Sited on the banks of Carter Creek where it flows into the Rappahannock River, Irvington boasts deep, protected waters and a quaint Colonial ambiance. The village once thrived as a stop for steamboats carrying goods and travelers across southern Chesapeake Bay, which is why The Steamboat Era Museum here is so popular today. For more history, head to Christ Church (finished in 1735), where you can tour one of the nation’s finest examples of Georgian architecture. Hit the farmers’ market for fresh seafood, meat and vegetables or visit one of the vineyards in the area. Dock at The Tides Inn Marina.
St. Michaels, Md.
Chesapeake Bay possesses a seemingly endless array of temptations for boaters, yet St. Michaels remains a perennial favorite for its sheer beauty and well-roundedness. Yes, it has picturesque streets lined with vintage homes leading to a gorgeous harbor. Yes, is has charming storefronts, trendy retailers and fine art galleries. Yes, it has spas and retreats for pampering and relaxation. Yes, it has fine dining from waterfront crab houses to gourmet brasseries. And yes, it even has the Chesapeake Bay Maritime Museum and the St. Michaels Museum on St. Mary’s Square. What’s not to love? Dock at St. Michaels Marina or at the Chesapeake Bay Maritime Museum, a members-only marina.
Cape May, N.J.
The entire city of Cape May is designated a National Historic Landmark due to its unprecedented concentration of Victorian buildings. It’s also called the nation’s oldest seashore resort and has all the trappings to back it up, including a two-mile boardwalk paralleling the beach with arcades, seafood joints and shopping galore. Cape May makes a great base for outdoor fun — bird-watching, boat tours, dolphin cruises, kayaking and canoeing — and the Naval Air Station Wildwood Aviation Museum is just a short cab ride away. Dock at South Jersey Marina or Canyon Club Resort Marina.
This village at the eastern end of Long Island’s North Fork is modest and casual with the look and feel of an authentic whaling town. Vessels of all sizes are moored in the deep-water harbor, seagulls soar overhead, and, occasionally, there’s a whiff of fried clams on the air. From the waterfront, you can walk to restaurants, shops and even a vintage carousel. Visit the East End Seaport Museum & Marine Foundation and the famous S.T. Preston and Son Chandlery for some nautical seasoning. Dock at Mitchell Park Marina or Brewer Yacht Yard at Greenport.
Well known as an old shipbuilding town, Mystic is also home to some of the finest modern marine facilities on Long Island Sound. There’s plenty to do, particularly for those cruising with kids. The waterside streets are lined with shops, galleries and restaurants, and there’s also a planetarium and children’s museum. No trip here is complete without a tour of Mystic Seaport, the nation’s leading maritime museum or the Mystic Aquarium & Institute for Exploration. Dock at Mystic Shipyard, Brewer Yacht Yard at Mystic or Seaport Marine.
Martha’s Vineyard, Mass.
The Vineyard, as locals call it, is the bigger, more outgoing sister of Nantucket. The island is closer to Cape Cod, making it a more convenient, and is adorned with picturebook beaches, elegant inns, and upscale dining and shopping, which draw celebrities and serious vacationers alike. Brightly painted gingerbread cottages line the streets of Oak Bluffs (also the home of the Flying Horses, the oldest working carousel in the U.S.). Visit Aquinnah Beach to see the famous color-streaked cliffs there. Dock at Oak Bluffs Marina, Vineyard Haven Marina or Edgartown Town Docks.
The world’s former top whaling port is now a remote summer vacation spot with a serene seaside look and feel. Restaurants and boutique stores line the streets of Nantucket Town, where you will also find the majority of dining and nightlife options, and the Museum of Nantucket History includes exhibits on the history of the island. Beachcombing, swimming, surfing and fishing are all glorious ways to spend a day, or a week, here. Bring your bike, too, as that is the best way to get around the 50-square-mile island. Dock at Nantucket Boat Basin.
Boston is one of the oldest cities in the U.S. and has an amazingly rich history and culture. You can still visit where many of the crucial events of the American Revolution occurred along the Freedom Trail, which is marked by a red line of bricks embedded in the ground. The Inner Harbor is home to the USS Constitution at the Charlestown Navy Yard as well as the Boston Tea Party Ships & Museum at Fort Point Channel. It also offers the Boston Harbor Islands National Recreation Area and numerous waterfront restaurants. Dock at The Boston Yacht Haven, Constitution Marina or Marina Bay.
It’s the Maine coast as it was meant to be. Lobster boats and schooners ply the harbor in front of a charming downtown studded with locally owned shops, galleries, seafood eateries and cafes — there’s even a beautiful public library right on the waterfront. Take a day-trip to the outlying islands and their 18 lighthouses, or head inland and experience Camden Hills State Park, a mecca for outdoor enthusiasts featuring 30 miles of scenic hiking and mountain biking trails, breathtaking views of the surrounding hills and lakes and well maintained campgrounds. Dock at Wayfarer Marine.
Dotted with historic homes and featuring the nation’s third-tallest monument, the 352-foot Doric column Perry’s Victory and International Peace Memorial, this village on South Bass Island is Americana at its best. It ranks in the top five confectionary destinations in the state, and its largest souvenir shop reportedly has 1,000 items with the town’s name on it. Enjoy winery tours, park tours, cave tours and home tours via rented golf cart, or spend your days kayaking, parasailing, fishing, biking, hiking or golfing. It’s the quintessential choose-your-own-adventure family vacation spot. Dock at Miller Marina or The Crew’s Nest.
Manitoulin Island, Ontario
The world’s largest freshwater island, Manitoulin in northern Lake Huron has been called “a place of convergence”. Indeed, history, culture and natural beauty merge in the two-dozen settlements spread across its 1,000 square miles of boreal forest, bluffs and meadows. The Holy Cross Mission and Ruins in Wikemikong commemorates early Jesuit visits to the island, which began around 1648. Sheguiandah holds a prehistoric quarry that has yielded stone pools and arrowheads dating back 9,000 years. Gore Bay, one of the larger communities, offers modern amenities such as shopping, restaurants and facilities for tennis and golf. Dock at Spider Bay Marina in Little Current.
With its megawatt downtown and world-famous attractions, it’s not surprising to see the Windy City listed here. Navy Pier, once a shipping and military training facility, is now a major tourist draw with 50 acres of promenades, shops, eateries and amusements. Shoreline Sightseeing operates nine touring boats and 11 water taxis that offer guided skyline tours, fireworks cruises, and special events such as Brew Cruises and Wine Tasting Cruises. Then, of course, there’s Michigan Avenue, Shedd Aquarium, Millennial Park, the Field Museum of Natural History and much more. Dock at DuSable Harbor, Burnham Harbor or 31st Street Harbor.
San Juan Islands, Wash.
The hundreds of islands breaching the sparkling blue waters here are everything you’ve heard — rugged, wild and richly fertile in scenery. May through September is the ideal time to visit, when the weather is mild and the whales (orcas, mainly) are on the move. You can take advantage of the many lovely resorts and lodges, the attractions of the charming seaside towns, or simply find your way to remote anchorages and deserted bays. Dock at Port of Friday Harbor on San Juan Island or Deer Harbor Marina on Orcas Island.