Rome, Florence, Milan, Venice
$999—Italy for 9 nights: visit 4 cities incl. flights
Connor White
Deal Expert
Explore Italy's greatest cities for $999.
Why We Love This Deal
We rarely see an Italy trip this extensive. On this vacation, you'll visit practically all of Italy's most popular cities. Plus, four-figure savings mean you'll have plenty of extra funds for and pasta and cannoli along the way.
Rome will make you fall in love with antiquity, and Florence, the Renaissance. Milan's fusion of baroque architecture and chic fashion are something of a spectacle. And the waterways of Venice always provide a dreamy welcome.
What's included in this $999-per-person offer:
- International airfare to Rome; return from Venice
- 9 nights at well-reviewed hotels: 3 nights in Rome; 2 nights each in Florence, Milan and Venice
- Train transfers between cities
- Daily breakfast
When to go: Depart on select dates November 2026–January 2027 from Boston, Newark or New York (JFK). Surrounding dates in April–October 2026 and February–March 2027 are also on sale, starting at +$100 per person. Departure dates vary by city; see website for more details.
Additional departures: Atlanta; Chicago; Dallas; Denver; Detroit; Houston; Las Vegas; Los Angeles; Miami; Orlando; Philadelphia; San Francisco; Washington, D.C., departures are available, starting at +$100.
For more information and a full calendar of dates, see our partner's website.
Additional itineraries: This offer is part of a larger sale on Italy packages. You can add time in an additional Italian city—Ischia, Sardinia, Sicily or Sorrento. Or add time in Barcelona, London or Paris; or Lake Como or Lake Garda.
Traveling alone? Travelodeal will waive the single supplement fee (limited to 25 reservations).
Book by April 15.
This offer is booked through, and is therefore subject to, the travel or entertainment provider's terms and conditions, including but not limited to refund and cancellation policy. Become a member to see all offer details and learn how to book.