BUDGET:
Getting there: Fly into Baltimore-Washington International (about a one-hour drive St. Michaels) from $69 one-way during frequent airfare sales; nonstop AirTran or Delta.
Stay: Harris Cove Cottages Bed N' Boat is a unique waterfront cottage village (five minutes from downtown) in the heart of a shallow and serene cove of Harris Creek. Explore 100 miles of Chesapeake Bay shoreline, take out a kayak or pedal boat (complimentary) or cook up some fresh crabs on the grill. Eight modern cottages sleep up to a family of four and have expansive waterfront views. Boat and motor rentals available. A two-night stay in a stateroom is $285; $370 for a two-night cottage stay; www.stmichaelscottages.com, 8080 Bozman-Neavitt Rd., 410-745-9701.
Eat: It's partytime during the summer at Foxy's Marina Bar with giant martinis, homemade blue crab cakes, fresh seafood and Angus burgers. Located on the dock, Foxy's draws the locals and tourists seeking an affordable menu and good times. Grilled entrees from $3.95 to $15.95. Steamed seafood items from $8.95 to $28.95 for the seafood Sampler; www.foxysstmichaels.com, 125 Mulberry St., 410-745-4340.
Experience: Enjoy learning about wines at the St. Michaels Winery, a laid back winery open year-round for tastings ($1 sample; $5 glass) without an appointment (suggested for groups of eight and up). Tastings include souvenir wine glass, cheese and crackers. The winery shop sells local cheeses, gourmet mustards made with St. Michaels wine, premium olive oils, tapenades, "Get Wobbly" T-shirts (named for the Gollywobbler wines) and more; www.st-michaels-winery.com, 605 S. Talbot St., 410-745-0808.
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MODERATE:
Getting there: One-way rates to Baltimore start from $107 and require a 21-day advance purchase; from $127 with 14-days; nonstop AirTran or Delta.
Stay: Compliment your stay in this quaint village on Maryland's eastern shore at the Five Gables Inn & Spa. The inn is made up of three charming 19th century homes with 20 well-appointed rooms, an Aveda concept spa, indoor pool, sauna and steam room and a few boutiques. Guests can explore the area with complimentary bicycles or walk to restaurants, upscale boutiques, antique shops and the marina. Rooms range from $260-$425 with expanded continental breakfast through Nov. 1 (weekdays $100 less per night); www.fivegables.com, 209 N. Talbot St., 410-745-0100.
Eat: Inspired by the bistro atmosphere in Paris, the Stein family converted their 100-year-old Victorian house into Bistro St. Michaels. The cozy eatery serves regional favorites, traditional American dishes and classic French cuisine with starters and small plates from $6 to $13; entrees $18 to $26; www.bistrostmichaels.com, 403 S. Talbot St., 410-745-9111.
Experience: The Chesapeake Bay Maritime Museum features nine exhibit buildings displaying regional maritime history and the craft of shipbuilding. The 18-acre campus has 15 unique attractions from the steamboat and oystering buildings to the Hooper Strait Lighthouse and a working boat yard. Admission is $13 adults; $6 children 6-17; www.cbmm.org, 213 N. Talbot St., 410-745-2916.
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SPLURGE:
Getting there: One-way, walk-up Business Class rates to Baltimore start from $438; from $488 into Washington National Airport (about a two-hour drive); nonstop AirTran or Delta.
Stay: The circa 1816 Inn at Perry Cabin has a misleading name. This historic colonial manor house and spa isn't primitive but posh, with intimate guest accommodations and a waterfront setting. Highlights include a heated horizon-edge swimming pool, a full-service spa and fitness center, complimentary bicycles, a movie library and 200-year-old cultivated grounds and gardens. A "Gourmet" package includes daily a la carte breakfast and dinner for two at the inn's Sherwood's Landing, access to the spa, newspaper and WiFi; from $385 per night; www.perrycabin.com, 308 Watkins Lane, 410-745-2200.
Eat: 208 Talbot offers a prix-fixe Chef's menu for $49 per person. Choose from oysters, salads, starters, specials, steaks, chops and dessert to create a personal four-course dinner. Chef Keegan, taught how to cook by his grandmother from Georgia, tweaks Italian and Spanish themes with a touch of "soul" food. A la carte entrees from $25 to $30; www.208talbot.com, 208 N. Talbot St., 410-745-3838.
Experience: Relax while celebrating a special occasion or join in to hoist the sails on the Selina II. This historic vessel heads out on the Miles River for two-hour sails with a narrated history of the picturesque waterfront ($50 per person) or for romantic sunset cruises ($65 each; maximum six passengers) with champagne, wine, beer, water, sodas and hors d'oeuvres; www.sailselina.com, 101 N. Harbor Rd., 410-726-9400.
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