things to do in Saint Michaels, MD

Sail a Historic 1935 Ketch on the Miles River

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

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

Choose your Gettysburg Licensed Battlefield Guide for a private 2–3 hour car tour

Discover Annapolis's Navy culture, history, and Chesapeake character

Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider

Cruise Chesapeake Bay aboard a 60-foot Viking with captain, crew and fuel included

Step inside a surviving Bucktown store tied to Harriet Tubman's early life

Paddle Deale’s quiet creeks and bays at your own pace

Take the controls for a Chesapeake Bay jet ski ride

Sample Six Curated Wines While Sailing Chesapeake Bay

Paddle with a guide, then explore Blackwater by bike at your own pace

Sail the Miles River with room to relax aboard Epiphany

Paddle the Chicamacomico River, then tour the winery and taste wine

Cruise Eastern Bay and the Chester River as autumn colors give way to sunset

Cruise the South River with spacious seating, storage, and an onboard toilet

Explore St. Michaels after dark through ghost stories and maritime history

Explore Deale's creeks, estuaries, and bay by kayak

Cruise the South River with 250 HP power and an onboard toilet

Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16

Anchor in protected waters for a gentle paddleboard yoga flow

Cruise Chesapeake Bay with your own drinks, music, and flexible stops

Propose aboard a private yacht with champagne and a harbor sail

Pedal through the countryside for a winery tour and tasting