Skip to content
Maryland Office of Tourism Logo
Maryland Office of Tourism Logo
      • Destination Maryland Magazine Order a free Destination Maryland magazine
      • Press Room
      • Group Travel
        • Chinese (Simplified)
        • Chinese (Traditional)
        • Dutch
        • English
        • French
        • German
        • Greek
        • Italian
        • Japanese
        • Korean
        • Portuguese
        • Russian
        • Spanish
        • Swedish
          • Chesapeake Bay Loop
          • Water Experiences
          • Only in Maryland
          • Underground Railroad
          • C&O Canal Experience
          • African-American Heritage
          • Civil Rights
          • Civil War
          • History & Heritage
          • The Star-Spangled Banner
          • Underground Railroad
          • Family Travel
          • Scenic Byways/Road Trips
          • Seasonal Travel
          • Trip Inspiration & Itineraries
          • Restaurants & Dining
          • Crabs & Seafood
          • Breweries, Distilleries & Wineries
          • Arts, Music & Entertainment
          • Attractions
          • Casinos & Racetracks
          • Events, Fairs & Festivals
          • Hiking, Biking & Recreation
          • Outdoors
          • Shopping
          • Sports
          • Water Experiences
          • Capital Region
            Frederick
            National Harbor
          • Central Maryland
            Annapolis
            Baltimore
          • Eastern Shore
            Ocean City
          • Southern Maryland
          • Western Maryland
            Deep Creek
            Hagerstown
          • Small Town Big Heart
          • Build Your Maryland Adventure
          • How to Get Here
          • Places to Stay
          • Maryland Welcome Centers
          • Deals and Discounts
          • Guide Request
          • Sign up For Enewsletter
Maryland Office of Tourism Logo
      • Destination Maryland Magazine Order a free Destination Maryland magazine
      • Press Room
      • Group Travel
        • Chinese (Simplified)
        • Chinese (Traditional)
        • Dutch
        • English
        • French
        • German
        • Greek
        • Italian
        • Japanese
        • Korean
        • Portuguese
        • Russian
        • Spanish
        • Swedish
Schooner Woodwind
Jennifer Kaye

Along Roots & Tides

From Annapolis to Prince Frederick

Schooner Woodwind
Jennifer Kaye

Explore the timeless traditions and deep maritime roots of Western Shore towns along the Chesapeake Bay. Go sailing, bird watching, museum hopping, or just relax on a sandy beach.

 

  • Drive the Roots & Tides Scenic Byway
  • Join a colonial-era guide on a walking tour of Maryland’s state capital of Annapolis
  • Take a 2-hour Schooner Woodwind cruise from Annapolis dock
  • See the beautiful woodland and ornamental gardens at Historic London Town & Gardens
  • Paddle the tidal marsh at Jug Bay Wetlands Sanctuary
  • Explore 22 miles of hiking trails at the American Chestnut Land Trust
  • Enjoy Chesapeake Bay views while lunching at the Rod n’ Reel Restaurant in Chesapeake Beach
  • Soak up the Tuscany vibes at Running Hare Vineyard
  • Walk the elevated boardwalk through the northernmost stands of bald cypress trees in North America at the Battle Creek Cypress Swamp
Send to Mobile

Places Mentioned

Scenic Byways-Roots and Tides Photo
Attractions, Accommodations, & Dining

Scenic Byways-Roots and Tides

Learn More
Racing Boats Sunset 1200x800 Photo
Attractions, Accommodations, & Dining

Annapolis Sailing Cruises: Schooner Woodwind

Learn More
Jug Bay Natural Area  Photo
Attractions, Accommodations, & Dining

Jug Bay Natural Area

Learn More
Attractions, Accommodations, & Dining

American Chestnut Land Trust

Learn More
Rod 'N' Reel Restaurant exterior view Photo
Dining

Rod 'N' Reel Restaurant

Learn More
Running Hare Vineyard Photo
Arts & Culture

Running Hare Vineyard

Learn More
People hiking Photo
Attractions, Accommodations, & Dining

Battle Creek Cypress Swamp Sanctuary

Learn More

Find Your Adventure on the Open Road

(*Note* Please contact the business directly for more information on their listed packages, deals, booking questions, or other inquiries.)

Filter Results:
  • (-) Accommodation (18)
  • Attraction (8)
  • Dining (4)
  • (-) GoVAX (1)
  • Shopping (1)
  • Capital Region (5)
  • Central Maryland (6)
  • Eastern Shore (6)
  • Southern Maryland (1)
  • Western Maryland (1)

Applied Filters

 
Couple having a romantic dinner Photo
Chestertown

Wine Country Date Night Special

Now Through Feb 10, 2026
[…]
Get Deal
Learn More
Beautiful waterfront guest room in the Manor House  Photo
Rock Hall

Memorial Day - Summer Kick Off Deal

May 22, 2025 Through May 27, 2025
[…]
Get Deal
Learn More
TRU by Hilton Bayside Ocean City
Ocean City

Ocean City 150th Anniversary Savings - Tru Ocean City Bayside

Now Through Dec 31, 2025
[…]
Get Deal
Learn More
Sleep Inn and Suites Cumberland/LaVale Photo
Cumberland

Stay 3 nights and receive 20% off your stay!

Now Through May 31, 2025
[…]
Get Deal
Learn More
Tanger National Harbor Shopping Photo
National Harbor

Enjoy These Exclusive Offers

Now Through Dec 31, 2025
[…]
Get Deal
Learn More
Bed, Breakfast and Valet Package Photo
Baltimore

Bed, Breakfast and Valet Parking Package

Now Through Dec 31, 2025
[…]
Get Deal
Learn More
Romance Package  Photo
Lord Baltimore Hotel
Baltimore

Romance Package

Now Through Dec 31, 2025
[…]
Get Deal
Learn More
  • <
  • Page 1
  • Current page 2
  • >
Open Road
Maryland Office of Tourism Logo
Copyright 2025 Visit Maryland, Maryland Office of Tourism Development. All rights reserved.
  • Accessibility
  • GDPR FAQ
  • Privacy
  • About Visit Maryland
    • Contact Us
    • Maryland Office of Tourism
    • Green Certification
  • Industry Links
    • Maryland.gov
    • Maryland Department of Commerce
    • Wes Moore, Governor
    • Customer Experience Survey
    • Group Travel
    • Press Room
    • Getting to Maryland
    • Maps & Brochures
    • Translate this page
  • TripAdvisor: Know better. Book better. Go better.
    Ratings and Reviews Powered by TripAdvisor