Dana Point and Laguna Beach, California
Thanks to a mother-in-law who calls Dana Point, California, home, I’m lucky to consider myself semi-bicoastal. I’m fortunate, because the crescent of coast from Laguna Beach to Dana Point and San Clemente is among my favorite strands on Earth.
Opened in 1971, Dana Point’s 2,400-slip harbor has been undergoing a locally contentious renovation for the past several years, but a couple of favorites among the locals and itinerant boaters are still here. Grab a plate of avocado toast or a stack of blueberry pancakes at the venerable Proud Mary’s before a waterfront stroll or bike ride past all the boats to the Dana Point Headlands. There you’ll find the Ocean Institute, a terrific small museum/aquarium that’s also home to the 118-foot tall ship Spirit of Dana Point (which offers offshore excursions, too). Atop the bluff above the harbor, there’s a stunning array of coastal hiking trails and expansive views from the iconic Chart House restaurant—no better spot exists for a glass of California chardonnay and a swordfish steak, finished off with the restaurant’s signature Hot Lava cake.
If you have bikes aboard, roll down the coastal bike trail that runs from the harbor past Doheny’s famous surf beach a few miles south to San Clemente. (You may want e-bikes for San Clemente’s moderate hills.) This beautiful, oceanfront route runs 20-plus miles farther south through San Onofre’s hallowed surfing grounds to Oceanside, but for our purposes, make for Del Mar Street and the Pier Bowl area for seared ahi at the excellent Fisherman’s restaurant atop the pier. Or try a plate of ravioli amour (with tomato cream sauce, artichoke hearts and sausage) off PCH at the four-decade-old Sonny’s restaurant.
No bikes? Grab a shuttle bus—they run all along the coast here—to downtown Laguna Beach. Must-stops include a myriad of art galleries, the local-artist-filled Sawdust Arts Festival, and the Pageant of the Masters, whose on-stage human re-creations of classic works of art must be seen to be believed. After a coastal hike north of Laguna’s main beach, what may be the best sushi on the planet can be found at Miki Sushi & Sake on Coast Highway. Downtown at Anastasia Cafe, the caramel French toast is amazing. And for lunch, hit up tiny La Sirena Mexican Grill for a local IPA and an avocado lime salad or a grilled ahi burrito. Trust me on that one. —Chris Dixon
New York Harbor
Like migrating birds returning from winter roosts, you can set your watch to the number of trawlers that flutter through New York Harbor en route to summer cruising grounds.
In late spring, well after the crocus and daffodils have pushed through the ground, the march of the power cruisers begins in earnest. You can stand on the Brooklyn Bridge and watch a parade of full-displacement yachts taking advantage of a favorable tide on the East River, bracing for the run through Hell Gate—the narrow, sometimes treacherous tidal strait that slices through Gotham.
I’ve talked to a fair number of liveaboards, both seasonal and full-timers, and many have said they generally bypass New York City. As a native New Yorker who has cruised here and entertained others passing through, allow me to personally invite you to stop in for a few days and take advantage of all this world capital has to offer.
Start by dropping the hook in the lee behind Liberty Island in the shadow of its famous statue, away from the heavy traffic and tidal currents of the harbor. After lunch, fire up the mains and head toward the southernmost point of Manhattan Island. Consider this to be your fork in the road: To port lies the Hudson River, and off your starboard bow, the borough of Brooklyn and the East River.
While Jersey City’s Liberty Landing is a fine choice, others opt to be in the belly of the beast. Both Manhattan’s Chelsea Piers and the Brooklyn Bridge Marina will oblige with transient slips that put you in the catbird seat. From there, it’s a short walk or bike ride to bistros, bakeries and other culinary heavyweights that’ll curl your toes with pleasure.
Walk off your meals with a museum visit or take in a show—there’s live music from just about every genre, every night. And if you had one too many Negronis, call an Uber to escort you back to your floating home. Just don’t forget to stop into Eataly for a mind-altering selection of the best Italian cuisine. That way, along with your memories, you can take a little piece of New York with you. —Jeff Moser
Connecticut River
I hated Connecticut. For three years, this drive-through state stood between where I grew up on Long Island and my new home in Newport, Rhode Island. I-95 was—and still kind of is—the devil. I would stop in the Nutmeg State only to use a rest area.
Ten years ago, I relocated to Connecticut to join the staff of Power & Motoryacht (sister publication of Soundings) in Essex, a small town on the Connecticut River. Just a stone’s throw north of a highway I disliked, Essex casts a powerful spell. What it lacks in five-star amenities it makes up for in Colonial charm. Spending a weekend here—grabbing an ice cream cone at Sweet P’s, a toy from Toys Ahoy or a pint at the storied Griswold Inn (allegedly opened in 1776)—feels like stepping back to a simpler time.
Newer establishments like Noah’s at 63 Main or Drift offer first-class cocktails and meals that rival those in larger ports like nearby Mystic. After a couple of nights slipping into the slower rhythm of Essex (and if you stay at Essex Island—which I can’t recommend enough—be sure to say hi), you can head north. There’s no need to obsess over the weather reports on this protected waterway. Spend a night on a mooring in Hamburg Cove, where waking to the morning sun cresting the pine-covered hills makes you feel like you’re in Maine—albeit with warmer, kid-friendly water.
Often overshadowed by more tourist-friendly Essex, Old Saybrook, Deep River and Chester also have marinas on the river that offer a quintessential Connecticut experience, along with proximity to excellent restaurants.
I understand from experience why so many people sleep on Connecticut—and more specifically, the river. Ports like Newport, Greenport and Montauk have long captured the cruising zeitgeist. But take it from me: Sometimes the best cruising grounds are hiding in plain sight. Be warned: A visit up this historic waterway has a way of hooking you for life. —Daniel Harding Jr.
Lake Champlain
Vermont is a landlocked state, known for mountains and farmland rather than its waterways. So when I moved here, I was excited to discover that it also harbors a hidden gem for boaters. The unofficial sixth Great Lake, Lake Champlain spans more than 400 square miles and is bordered by Vermont’s Green Mountains, New York’s Adirondack range and Quebec. While the lake might feel out of the way for some boaters, Great Loopers can enter through the Champlain Canal (bridge clearance 17 feet) and exit through the Richelieu River, which flows north into the St. Lawrence. Once on the lake, you are surrounded by spectacular mountain scenery and have access to sheltered bays, historic sites and unique small towns.
I recommend visiting downtown Burlington on the lake’s eastern shore, where you can grab a slip at the Community Boathouse Marina, eat at the dockside restaurant Splash, and explore the local shops along the pedestrian-only Church Street Marketplace. Burlington also hosts regular waterfront concerts and festivals throughout the summer.
Just south of Burlington is Shelburne Bay. Dock at Safe Harbor Shelburne Shipyard and visit Shelburne Farms, a 19th-century estate turned environmental education nonprofit. Still a working farm, it offers tours, workshops and overnight stays at the original mansion.
On Lake Champlain’s western shore in New York is Fort Ticonderoga, an 18th-century star fort that played an important role in the Revolutionary War. Also on this side of the lake is Valcour Island, where boaters can enjoy protected bays, deep anchorages, quiet beaches and more than seven miles of hiking trails.
Lake Champlain may not draw the same crowds as other boating destinations in the Northeast, but that’s part of the appeal. The scenery alone makes it worth the journey, and the small towns, parks and historic sites along its shores only add to the experience. —Carly Sisson
Salem, Massachusetts
When I started at Sail (Soundings’ sister publication), we worked from a seaside office nestled between a North Sails loft and Dion’s Yacht Yard in Salem, Massachusetts. I was immediately smitten. It was an ideal location for a marine magazine, just a stone’s throw from the dock in the beating heart of one of the state’s thriving marine communities.
From the office, I used to take long, rambling walks to get to know the parks, public beaches and lovely downtown. Though a little thick on the witchy tourism for me—the Salem Witch Trials took place in modern-day Danvers, not Salem itself, but every October the traffic stops and the tourism dollars flow anyway—the downtown is beautiful. It’s also home to excellent restaurants and myriad quaint shops where you can find everything from antiques to souvenirs to sailboat-themed chocolates.
With a naturally deep and protected harbor, Salem was one of America’s most important shipping ports during the 18th and 19th centuries, resulting in a rich and complex maritime history that is still part of the city’s culture. Don’t miss the Peabody Essex Museum, which showcases a unique blend of cultural craftsmanship and art from around the world, including a room dedicated to figureheads from ships of yesteryear and a 16-bedroom Qing Dynasty home from the Huizhou region of China reconstructed in its entirety within the museum’s walls. If history is your thing, plan a walking tour. The city is full of Colonial homes from the 1600s onward that are still standing.
Salem and neighboring Marblehead cup two harbors that are packed with moorings and docks for marine businesses and yacht clubs. A short distance away, islands like Baker’s and Misery make for excellent day trips. An easy commuter rail or a ferry will get you into Boston if you’d rather have a lay day in the city.
The magazine’s offices have since moved, but I’ll always fondly remember our time in Salem. It’s a cultural gem with centuries of maritime history, and it is well worth a visit. —Lydia Mullan
Sanibel Island, Florida
Florida has changed so much since I first moved here in 1979 that I hardly recognize the place. When I was a kid, it was more undeveloped wilderness and orange groves than subdivisions. That Florida is gone, replaced by urban sprawl and high-rises standing like sentries along the beaches. Rapid growth is the norm everywhere in the Sunshine State. Everywhere, that is, except Sanibel.
Anchor off Point Ybel or drive over the bridge from Fort Myers, and you’ll go back in time. With roughly 67 percent of the island designated as a wildlife refuge or protected land, and the condos, where they’re allowed, limited to four stories or less, this is the Florida of my youth. There are miles of white sand beaches, the green blue waters of the Gulf, and just enough restaurants and services to keep the residents taken care of.
Sanibel Marina offers transient slips and can accommodate boats up to 70 feet. It may be tough to find a spot during the winter high season on a weekend, but with plenty of protection behind this island, or behind Captiva to the north, it is one of my favorite anchorages along the Gulf Coast. Drop the hook, come ashore and make your way to the shops along Periwinkle, where you can rent bikes from Billy’s Rentals. Head to the beaches for the best shelling in the Western Hemisphere, and know there will be dolphin sightings. When it’s time for lunch, you can’t go wrong at Grandma Dot’s at the marina or The Blue Giraffe. If you have time and can get a reservation, the Blue Rendezvous is open from October to June and is, for my money, a better meal than anywhere within 100 miles.
If you are looking for nightlife, forget it. The streets roll up at night. We douse our porch lights so as not to confuse nesting sea turtles, and by 9 p.m. all you can hear is the breeze through the palms and, if there is an onshore wind, the breakers. Every now and then, a coyote howls from the preserve; there are about 20 on the island.
Sanibel is the Florida that was. It’s not bright lights or glamour or too many choices for dinner. Sanibel is what drew people to Florida in the first place. — Mario Vittone
Charleston, South Carolina
There’s a reason my hometown has been featured so much as a destination in the past couple of decades. Charleston is simply a remarkable old city. If you live here and have a boat, it’s more remarkable still. Cruisers pass through Charleston all the time, of course, but there are some beautiful detours off the beaten path, too.
Meandering off the ICW down the Stono River, you’ll reach the northern end of Kiawah Island. The water’s pretty deep almost right up to Sandy Point’s beautiful, uninhabited beach. (We pulled a Scout 670 right up to the sand). It gets crowded during summer weekends, but the rest of the time, you’ll have a huge stretch of coast mostly to yourself. If the tide’s not too low and your depthfinder’s working, follow the channel north, tuck in behind Bird Key and cruise up Folly River to Bowens Island restaurant on Folly Creek. Tie off at the dock of this classic fish camp (and setting for Netflix’s Outer Banks) with your tender or smaller cruiser (leave room for the locals’ boats), or paddle right up to the kayak and boat landing for a bowl of shrimp and grits or a fried grouper sandwich. Just down from Bowens is my funky hometown of Folly Beach—hit up Sunset Cay Marina for an overnight mooring. Folly is bike-friendly (bike lanes will take you from Folly to Bowens Island, too) with a fishing pier, good surfing (rent a board from McKevlin’s surf shop), and terrific food. The Lost Dog Cafe is a fave for lunch and breakfast, and you can’t go wrong with fish tacos at Catch 23 or a sunset view at Lolo’s restaurant. The outdoor Chico Feo taco stand has great acoustic acts and an iconic local bar.
In the historic downtown, overnighting at Safe Harbor Charleston City is always a solid bet. After a crab Benedict at the marina’s new Fin & Crab, jump on one of their shuttles or your bikes and make for the world-class South Carolina Aquarium, the newly opened International African American Museum, the Marion Square Farmer’s Market, and the historic King Street District. For dinner, it’s tough to beat Charleston’s legendary Husk followed by a nighttime stroll through the hallowed surrounding neighborhoods, where maritime ghosts still tread. —Chris Dixon
Mackerel Cove
Years ago, my wife and I owned a beautiful Airstream trailer that we used for family camping trips. Because I spent a lot of time on the water for my work as a marine photographer, I longed for the smell of pine trees and campfire smoke in my leisure time. But the problem was that every other New Englander had the same desire, so we’d have to drive many hours north to find good campsites, and even those were packed. After years of great adventures, we decided to sell the Airstream and get a boat. After all, we lived in Jamestown, Rhode Island, near some of the best cruising grounds on the East Coast.
We bought a 1987 Grand Banks 32 and have been exploring the New England coast, including iconic destinations close to home, such as Block Island and Cuttyhunk. But our favorite “just around the corner” anchorage is Mackerel Cove, which is south of the main mooring field of Jamestown and directly across the bay from the Castle Hill Lighthouse. Sunday afternoons get busy, but if you go during the week, you will have the cove to yourself. From our mooring off the Conanicut Yacht club on the east side of Conanicut Island (also known as Jamestown), it’s a 3-mile steam out. Mackerel Cove is about 1 mile long by 0.3 of a mile wide. It has a sandy bottom that makes for perfect holding ground and runs pretty much in a north/south direction, so it’s protected from the prevailing southwest sea breeze. The only direction it’s exposed to is a southerly, and if there is a swell running, conditions get a bit rollie.
The cove is surrounded by a handful of beautiful homes and a rocky shoreline with tons of trees. Sunsets are beautiful, and it’s the perfect place for a swim, a barbecue and a peaceful night on the hook. It’s a no-brainer for a one- or two-night stay at anchor in a peaceful anchorage that looks and feels more like Maine than Rhode Island. And it’s just 20 minutes from our home when running at 8 knots. That’s a far cry from the 4-hour drives we used to take with the Airstream to find the same kind of solitude. I’m so glad we made the switch. —Onne van der Wal
St. Michaels, Maryland
Local lore has it that in the predawn hours of August 10, 1813, as a dozen British war barges headed for the tiny boatbuilding community of St. Michaels, Maryland, the townspeople thought fast, stringing lanterns from masts and trees to draw fire from the invading troops well above the town. “We were fortunate enough not to have a man hurt, although the grapeshot flew like hail in the town, and their balls passed through a number of houses,” read a letter from St. Michaels that was published in Baltimore’s Niles’ Weekly Register.
Something of that spirit seems to linger in this town, whose many high-profile residents somehow manage a low profile while delighting in the picture-perfect Federalist architecture, shopping, gallery-hopping and dining. Whether you’re spending a whole summer cruising Chesapeake Bay or you’re simply looking for a stop that avoids the bustle of Annapolis (or Baltimore), St. Michaels accommodates.
Home to hardly more than 1,000 year-round residents, there is a surprising number of accommodations, watering holes and eateries, all brimming with Eastern Shore flavor and hospitality. The Inn at Perry Cabin—with dock space—is a renowned and somewhat tony choice, made all the more famous after it was featured in the popular early-aughts rom-com Wedding Crashers. Oysters, she-crab soup and crab dip are a must here—and just about anywhere dockside.
The Crab Claw bears a simpler dockside atmosphere with all-you-can-eat blue crab, and is front and center for the annual Chesapeake Cowboys contest, a theatrical, high-speed docking competition between working watermen.
For a little less fanfare, Talbot Street is rife with all the culinary offerings and down-home Eastern Shore hospitality you could want, with a tavern, a steakhouse and several white-tablecloth options fit for the D.C. crowd that flocks here on weekends during summer months. Somehow, through it all, St. Michaels maintains its distinct yachty soul. —Owen Burke
Penns Landing
Few cruising locales can match the depth and breadth of history as Penns Landing, located in the heart of Philadelphia’s waterfront on the Delaware River. It combines breathtaking views of one of the oldest cities in America with a vibrant nightlife and nautical adventures that will pique the interest of any sailor worth his or her salt.
Start the trip by reserving a slip at Penns Landing Marina. You can ask for their friendly dockmaster Richard Goodman. Penns Landing is where Quaker William Penn made landfall in 1682 and quickly established the area as a vital maritime and commercial hub. Today, it is a protected marina surrounded by landscaped parkland and home to a wonderland of historic vessels. The USS Olympia is the oldest floating steel warship in the world. Launched in 1892, it served as Commodore Dewey’s flagship during the Spanish-American war, saw action in WWI and ferried home the Unknown Soldier in 1921. Now lovingly restored, her gleaming white-and-red hull beckons history buffs aboard. Alongside her is Becula, a WWII submarine open for tours, and Moshulu, a historic four-masted steel barque and the world’s largest remaining original windjammer. She’s outfitted as an extravagantly decorated restaurant with decadent cuisine and beverages, and the night views from her decks are worth the trip.
Hop on the nearby ferry for a five-minute ride across the river to theBattleship New Jersey Museum & Memorial on the Camden waterfront, and while there make a visit to the acclaimed Adventure Aquarium, which will thrill adults and kids alike.
A five-block walk from your berth at Penns Landing puts you in the heart of Philadelphia’s historic district, where you can visit the first Free Quaker Meeting House, Independence Hall, the Liberty Bell, Congress Hall, Edgar Allan Poe’s house, the Benjamin Franklin Museum and Franklin Court, where you’ll see fragments of his house and a completely restored printing office. I can’t think of a better place to cruise during this 250th anniversary of the United States. While you are there, don’t forget to try a famed Philly cheesesteak. That culinary staple is just one of the reasons Penns Landing continues to be one of my favorite trips. Maybe it will become one of yours, too. —Gary Caputi
This article was originally published in the July 2026 issue.
