If you want to get under the surface of the city, Context Travel ★★ (www.contexttravel.com; (tel) 800/691-6036 in the U.S. or 06-96727371 in Italy) offers insightful culture tours led by academics and other experts in their field in a variety of specialties, from the gastronomic to the archaeological and artistic. Tours are limited to six people and cost around 95€ per person. Context also conducts a guided walk through the Vasari Corridor. The quality of Context’s walks are unmatched, and well worth the outlay.

Offerings from CAF Tours (www.caftours.com; tel. 055/283-200) include several themed walks and cooking classes costing from 19€ to over 100€. I Just Drive (www.ijustdrive.us; tel. 055/093-5928) offers fully equipped cars (Wi-Fi, complimentary bottle of Prosecco) plus an English-speaking driver for various themed visits; for example, you can book a ride in a luxury Bentley or Mercedes up to San Miniato al Monte at dusk (1.5 hr.; 129€). They also operate full-day and half-day private and group food and wine tours into the Chianti hills. For more options, surf to Viator.com, a marketplace site that lists a wide range locally organized tours and activities, reviewed by travelers.

Tour marketplaces (and apps) such as Viator.com and GetYourGuide.com also have a vast range of locally organized tours and activities, reviewed and rated by users. Note: Don't be tempted to book airport or rail station transfers via the tour companies—it is much cheaper to call a cab and pay the very reasonable fixed local rates.

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Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.