Guided Trip To Annapolis
A 4-hour boat ride from South River, Maryland, to Annapolis.
A guided trip to Annapolis is a relaxing and scenic trip through the Chesapeake Bay’s tributaries. The South River is just a few miles southwest of Annapolis, so to stretch this ride into four hours, you’d likely be cruising at a leisurely pace, possibly exploring some of the creeks and landmarks along the way.
Guided Annapolis Trip Itinerary
Departure from South River 9:30 am or 2 pm
You’ll start in the South River, a beautiful estuary lined with waterfront homes, marinas, and
quiet coves. The river has several small inlets, such as Glebe Bay, Harness Creek, and Church
Creek, where you might spot herons, ospreys, and even bald eagles.
- Quiet Waters Park: As you head toward the mouth of the river, you’ll pass by this
scenic park with wooded trails, kayak rentals, and a dog beach. - Londontowne & Historic London Town and Gardens: On the southern shore of the
river, this historic site features colonial-era buildings and beautiful gardens.
Entering the Chesapeake Bay
As you leave the river and enter the Chesapeake Bay, the water opens up, and you’ll feel the
salty breeze. The bay can get a bit choppy depending on the weather, but the views are fantastic.
- Thomas Point Shoal Lighthouse: A must-see! This is one of the last remaining screw-
pile lighthouses in the Chesapeake, standing on stilts above the water. It’s a famous
landmark and an excellent photo opportunity.
Exploring the Severn River (Optional Side Trip)
Before heading into Annapolis, you might take a detour up the Severn River. This river is home
to some of the most beautiful waterfront properties and offers a chance to see:
- Naval Academy Bridge: A large steel bridge that provides great views of downtown
Annapolis. - United States Naval Academy: You’ll see the academy’s impressive buildings along the
river, including Bancroft Hall, the largest dormitory in the world.
Arrival in Annapolis 10:45am or 3:15 pm Depart Annapolis 12:15pm or 4:45pm
As you approach Annapolis Harbor, you’ll be greeted by the city’s historic skyline, with the
Maryland State House dome visible above the treetops.
- Ego Alley: This narrow waterway is a famous spot where boats parade up and down for
all to see. It’s a great place to dock and watch the bustling harbor activity. - City Dock: The heart of Annapolis, lined with restaurants, bars, and boutiques. You
might tie up at Pusser’s Caribbean Grille for a drink or grab some fresh seafood. - Annapolis Waterfront Hotel & Marinas: A picturesque spot to end your ride, with plenty of space to dock and enjoy the lively atmosphere.
Other Sights Along the Way
- Wildlife: Keep an eye out for dolphins (occasionally seen in the Bay), ospreys nesting on
channel markers, and crabs scuttling near the docks. - Sailboats: Annapolis is the sailing capital of the U.S., so you’ll likely pass by dozens of
sailboats, from small dinghies to massive yachts.
Back to the South River at 1:30 pm or 6 pm
This trip offers a mix of natural beauty, history, and classic Chesapeake Bay charm—whether
you’re cruising slowly, stopping to explore, or just enjoying the ride!
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⭐⭐⭐⭐⭐
Seriously so amazing!!! The best experience ever. We did a pontoon and it was the funnest time. Great employees and amazing captain. You will not be disappointed!
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Explore Annapolis
Why Choose Us
We specialize in power boat rentals and charters on the Chesapeake Bay for family, social and corporate outings. Knowing you have lots of choices when planning your next outing, we work hard to make sure your experience is one that you will want to repeat again and again!
About us
Over 30 Years Of Serving Boat Rentals On The Chesapeake Bay.
Contact us now to book your Chesapeake Bay Experience on a boat from South River Boat Rentals!
Leading Boat Rental Company on the Chesapeake Bay
Tubing, Skiing, Wakeboarding and Kneeboarding Options
Captains Hold US Coast Guard 50 Plus tonnage Master Licenses
Our Fleet Of Power Boats Is Professionally Maintained
Our Customers Love Us!
Just Google "South River Boat Rentals" to see all the positive reviews we have earned throughout the years. Customer service and ensuring you have an excellent day on the water is our top priority.
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