$1199—Italian island vacation w/flights & car

Just off the "toe" of Italy's boot, Sicily is a storied island with a long history and treasured cuisine. For a week, you'll cruise in your rental car between attractions in the shade of mighty Mt. Etna, stopping to take in Roman ruins or delicious cannoli. Palermo is the island's historic capital, and Ragusa is famous for its twin city centers and Baroque architecture. In Taormina, you can sit in the seats of the ancient Greeks at the Teatro Antico.

What's included in this $1199-per-person offer:

• Roundtrip flights from the U.S. to Catania, Sicily
• Rental car throughout; pickup and drop-off at Catania Airport (CTA)
• 7 nights at well-reviewed hotels
  • 2 nights in Ragusa
  • 3 nights in Palermo
  • 2 nights in Taormina
• Daily breakfast

When to go: Depart on select dates in December 2026–April 2027 and October 2027 from Boston, Chicago (ORD) and New York (JFK). Surrounding dates in November 2026 and May–September 2027 are also on sale, starting at +$100 per person. Departure dates vary by city; see website for more details.

Additional departures: Atlanta; Dallas; Denver; Detroit; Houston (IAH); Las Vegas (LAS); Los Angeles; Miami; Newark; Orlando; Philadelphia; San Francisco; and Washington, D.C., departures are available, starting at +$100 per person.

For more information and a full calendar of dates, see our partner's website.

Additional itineraries: This offer is part of a wider sale on Italy packages. You could add 3 nights in Malta to your week in Sicily; or Sorrento or Sardinia. You can also go north and add 3 nights in Rome, Florence or Venice.