Catalina Island, California
Just 22 miles southwest of Los Angeles, Catalina Island is a slice of southern California heaven plunked down in the Pacific. Cars are restricted (there’s not a single stop light) so golf carts and bicycles rule the roads. The one incorporated town, Avalon, and the tiny village of Two Harbors have adorable shops and cafes, but the real scene stealer here is the natural splendor — bald eagle soars over hiking trails that cut through canyons and along the coast; giant kelp forests rise up from the sparkling clean waters to the delight of kayakers and snorkelers. Spots to Hit
The rugged backcountry is perhaps best seen from the passenger seat on a Jeep Eco-Tour
Catalina Country Club, open to the public, has a terrific golf course that overlooks the town of Avalon
Don’t-Miss Events
Explore Avalon’s finest eateries all in one night during the annual Taste Around Avalon (June 2, 2011)
As many as 30 jazz musicians perform during the three-weekend Catalina Island JaxxTrax Festival (September 30 to October 2, 2011)
Dockage
Two Harbors and the outlying coves have loads of moorings; arrive early as they’re assigned first come, first served. Contact the Harbor Department via VHF Channel 9.
Charleston, South Carolina
Gracious Charleston casts a spell over boaters and land-lubber visitors alike. The blend of beautiful mansions, historic cobblestone streets, and southern hospitality is all but irresistible. The city is also a legendary food destination that has only grown in renown the past few years—down-home cooking and sophisticated sass come together in dishes that have even Yankees asking for more. Spots to Hit
The lush grounds and Antebellum-era cabin at Magnolia Plantation & Gardens
Charleston City Market, four blocks of galleries and crafts shops with souvenir-worthy items like woven sweet-grass baskets
Don’t-Miss Events
Slurp bivalves and watch the area’s best shuckers during the Lowcountry Oyster Festival (January 30, 2011)
Charleston Boat Show is the region’s biggest boating expo (January 21-23, 2011)
Charleston Harbor Marina: South Carolina’s largest marina, with views of Fort Sumter, a terrific restaurant, and trolley service to the historic city center. 24 Patriot’s Point Rd., 843-284-7062, www.charlestoncitymarina.com
Chicago, Illinois
The Windy City is known for its deep dish pizza, stunning skyscrapers, world-class museums—and knock-out appeal for boaters. Set on enormous Lake Michigan, Chicago lets the most die-hard captains and skippers embrace their inner city slickers without having to sacrifice their beloved crafts, the best of both worlds, indeed. Spots to Hit
Catch a ball game at Wrigley Field, home of the Chicago Clubs since 1916
The Field Museum sits within the famous Chicago Museum Campus; don’t miss saying hi to Sue, the world’s largest and most complete Tyrannosaurus Rex skeleton
Don’t-Miss Events
Taste of Chicago, in Grant Park, is a 10-day-long celebration featuring food from more than 70 restaurants (June 24-July 4, 2011)
Watch classic films under the stars during the Chicago Outdoor Film Festival, which takes place every Tuesday from mid-July through August
Fort Lauderdale, Florida
Over the years Fort Lauderdale has evolved from a rowdy spring break town into a polished resort destination—and a hub for boaters and megayachters. With unbeatable marine services; a semi-tropical climate; lovely beaches; and loads of first-rate shopping, dining, and entertainment, it’s no wonder the partying undergrads have given way to decidedly discerning cruisers. Spots to Hit
Las Olas Boulevard is popular with visitors and locals alike for upscale shopping and some of the city’s best food.
The excellent Museumof Discovery & Science has exhibits that vividly bring the nearby Everglades to life
Don’t-Miss Events
Fort Lauderdale International Boat Show is the world’s largest in-water boat show, with vendors from around the globe (October 27-November 1, 2011)
The Fourth of July Spectacular is an all-day event with live music, kids’ contests, and a fabulous fireworks display
Dockage
Lauderdale Marine Center: At 50-acres, one of the largest marinas in the country, plus a superb full-service boatyard to boot. 2001 SW 20th St., 954-713-0333, www.lauderdalemarinecenter.com
• Marina Bay Marina Resort offers an impressive array of amenities from a stunning clubhouse to lighted tennis courts along with dockage for boats up to 150 feet. 2525 Marina Bay Drive West,954-791-7600, www.marinabay-fl.com
Key West, Florida
Funky, surprisingly sophisticated, and utterly low-key, Key West is at the extreme southeast end of the United States—so extreme, in fact, that it’s closer mile-wise to Cuba than to mainland Florida. Beyond that, the only thing extreme about it is how extremely delightful it is. Traditional Conch-style cottages and thatched roof open-air bars share street space with excellent boutiques and fine dining restaurants. Tie up, rent a bike, and follow your whims.Wherever you end up you won’t be disappointed. Spots to Hit
Tour Pappa’s Old Key West residence—and glimpse his fantastic study—at the Ernest Hemingway House, now home to more than 60 cats descended from Hemingway’s own felines
The Key West Butterfly & Nature Conservatory is a haven with more than 50 different species of the winged creatures
Don’t-Miss Events
Grow your beard for the 31st Annual Hemingway Look-Alike Contest at Sloppy Joe’s Bar (July 21-24, 2011)
Fantasy Fest is the partying town’s ultimate party: extravagant costumes and debauchery galore (October 21-30, 2011)
Dockage
Conch Harbor Marina: Next to the historic bight, can accommodate vessels to 185 feet. 951 Caroline St., 305-294-2933, www.conchharbormarina.com
The Galleon: 91 slips in a resort-like setting, two blocks from Duval Street. 609 Front St., 305-292-1292, www.galleonmarinakeywest.com
Lake Washington, Washington
An expansive fresh-water lake surrounded by the cities of Seattle, Bellevue, and Kirkland, Lake Washington is an ideal spot for dipping into the area’s vibrant maritime activities and sampling some of its wonderful urban attractions. The Bellevue Collection has an alluring selection of upscale department stores and designer shops; for edgier boutiques, explore Seattle’s Fremont and Ballard districts. The region is justly known as a foodie mecca, and there are stellar restaurants at almost every turn, but also don’t miss a provisioning bonanza: the extraordinary farmers markets sprinkled throughout the neighborhoods. Spots to Hit
Pike Place Market is a vibrant mix of farmers, artisanal food purveyors, and shops; enjoy locally brewed beers and sip coffee from the world’s first Starbucks
Watch the boats come through the working Chittenden Locks; when they’re running, salmon jump through too
Don’t-Miss Events
During SeafairWeekend enjoy hydroplane races & the Boeing Air Show (August 5-7, 2011)
Bumbershoot is a kaleidoscopic celebration of the arts and each year features some of the world’s top musical acts (September 3-5, 2011)
Dockage
Carillon Point Marina located on the shores of Lake Washington with stunning views of the Olympic mountains and Seattle’s skyline, and shopping, restaurants nearby. 3240 Carillon Point Blvd, 425-822-1700, www.carillonpoint.com
Bell Harbor Marina: Lots of moorings, and within easy reach of downtown’s best restaurants and shops. 2203 Alaskan Way, 206-787-3952, www.portseattle.org
Naples, Florida
Edged in sugar-soft white-sand beaches perfect for lounging, cocktail in hand, Naples has just enough glamour to give it a certain fizz but not enough to wipe out the infectiously easy-going attitude. The waters are calm, the weather is balmy, and there’s plenty to do if you tire of lolling (a big if): tennis, deep-sea fishing, and what seem like an endless string of championship golf courses. Spots to Hit
Shop downtown Old Naples along Third and Fifth Streets South for café’s, world-class art galleries, and chic boutiques
Naples Zoo at Caribbean Gardens includes a paved path that winds past exotic animals in an incredible tropical setting
Don’t-Miss Events
Naples Winter Wine Festival brings more than 30 vintners and 17 chefs from around the globe for a 3-day extravaganza (January 28-30, 2011)
The open-air Naples National Art Festival hosts more than 275 artists from around the country (February 26-27, 2011)
Dockage
Naples Bay Resort: Full-service marina with 97-slips and resort amenities including restaurants, swimming pools, tennis courts and a full-service spa. 1500 5th Avenue South,239-530-5134, www.naplesbayresort.com
Newport, Rhode Island
Newport is a diverse and vibrant seaside burg with big-city appeal and a small-town vibe. For many years it hosted the America’s Cup race and it’s still one of the country’s premiere yachting centers. Top-notch art galleries and boutiques populate the walkable neighborhoods, most of which have a distinct maritime charm. Add the miles of New England coastline and breathtaking Gilded Age mansions, and it’s clear why the town is a perennial boaters’ fave. Spots to Hit
The 3.5-mile Cliff Walk,which wends past historic manses and along dramatic coasts
Bannister’s Wharf and Bowen’s Wharf for boutiques running from tony to quirky
Sumptuous Rosecliff, the estate built 1899 for a Nevada silver heiress
Don’t-Miss Events
Sip syrah dockside at the Newport Wine Fest (Aug 19-21, 2011)
Joan Baez and Bob Dylan both had their national debuts at the Newport Folk Festival—what else is there to say? (July 29-31, 2011)
Dockage
Newport Harbor Hotel & Marina :Home port of six sleek vessels that competed for the America’s Cup, with 60 slips for transients. 49 Americas Cup Ave., 401-848-3310, www.thenewport-hotel.com
Newport Yachting Center: Smack in the middle of town, with floating docks to accommodate boats to 180 feet. 4 Commercial Wharf, 410-846-1600, www.newportyachtingcenter.com
Newport Marina: Recently upgraded private wharf with a convenient downtown location. Lee’sWharf, 401-849-2293, www.newportmarina.com
Sag Harbor, New York
The 300-year-old village of Sag Harbor was once a thriving whaling port; now it’s a deliciously laid-back alternative to the go-go Hamptons nearby. The deep-water port is tucked inside Long Island’s South Fork, and everything you could need is easily accessible either on foot or by bike. Spend the day pedaling along sand dunes and along country lanes; then sneak into the Hamptons that night to sample the white-hot action. Spots to Hit
Savor a leisurely cocktail on the porch of the American Hotel and watch the world go by on Main Street
The restored Windmill on Long Wharf is a replica of the original 1806 Beebe mill
Don’t-Miss Events
Sag Harbor HarborFest is aweekend-long celebration that kicks off with a lobster bake and whaleboat races (September 2011)
Dockage
Sag Harbor Yacht Club: Centrally located and can accommodate boats up to 200 feet; the concierge can help with hard-to-get dinner reservations. 27 Bay St., 631-725-0567, www.sagharboryc.com
St. Michaels, Maryland
One of the most picturesque towns on the Chesapeake Bay, St.Michaels draws boaters from across the Eastern Seaboard. The rich watermen’s history and bounty of fresh seafood (try to visit during summer, when steamed blue crabs are in season) belie the area’s industrious heritage. The quaint downtown with its specialty shops and stand-out food proves the locals enjoy life’s finer things, too. Spots to Hit
Stretched across 18 acres along the Miles River, the Chesapeake Bay Maritime Museum exhibits include examples of historic bay working boats, ship models, and more
Sample tasty novelties such as chocolate zin and chambourcin at St. Michaels Winery
Don’t-Miss Events
Annual Antique & Classic Boat Show held at the Maritime Museum showcases a variety of Antique & Classic boats (June 17-19, 2011)
Oysterfest brings live music, boat rides, and oyster stew tastings to the pretty hamlet. (November 5, 2011)
Dockage
Bob Pascal’s St. Michaels Harbour Inn Marina & Spa: 52 transient slips in a tranquil, resort-like setting. 101 N.Harbor Rd., 410-745-9001, www.harbourinn.com
St. Michaels Marina: In the center of town,with a pool, bike rentals, provisioning store, and dockage for boats up to 220 feet. 305 Mulberry St., 800-678-8980, www.stmichaelsmarina.com