1. The Mogul
Newport, R.I. - For those who wait all year to slouch into a gold-buttoned navy blazer, slip on boat shoes, and entertain clients or family on a classic American sloop, here's the best way to sail from New York City to the nautical heartland of Newport.
The yacht: The Mariner III, a 1920s-era, 122-foot boat that has drawn celebrities (John Barrymore, Madonna, Harrison Ford) with gilded teak-paneled staterooms. The six-person crew can host up to 80 guests. Depart New York's Chelsea Piers around 8 a.m. to reach Newport in time for sunset cocktails ($4,500 for a day trip, $8,000 per night). Stay: If you're not in the water, see it in all its splendor from the 20-room The Chanler at Cliff Walk hotel. Book the plush Nantucket Ocean Villa (around $1,000 a night) for private gardens with panoramic Atlantic views. Eat: Meaty, fresh No-Nonsense Lobsta Rolls at Flo's Clam Shack have been the perfect Newport nosh since 1936. Drink: New Englanders began guzzling Narragansett Draft Lager in 1890; have yours at Midway Bar, an alfresco people-watchers' paradise at the 18th century Clarke Cooke House. Shop: Before embarking from Manhattan, stop in SoHo's Opening Ceremony boutique to buy a pair of limited-edition, retro water shoes ($95) inspired by Timberland classics. See: Get your fill of maritime history at the Museum of Yachting, which is restoring the 133-foot Coronet schooner, built in 1885. Tip: Fans of rope-and-buoy-inflected decor will love the Newport Yachting Center's Arts Festival, Aug. 28-29.
2. The Family
Eastern Caribbean - One key to bringing the brood together is being able to spend time apart. For all their flaws, cruises balance family and free time: You'll find activities aplenty—and containment that eases (some of) your worries about the kids.
Cruise: Gargantuan and enjoyably over the top, Royal Caribbean's Oasis of the Seas is a 100,000-ton floating resort with a shady park, zip line, surfing simulator, ice rink, boardwalk, four pools, and a massive, slow-moving elevator that doubles as a bar. The Eastern Caribbean Cruise option (from $750 per person for seven nights) sets sail from Ft. Lauderdale and affords full days in Nassau, St. Thomas, and St. Martin, which means at least 24 hours on turquoise-water-fronted white sands. Stay: The Royal Family Suite (from $1,750 per person for seven nights) sleeps eight. Eat: Send the kids to Johnny Rockets and try 150 Central Park, with its seven-course menu and expansive wine list. Reserve well in advance. Drink: Perched on the boat's 17th deck, Viking Crown Lounge has a view that's worth the hike. Shop: On St. Thomas, pick up colorful quadrille dancer dolls ($39-$64) at the Native Arts & Crafts Cooperative. See: Sign the family up for the cruise's Voluntourism Program at St. John Virgin Islands National Park. You'll be picked up at St. Thomas and spend a day fixing jungle trails or cleaning beaches. Tip: Rent iPhones ($17.50 per voyage) through the Royal Connect program to avoid hefty roaming charges and track the kids'—or Grandma's—whereabouts.
3. The Twenty-something
San Francisco Bay Area - Neither too remote nor too trafficked, the Bay Area is ideal for those who couldn't bear to be too far from it all: In Berkeley Harbor, you'll get epic wind, choppy waters, and access to San Francisco's locavore bistros and stylish bars.
Sail: In Berkeley, Olympic Circle Sailing Club offers a "Learn to Sail" course ($995 for two weekends or five weekdays); graduates are able to singlehandedly skipper a small boat. Stay: You're better off crossing the bridge to sleep in San Francisco, where the design-focused Clift Hotel sits within steps of quiet, storied Nob Hill. It remains popular for its surreal Philippe Starck lobby, sceney bar, and mod rooms (from $285 per night). Eat: The menu is entirely seasonal at Frances, an already acclaimed new Castro neighborhood spot with a young chef, Melissa Perello, who scours Northern Californian farms for fresh ingredients. Drink: Sip a cucumber gimlet at The Owl Tree, a dive bar turned swanky cocktail spot (with only a few owl-influenced touches) a few blocks from the Clift. Shop: Sailing? There's an app for that: iNavX Marine Navigation ($50) has all the charts you'll need to navigate U.S. coastal waters. See: Arrange to have your lesson on the weekend of July 31 to catch the 22nd Annual Berkeley Kite Festival, which also benefits from the city's gusts. Tip: Avoid seasickness by popping a few ginger tablets (try GNC Natures Fingerprint Ginger Root) before setting sail.
4. The Landlubber
Bryson City, N.C. - If the mere thought of sailing makes you seasick, head to Bryson City, where three of the nation's great rivers drain out of the Smoky Mountains. It's a whitewater paradise, 400-year-old forest, and quaint town all in one.
Paddle: Kayak lessons ($99 per person for a one-day course) at Nantahala Outdoor Center include gear, a picnic lunch, and tuition from champion paddlers. Stay: Watershed Cabins is nestled amid poplars at the top of a windy mountain road. Reserve the Moonstruck (from $215 per night), a grand log-and-stone cabin with a hot tub, outdoor fireplace, and gorge views. Eat: After a long day in the kayak cockpit, savor wild mushroom fritters and brook trout (known locally as "specks") at Reila's Garden, a literal stone's throw from the river. Drink: Sample Nantahala Brewing Co.'s Noon Day IPA at Across the Trax, a woodsy joint loved by travelers and townies alike. Shop: The NOC Gear Shop peddles activewear like Vibram's Fivefingers Sprint, waterproof shoes made to mimic bare feet. See: In Smoky Mountain National Park's western wilds, large stands of old-growth forest are preserved above Appalachian-settlement ruins on the upper reaches of Noland Creek trail. Tip: Flying in and out of Asheville Regional Airport instead of Atlanta or Charlotte saves you four hours in the car, round-trip. Direct flights come from 10 cities, including Chicago, Houston, and New York (a round-trip from O'Hare costs upwards of $370).