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!

⭐⭐⭐⭐⭐

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!

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.

As a privately-owned company with over 30 years of experience, our reputation is based on the quality and our belief in first-class customer service. Our friendly and knowledgeable team will help you choose the right boat and will also recommend destinations, activities, and enhancements to ensure your outing is all that you imagined.

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.

"

We used South River boat rentals this past weekend for a bachelorette party and had the absolute best time. Special thanks to Captain Chris and the rest of the crew who were all kind, courteous, and informative. Definitely will be returning! - Gabby Cooper

Amazing day on the pontoon boat with our extended family. Graham was a WONDERFUL captain and host. He took us to a quiet area to swim, dragged all 4 kids in the tube, and slowed the boat so we could look at wildlife up close. Worth every penny! Highly recommend requesting Graham as your captain. - Meredith Bove

Thank you for a memorable experience. Would recommend this place to everyone. Can’t wait to make another reservation in the future. A big thank you to Nancy for your amazing customer service and friendly personality!! - Nicole Wilkinson

Thank you for an amazing time. We rented the 26' Chaparral for a day of cruising and tubing. We could not be more grateful. The boat ran perfectly and the staff was king, courteous and accommodating. We will return! - Garrick Muench

Had a great experience with them. I even had to reschedule for a later date and they were able to accommodate! Would definitely recommend the 50' Trawler! - Kourtney Ramseur

Such an amazing company to work with!!! From scheduling, to weather related rescheduling, the captain, and the overall boat condition and experience - I cannot say enough good things about South River Boat Rentals! Definitely will return! - Tara Klimovitz

The boat was ready and waiting for us; the service was good from booking to returning the boat. South River made it an easy and enjoyable experience. - Judy Graham

So much fun renting a boat for the day. Our Captain Wayne was awesome and took us wherever we wanted to go. He gave suggestions based on weather/water conditions/our ideas of what we wanted to do. It was really a great day! - Sarah Edwards

Outstanding Labor Day out on the water thanks to South River Boat Rentals! Best prices in the area, great vessel, easy to use, a lot of fun for our family! - Mark Fratto

The staff was awesome and super hospitable. They walked us through everything and made sure we felt comfortable on the boat. Boat was in great condition too! - Dylan Stoskus

We had a wonderful experience with South River Boat Rental! The boat was in perfect condition, very clean, and the staff was a pleasure to work with. Would highly recommend! - Liz Gillette

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