Chesapeake Windsail Cruises

Chesapeake Windsail Cruises We offer 4 daily sailing cruises on the Chesapeake Bay, Tues. - Sun. Radios issued to groups of 5 or more walkers.

on a 42’ sailing Yacht and 5 daily guided walking tours of the Twin Beach Towns of Chesapeake Beach and North Beach, MD., Wed. - Sun.

06/10/2026

Today was a beautiful day for sailing! Our guests from Denver were amazed by the beauty of the Chesapeake Bay.

Isn't it time for you to come out and join us?

Bring Your Crew Aboard!Gather four or more friends, family members, or coworkers andset sail on the Chesapeake Bay for a...
05/13/2026

Bring Your Crew Aboard!
Gather four or more friends, family members, or coworkers and
set sail on the Chesapeake Bay for a private experience you won’t forget. With room for up to six guests, it’s the perfect way to celebrate, reconnect, or simply unwind on the water together. Reserve your sailing date today and make the Bay your backdrop.

BOOK NOW

Save 10% Off, when using the below Promo Code: 4MORE2026

We are 18 minutes, North of Chesapeake Beach & North Beach.
Chesapeakewindsailwruises.com

05/03/2026

Our 2026 season begins May 20th. Book Your Group of 4-6 persons Now and save 10%! chesapeakewinfsailcruises.com

05/03/2026

Our 2026 season begins May 20th. Book Your Group of 4-6 person Now and save 10%!

04/22/2026

HELP WANTED
Accounting Manager

We are seeking a part-time Accounting Manager. The ideal candidate will have 10+ years of accounting experience and proficiency with QuickBooks Pro. Experience in the tours and activities, sightseeing, or amusement industry is a plus.

Qualifications:
AA or BS in Accounting
Strong accounting background with hands-on QuickBooks Pro experience

Compensation:
Pay is commensurate with experience.

To apply, please send your resume to: [email protected]. For more information, call 855-561-8810 ext. 105.

Call now to connect with business.

02/25/2026
End Of The Month Blow-Out Sale!. 50% Off All Cruises and Walking Tours !Take advantage of this incredible limited-time ...
02/24/2026

End Of The Month Blow-Out Sale!.
50% Off All Cruises and Walking Tours !

Take advantage of this incredible limited-time offer and feel the summer breeze. Book that family cruise or a friends' cruise for you and your special friends today, and when summer arrives, you’ll be celebrating in unforgettable style. Book Now. Sail Later. Love Every Moment.
50% off when you USE PROMO CODE: BLOWOUT2026 Book Now at chesapeakewindsailcruises.com

Address

453 Deale Road, Dock C , Slip 18
Deale Beach, MD
20751

Opening Hours

Tuesday 9am - 6pm
Wednesday 9am - 6pm
Thursday 9am - 6pm
Friday 9am - 6pm
Saturday 9am - 6pm
Sunday 9am - 6pm

Telephone

+18555618810

Website

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