Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits.
Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits.
With Picture Perfect Sailing, the options are virtually endless!
Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!
Duration: 3 hours (leaves and returns to Annapolis)
Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.
Duration: 2.5 hours (leaves and returns to Annapolis)
Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.
Duration: 6 hours (leaves and returns to Annapolis)
Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.
Choose one or two overnights: (leaves and returns to Annapolis)
Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages.
Double (two) overnights: typically departs at 9am, one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests. Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.
The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels.
What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.
How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.
*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders. Contact Picture Perfect Sailing for more information and to book a sailing cruise today!
You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.
With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all!
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