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Boating in Chesapeake Bay: Must-Visit Spots and Storage Solutions

When it comes to iconic boating destinations on the East Coast, it’s hard to beat the charm, beauty, and history of Chesapeake Bay. With over 11,600 miles of shoreline and water from over 150 rivers and streams, America’s largest estuary is a hub for fishermen, tourists, and boating enthusiasts from all over.

Whether you’re a Maryland local searching for new spots to explore or a family seeking a waterfront vacation, cruising around the Chesapeake Bay is the perfect getaway. We’ve compiled a guide to exploring all the bay has to offer, from restaurants to attractions, in addition to helpful tips and tricks for planning your trip to the great shellfish bay.

Things To Do in Chesapeake Bay

With something to offer everyone from history buffs to seafood fanatics, the most challenging part about visiting Chesapeake Bay is deciding what to do first! It’d be a tall order to explore all 4,480 square miles, so you’ll need to decide whether you want to use Maryland’s shores or the Virginian coast as your home base. From Baltimore down to Norfolk, read on for some essential attractions to add to your itinerary.

Chesapeake Bay Attractions in Maryland

A visit to Maryland wouldn’t be complete without a boating trip around the bay! Hop on a scouting trip to tour the historic lighthouses throughout the Great Chesapeake Bay Loop. Head to Annapolis for an internationally renowned boat show celebrating sailors and vessels from around the world. Go back in time in Saint Michaels at the Chesapeake Bay Maritime Museum to learn about the bay’s past while watching boats be restored in real time.

Maryland’s coast is dotted with must-visit iconic seaside towns. Below are just a few of the places we recommend docking:

• Baltimore. Peruse cobblestone streets and dive into oceanside cuisine at Thames Street Oyster House.
• Annapolis. After checking out Ben Franklin’s lightning rod on the statehouse dome, feast on crab cakes at Boatyard Bar & Grill.
• Cambridge. Walk the same historic paths as Harriet Tubman before grabbing beignets at Ava’s Pizzeria & Wine Bar.
• Kent Narrows. Enjoy a relaxed destination for sunset boating after some delicious surf and turf at Knoxie’s Table.
• Saint Michaels. Explore this well-rounded town with museums and shopping galore, and sip on an award-winning beer at Eastern Shore Brewing.

Chesapeake Bay Attractions in Virginia

If the excitement of Maryland isn’t quite your speed, you may find yourself drawn to the quieter waters off the coast of Virginia. A nature lover’s paradise, spend an afternoon on the beach at Westmoreland State Park and a night camping in Caledon State Park after crossing the iconic 17-mile Chesapeake Bay Bridge-Tunnel. Explore the historic Battleship Wisconsin at Nauticus before enjoying a sunset bay cruise. 

A slower speed than Maryland, southern Chesapeake Bay is ideal for families wanting to spend more time on the water than on land. If you need a place to head ashore in Virginia, check out the following cities:

• Norfolk. Meander through naval museums and botanical gardens before chowing down on bangers and mash at Grace O’Malley’s Irish Pub & Restaurant.
• Cape Charles. This quaint beach town is ideal for outdoor adventures and water-to-table seafood at The Oyster Farm at Kings Creek.
• Urbanna. If you visit in early November, don’t miss the annual Urbanna Oyster Festival.

Chesapeake Bay Boating Tips

Does a trip to Chesapeake Bay sound like the perfect vacation for you and your family? It’s time to put pen to paper and create a plan of how to make the most of your boating trip.

When Is the Best Time To Visit Chesapeake Bay?

While Chesapeake Bay attracts visitors year-round, you’ll likely have the best trip possible if you come in the spring or fall. Though summer may be ideal for bringing along children, July and August usher in sweltering heat, bustling crowds, and hiked prices. For sailing fans, late spring and early fall are the most popular times to set sail on the water, and you’ll also have the best shot at catching rockfish and striped bass.

Bringing a Boat to the Chesapeake Bay

Whether renting a boat in the bay or bringing your own, know where you plan on loading in and docking. The municipal public boat ramp in Chesapeake Beach, MD, offers affordable launch fees and bountiful trailer parking spots near the ramps. Down in Norfolk, VA, the Willoughby Boat Ramp is an ideal place to lower your vessel into the water. 

As far as docking goes, most major waterfront towns and cities will have a plethora of marinas and boat slips to choose from. It’s worth noting that the busier it is when you visit, the harder it is to find a place to dock, so have a float plan in place.

Store Your Chesapeake Bay Boat at Self Storage Plus

Don’t let the uncertainty of finding a secure, trustworthy place to park your boat keep you from enjoying all that Chesapeake Bay offers. Self Storage Plus is your premier destination for boat storage in the bay area, and our abundance of affordable options means you can always find an ideal place to park. Our goal is to give our customers room to pursue life, and that means giving your vessel a convenient place to stay that keeps it from clogging up your garage.
To get started, contact us today and find us at a location near you!