Guided Trip To St. Michaels, Maryland

Up to 30 Passengers • Many Landmarks! • 8 Hours

by South River Boat Rentals· Edgewater, MD
From$1050
Group sizeUp to 30 People

What to Expect

An 8-hour boat ride from South River, Maryland, to St. Michaels, Maryland takes you through some of the most scenic and historic waterways of the Chesapeake Bay. The journey covers approximately 35-40 nautical miles, depending on your exact route, and offers breathtaking views, wildlife, and notable landmarks.

Includes

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!

Duration

8 hours

Address

South River Boat Rentals Pickup Location

Pricing

19' Hurricane · 5 Passengers • Captain Included$1165.50
21' Kencraft · 5 Passengers • Captain Included$1165.50
23' Parker · 5 Passengers • Captain Included$1165.50
26' Bennington Pontoon · 11 Passengers • Captain Included$1720.50
26' Crest Tritoon · 11 Passengers • Captain Included$1720.50
46′ Carman · 29 Passengers • Captain Included$4107
50′ Viking · 11 Passengers • Captain Included$4384.50

Prices are typical; see the booking calendar for live availability and rates.

Cancellation Policy

Cancel up to 2 days before the start time.

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