that the experience was terrific. 

- - Rock Hall, MD

Sail 

5 stars

 Our experience was awesome. The trip was beautiful and the captain and first mate couldn't have been any nicer. Also, we were pleasantly surprised with the complimentary drinks. 

- - Maryland

Great! 

5 stars

 Ny wife and I had a wonderful time with captain mark and the margaritas! 

- - Rock Hall

Chesapeake Sailing 

5 stars

 We had a wonderful time. 

- - Springfield, VA

Chesapeake Bay Sailing 

5 stars

 A lovely experience. The Captain was welcoming, attentive, knowledgeable and fun. 

- - Oakton, VA

Awesome Experience 

5 stars

 My BF was surprised and enjoyed the ride. Thank you for helping me pull it all together. Captain Mark and his first mate were amazing. I am already thinking of my next trip for next year. Thanks again for helping me to celebrate my BF's birthday. 

- - Alpharetta, GA

Great Sailing Trip! 

5 stars

 The sailing trip was great! perfect sunny day with just the right amount of wind. The Crew was both friendly and informative! Would recommend. 

- - Baltimore, MD

Afternoon Sail on Chesapeake 

5 stars

 Beautiful! Captain Mark and Suzanne were great! My girls were at the helm and used the antique spy glass to look for pirates. It was quiet, serene, and stunningly beautiful. Wonderful memories which will live on forever. If only they could figure out how to outlaw power boats on the bay! 

- - Rock Hall, MD

Sunset Sail 

5 stars

 Wonderful, relaxing experience - definitely exceeded all of our expectations! 

- - edgewater, md

Chesapeake Sailing Charter 

5 stars

 This was an awesome birthday gift from my wife. Each and every one of my guest on the sail had a wonderful time. The boat, captain and first mate are all top notch and made sure we left with smiles on our faces and wind in our hair. 

- - Virginia

July 4, 2010 Sailing 

5 stars

 I want to thank Captain Mark and his crew for making my 39th Birthday a beautiful experience. We sailed and watch the fireworks. WoW what a wonderful time. I will return next year.... As Captain Mark says ' who sail better than we do' NOBODY! 

- - Upper Marlboro MD

Chesapeake Sailing Charter 

5 stars

 This was an extrodinary experience for me, my wife, and our guests. Capt. Mark was extremely proficient in his boat handling the weather and bay conditions were perfect! We had good food and wine. Who lived better than us? NOBODY! 

- - USA

Sailing for Two 

5 stars

 We really enjoyed our sailing excursion Saturday evening. The weather was good, even though we did not have enough wind to really sail, the crew did their best to ensure we had wonderful views of the sunset and the surrounding areas. 

- - Westminster, MD

Chesapeake Sailing Charter 

5 stars

 This was a wonderful day! We could not have asked for a better way to celebrate Jack's birthday. Thank you!!!! 

- - Virginia

Amazing Experience 

5 stars

 This was the perfect gift for my boyfriends birthday. Captain Mark and Susan were amazing and we had a great time. 

- - Rock Hall, MD

Perfect 26th Birthday Gift for the Perfect Boyfriend 

5 stars

 Absolutely in awe the moment we arrived at the dock. We got caught in traffic and arrived a tad bit later than expected. They tried calling us but we did not receive the calls until we parked. By the time we had called them back, they had already pulled off but came back to get us and it was amazing. Mark and 1st mate, Suzanne, were great hosts and they made my boyfriend's 1st ride on a yacht a memorable one. We loved the people we experienced it with as well. Thanks again and we will be doing this again in the future!!!!! 

- - Washington, DC

Sail Away 

5 stars

 We loved this sail experience! We recommend this voyage! Mark was a great captain/host! 

- - Ridgely, MD

Sunset Sail 

5 stars

 This was an amazing experience. Cute town, friendly people and a beautiful boat. Capt Mark and Suzannes were terrific. Can't beat this sunset! 

- - Leesburg, VA

Blue Crab Sailing 

5 stars

 Wonderful sunset sail with Captain Mark and 1st mate Suzanne aboard the Blue Crab. Highly recommended as a memorable gift. 

- - Washington DC

Chesapeake Bay Sailing 

5 stars

 It was a great time! Beautiful weather, and a nice capt. and crew! 

- - Maryland

A Magnificent Experience 

5 stars

 As a third year anniversary present, we received an Experience Days certificate for a sunset sailing cruise for two on the Chesapeake Bay. From the moment we arrived in Rock Hall, we found ourselves in awe at the beauty of the bay and the hospitality of our hosts. The sail was magnificent - much better than we ever could have imagined. We look forward to a new annual tradition of sailing with Blue Crab Charters and relaxing on the bay. 

- - Philadelphia

Sailing Chesapeake Bay 

5 stars

 Wonderful, beautiful day. Weather was perfect, Captain Mark and Suzanne were very nice. One recommendation: Perhaps a bag of chips or nuts to go with the drinks! Of course, we wished it hadn't ended so soon - would have enjoyed another hour or two! 

- - Rock Hall, MD

Sailing Chesapeake Bay 

5 stars

 Had a wonderful time on the sunset sail. The weather was beautiful, the Captain and First Mate Suzzane were great. I would definitely recommend this to anyone and hope to sail with Captain Mark and Suzanne again. 

- - Manassas, VA

Chesapeake Bay - Great Sailing! 

5 stars

 A wonderful time, very relaxing and very unique-a must! 

- - Rock Hall

Sailing Chesapeake Bay 

5 stars

 It exceeded all of our expectations. We had a wonderful time, and Mark made the experience even more enjoyable with his friendly conversation. 

- - Newark, DE

Chesapeake Bay Sailing 

5 stars

 Our weather was spectacular (in spite of the weatherman looking to rain on our sail!), the visibility on the Chesapeake was outstanding, the boat was excellent and Captain Mark was very accommodating. A day to be remembered for a long time. 

- - Rock Hall, MD

Sailing Experience 

4 stars

 We had a great ride and the crew was very friendly and helpful. 

- - Falls Church

Chesapeake Bay Sailing for Two 

5 stars

 We had FABULOUS weather and a very delightful and relaxing boat trip. It was a great antidote to the normal daily grind. 

- - Washington, DC

Sailing for Two 

5 stars

 Beautiful boat - beautiful day! We had a great time and this is definitely something we'd consider doing again. Would also make a really great gift for another couple! Thanks for a great day! 

- - Baltimore

Sunset Sail 

5 stars

 Wonderful sail. The Captain and his 'First and Only Mate' were terrific and made sure everyone enjoyed the evening. 

- - Washington, DC

Sailing for 2 

5 stars

 It was a beautiful day on a beautiful boat! We had a great time! 

- - Rock Hall, MD

Question: I received a gift card for a Chesapeake Bay Sailing Trip for Two for Christmas. When will dates become available for this sailing adventure?

Answer: The Chesapeake Bay Sailing Experience is offered seven days a week April thru October, subject to availability. Sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset.

Question: Does this include food and beverages? Does it sail rain or shine?

Answer: The Chesapeake Bay Sailing experience does not include food or beverages, but participants may bring their own onboard. Sails may be cancelled by the Captain due to high winds, heavy rain, fog or other inclement weather. Any reserved sail cancelled by the Captain may be rescheduled at the participants' convenience.

Question: Hi there -- I want to purchase this as a gift for my fiance but we will not have a chance to use it this year? Is there an expiration -- will it be valid next April - July? I want to ensure that if I am going to purchase it I have a guarantee. thanks!

Answer: Thank you for your inquiry. The certificates do not expire and Experience Days certificates always retain their original value. If you do not use the certificate within 12 months of the issue date, and the price of the experience has increases, then you are responsible for the difference. You may also exchange the value of your certificate towards the purchase of another activity on the website for yourself or another.

Question: How many people sail at a time?

Answer: The Chesapeake Bay Sailing For Two Experience Certificate® is for two participants. There will be approximately four additional participants on the sail.