Escape to the breathtaking coastlines and ancient wonders of Southern Italy with an exclusive seven-night package starting at just $1,599 per person, complete with flights, four-star hotels, a rental car, and immersive local experiences.

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The rugged coastlines, ancient ruins, and culinary triumphs of Southern Italy are now within reach thanks to a spectacular vacation package starting at just $1,599 per person. Negotiated exclusively for Travelzoo members, this sweeping seven-night getaway bundles together everything needed for a dream Italian escape: roundtrip international flights, two distinct four-star hotel stays, a manual rental car, daily breakfast, and unforgettable guided experiences that highlight the region’s incredible history and cuisine.

Two Sides of Southern Italy

This itinerary perfectly balances the electric energy of Naples with the coastal tranquility of Castellammare di Stabia. Naples is Italy turned up to eleven — a chaotic, gorgeous, and deliriously alive metropolis resting beneath the watchful gaze of Mount Vesuvius. Spend your first few days exploring the Centro Storico, a labyrinth of centuries-old streets, hanging laundry, and Baroque churches. Do not miss the Cappella Sansevero to view the Veiled Christ, one of Italy’s most haunting sculptures, or the Museo Archeologico Nazionale, which boasts the best Greco-Roman collection outside of Rome. Stroll down Spaccanapoli, the main artery of old Naples, and grab an authentic pizza a portafoglio before heading to the Lungomare to watch the sun drop over the Bay of Naples.

After diving into the heart of the city, the journey continues south to Castellammare di Stabia. While Naples brings the drama and art, Castellammare is all about relaxation and breathtaking views. Think palm-lined promenades, serene marinas, and steep hills that look plucked straight out of a Renaissance painting. It serves as a perfect, peaceful base near the Amalfi Coast. From here, travelers can easily explore the local thermal baths (Terme di Stabia), wander through the ruins of Villa Arianna and Villa San Marco, or hop on a ferry for a quick ride to the glamorous islands of Capri and Sorrento.

What Is Included in the Package?

This robust deal takes the stress out of international travel planning by bundling the essentials and tossing in generous, exclusive perks. The package includes:

  • International flights from the U.S. to Naples
  • A manual rental car for the entire duration of the trip (upgrades to automatic are available)
  • 3 nights at the Hotel San Francesco Al Monte in Naples, a unique former 16th-century monastery turned four-star hotel
  • A welcome bottle of prosecco during the Naples hotel stay
  • 4 nights at La Medusa Dimora di Charme, an elegant four-star property in Castellammare di Stabia
  • Daily breakfast
  • A guided half-day tour of Pompeii with priority access, allowing visitors to explore the ancient city frozen in volcanic time
  • An authentic Neapolitan pizza and tiramisu cooking class
  • All base taxes and fees

Departure Cities and Pricing

Pricing is tiered based on the departure airport. The per-person prices based on double occupancy are as follows:

  • $1,599: Boston, San Francisco
  • $1,649: Los Angeles, Miami, New York (JFK), Newark
  • $1,699: Chicago, Washington, D.C.
  • $1,799: Philadelphia
  • $1,899: Atlanta

Note: Other departure cities are available.

When to Travel and How to Book

The absolute lowest pricing of $1,599 can be found for travel dates spanning November and December. For those looking to travel during a warmer shoulder season, dates in September and October are also on sale, though pricing will vary depending on the exact dates chosen.

Deal Caveat: The provider has not listed a specific booking expiration date, booking window, or exact blackout dates for this offer. Because this crucial timeline information is missing from the deal terms, travelers are highly encouraged to act quickly and confirm availability directly with the provider before the inventory sells out.

This exclusive rate is provided via Travelzoo, meaning a membership is required to access and complete the booking. Travelzoo memberships cost $50 annually, but new users can currently take advantage of a $1 trial for 30 days to secure this vacation.

As with all travel deals, this offer is subject to availability, and prices or terms are subject to change without notice. Always verify specific date restrictions, final flight routes, and any additional taxes or fees directly on the booking page before securing your reservation.

Some or all of this article was crafted with help from AI. All deal content comes from Travelzoo, and all destination content comes from Fodor’s Travel. An editor reviewed and vetted this article before publishing.