You might be whisked into a shopping frenzy at Pryde's Old Westporta famous local kitchen store.
Saturday--Where the Locals Go
Resist the urge to linger in bed because early birds get the sunniest tables at Succotash, a charming little open-air cafe that provides a front-row seat at City Market, the bustling local bazaar. Grin back at the Cake and a Smile breakfast ($5.25), an anthropomorphic pancake with a bacon smirk. After breakfast, stroll to Dutch Flowers to buy a fresh-off-the- waffle-press stroopwafel, an authentic Dutch sweet that's hard to get outside of Holland.
You'll probably desire more shopping at the Plaza, but swing by a few local gems on the way. Head down Grand, and look for the wall-size mural that welcomes you to Bob Jones Shoes, a sole-searcher's paradise. You'll find dozens of bags, 100,000 pairs of shoes, popular brands marked down at least 20%, and a whopping clearance rack. Your next stop is Pryde's Old Westport, a kitchen store overflowing with must-have gadgets, painted stoneware, specialty bakeware, and pretty linens. The friendly employees will offer you a complimentary mug of fresh coffee or tea. We dare you to leave empty-handed.
Wander around Westport, a charming neighborhood full of antiques stores and little shops. You might find a first edition Hemingway, a 100-year-old map, or a personal note signed by JFK at Spivey's Rare Books, Maps, and Fine Arts. For lunch, pop into Cupini's, a little Italian deli with an ample selection of hot panini sandwiches, homemade pastas, and spinach pies--all for around $6. Get a good whiff of the olive bar, and shop for imported goods in their market next door.
Spend the afternoon shopping at the Plaza; then stroll over for an aperitif at The Lounge at The Fairmont, an upscale place that's classy but not stuffy. The nightly live jazz starts at 5 p.m., and there's no cover charge, so you can splurge on a chocolate martini. They have enough specialty drinks for you to try a new one every day of the year. Plus, you can order sushi for $1 a piece--a steal! It's a fun, affordable way to enjoy the city's fanciest hotel.
Head a few blocks south for wining and dining at Joe D's Winebar-Café and Patio. You gotta love a restaurant with a one-page menu and a four-page wine list. A local favorite, its changing menu features pastas, seafood, and entrées with a European flair ($14 to $25), not to mention plenty of vino (50 selections by the glass, 200 by the bottle).