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This trip hands you the keys to unlock some of Italy’s most romantic destinations, with personalized guided tours and insider experiences through Ancient Rome, the dramatically beautiful Amalfi Coast, Florence’s art historical wonders and the rolling hills, villages and vineyards of Tuscany.

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Staying in two of Italy’s most sought-after and dreamed-about locales—perched first on the beautifully dramatic Amalfi Coast and then amid the rolling hills of Tuscany or Umbria—you’ll explore the best and most authentic cultural, food and wine experiences of these two distinct, and distinctly magical, regions.

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Crisscross the Italian boot from the turquoise waters of the Amalfi Coast to the rolling hills, medieval villages and boutique wineries of Tuscany to the cultural capitals of Rome, Florence and Venice. Enjoy the personalized attention of private local guides, soaking up authentic, insider experiences at every stop

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Discover the magical canals of Venice and cobblestoned streets of Florence, the authentic charms of the villages and vineyards of the pastoral Tuscan countryside, and the hidden gems of the Italian Riviera and Cinque Terre.

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Experience the best of Italian food and wine, art and antiquities in the cultural capitals of Rome, Florence and Venice—visiting both well-known highlights and off-the-beaten-path finds—and discover the pastoral charms of Tuscany’s most picturesque villages and sought-after wineries.

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Travel through some of Italy’s most picture-perfect regions of the north, beginning with the luxury of Lake Como (or, alternatively, the fashion capital of the world, Milan). From there, continue on exploring the lush countryside of Piedmont, full of verdant hills, renowned vineyards and culinary delights. Close out the trip in the idyllic Italian Riviera, finding your perfect balance of relaxation and adventure in this seaside paradise.

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Abounding in ancient Greek temples, majestic seaside and rugged landscapes, the island of Sicily boasts an enticing balance of natural beauty, food, wine, history and culture. Given Sicily's proximity to northern Africa and Greece, its churches mix Norman and Arab influences, while its cuisine embodies southern Italian with an exotic flare.

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Venture to some of Italy’s northernmost stretches, starting with the romantic shores, charming coastal villages and alpine landscapes of chic and charming Lake Como. From there, continue on to the storied canals and palazzos of Venice and the cobbled streets and architectural icons of Verona— the setting of Shakespeare’s celebrated Romeo & Juliet.

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Experience the iconic splendor and picturesque resort towns of the Dolomite mountains, hitting famed ski slopes and warming up in charming lodges. Bookend your time in the Alps with other adventures through Italy's Veneto region in the northeast corner of the boot, from the floating city of Venice to the holiday markets of Verona. Summer travelers will enjoy hiking and biking the majestic Dolomites, with the option to end their trip in the peaceful paradise of Lake Garda.