Terrific Charter Itinerary Ideas in the Southeast

The heart of summer is a perfect time to charter a yacht and explore along the U.S. southeast coast. From the Chesapeake Bay to the Carolinas, Florida and Bahamas, there are some fantastic itineraries that will lead you to hot spots and hidden gems ripe for discovery by sea and shore.

Chesapeake Bay
“There are so many different places to go on the Chesapeake, more than people could ever see in a lifetime, so you can make each trip here different,” explains Erin Minner, manager at Dream Yacht Charter’s base in Annapolis, Md. “The fact that our home base is right in Annapolis is great. People can see the town and all its charm, and then take off sailing for however long they want!”

Wind and weather can always throw a monkey wrench in the best-made sailing plans. When the breeze is blowing out of the north, consider the following itinerary:

Day 1:  Annapolis to Herrington Harbor. Here, on the western shore of the Chesapeake Bay, are overnight slips and the opportunity for waterfront dining in a classy-casual setting. It’s best, especially in the summer season, to reserve a slip in advance.

Day 2: Enjoy a leisurely sail to Oxford on the eastern shore. There you will enjoy a boater-friendly feeling as well as an easily walkable downtown with restaurants and shops.

Day 3: Cruise to Cambridge, the oldest town in Maryland, established in 1684. Cambridge Creek is a good, protected spot with ample room to drop anchor. Attractions include the Brannock and the Richardson Maritime Museums.

Day 4: Cross the Bay to St. Leonard’s Creek. Vera’s Beach Club, Restaurant & Marina is a good place to dock or anchor out. It’s a beautiful area surrounded by rolling hills, lush woodlands and shoreline marshes. Vera’s is one of the top seafood restaurants in the area.

Day 5: Seven miles downriver from Vera’s is picturesque Solomon Island. Stroll the Riverwalk, tour the Drum Point Lighthouse at the Calvert Marine Museum or enjoy one of several waterfront eateries.

Day 6:  Enjoy an easy sail across the bay to St. Michaels. This is a lovely town with a lively shop- and restaurant-filled Main Street. There are marinas downtown or anchor out and dinghy in.

Day 7:  Spend your last day under way for the 25 nautical miles (nm) or five to seven hour sail back to Annapolis.

North Carolina

The waterways, places to visit and people make this area ideal to charter. “There are a variety of creeks, rivers, and sounds to explore, as well as access to the ocean and beaches,” says Jules Norwood, vice president at Carolina Wind Yachting Center, in Washington, N.C.

Places to visit range from small historic villages to the unspoiled bight at Cape Lookout.

“If I had a week, I would definitely plan my trip around Cape Lookout,” suggests Norwood. “I would take a couple of days to get there, with perhaps one night anchored out and another at a marina in Beaufort or Morehead City to top up the tanks and pick up supplies. When I left Beaufort Inlet, I’d sail out into the Atlantic for a while before sailing back to the anchorage at Cape Lookout. I’d spend at least a night or two at Cape Lookout Bight, then make my way back toward our base in Washington. Oriental would make a nice stop along the way. There’s a beautiful marina called River Dunes with a pool, Jacuzzis, and a wonderful restaurant overlooking the docks.”

South Florida, Florida Keys & the Bahamas

“South Florida and the Bahamas are a paradise right in our backyard. They represent the quintessential Caribbean experience, but with the ease of travel and a familiar language and currency,” says Ian Pedersen, assistant marketing manager at The Moorings, headquartered in Clearwater, Fla.

A week’s charter from Dream Yacht Charter’s base in Ft. Lauderdale, Fla., can include several stops along the way to Key West. “You can even sail as far as the Dry Tortugas,” says base manager, Hannah Allison.

One itinerary, for example, starts with a first night in Key Largo, then leap-frogging down the chain of keys to Islamorada, Duck Key, Marathon, Little Palm Island to Key West. If you have longer than one week, the Keys extend another 68 nm westward to the Dry Tortugas. Here the attraction is Fort Jefferson and the Dry Tortugas National Park.

The main attractions in the Bahamas are Freeport and Nassau. Just north of Nassau is the lesser known region of the Abacos. The Moorings has a base in Marsh Harbor. A great one-week charter from here is the approximately 110-nm route to Man-O-War Cay, Great Guana Cay, Green Turtle Cay, Treasure Cay, Hope Town, Little Harbor and Elbow Cay, and then back to Marsh Harbor.

The Moorings Pedersen says of the Abacos, “Life here is still laid-back and the snorkeling is as good as it gets.”

Carol Bareuther has written for ALL AT SEA since 2004.