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Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.

Tucked away on an eight-acre estate at the top of St. Helena’s main street, Harvest Inn could easily be mistaken for a private country manse somewhere in England, or even northern France. Its lush gardens are traversed by winding pathways, and its brick-accented, Tudor-inspired architecture suggests somewhere far more Old World than upstart Napa. Even its sinuous pools and cozy rooms (many with fireplaces and private outdoor hot tubs, mind you) are reminiscent of a style somewhat less rustic-chic than tends to be in vogue here in wine country. Indeed, by Napa Valley standards, the intimate inn is part of the old guard, its original 25 rooms dating back to 1975, just after the famed Judgment of Paris tasting brought the region’s New World wines into the international spotlight.

But the Harvest Inn is no less luxurious than the new resorts popping up all over Napa Valley. It has one of the most desirable locations in one of the most desirable parts of the world, surrounded by celebrated vineyards and presiding over arguably the most picturesque town in wine country. It also features a popular restaurant, Harvest Table, which serves dishes full of ingredients from the hotel’s on-site vegetable and herb garden.

At this Charleston hit, James Beard Award–winning chef Sean Brock reinterprets traditional Southern dishes with a steadfast commitment to local and regional ingredients—the restaurant even has its own garden. Constantly changing, the menu is filled with inventive new takes on Southern cuisine, such as pig’s ear lettuce wraps done up “buffalo” or “Kentukyaki” style.

Don’t miss the Carolina Grouper—it’s one of the most beautiful dishes at this establishment, and a regional classic you have to try while visiting Charleston.

Note that the restaurant also has locations in Nashville, TN and Savannah, GA.

Local chef Donnie Masterton long ago refined the art of matching sensory experience to fine food, and The Restaurant, on Sollano in the Centro, offers thrills on every level. Dinner here is an occasion for shirts with collars for men and shoes otherwise reserved for dancing for the women. (Dancing, by the way, often erupts in the bar in the wee hours, so it’s good to be prepared.) And while every night at Donnie’s proves a visual treat, Thursday nights are the see-and-be-seen scene, when locals stop in for gourmet burgers—available that night alone—with their Chateau Puy Blanquet St. Emilion Grand Cru.

Formerly the private residence of Gioacchino Murat, king of Naples and Napoleon’s brother-in-law, Palazzo Murat has the mark of aristocracy—white-walled interiors are outfitted with elegant antiques, oil paintings, and decorative tiled floors—but also the welcoming atmosphere of a dear friend’s home. The 18th-century villa is tucked away behind cascades of bright bougainvillea and greenery-filled grounds fragrant with jasmine and citrus trees yet centrally located in Positano’s pedestrian zone, making it an ideal base for shopping holidays and seaside idylls alike. The pool is especially impressive, flanked by a lawn studded with chic sunbeds and backed by a storybook scene of pastel-hued houses stacked higgledy-piggledy along the hillside. Just steps away is the charming Al Palazzo restaurant, which incorporates ingredients from its vegetable patch and twinkles with candlelight in the evenings. As for the guest rooms, soothing white spaces are accented with pops of blue and lemon yellow, and French doors open onto lovely balconies with views of the gardens, town, or sea.

A buzz surrounds the Smyth, located smack in the heart of TriBeCa, with its recent reinvention: Chef Andrew Carmellini has revitalized the restaurant space, making it a destination for diners from across the city, and a redesign from Gachot Studios has brought a fresh feel to the decor. The new residential-feeling lobby is meant to be your TriBeCa living room, with all the neighborhood’s shopping, galleries, spas, Michelin-rated restaurants, and attractions right on the doorstep. One of downtown’s most poignant landmarks, the 9/11 Memorial, is a few short blocks away. Mirroring the neighborhood’s style, this hotel is understated and chic. Grab a stool next to TriBeCa’s designers, filmmakers, and photographers for a cocktail at the Evening Bar.

Saline is the most beautiful and the most famous beach in St. Barths. From the shore, you cannot see any building: no fancy bar, no posh restaurant, nothing. Just the wild beach and you. Saline Beach never really gets crowded, as the island is too small to have actual crowds. But it is a true luxury, early morning, to come there for a nice swim. More than once, I’ve been able to be the only one there. This long, beautiful, renowned beach was just mine! It is okay to do nude sunbathing in Saline, but it’s better if you do it on the far sides of the beach. Indeed, the middle part is where the trail arrives from the parking lot and you do not want to make families feel uncomfortable. Even if nobody really cared. Again, early morning, it is just a couple of people here and nobody minds if you swim naked in this pure Caribbean blue water. Vive la liberté ! My tip: Bring a bottle of water if you are planning on staying for long, as there is no store on the beach. Nothing!

Rugged Monhegan, aka the Artists’ Island, lies about a dozen miles out to sea, and is reachable only by passenger ferries. About 60 hardy souls live here year-round, most making a living from the sea. If you get a sense of déjà vu when visiting Monhegan, it’s likely because so many of the island’s icons and vistas have been painted by American masters, including Robert Henri, Rockwell Kent, Jamie Wyeth, George Bellows, Edward Hopper, James Fitzgerald, Andrew Wyeth, Alice Kent Stoddard, Reuben Tam, and William Kienbusch. Artists and art lovers come in summer; bird-watchers flock here in spring and fall. Hiking trails access remote rocky beaches and craggy headlands. Go for the experience, the art, and the hiking, and don’t miss the museum at the lighthouse.

At Point Udall, on the east coast of St. Croix, a sundial called Millennium Monument was erected for the New Year’s celebration in 2000. The stark sculpture represents the azimuth of the first sunrise of that year, the new millennium, at this easternmost point of the United States. Point Udall also affords visitors panoramic views and marks the starting point of a hike that leads to the beach at Isaac Bay.

Located in some of the last remaining coastal canyons in Southern California, Laguna Coast Wilderness Park offers some 40 miles of hiking trails that wind through oak and sycamore woodlands and up onto ridges with sweeping ocean views. The park is also part of the Natural Community Conservation Planning program, which helps protect rare and endangered species, so visitors should keep their eyes peeled for animals like the California gnatcatcher and the orange-throated whiptail. You might even spot mule deer, long-tailed weasels, bobcats, and red-tailed hawks while exploring the park’s 7,000 acres of pristine wilderness. Stop by the Nix Nature Center on your way in for maps, information, and anything else you might need for an epic hike.

Established in 1993, Dawson Cole Fine Art is one of Laguna’s top galleries, with works by such big names as Picasso, Matisse, Chuck Close, Wayne Thiebaud, and more. Here, the focus is on contemporary and modern art, with everything from sculpture to drawings to prints on display. When you’re done browsing the showroom, head out back to the stunning sculpture garden, where you can check out even more art while soaking up the California sunshine.

You can find stunning tide pools all along the coast of Laguna Beach, but the ones at Wood’s Cove are unique because they’re deep enough for swimming. Part of a rocky outcropping called Cactus Point—which is also home to Orange County’s only blowhole—the pools are full of exciting marine life, from hermit crabs and sea stars to colorful sea anemones. When swimming here, just be sure to leave everything exactly as you found it. The tide pools fall within a protected area, meaning that taking shells, rocks, sand, or other objects is strictly forbidden. And keep an eye on the tides—it’s best, and safest, to visit at low tide when the risk of crashing waves is minimal.

Though there are plenty of surf shops to be found around Laguna and Dana Point, none is more important to the community than Hobie. Way back in 1950, Hobie Alter started shaping surfboards in his family’s Laguna Beach summer home. In 1954, he opened Southern California’s first surf shop in Dana Point, where his brand became synonymous with innovation and craftsmanship. Some 70 years later, his surfboards remain a favorite of top athletes like Phil Edwards, Joey Cabell, and Corky Carroll and continue to inspire surfers all over the world. Stop into the shop, which now stands just two blocks from the original location, to pick up a board of your own, plus apparel, accessories, and everything else you need for hanging ten.

Just steps from the sea, on the pine-shaded terrace of the Cheval Blanc St. Tropez (formerly La Résidence de la Pinède hotel), the Vague d’Or celebrates the riches of the sea. Chef Arnaud Dockele’s passion for the region is evident in each bite—and Michelin inspectors have given three stars to the kitchen to reward his creativity in dishes like spider crab in a citrus bath; a verbena-infused bouillon; and abalone served with locally grown onions. Pastry chef Guillaume Godin picks his inspirations from nearby orchards with desserts based on apricots and almonds and local lemons that make the perfect end to a meal under the stars.

Mollusk is a neighborhood surf shop that sells clothing and great boards. They carry my surfboards and handplanes [for body surfing]. They occasionally host art shows and live music. The shop is sort of like the cornerstone of the Sunset. 4500 Irving St., (415) 564-6300, mollusksurfshop.com. This story appeared in the January/February 2012 issue.