Tuscany: Rolling Hills & Renaissance Wonders

Wine, Art & Timeless Landscapes

Wine, Art & Timeless Landscapes

Indulge in the ultimate Tuscan escape, where Renaissance art, world-class wines, and breathtaking landscapes blend seamlessly in this exclusive 7-day itinerary. Begin in Florence, the heart of Italian culture, where you’ll explore iconic landmarks, savor Michelin-starred dining, and embark on an authentic truffle hunting experience. Journey through the rolling hills of Chianti and Val d’Orcia, tasting prestigious wines and discovering charming medieval villages like Siena, Montepulciano, and San Gimignano. From hands-on cooking classes to private vineyard tours, this immersive adventure is designed for travelers who seek the perfect balance of culture, cuisine, and luxury. Whether admiring Botticelli’s masterpieces or savoring a glass of Brunello under the Tuscan sun, this journey offers an unforgettable taste of Italy’s finest treasures.

Tuscany: Rolling Hills & Renaissance Wonders

Tentative Itinerary

  • Private car pick-up from airport
  • transfer to luxurious hotel in Florence
  • welcome lunch overlooking the Arno
  • private guided tour of historic center
  • Duomo and Ponte Vecchio
  • dinner at a Michelin-starred restaurant.

  • breakfast at hotel
  • truffle hunting in the Tuscan countryside
  • picnic lunch (local cheeses, cured meats, fresh bread)
  • return to Florence
  • Uffizi Gallery (Botticelli, Michelangelo, Leonardo)
  • dinner at a cozy wine bar.

  • private wine tour in Chianti
  • lunch at a charming winery paired with Chianti wines
  • visit several renowned wineries
  • return to Florence
  • relaxed dinner at a local restaurant.

  • private transfer
  • check in to luxurious hotel in city center
  • lunch with traditional Sienese dishes
  • explore historic center
  • Piazza del Campo and Siena Cathedral
  • wine tasting at a local enoteca
  • dinner at a top-rated restaurant.

  • breakfast
  • scenic drive through Val d'Orcia (UNESCO)
  • Pienza lunch (pecorino) at a trattoria
  • Montalcino and Montepulciano
  • wine tastings
  • return to Siena
  • cozy dinner.

  • breakfast
  • private transfer to San Gimignano
  • explore streets and shops
  • café lunch with gelato
  • private cooking class + enjoy the meal you prepared
  • return to Siena
  • leisurely evening.

  • leisurely breakfast
  • last-minute shopping/sightseeing in Siena
  • private transfer to Florence Airport.

Pricing

Double occupancy: $6,995.00

Single occupancy: $8,395.00

25% Deposit DUE upon reservation

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Departure Dates

Year Dates Price pp (double occ.)
2025 July 20-26, 2025 $5,995.00
2026 September 20-26, 2026 $7,195.00
2027 May 23-29, 2027 $7,795.00
2028 June 11-17, 2028 AND June 18-24, 2028 $8,195.00

Essential Travel Guide

Entry & Travel Requirements: ETIAS authorization (2025+) for visa-exempt countries; passport valid 3+ months beyond Schengen departure.
Currency & Payments: Euro; cards widely accepted, carry some cash; tipping discretionary.
Airport: Florence Airport (FLR) Amerigo Vespucci.
Luggage & Packing: 1 personal item, 1 carry-on, 1 checked (50 lbs/23 kg economy); Type E plugs 230V/50Hz, adapter needed from US.

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