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Water Activities and Boat Tours in St. Michaels, Maryland

Located on St. Michaels Harbor near the Miles River and Chesapeake Bay, Log Canoe Inn gives guests easy access to a variety of water activities in St. Michaels, Maryland. Nearby options include kayaking, paddleboarding, sailing charters, fishing...

Many of these waterfront experiences are within walking distance or a short trip from the inn, making it easy to explore St. Michaels from the water. Couples, families, and outdoor enthusiasts can choose from relaxing sightseeing cruises, active paddling adventures, private charters, and scenic trips across the Miles River and Chesapeake Bay.

Log Canoe Races

Chesapeake Bay Log Canoe Racing

Chesapeake Bay log canoe racing is a centuries-old Eastern Shore tradition that brings historic wooden sailing vessels together for fast-paced summer competition. Crews rely on teamwork, balance, and sailing skill as the canoes race across the Bay and its tributaries. Visitors can view scheduled races from the shoreline, aboard local charter boats, or near participating yacht clubs. Visit the Chesapeake Bay Log Canoe Racing website for a schedule of log canoe racing events. 

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Cruises

Patriot Cruises

Patriot Cruises offers narrated sightseeing tours aboard a classic Chesapeake-style vessel. Guests enjoy scenic views of St. Michaels Harbor, the Miles River, waterfront estates, historic landmarks, and local wildlife while learning about the area's maritime history and Chesapeake Bay culture.

(410) 745-3100
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Distance: 0.4 miles

St. Michaels Sailing Charters

St. Michaels Sailing Charters offers public sails, private charters, sunset cruises, tasting cruises, sailing lessons, and custom excursions from Harbour Inn Marina in St. Michaels, Maryland. Guests can sail the Miles River and Chesapeake Bay aboard Lady Patty, a restored 1935 Maryland-built ketch, or Epiphany, a spacious 44-foot catamaran. The company’s trips are suitable for couples, families, and small groups seeking a scenic cruise, romantic sunset sail, or private Chesapeake Bay charter. Each excursion includes views of St. Michaels Harbor, local waterways, and the region’s maritime landscape.

(410) 849-9864
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Distance: 0.8 miles

St. Michaels Harbor Shuttle

St. Michaels Harbor Shuttle offers harbor tours, sunset cruises, private charters, water taxi service, eco-tours, and narrated history cruises in St. Michaels, Maryland. USCG-licensed captains guide guests through St. Michaels Harbor, nearby creeks, and local waterways while sharing information about the area’s maritime history, ecology, wildlife, and waterfront landmarks. The company serves couples, families, groups, boaters, and wedding parties, with customizable trips and transportation throughout the St. Michaels harbor area. Select tours are BYOB and pet-friendly, making them a flexible option for sightseeing, private events, and relaxed Chesapeake Bay outings.

(410) 819-9606
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Distance: 0.8 miles

Fishing Charters

Ferry Cove Charters

Ferry Cove Charters offers private boat charters, fishing trips, sightseeing cruises, sunset excursions, and custom outings near St. Michaels, Maryland. Guests can explore the Miles River, Eastern Bay, Oxford, Tilghman Island, and surrounding Chesapeake Bay waterways with knowledgeable local captains. 

Trips are available for sightseeing, fishing, private celebrations, and relaxed sunset cruises. Along the way, guests may see historic skipjacks, working crab boats, local wildlife, and waterfront scenery that reflects the maritime heritage of Maryland’s Eastern Shore.

(410) 924-6157
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Distance: 0.8 miles

Kayaking & Paddle Boarding

Shore Pedal & Paddle

Shore Pedal & Paddle offers kayak, paddleboard, bicycle, and electric bike rentals for visitors looking to explore St. Michaels and the surrounding waterways at their own pace. Their waterfront location makes launching a kayak or paddleboard easy and convenient.

(410) 745-6006
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Distance: 0.2 miles

Stay Near the Best Things to Do in St. Michaels

Log Canoe Inn places guests near the harbor, downtown restaurants, shops, museums, and waterfront activities. Explore the inn’s six rooms and check availability for your visit. Traveling with a family? We also have a family-friendly cottage just 4 miles from the inn. 

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