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Lighthouse Adventure Cruise

Lighthouse lovers cruise the Bay and visit Point No Point, Point Lookout and Smith Point Lighthouse before stopping for lunch at the Bayside Inn on Smith Island. After lunch, cruise continues to Solomons Lump and Hooper Island Lighthouses. 7:45am at Calvert Marine Museum, Solomon’s. $125 w/discounts; rsvp: 410-326-2042 x41; www.calvertmarinemuseum.com.

Last Day of Summer Cruise

Board the Wm. B. Tennison and celebrate the end of summer and beginning of fall along the Patuxent River and get your first glimpse of leaves changing colors. Drinks and appetizers included. 5-6:30pm at Calvert Marine Museum, Solomons. $25; rsvp: 410-326-2042 x 41; mccormmj@co.cal.md.us.

Cambridge Skipjack Race • free

Skipjacks race to preserve the vanishing heritage in the Choptank Heritage Skipjack Race. Captains and crews meet at 7am for coffee, donuts and a briefing. Onlookers get the best view at Long Wharf starting at 10am. While sailors race, enjoy the vendors and exhibitions; then head to the trophy presentation at 2pm. Move to Snapper’s Tiki Bar at 3pm and party until closing time. 7am-3pm at Cambridge waterfront: 410-770-9410; www.skipjack-nathan.org.

33rd Annual Hospice Cup

Raise a glass for sailors at the Blessing of the Fleet F Sept. 20 from 6:30-8:30pm at Annapolis Yacht Sales. Sailors race Sa Sept. 21. Post-race, bid at silent auction for luxury vacations and unique signed memorabilia (3-7pm) at Annapolis Sailing School. Enjoy live music, open bar, a full-catered meal, including fresh shucked oysters and side dishes from Graul’s Market (3-8pm) at the Shore Party at Annapolis Sailing School to benefit Hospice programs throughout Maryland, D.C. and Virginia. $85: www.hospicecup.org.

Wine in the Wind

Sample wines and hors d’oeuvres while cruising aboard the Schooner Woodwind. 2-5pm at 80 Compromise St., Annapolis. $99;rsvp: 410-263-7837; www.schoonerwoodwind.com.

Sail Free

Disabilities won’t stop you from sailing the high seas at the Chesapeake Region Accessible Boats first Sail Free, where people of all sorts of abilities, their families and caregivers sail on the Bay. Bring sunscreen, a hat, drinking water and a snack; life vests provided. 9:30am-3:30pm at Sandy Point Park, Annapolis. $5/car admission: 410-626-0273; www.crabsailing.org. 

Sailing in Annapolis

Sail with Molly Winans and learn about the history of the sailing capital of the world aboard the 74-foot Schooner Woodwind. 6:30pm at Annapolis Marriot Waterfront Hotel. $42 w/age discounts: 410-263-8994; www.annapolis.org. 

Sailing in Annapolis

Sail with Molly Winans and learn about the history of the sailing capital of the world aboard the 74-foot Schooner Woodwind. 6:30pm at Annapolis Marriot Waterfront Hotel. $42 w/age discounts: 410-263-8994; www.annapolis.org. 

Sailing in Annapolis

Sail with Molly Winans and learn about the history of the sailing capital of the world aboard the 74-foot Schooner Woodwind. 6:30pm at Annapolis Marriot Waterfront Hotel. $42 w/age discounts: 410-263-8994; www.annapolis.org. 

Brunch and Sailing

Take dad for a cruise on Schooner Woodwind and enjoy a Bloody Mary or Mimosa, scones, quiche, baked citrus salmon, grilled flank steak and a fresh fruit salad. 10am-1pm at 80 Compromise St., Annapolis. $86 w/age discounts;rsvp: 410-263-7837; www.schoonerwoodwind.com.