$789 & up – Tuscany: 4-City Road Trip w/Flights

TOP 20 - Sells out quickly!
Christian Alcantara
Deal Expert
Tuscany in December is perfect for thermal baths, food festivals and signs of Christmas everywhere.

The Deal

You could write your own Tuscan romance novel with this self-drive itinerary from Tripmasters that starts and ends in Florence, resplendent with colorful lights and holiday decorations. Siena's narrow medieval streets are the pathway to indulging at its Christmas markets, after which you can take the obligatory Leaning Tower of Pisa selfie, then keep shopping in Lucca at Piazza Napoleone — all with this itinerary from Tripmasters starting at $789 per person.

  • Roundtrip flights from the U.S. to Florence, on a full-service airline such as Delta
  • Stay 2 nights in Florence, 1 night in Siena, 1 night in Pisa, 1 night in Lucca and 1 final night in Florence; hotel upgrade options are available
  • Rental car for 4 days
  • All taxes and fees

At the time of publication, we found the lowest pricing to be $789-$889 for departures from New York City (all airports) arriving Nov. 11-18, 20-22, 25-30; Dec. 1-10 (additional departures available year-round).

Additional departure cities available from $799 (lowest price based on Nov. 20 arrival): Atlanta; Boston; Chicago; Dallas; Denver; Ft. Lauderdale; Houston; Kansas City; Los Angeles; Miami; Minneapolis; Nashville; New Orleans; Orlando; Philadelphia; Pittsburgh; Portland, Oregon; San Francisco; Seattle; Tampa; Tulsa; and Washington, D.C.

All itineraries can be customized with dozens of hotel options available, including some within walking distance of top attractions. When booking, travelers will see available hotels and airlines at featured prices or can upgrade to other accommodations and airlines. Sightseeing tours are also available.

Book by Oct. 30.

* Pricing is per person, based on two travelers sharing a room. Solo traveler pricing is available upon request. Air, hotel and tourism taxes are covered. All packages are based on the lowest hotel/air classes available at time of publication, capacity controlled, subject to availability and may change without notice. Restrictions/blackout dates may apply. Please see the individual air carrier’s website for a full, detailed description of baggage charges before making your purchase.

$789 & up

at Tripmasters

When You Can Go



Over $140 vs. DIY pricing

How to Book

Continue to Tripmasters

Use the "Customize and Book" feature to enter departure city and arrival date. Note: The departure date may be different from the arrival date if you have booked an overnight flight.

Book this deal by phone

Call Tripmasters at 1-800-430-0484.

Mention the Florence-Siena-Pisa-Lucca-Florence 6-night deal you saw on Travelzoo.

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$789 & up -- Tuscany: 4-City Road Trip w/Flights

$789 & up

Top 20 Deal — Sells Out Quickly