Dana Point and Laguna Beach, California
Thanks to a mother-in-law who lives in Dana Point, I’m lucky enough to be semi-bicoastal. The short stretch of coastline from Laguna Beach down to Dana Point and San Clemente is one of my favorite coastal cruising corridors.
Dana Point Harbor, opened in 1971 and home to roughly 2,400 slips, has been under renovation in recent years, but many beloved local spots remain. Start your morning with avocado toast or blueberry pancakes at the long-standing Proud Mary’s, then take a waterfront walk or bike past the marina to the Dana Point Headlands. The Ocean Institute there is a compact, engaging museum and aquarium, and it also serves as home base for the 118-foot tall ship Spirit of Dana Point, which runs occasional offshore trips. Climb the bluff above the harbor for coastal hiking trails and broad ocean views, and treat yourself to a meal at the iconic Chart House—an unbeatable spot for California chardonnay, swordfish, and the restaurant’s famous Hot Lava cake.
If you carry bicycles, the coastal bike trail is a highlight: it runs from the harbor past Doheny State Beach and continues south toward San Clemente. For the rolling hills of San Clemente, consider e-bikes. The shoreline route stretches much further for dedicated cyclists—through San Onofre and down toward Oceanside—but for a pleasant ride, pedal to Del Mar Street and the Pier Bowl for excellent seared ahi at Fisherman’s atop the pier. Another classic option is Sonny’s on the Pacific Coast Highway, a four-decade staple known for hearty plate fare like ravioli amour.
If you arrive without bikes, take one of the frequent coastal shuttles into downtown Laguna Beach. The town is rich with art galleries, the Sawdust Arts Festival showcasing local makers, and the Pageant of the Masters, famous for its live re-creations of classic paintings. After a coastal hike north of the main beach, try Miki Sushi & Sake on Coast Highway for outstanding sushi. For breakfast, Anastasia Cafe’s caramel French toast is a treat, and for a casual lunch, La Sirena Mexican Grill serves a solid local IPA with favorites such as an avocado-lime salad or a grilled ahi burrito. —Chris Dixon
New York Harbor
Each spring, pleasure boats surge through New York Harbor like migrating birds heading to summer waters. By late spring, full-displacement yachts and cruisers begin their seasonal passages, often timing tides through the East River and the challenging Hell Gate stretch.
Many liveaboards say they avoid New York City, but as a native and frequent boater here, I recommend stopping for a few days to experience what this global city offers to visiting cruisers. Anchor in the lee of Liberty Island to enjoy the statue’s shadow while staying clear of the harbor’s heaviest traffic and strongest currents. From there, run toward southern Manhattan and choose your next route: port leads to the Hudson River; starboard opens to Brooklyn and the East River.
Options for transient berths include Jersey City’s Liberty Landing, Manhattan’s Chelsea Piers, and Brooklyn Bridge Marina—each places you within easy walking or biking distance of top restaurants, bakeries and cultural attractions. Walk off a big meal with a museum visit or a live show—New York’s music scene offers something every night. Dockside, snap up specialty foods at Eataly for exceptional Italian selections to take home with you. An overnight stay in the harbor lets you combine maritime adventure with the unmatched dining and entertainment of one of the world’s great cities. —Jeff Moser
Connecticut River
For years I thought of Connecticut as just a drive-through state along I-95. That changed when I moved to Essex on the Connecticut River to work for a boating magazine. Essex is small but full of Colonial charm: grab an ice cream cone at Sweet P’s, browse Toys Ahoy, or enjoy a pint at the historic Griswold Inn, which dates back to the 18th century.
Newer spots like Noah’s at 63 Main and Drift offer refined dining and cocktails that rival larger coastal ports nearby. Slow down for a weekend or more, and consider staying at Essex Island for easy access to town. The Connecticut River is a sheltered cruising waterway—drop onto a mooring in Hamburg Cove and wake to pine-covered hills and calm mornings that feel almost like Maine, but with warmer swimming water.
Other river towns—Old Saybrook, Deep River and Chester—have marinas with classic New England character and plenty of good restaurants. Often overlooked in favor of Newport or Montauk, the Connecticut River rewards those who explore it: quiet anchorages, historic harbors and close-knit small towns that can quickly become favorite cruising grounds. —Daniel Harding Jr.
Lake Champlain
Lake Champlain, the unofficial sixth Great Lake, spans more than 400 square miles between Vermont, New York and Quebec. Framed by the Green Mountains and the Adirondacks, the lake offers scenic open water, protected bays, historic sites, and small towns with a strong boating culture.
Burlington on the eastern shore is a great stop: Community Boathouse Marina provides slips, the dockside restaurant Splash is convenient for meals, and Church Street Marketplace offers pedestrian shopping and seasonal waterfront events. South of Burlington, safe harbor moorings at Shelburne put you within reach of Shelburne Farms, a 19th-century estate now focused on conservation and education.
On the New York side, historic Fort Ticonderoga anchors the region’s Revolutionary War story, while Valcour Island delivers protected anchorages, quiet beaches and miles of hiking trails. Lake Champlain sees fewer crowds than many East Coast boating destinations, and that quieter pace—combined with mountain vistas and historic charm—makes the lake a rewarding destination for cruisers. —Carly Sisson
Salem, Massachusetts
When I worked for a sailing magazine in Salem, Massachusetts, I fell for the town’s maritime roots and compact waterfront culture. Nestled between marine businesses and classic New England architecture, the downtown is full of shops, galleries and restaurants, and it’s easy to explore on foot from the docks.
Salem’s tourism leans into its witch-trial legacy each October, but the town’s true strengths are its maritime museums, Colonial homes and cultural institutions. The Peabody Essex Museum is a standout, with global art, maritime artifacts and even a reconstructed Qing Dynasty house gallery. Walking tours reveal centuries of history and well-preserved homes dating back to the 1600s.
Salem and nearby Marblehead share busy harbors with commercial marine activity, yacht clubs and moorings. Islands like Baker’s and Misery are excellent short trips, and convenient ferries or commuter rail links make Boston an easy destination for a city day. Salem’s combination of history, maritime culture and charming downtown makes it a worthwhile stop for cruisers. —Lydia Mullan
Sanibel Island, Florida
Florida has changed dramatically since the late 1970s, but Sanibel Island remains a rare holdout of low-rise, conservation-oriented coastal life. About two-thirds of the island is wildlife refuge or protected land, and building heights are limited, preserving a relaxed, natural atmosphere.
Sanibel Marina accepts transient boats up to 70 feet and can be busy in winter, but the island provides well-sheltered anchorages behind the barrier islands. Onshore, Periwinkle Way hosts shops and restaurants; Billy’s Rentals offers bikes for exploring; and the beaches provide some of the best shelling in the hemisphere. Expect frequent dolphin sightings and quiet evenings—the island dims lights to protect nesting sea turtles, and nightlife is intentionally subdued.
For dockside dining, Grandma Dot’s at the marina and The Blue Giraffe are reliable choices, and the seasonal Blue Rendezvous (open October through June) is a standout if you can secure a reservation. Sanibel is classic Florida: unhurried, natural and ideal for boaters seeking calm anchorages and island rhythms. — Mario Vittone
Charleston, South Carolina
Charleston’s historic streets, food scene and deep maritime culture make it a perennial favorite. For boaters, it’s an ideal base to explore classic Lowcountry waters and nearby islands.
Cruise off the ICW down the Stono River to reach the north end of Kiawah Island and the unspoiled sand of Sandy Point, or follow channels into the Folly River and tie at Bowens Island restaurant for seafood in a rustic fish-camp setting. Folly Beach—accessible via Sunset Cay Marina—offers surf, a fishing pier, bike-friendly streets and casual dining at local favorites like The Lost Dog Cafe, Catch 23 and Lolo’s for sunsets and seafood.
In downtown Charleston, Safe Harbor Charleston City provides a convenient berth. From there you can visit the South Carolina Aquarium, the International African American Museum, Marion Square’s markets, and the storied King Street shopping and dining district. For a special meal, try Husk, then stroll Charleston’s historic neighborhoods to soak up the city’s maritime atmosphere and layers of history. —Chris Dixon
Mackerel Cove
After years of camping with an Airstream, my wife and I traded long drives for a boat and discovered New England anchorages close to home. Living in Jamestown, Rhode Island, put destinations like Block Island and Cuttyhunk within easy reach, but our favorite nearby anchorage became Mackerel Cove.
Mackerel Cove lies south of Jamestown’s main mooring field and faces Castle Hill Light across the bay. It’s roughly one mile by a third of a mile, with a sandy bottom that provides good holding and protection from prevailing southwest breezes. Weekends can be busy, but weekday visits often leave the cove nearly deserted. The tree-lined shoreline and quiet atmosphere make it ideal for swimming, barbecues and peaceful nights on the hook—an anchorage that feels more like Maine while being just minutes from home. —Onne van der Wal
St. Michaels, Maryland
St. Michaels retains the hardy spirit of a Chesapeake Bay watermen’s town. In 1813, locals famously hung lanterns to confuse attacking British barges—an anecdote that still colors local pride. Today, the town blends historic charm with approachable waterfront dining and marine services.
With roughly 1,000 year-round residents, St. Michaels packs a surprising number of inns, restaurants and marinas. The Inn at Perry Cabin, with its dock space, is a well-known upscale choice; dockside dining often features oysters, she-crab soup and crab dip. The Crab Claw offers a simpler, lively dockside scene with all-you-can-eat blue crab and hosts the Chesapeake Cowboys docking competition each season.
Talbot Street is the town’s culinary hub, offering taverns, steakhouses and white-tablecloth options that draw weekend crowds from the D.C. area. Through all the visitors, St. Michaels maintains its authentic Eastern Shore character and remains a welcoming stop for Chesapeake cruisers. —Owen Burke
Penns Landing
Penns Landing sits on Philadelphia’s Delaware River waterfront and offers a rare blend of rich American history, maritime museums and an energetic urban waterfront. Reserve a slip at Penns Landing Marina and enjoy green parkland, historic ships, and easy access to the city’s cultural core.
Historic vessels moored near the marina include the USS Olympia, the oldest surviving steel warship, as well as other museum ships that draw history-minded visitors. A short ferry ride across the river reaches the Battleship New Jersey Museum & Memorial and the Adventure Aquarium in Camden. On land, a brief walk from the docks places you in Philadelphia’s historic district with Independence Hall, the Liberty Bell, the Benjamin Franklin Museum and a variety of colonial-era sites and museums.
Between maritime attractions and world-class food—including the city’s famed cheesesteaks—Penns Landing offers cruisers a compelling mix of history, culture and waterfront amenities. It’s an excellent urban stop for boaters exploring the Mid-Atlantic. —Gary Caputi
This article was originally published in the July 2026 issue.