The Chesapeake Bay is approximately 200 miles long, stretching from Havre de Grace, MD, to Virginia Beach, VA. It is the largest of more than 100 estuaries in the United States and the third largest in the world. The Chesapeake watershed comprises about 64,000 square miles and includes parts of six states: Delaware, Maryland, New York, Pennsylvania, Virginia, and West Virginia, and the District of Columbia. The Bay and its tidal tributaries encompass more than 11,684 miles of shoreline, more than the entire length of the U.S. West Coast. In a space like that, the Chesapeake Bay boating possibilities are endless.

chesapeake bay boating
On the Chesapeake Bay, the boating possibilities are endless. 

Boating License Requirements

First things first: both Maryland and Virginia require a boating license to operate a boat on the Chesapeake Bay.

Maryland law requires that anyone born on or after July 1, 1972, must have a Certificate of Boating Safety Education in order to operate a mechanically propelled vessel on Maryland waters. You can take the class online at, or you can find a class through your local power squadron. 

In Virginia, beginning July 1, 2016, all motorboat operators of 10 hp or greater, regardless of age, and all PWC operators 14 years old or older must take a boating safety course. No one under the age of 14 may operate a PWC. Operators 14 and 15 years old must show proof of completing education. Click to to take the class online.

What Powerboat is Right For You?

There are so many powerboats to choose from, and depending on the type of boating you wish to do, not every type of boat will fit the mold. Here are some of the options, courtesy of BoatU.S. (click on the link for more detailed descriptions and photos of each boat).

  • Bass Boat: generally 14 to 23-feet long and typically used for freshwater fishing. 
  • Bay Boat: generally 18 to 24 feet in length, and designed for use in shallow bays, estuaries, or near shore.
  • Bowrider: designed with an open bow area designed for extra seats forward of the helm. Great family boat; good for watersports.
  • Center Console: so-named because their helm is on a console in the center of the boat. Most are powered by outboard engines, and the open hull also anglers to walk unimpeded from bow to stern.
  • Convertible Fishing Boat: generally 35 feet or larger; suited for offshore fishing and cruising.
  • Cruiser: have a cabin in the bow; designed for short, overnight stays onboard.
  • Cuddy Cabin: have a small cabin for storage; may accommodate a berth and/or a head.
  • Deck Boat: features an open deck with plenty of seating; V-shaped hull offers more performance than a pontoon boat.
  • Dinghy: a small boat generally carried or towed by a larger boat for going ashore.
  • Downeast Cruiser: also called lobster boats; they are built for offshore cruising and fishing. Native to coastal New England.
  • Dual Console: has two dashboards and windshields with space to walk between them.
  • Express Fisherman: designed for high speeds to get to offshore fishing grounds in a hurry.
  • Fish n' Ski Boat: used for fishing and/or waterskiing with accessories for each application, including livewells for fishing and elevated tow bars for watersports.
  • Flats Boat: smaller boats with shallow drafts designed to navigate shallow waters.
  • High Performance Boat: built for speed, powered by high performance engines. They have spartan cabins; cockpits seat two to six passengers.
  • House Boat: floating houses with a kitchen, bedroom(s) and living and dining areas.
  • Inflatable Boat: generally six to 14 feet in length and often powered by outboard motors. They deflate and are easy to transport; often used as dinghies on larger boats.
  • Jet Boat: have single or multiple jet drives instead of a propeller for propulsion. Very maneuverable; generally used for watersports.
  • Jon Boat: small, utility craft often made of aluminum or fiberglass. Inexpensive; used for boating or fishing in shallow water.
  • Multi-Species Boat: made for fishing a variety of species; designed to travel in rougher water than bass boats.
  • Pilothouse Boat: features a fully enclosed pilot house; built to endure rougher seas while keeping the helmsman dry.
  • Pontoon Boat: have two or three aluminum tubes that support a broad open platform. Very stable; used for fishing, cruising, and watersports.
  • Power Catamaran: dual-hull boat; provide a more stable ride than monhulls.
  • PWC (Personal Watercraft/Jetski): powered by a jet drive; depending on the model can fit from one to four people.
  • Rigid Inflatable: or RIB. A fiberglass or aluminum hull is attached to inflatable outer tubes. Usually faster, larger, and can carry more weight than flexible floored inflatables. 
  • Runabout: generally defined as a small powerboat in the 14-24 foot range; suitable for watersports, cruising, or fishing.
  • Sedan Bridge Boat: intended for extended cruising with accommodations below; ranging from 35-65 feet. The bridge allows for greater visibility. 
  • Ski and Wakeboard Boat: designed specifically for watersports; can be ballasted to produce a higher wake.
  • Skiff: similar to a Jon Boat; great for boating in shallow water, often with flat hulls.
  • Utility Boat: made for tough use; relatively lower cost. Generally made of aluminum with outboard power.
  • Walkarounds: allow an angler to walk around the cabin; generally 20-30 feet in length.


There are other times of boats available that don't require a trip to the fuel dock. Paddleboards, kayaks, canoes, and other paddle craft can be a great way to get out and explore the tributaries of the Bay, and get a workout while you're at it. There are a multitude of rental agencies around the Bay, as well as how-to classes and educational paddle tours to get your feet wet in the sport. There is also a growing group of kayak anglers on the Bay. Click to to learn more.

Chesapeake Bay Boating Destinations

With so much shoreline to explore, it can be dizzying trying to choose a location to start. Lucky for you, we have a massive library of destination articles around the Bay that we can personally vouch for. Click to our See the Bay section to get started. Also be sure to check out our Dock Bars for an interactive map of the best dockside bars in Chesapeake country.

Cruising Tips and Stories

Interested in winterization and spring commissioning tips? How about DIY maintenance on your boat? Visit out Cruising section for expert tips, first-hand accounts of cruising the Chesapeake Bay, and tips and stories from Chesapeake boaters who have then chartered off the Chesapeake, in places like the British Virgin Islands.


Unless you live on the water, you'll need to either find a marina to keep your boat, or if it's small enough, you can keep it in your driveway on a trailer. Either way, you're going to want to know where you can launch your boat and what amenities are available at marinas near you. Click to our interactive Marinas page for a list of amenities and a map of marinas around the Bay.

Powerboat Racing

Interested in high speed powerboat racing on the Chesapeake Bay? The Chesapeake hosts several large-scale race events on the Chesapeake each year, including the Cambridge Classic and the Hampton Cup Regatta, as well as a series of smaller events through the Smith Island Crab Skiff Association and the Cocktail Class Wooden Boat Racing Association. Visit our Racing section for profiles on competitors, spectator's guides to big events, details on upcoming races, as well as race results and photos.

Charter Fishing

No matter the season, the Chesapeake Bay is an anglers playground. If you're new to fishing or simply want to go out with an experienced captain who can put you directly in the action, look no further than our Charter Fishing Guide, organized by Bay regions. You can also check out our Fishing section for how-to articles on catching various Chesapeake species, as well as fishing tournament results, fishing getaways, and more.

Boats for Sale

Ready to jump right in and become a boat owner? Check out our library of comprehensive Boat Reviews, then click to our Boats for Sale page to start shopping for that perfect new-to-you boat.