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  • 12 Best Heritage Train Rides in America for Your Travel Bucket List
  • Best 86

    things to do in Church Creek, MD

    Showing 25-48 of 86 results
    Wine Tasting Sailboat Cruise in St. Michaels, MD

    Wine Tasting Sailboat Cruise in St. Michaels, MD

    Sip six curated wines while sailing St. Michaels’ waterfront

    5.0 • 1.4K reviews
    $187/ person
    Sunset Paddleboard Tour on Rockhold Creek

    Sunset Paddleboard Tour on Rockhold Creek

    A Friday evening creek paddle with live music and a lighted ride back

    4.6 • 36 reviews
    $27/ person
    Chesapeake Bay Sunset Champagne Sail in St. Michaels

    Chesapeake Bay Sunset Champagne Sail in St. Michaels

    Sail Chesapeake Bay at sunset with champagne and light bites

    5.0 • 1.4K reviews
    $298/ person
    Paddle Board Rental in Deale

    Paddle Board Rental in Deale

    Explore Deale's creeks and bay at your own pace on a paddle board

    4.6 • 36 reviews
    $32/ paddle board
    2-Hour Beer Tasting Cruise in St. Michaels

    2-Hour Beer Tasting Cruise in St. Michaels

    Sample six rotating craft beers aboard a modern catamaran

    5.0 • 1.4K reviews
    $298/ person
    Sunrise Paddleboarding Tour in Deale

    Sunrise Paddleboarding Tour in Deale

    Greet the day with a guided paddle at sunrise on Chesapeake Bay

    4.6 • 36 reviews
    Contact for pricing
    Deale Paddle & Brunch Tour

    Deale Paddle & Brunch Tour

    Paddle the creek, then pause at a local waterfront restaurant for brunch

    4.6 • 36 reviews
    $27/ person
    Self-Launch Kayak & SUP Access in Deale Near Chesapeake Bay

    Self-Launch Kayak & SUP Access in Deale Near Chesapeake Bay

    Launch from a private ramp less than a 10-minute paddle from Chesapeake Bay

    4.6 • 36 reviews
    $11/ person
    Bachelorette & Bachelor Party Cruise in St. Michaels

    Bachelorette & Bachelor Party Cruise in St. Michaels

    Celebrate the bride or groom aboard a historic private sailboat

    5.0 • 1.4K reviews
    $1,792
    Private Half-Day Sail on a 1935 Ketch in St. Michaels

    Private Half-Day Sail on a 1935 Ketch in St. Michaels

    Sail the Miles River aboard a historic 1935 ketch

    5.0 • 1.4K reviews
    $3,453
    Marriage Proposal Cruise in St. Michaels

    Marriage Proposal Cruise in St. Michaels

    Plan a private proposal aboard a historic 1935 ketch

    5.0 • 1.4K reviews
    $1,792
    Sunset Champagne Cruise in St. Michaels

    Sunset Champagne Cruise in St. Michaels

    Sail a historic ketch at sunset with champagne and Chesapeake Bay views

    5.0 • 1.4K reviews
    $187/ person
    2-Hour Chesapeake Bay Sailing Cruise

    2-Hour Chesapeake Bay Sailing Cruise

    Sail the Miles River aboard a spacious catamaran

    5.0 • 1.4K reviews
    $270/ person
    Private Half-Day Sailing Charter in St. Michaels

    Private Half-Day Sailing Charter in St. Michaels

    Harbor views and wind-powered sailing on the Miles River

    5.0 • 1.4K reviews
    $2,899
    2-Hour Beer Tasting Cruise in St. Michaels

    2-Hour Beer Tasting Cruise in St. Michaels

    Savor rotating craft beer tastings aboard the historic Lady Patty

    5.0 • 1.4K reviews
    $187/ person
    2-Hour Sailing Lesson in St. Michaels

    2-Hour Sailing Lesson in St. Michaels

    Build Practical Sailing Skills With Private, Hands-On Instruction

    5.0 • 1.4K reviews
    $1,377
    Historic Ketch Sailing Lesson in St. Michaels

    Historic Ketch Sailing Lesson in St. Michaels

    Take the Helm and Learn Hands-On Sailing Skills

    5.0 • 1.4K reviews
    $1,792
    Sailboat Wedding & Elopement Cruise in St. Michaels

    Sailboat Wedding & Elopement Cruise in St. Michaels

    Make your vows your own aboard a private Chesapeake Bay catamaran

    5.0 • 1.4K reviews
    $1,859
    Sailboat Wedding & Elopement Cruise in St. Michaels

    Sailboat Wedding & Elopement Cruise in St. Michaels

    Exchange vows aboard a historic sailboat with a ceremony shaped around you

    5.0 • 1.4K reviews
    $2,274
    Cambridge Haunted High Street Ghost Tour

    Cambridge Haunted High Street Ghost Tour

    Hear true local ghost stories on a nighttime walk through historic Cambridge

    4.6 • 167 reviews
    $27/ person
    Blackwater Refuge Bike Rental in Cambridge

    Blackwater Refuge Bike Rental in Cambridge

    Pedal refuge and marsh roads with a bike, helmet, and map

    4.9 • 556 reviews
    $23/ bike
    Full-Day Private Sailing Charter in St. Michaels

    Full-Day Private Sailing Charter in St. Michaels

    Private Chesapeake Bay sailing aboard a 1935 ketch

    5.0 • 1.4K reviews
    $3,868
    5-Hour Bottom Fishing Trip in Solomons

    5-Hour Bottom Fishing Trip in Solomons

    Bottom-fish with room to cast on a 16-angler boat

    4.9 • 188 reviews
    $74/ person
    Tropical Harbor Cruise on Solomons Island

    Tropical Harbor Cruise on Solomons Island

    Chesapeake water views with a laid-back island vibe

    4.9 • 153 reviews
    $69/ person
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    • Paddleboarding4
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