Sailing
2–3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 95% of travelers
95% of reviewers gave this product a bubble rating of 4 or higher.
from
$102
per adult
Chesapeake Windsail Cruises Corporation
Chesapeake Windsail Cruises Corporation
Chesapeake Windsail Cruises Corporation
4.5
9:00 AM - 6:00 PM
Tuesday
9:00 AM - 6:00 PM
Wednesday
9:00 AM - 6:00 PM
Thursday
9:00 AM - 6:00 PM
Friday
9:00 AM - 6:00 PM
Saturday
9:00 AM - 6:00 PM
Sunday
9:00 AM - 6:00 PM
Full view
About
Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay.
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Chesapeake Windsail Cruises sails out of the beautiful Chesapeake Beach Resort & Spa located in the bay-side town of Chesapeake Beach, Maryland.
Chesapeake Beach, Maryland
Tours and Tickets by Chesapeake Windsail Cruises Corporation
Sailing
2–3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$123
per adult
Likely To Sell Out
1–2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$41
per adult
Historical Tours
1–2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$41
per adult
Sailing
2–3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$651
per group
Travelers talk about
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
4.5
65 reviews
Excellent
58
Very good
3
Average
1
Poor
0
Terrible
3
Kristine M
1 contribution
Jul 2021
Our trip on Chesapeake Windsail Cruises was everything we expected! Our captain and first mate were very pleasant. We didn't have much wind, so, the cruise was relaxing and very enjoyable. After the cruise, we had a late lunch and enjoyed live music outside at the restaurant by the dock. Such a great way to spend the afternoon!
Written August 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Gary G
3 contributions
Jul 2021 • Family
Lovely afternoon on the water with a professional and friendly crew. While the winds were predictably light on a summer afternoon the crew found enough to make it a relaxing sail. They were very polite and friendly but were also very safety conscious and knowledgeable about the area.
Written July 22, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
dskaddan
Fairfax Station, VA18 contributions
Jun 2021
The 2 1/2 hour charter departs from the Chesapeake Beach harbor. Parking readily available. ~40 foot sailboat, spotless clean and in great shape. First mate Nate is competent, friendly, attentive and informative. Our Captain I believe was new, but clearly loved to sail. You are free to bring a cooler with beverages and snacks or sandwiches. I believe the max number of passengers is 6--it could be fun to rent out the charter with friends. We could not have asked for a nicer sailing experience.
Written June 3, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tracy F
Narvon, PA41 contributions
Jul 2024 • Friends
We had a great time sailing with Chesapeake Windsail. The crew was personable, considerate and friendly. First mate worked his butt off and he and the captain went out of their way to make it a pleasant experience for all of us.
They were both very knowledgeable and pleasant and regaled us with tales from their experiences. We truly enjoyed our trip and would highly recommend this trip to anyone.
They were both very knowledgeable and pleasant and regaled us with tales from their experiences. We truly enjoyed our trip and would highly recommend this trip to anyone.
Written July 4, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
InfrequentReviewer
1 contribution
Aug 2021 • Family
Amazing crew, great boat and overall a very fun experience! We went out at 9am and the water was great. The day before we could not go out because of strong wi da and they were very good at handling our rescheduling. Highly Recommend!
Written August 6, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Penny O
41 contributions
Jul 2021
We had a perfect day for sailing, sunny and breezy in the mid-80s, low humidity. Couldn't have asked for a better day. Priscilla (first mate) was delightful and shared some history of the area and about the cliffs. The captain was very nice as well and invited guests to have a turn at steering. Would have liked to have sailed along the shore or cliffs to have seen something more than just out to the middle and back. Still, overall, great experience.
Written August 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Cavi W
2 contributions
Jun 2021 • Family
Nate and Priscilla were very warm and welcoming. We felt safe the entire time. The ride was amazing, the day was perfect. Looking forward to a sunset cruise :) 2.5 hours were ample. Thank you 😎
Written June 17, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Gtt1908
Maryland2 contributions
Jun 2021 • Couples
We booked for Father’s Day and it was one for the books! The captain and crew were super friendly and made us feel comfortable right away.Our captain shared his extensive sailing experience some interesting bay facts. We even saw dolphins! Highly recommended this company to anyone looking to spend a relaxing day on the water.
Written August 29, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jeaninne S
2 contributions
Jul 2023 • Couples
We had a wonderful time, Captain Andy and First mate Priscilla were great, we would sail with them again anytime!!! They were so knowledgeable about sailing in general as well as about they bay and all it has to offer. They even gave us their favorite restaurants in the area, we enjoyed trying a few while we were in Annapolis. Thank you both!!
Written July 21, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CherylMW4
Pittsburgh, PA6 contributions
Jun 2019 • Couples
We booked a Sunday afternoon sail with Nate. He was very friendly on the phone & during the sail. However, we were NOT told that the main sail was nonexistent! So, we didn’t “sail”, we floated. Also, we understand being cautious, but we had to (1) sign a waiver (2) wear very uncomfortable life jackets to sit out on the boat (instead of uncover with other guests just talking with crew) (3) had to have an ‘escort’ out on the boat! Good grief- the boat was barely moving & we’re grown adults (& good swimmers). We could have tolerated being treated like helpless children IF we were actually sailing. Such an expensive disappointment.
Written June 5, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks CherylMW4 for your review and feedback. I am sorry that your sailing experience with us was disappointing to you. We greatly appreciated your input as well as input from all of our passengers. Your input is important and it will receive top priority as we address any positive or negative sailing experiences.
On your cruise as well as many cruises this year and last year, we have sailed without the mainsail. Had we sailed the main, it would have not made much difference, because we had very little wind and our boat speed was less than 2 knots.
We ask all of our passengers to sign a waiver so that they would understand the inherent dangers of sailing. The US Coast Guard advises that everyone should wear a life jacket when on the water. According to a Coast Guard publication… "One-half of all recreational boating fatalities happen in calm water. These fatalities occur close to shore and are caused by drowning. Also, in most cases, life jackets are stowed on board, but not worn. And all are unexpected. The U.S. Coast Guard recommends that you wear — not just carry — a life jacket while boating." However, our policy is that if you leave the cockpit to go onto the deck, you MUST wear a life jacket. Children under 12 must wear a life jacket AT ALL TIMES.
I am very sorry that the life jackets were uncomfortable, but our U.S. Coast Guard Approved Type 1 Offshore life jackets, are designed so that in the event of a passenger going overboard, conscious or unconscious, the life jackets will turn you face up to increase your chance of survival.
In the unfortunate event of a person going over board, the first mate is the spotter to identify the location of the person and to make the captain aware that the Man Over Board (MOB) maneuver is in effect. This is why a first mate is on the deck with you regardless of the wind speed.
Our mission is that our passengers’ safety will always come first as we provided them with a unique, wonderful and memorable sailing experience on the bay.
Thank you once again for your review and input. We hope that in the future, we will have a chance to share with you why so many of our passengers love sailing on the Chesapeake Bay. When you come back, please bring some wind with you! (smile). Hope to see you on the bay.
Written June 6, 2019
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
No questions have been asked about this experience
*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.