Phipps Trips
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Grand Italy & Sicily - Classic Group

Tour, Escorted tour

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Grand Italy & Sicily - Classic Group
Art, food, and scenery combine in this 17-day guided tour through Italy. Revel in Renaissance artwork housed in the Vatican Museums and gaze at Michelangelo’s famous ceiling in the Sistine Chapel. See Rome’s iconic Colosseum as a Local Expert shares its history. In coastal Cinque Terre, stop in a fishing village and cruise the rugged Ligurian coast, admiring the colorful homes perched on the cliffs. See statues of Neptune, Hercules and Cacus, and feast on a steak dinner and local wine in Florence. In Sorrento, meet a Local Expert for a cruise to Capri, where you ascend to Capri town for an unapparelled view of the Mediterranean Sea. In the UNESCO World Heritage Site of Alberobello, meet a restaurateur who will share his farm-to-table philosophy and serve you freshly made orecchiette pasta.


Dining Summary
  • 1 Dinner (D)
  • 16 Breakfast (B)
  • 7 Dinner with Wine (DW)
Choice Highlights
  • Choose between two carefully selected activities
  • Florence: Stand beside Michelangelo's monumental statue, 'David', in the Accademia Gallery, and admire the exquisite technique and absorbing history behind the world's most famous sculpture.
  • Florence: Take a stroll with your Travel Director to Piazza Santa Croce and immerse yourself in the essence of la dolce vita of Florence while you enjoy a typical Italian treat in a local cafe.
Additional Included Highlights
  • Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
  • Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.
  • We carry your bags for you and promptly deliver them to your hotel door.
  • From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
  • Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
  • If your arrival and/or departure flights are as per the itinerary start and end dates, then transfers are available at scheduled times. If your flights are outside these times, or you have booked additional nights accommodation with Insight Vacations, you may purchase transfers or make your own way from/to the airport.
Authentic Dining
  • Rome: Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
  • Florence: Enjoy a traditional Bistecca alla Fiorentina steak dinner paired with delicious local wine, a specialty not to be missed.
  • Alberobello: Learn about local life while savoring a freshly prepared Farm-to-Table meal featuring recipes and flavors typical of the region.
  • Palermo: Experience local customs as you delve into tantalising flavors and rustic dishes served with local wine.
Insight Choice
  • Florence: Stand beside Michelangelo's monumental statue, 'David', in the Accademia Gallery, and admire the exquisite technique and absorbing history behind the world's most famous sculpture.
  • Florence: Take a stroll with your Travel Director to Piazza Santa Croce and immerse yourself in the essence of la dolce vita of Florence while you enjoy a typical Italian treat in a local cafe.
Insight Experiences
  • Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
Make Travel Matter
  • Venice: Witness the ancient skill of glassblowing, now practised by precious few masters. Watch artisans create delicate works of art using rare traditional practices. The workshop's master craftsmen teach visitors about the traditional craft of glassblowing and its history which dates back to the 15th century. Every visit helps to support the workshop and the survival of this traditional craft.  This workshop directly supports United Nations Sustainable Development Goal 11: Sustainable Cities and Communities.
Top Rated Highlights
  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Pisa: Your Local Expert will show you the baptistery bristling with marble spines, and the colonnaded bell tower lurching behind the 11th-century cathedral - the famous Leaning Tower in the Square of Miracles.
  • Cinque Terre: Led by your Local Expert, visit the UNESCO World Heritage Site with dedicated time to explore one of the charming fishing villages.
  • Portofino: Visit this elegant fishing village and admire the colored houses and yachts moored in the harbor.
  • Lake Maggiore: Experience the charming traditional social ritual of la passeggiata in the Italian Lake District. All across Italy, in cities, towns and villages people leave their houses to gently walk streets, from babies in strollers to the most senior citizens. Savor a gelato or glass of wine along the way and observe, as new romances, new babies and new shoes are all put on display. Note the ever-stylish Italians love to dress up for the occasion so feel free add a touch of flair to your outfit!
  • Venice: With your Travel Director cruise to St. Mark's Square and see the Doge's Palace, Bridge of Sighs and St. Mark's Basilica.
  • Venice: Delight in the magic of this charming city as you glide along the canals by gondola.
  • Florence: Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
  • Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
  • Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
  • Capri: Explore Capri town with your Local Expert and see the whitewashed houses, winding alleyways, small cafes, fashionable boutiques and artisans studios.
  • Matera: With your Local Expert explore this town that Mel Gibson chose as the setting for his film 'The Passion of the Christ.'
  • Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
  • Messina: Cross the Straights of Messina to Sicily by ferry.
  • Taormina: Visit the ancient Greek Amphitheater with your Local Expert. Set on a cliff, open to the sky, take your seats and enjoy the view through the crumbling arches to Mount Etna.
  • Taormina: Visit Taormina with a Local Expert and enjoy free time to stroll along Corso Umberto to Piazza IX Aprile.
  • Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.
Well-being
  • Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.
  • Hand sanitizer is freely available on board for you to use throughout the day.

16 Nights Starting At
July 04, 2025 through August 01, 2025
Book by:
July 28, 2025 7:00 PM
Book by 2025-03-06 to receive $679.00 Last Minute Deal Discount. Airfare not included, Various departures
Last Minute Deal: Must book by 2025-03-06
Itinerary Map
Dates & prices
Additional
Offers
Starting From Additional Details
16 Nights from $6,116.00 (USD) Per Person
Book by 2025-03-06 to receive $679.00 Last Minute Deal Discount. Airfare not included, Various departures
July 28, 2025 7:00 PM
16 Nights from $6,925.00 (USD) Per Person
Please Call, Airfare not included
March 31, 2025 7:00 PM
16 Nights from $7,375.00 (USD) Per Person
Airfare not included
April 21, 2025 7:00 PM
16 Nights from $7,500.00 (USD) Per Person
Airfare not included
April 28, 2025 7:00 PM
16 Nights from $7,875.00 (USD) Per Person
Airfare not included
May 05, 2025 7:00 PM
16 Nights from $7,675.00 (USD) Per Person
Airfare not included
May 19, 2025 7:00 PM
16 Nights from $7,475.00 (USD) Per Person
Please Call, Airfare not included
May 26, 2025 7:00 PM
16 Nights from $7,500.00 (USD) Per Person
Airfare not included
June 09, 2025 7:00 PM
16 Nights from $6,566.00 (USD) Per Person
Book by 2025-02-20 to receive $729.00 Last Minute Deal Discount. Airfare not included
June 16, 2025 7:00 PM
16 Nights from $7,195.00 (USD) Per Person
Airfare not included
August 11, 2025 7:00 PM
16 Nights from $6,566.00 (USD) Per Person
Book by 2025-04-24 to receive $729.00 Last Minute Deal Discount. Airfare not included
August 18, 2025 7:00 PM
16 Nights from $7,395.00 (USD) Per Person
Airfare not included
August 25, 2025 7:00 PM
16 Nights from $7,750.00 (USD) Per Person
Airfare not included, Various departures
September 08, 2025 7:00 PM
16 Nights from $7,795.00 (USD) Per Person
Airfare not included, Various departures
September 22, 2025 7:00 PM
16 Nights from $7,895.00 (USD) Per Person
Airfare not included
September 29, 2025 7:00 PM
Additional
Offers















About Insight Vacations
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Learn More About Insight Vacations
More trips from Insight Vacations

There's more to travel than simply visiting new places – join us for experiences that spark your curiosity and take you beyond traditional sightseeing. On our premium guided tours, every day is filled with fascinating facts and intriguing stories, while superior dining nourishes the body and stylish hotels rest the soul.

When you join a guided tour, you travel hassle-free. But when you join an Insight Vacations tour, you travel ‘business class’ - with all the perks.

Discover the superior touring experience you deserve.

Read More

About Insight Vacations

There's more to travel than simply visiting new places – join us for experiences that spark your curiosity and take you beyond traditional sightseeing. On our premium guided tours, every day is filled with fascinating facts and intriguing stories, while superior dining nourishes the body and stylish hotels rest the soul.

When you join a guided tour, you travel hassle-free. But when you join an Insight Vacations tour, you travel ‘business class’ - with all the perks.

Discover the superior touring experience you deserve.

Read More

Learn More About Insight Vacations
More trips from Insight Vacations
Prices are per-person based on double occupancy, unless otherwise noted.