Schooner Woodwind Sailing Cruises

Location: 80 Compromise St, Annapolis, MD 21401
Our Experience: Five Stars

Is sailing a sailboat one of your life goals? Have you thought of sailing a sailboat that was filmed in “The Wedding Crashers” with Vince Vaughn and Owen Wilson? If yes, then you gotta check out Schooner Woodwind Sailing Cruises in Annapolis, MD!

We got a chance to ride and drive the racer sailboat, which is the one that wins races frequently. They’ve never lost a passenger since they were in business, which is a good thing know! One of the nice things about riding with Schooner Woodwind Sailing Cruises is that your ticket comes with a free drink and snack. If you’re a beer fan and decide to buy a koozie with them, you’ll get free beer in the next trip.

They sail multiple times daily, and we got a chance to do the sunset sail, which was breathtaking. We enjoyed it so much that 2 hours went by so quickly, and we didn’t get seasick at all! When you’re on the sailboat, you’ll get to see beautiful homes, peaceful scenery kickback, United States Naval Academy, Chesapeake Bay, and if you’re lucky enough you’ll get to see Bay Bridge and Thomas Point Lighthouse as well. They are all depend on the speed and wind direction.

This can be a fun idea for birthdays, anniversaries, wedding receptions or if you just want to have a relaxing experience. They also offer frequent sailing points, ride 4 times and get 5th ride free. If you’re a seafood lover, you’ll have plenty of restaurants to explore since Schooner Woodwind Sailing Cruises is really close to so many seafood restaurants.

Watch out for traffic! Weekend traffic in downtown area is very busy. GPS said 20 minutes the night before, and it took us 75 minutes to get there and park. Unless your staying at the Marriott waterfront plan some extra time to get there. Here is a tip on how to find this sailing cruise company. It’s hidden behind the Marriott hotel, and you should look for yacht club parking lot. Also, bring rain jacket as waves splash up on boat and you’ll get wet. We hope you have a wonderful time there and let us know what you think about this place!


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