Sailing Destinations

1. Kiawah Island, South Carolina
This exquisite barrier island is home to 10 miles of unspoiled fine-sand beach; wild-growing palmetto, oak, and magnolia trees; a veritable Noah's ark's worth of mammals and rare birds; and 1,626 lucky residents. With small-town charms and proximity to the gracious urbanity of Charleston, Kiawah makes the ideal possible: a vacation-like lifestyle with easy access to commerce and culture. Home to five award-winning golf courses,  30-plus miles of paved paths ideal for biking, and shopping at local hub Freshfields Village, residents often kayak down the tree-shaded Kiawah River to watch egrets, herons, and bald eagles enjoying their sanctuary


2. Naples, Florida
Credit the romanticism of promoters in the late 1800s, who saw a town much like its Italian namesake, with abundant fishing, the temperate climate on the Gulf of Mexico, and a view that surpassed the Bay of Naples in its grandeur. This lively town lives up to its international reputation.

With rich cultural offerings (including resident orchestral and theater groups), this town of just fewer than 20,000 people offers big-city-pay-offs minutes from beaches with some of the finest snowy white sand in the region. A strong arts community has kept the downtown scene as beautiful as the shoreline. Shopping mavens love to scout for antiques and artisans finds at Tin City, an open-air marketplace. Always a center for fresh seafood, the town as undergone a recent culinary boom. And with so much within reach of its neighborhoods, it's one of the most walkable cities on our list.

 

3. Sausalito, California
Perched on the steep, wooded hillsides that give way to Marin County's Richardson Bay, this town of more than 7,000 lucky souls just north of the Golden Gate Bridge is surrounded by the lush Golden Gate National Recreation Area. (Locals rave about nearby Muir Beach's clean white sands and crystal-clear water.) Sausalito is home to about 400 houseboats, as well, and has one of the only open marinas on San Francisco Bay's coast.

The zeitgeist here echoes its bohemian roots as an artists' colony while also hosting well-heeled inhabitants. Café life informs the pace—start your morning like locals do, with an espresso at Poggio, Sausalito Bakery & Café, Il Piccolo Café, or Caffe Tutti. Then wind down your day with wine tasting—and if you score a night on a Sausalito houseboat, your life is pretty much complete.

4. Tiburon, California
Don't be put off by the fact that its name is the Spanish word for shark—Tiburon is one benign and happy place, settled on the steep-hilled tip of the Tiburon peninsula. One of the many lovely things about living in this town of fewer than 10,000 folks is that you can commute to San Francisco by fast ferry: no gridlock. A revitalized Main Street that made all the town's popular boutiques and restaurants handicapped accessible without forgoing quaint streetscapes is testimony to the beating heart in Tiburon. So are the top-notch schools, which brought in the highest rankings in our survey.

Perhaps most emblematic of the welcome in Tiburon is in the philosophy of one of its oldest restaurants, the beloved waterfront hangout Sam's Anchor Cafe (one of the only restaurants in the San Francisco Bay with a public dock): &;;;;;;;;Pull up. Tie up. Stay a while.&;;;;;;;; It's that kind of place.

5. Laguna Beach, California
Among Orange County's high-profile, high-priced developments, this quaint, artistic village anchored by a walkable downtown has always marched to its own drummer. From its founding as an artists' colony, Laguna Beach embraces the diverse, with funky downtown restaurants, surfing culture, and a summer full of art festivals. (Luxe outposts like the Ritz-Carlton and Montage offer high-end comforts, too.)

While some other California coastal towns piled up commerce on their shores, Laguna fought for open space, and now its nearly 25,000 residents reap the benefits of sweeping views and unparalleled public access to some of the most unspoiled coves in America
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6. Half Moon Bay, California
Everyone's first visit to Half Moon Bay feels as close to a &;;;;;;;;eureka!&;;;;;;;; discovery moment as there is. Your car navigates that vertiginous road over the coastal hills from sprawling Silicon Valley, and then you descend upon this little gem nestled against the Pacific. The place is simply overwhelmed by the abundance of organic produce grown there. (Go in fall and you'll see a sea of the town's famed pumpkins.) That's the magic of this fertile township of more than 12,000 residents that was first discovered and cultivated by 18th-century Spanish settlers, and proudly maintains its agricultural heritage into the iPad era.

7. Chatham, Massachusetts
Cape Cod, redolent with the summer perfume of suntan lotion and the tang of saltwater taffy, holds in the crook of its sandy elbow this historic little town. Pure New England in its shingled cottages, cozy along its narrow streets, Chatham maintains the small-scale beauty of its 18-century beginnings. A sense of community permeates the town (the year-round population of 6,625 more than triples in the summer), particularly among the family-owned and operates shops, restaurants, and businesses that dot downtown. Add to that a pretty little gazebo on Main Street for concerts, the bleached-white stalwart beauty of the Chatham Lighthouse, the 2 p.m.-to-4 p.m. ritual of strolling to the pier to watch the fleet come in, and the colorful presence of a local baseball team, the Chatham Anglers, for more old-fashioned fun.

8. Jupiter, Florida
Hundreds of rare loggerhead turtles know a paradise when they find one. Juno Beach, a white strand of sand along the southern Florida coast, is one of their favorite nesting places. Just north of that beach sits Jupiter, a relaxed beachfront town with 40,000 year-round residents who've chosen to nest along this network of inlets and waterways.

Life in Jupiter is easygoing and low-key, and yet there's access to plenty of luxury amenities, whether you're a visitor or a resident. On the down-home front, baseball devotees love the proximity to spring training—both the St. Louis Cardinals and Miami Marlins train and play at Jupiter's Roger Dean Stadium. And tying it all together are those lovely Florida Atlantic coast beaches—long, broad, and ranked consistently among the healthiest beaches on our list.

9. Lahaina, Hawaii
T
he Hawaiian kings knew that Lahaina was the crown jewel of the islands. Which is why this town of 11,700 was once the royal capital of Maui Loa in antiquity. Now it's the charming gateway to Maui's world-famous Ka'anapali and Kapalua beach resorts to the north. Its banyan trees add a courtly air to the downtown, and its brightly colored Front Street, busy with shops and galleries, keeps things lively. Lahaina has nearly perfect air quality, and when you add its dry, sunny climate in a tropical paradise, that makes life pretty ideal.

Long a favored harbor for American whaling vessels, Lahaina maintains an exotic tinge of a mid-19th-century Hawaiian seaport in its architecture and vibe. The seafaring tradition continues each year, when the town hosts the finish of the Vic-Mauo Yacht race, the longest offshore sailboat race on the West Coast, held every June through July
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10. Marblehead, Massachusetts
A great harbor will always make a great coastal town, and Marblehead is exhibit A. With a sheltered harbor ringed by a rocky peninsula and a sandbar, this proud town of 19,800 on Massachusett's North Shore has spawned generations of great sailors.

Since the late 1800s, Marblehead has been able to claim its title as yachting capital of the United States, counting six yacht clubs and the oldest junior yacht club in America. On any weekend, the harbor fills with the furled sails of regatta competition. Less than an hour from Boston, Marblehead boasts a highly educated population that has driven the town to maintain some of the highest-ranked schools on our list.

11. Stinson Beach, California
Living in Stinson Beach is like being on a perpetual honeymoon. It's that romantic. Maybe because the area used to be only accessible from San Francisco by schooner, or by foot over the Dipsea Trail. Eventually, a dirt road was carved along the coast from Sausalito, and a tent c sprang up among the willows. Now, 773 homes dot this Route 1 gem about 25 miles north of San Francisco—with 3 1/2 miles of sand that are among the cleanest stretches of beach in California. Plus, there are surfers, rugged natural beauty everywhere you look, and lots of sand dollars for shell-collecting walks.

12. Cohasset, Massachusetts
Insiders who know New England coastal life know that Boston's South Shore has some of the most picturesque (and hard to get to) towns there are. And those townfolk are all the luckier for their splendid isolation. Chief among those secret-treasure towns may be Cohasset, a former fishing village tucked in along the rocky shores where greater Boston Harbor ends and Massachusetts Bay begins.

Cohasset's beauty drew painter Maurice Prendergast, who captured its colors in famous oils. With only 7,500 residents, Cohasset offers a large park, two beaches for residents, and a wildlife sanctuary. Shh. Don't tell another

13. Duxbury, Massachusetts
While New England's Wanoag Indians had enjoyed the sea-borne bounty of this shoreline on Cape Cod Bay for centuries, it was pilgrim Myles Standish who settled in an area now known as Standish Shore, in 1637.

Did that famous Pilgrim envision the community that would grow here, out of shipping and farming (Duxbury is dotted with the deep red of cranberry bogs, and its oyster farming is on the rise), to hold one of the United States' top 12 public high schools? Perhaps. A community commitment to education keeps this town of 14,200 residents a desirous outpost for Boston commuters. And clean air and spacious views of the bay make it a yea

14. Solomons Island, Maryland
Tidewater living is about some fresh oysters for dinner and an icy beer, about summer hospitality and quiet pride in community. It's about a legacy of fishing, shellfishing, and explorations. And Solomons, tucked along where the Patuxent River meets Chesapeake Bay, breathes these qualities among its tidy, whitewashed homes and businesses.

A favorite getaway spot for the Baltimore-Washington area, this tiny settlement of 2,400 boasts marinas, seafood joints (including a heralded spot, Stoney's Seafood House), a well-worn boardwalk forstrolling, and the gorgeous Annmarie Sculpture Garden and Arts Center, which shows world-class work on loan from the National Gallery of Art or the Smithsonian. It's like finding a pearl. And still getting to eat the oyster. Every day.