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Downrigging 2026 Sailing Experience

Ages 18+ • 4 days

Quick Details

People

Ages 18+

$ 1,395

Schooner Adventurer will be attending Downrigging this year and we hope you’ll consider joining us for “A Weekend of Tall Ships, Music, & Community.” Sultana Downrigging combines the largest annual gathering of Schooners in North America and a high-energy Bluegrass festival – all set against the backdrop of Chestertown, the coolest small town in America.

What’s included

  • Maximum of 5 passengers
  • Sailing on schooner Adventurer to from Annapolis to Chestertown, MD
  • Meals while underway
  • On-board accommodations Thursday-Sunday
  • Passes to the Music Village
  • Bathhouse facilities at Chestertown Marina

Itinerary

Adventurer will provide meals while underway (Thurs & Sunday) and will also provide passengers with tickets to the music festival tent Friday and Saturday. While we’re in Chestertown, Downrigging provides opportunities to see and tour these historic ships, take rides, enjoy exhibits from around our region, tap your feet to some amazing music, and just stroll the streets of this charming town.

Highlights

Each year the Sultana Foundation hosts a weekend celebration of schooner Sultana’s past year; Downrigging! It’s a big deal and schooners from all over the bay converge on Chestertown, Maryland to see and be seen.

Additional Information