$799 & up – Italy in Holiday Season: 4-City Trip incl. Air

TOP 20 - Sells out quickly!
Christian Alcantara
Deal Expert
'Tis the season to upgrade your Italy vacation to all 4-star hotels for just $30 more per person.

The Deal

UPDATE 11/4/19: Due to fluctuations in airfare, the price has dropped to $799 for a Dec. 3 departure.

Your arrival in Rome will be met with festive lights and decorations; then, in Cinque Terre, enjoy the scenic hilltop views without battling the peak summer crowds; once in Florence, put the finishing touches on your holiday shopping list with unique gifts from the Christmas Market in Piazza Santa Croce; finally, in Venice, enjoy a cup of hot chocolate at Italy's oldest coffee house after a canal visit — all with this itinerary from Tripmasters starting at $799 per person.

  • Roundtrip flights from the U.S. to Rome, returning from Venice, on a full-service airline such as Alitalia
  • 3 nights in Rome, 2 nights in Cinque Terre area, 2 nights in Florence and 2 nights in Venice; hotel upgrade options are available
  • Train transfers between Rome and Cinque Terre, Cinque Terre to Florence and Florence to Venice
  • All taxes and fees

Customize: Want to customize your trip with an additional night in your favorite city; a hop on, hop off panoramic tour in Rome; Pisa Bus tour near Cinque Terre; Florence city walking tour; or a private gondola ride with serenade in Venice? Tripmasters itineraries can also be customized with dozens of options/upgrades including airlines and hotels, some within walking distance of top attractions.

At the time of publication, we found the lowest pricing to be $799-$959 for departures from New York City (all airports) arriving Nov. 25-27, 29-30; Dec. 1-10 (additional departures available year-round).

Additional departure cities available from $929 (lowest price based on Dec. 9 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.

Book by Dec. 11.

* 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.

$799 & up

at Tripmasters

When You Can Go

November-December; additional dates available year-round


Over $200 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 Rome-Cinque Terre-Florence-Venice 9-night deal you saw on Travelzoo.

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