Guided Scenic Trip To St. Michaels, Maryland

Great for 1 – 30 Passengers

The Route & Sights Along the Way

1. South River Departure (Departs at 10am)

• You’ll start your journey from South River, just south of Annapolis. This river is
  known for its picturesque waterfront homes, marinas, and quiet coves.
• As you exit the river into the Chesapeake Bay, you may spot sailboats, ospreys,
  and herons along the shoreline.

2. Chesapeake Bay Crossing

• Heading east across the Bay, you’ll see Thomas Point Shoal Lighthouse, one of
  the most famous and last-standing screwpile lighthouses on the Chesapeake.
• The open water here is known for its stunning sunrises if you depart early.
• Keep an eye out for pods of dolphins, bald eagles, and working watermen
  harvesting crabs and oysters.

3. Eastern Bay Entrance

• Turning into Eastern Bay, the waterway narrows slightly, offering calmer waters.
• You’ll pass by Bloody Point Lighthouse, a historic beacon marking the southern
  tip of Kent Island.
• Along the shores of Kent Island, you may see waterfront homes, small beaches,
  and fishermen.

4. Miles River Approach

• As you enter the Miles River, you’re getting close to St. Michaels.
• This section of the trip offers serene landscapes, with lush tree-lined shores and
  historic estates.
• Keep a lookout for sailboats and classic Chesapeake Bay deadrise boats.

Things to Do in St. Michaels (Arrive at 12:30pm Depart at 3:30pm)

Once you arrive in St. Michaels, a charming and historic town, there’s plenty to explore:

1. Chesapeake Bay Maritime Museum

• A must-visit spot featuring historic boats, a lighthouse you can climb, and exhibits
  on the Bay’s maritime heritage.

2. St. Michaels Harbor & Waterfront Dining

• Enjoy dock-and-dine restaurants like The Crab Claw or Ava’s Pizzeria & Wine
  Bar with fresh seafood and waterfront views.

3. Shopping & Strolling in Downtown St. Michaels

• The town has boutique shops, art galleries, and quaint streets perfect for walking.

4. Wine, Beer, & Spirits Tasting

• Visit St. Michaels Winery, Lyon Distilling Company, or Eastern Shore
  Brewing for local drinks.

5. Historic Walking Tours

• Learn about the town’s role in the War of 1812 and its nickname, “The Town
  That Fooled the British”

Back to the South River at 6PM

Final Thoughts

This boat trip offers a mix of adventure, history, and relaxation, making it an unforgettable
journey through Maryland’s Eastern Shore. Whether you enjoy nature, food, or maritime
heritage, St. Michaels provides a fantastic destination at the end of your voyage!