Isola Bella in the middle of Lake Maggiore, Italy.
country flag

Italy Vacation Ideas: 14 Amazing Italy Itinerary Packages

Ratings of Zicasso's Service
<p>It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation Ideas is here to provide you with the inspiration you need to create a personalized experience tailored to your interests. From wine tasting in Tuscany to trekking in the Dolomites and swimming in the Mediterranean, a grand trip awaits. Explore the endless opportunities with the sample itineraries below.</p>

It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation...

It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation Ideas is here to provide you with the inspiration you need to create a personalized experience tailored to your interests. From wine tasting in Tuscany to trekking in the Dolomites and swimming in the Mediterranean, a grand trip awaits. Explore the endless opportunities with the sample itineraries below.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
Positano, Italy

Italy Family Vacation: Coastline, History, and Food

Places Visited: Sorrento, Pompeii +5 more
Places Visited: Sorrento, Pompeii, Positano, Rome, Florence +2 more

10 Day Custom Tour

From $4,500

Civita di Bagnoregio is one of the most unusual sights in Italy.

Immersive Italy Vacation: North to South

Places Visited: Milan, Venice +7 more
Places Visited: Milan, Venice, Florence, Bologna, Rome +4 more

12 Day Custom Tour

From $5,400

Medieval city of Matera in Southern Italy during a sunset

Exclusive Southern Italy Vacation: Sorrento, Matera, Ostuni

Places Visited: Sorrento, Capri +10 more
Places Visited: Sorrento, Capri, Herculaneum, Paestum, Matera +7 more

12 Day Custom Tour

From $11,700

Mountain side village of Castelmezzano in the Potenza Province of Southern Italy

10 Days Off the Beaten Path Tour of Southern Italy and Sicily

Places Visited: Naples, Sorrento +4 more
Places Visited: Naples, Sorrento, Palermo (City), Matera, Cosenza +1 more

10 Day Custom Tour

From $4,500

Aragon Castle on Ischia Island.

Gems of the Mediterranean Italy Vacation

Places Visited: Capri, Ischia +3 more
Places Visited: Capri, Ischia, Ponza, Ventonete, Rome 

9 Day Custom Tour

From $6,600

Couple taking sunset gondola ride on the Grand Canal in Venice, Italy

Romantic Italy Getaway: Art, Food, Gondolas & More

Places Visited: Florence, Pisa +6 more
Places Visited: Florence, Pisa, Lucca, Vernazza, Riomaggiore +3 more

7 Day Custom Tour

From $3,200

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
Explore the ancient Roman city of Pompeii, near Naples

A Serene Senior’s Tour of Southern Italy and Sicily

Places Visited: Palermo (City), Taormina +3 more
Places Visited: Palermo (City), Taormina, Sorrento, Naples, Matera 

7 Day Custom Tour

From $3,200

Explore the streets of Renaissance Florence, Palazzo Vecchio.

Highlights of Italy Tour: Venice to Sorrento

Places Visited: Venice,  Florence +10 more
Places Visited: Venice,  Florence,  Siena,  Chianti,  Pisa +7 more

13 Day Custom Tour

From $5,900

Statues of saints on top of St. Peter's Basilica in Rome, Italy

10-Day Italy: Rome, Florence and Venice

Places Visited: Rome, Florence +8 more
Places Visited: Rome, Florence, Sorano, Montalcino, Siena +5 more

10 Day Custom Tour

From $4,500

Italy Tour for Food Lovers

Italy Tour for Food Lovers

Places Visited: Venice, Florence +3 more
Places Visited: Venice, Florence, Rome, Tuscany, Sorrento 

12 Day Custom Tour

From $5,400

Frediano castle in Florence, Italy

Essence of Italy Tour: Cities, Ruins, Canals, History & Beauty

Places Visited: Rome,  Naples +7 more
Places Visited: Rome,  Naples,  Pompeii,  Assisi, Deruta +4 more

11 Day Custom Tour

From $5,000

St. Francis of Assis Basilica in Umbria, Italy

Perfect Italy Vacation for Senior Travelers

Places Visited: Milan, Bellagio +12 more
Places Visited: Milan, Bellagio, Santa Maria delle Grazie, Pinacoteca de Brera, Venice +9 more

17 Day Custom Tour

From $7,000

Show More(2 itineraries)

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Travel Agents with the Best Italy Vacation Ideas

See all Agents

Reviews of Zicasso's Referral Service

4.9 stars based on 5892 reviews.

Italy 25th Anniversary Travel Review: Positano, Sorrento,...

This was possibly the best vacation we have ever taken. A fitting trip to mark our 25th anniversary, we will remember our days in Positano and Sorrento forever. Everything was perfect and the service and support were extraordinary.

Zicasso's travel specialist and the other people were always super-helpful and friendly. The hotels they chose for us in particular were exactly what we wanted. I can’t think of a single issue. Transport, transfers, etc., were perfect. The only bad part was that we had to return to normal life afterwards! We highly recommend our travel company to anyone! Grazie mille!

Reviewed By Mauro A.

Italy Trip Review: Amalfi Coast, Herculaneum, Vatican, Capri,...

We had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

Reviewed By James T.

Italy Vacation Review: Positano, Boat Tour, History, 16-Day...

I want to give a huge shoutout to Zicasso's trip coordinator. She was our coordinator through WhatsApp. She was always available, provided quick solutions and documents whenever we needed them. Given a few airline delays, we needed to adapt our itinerary rapidly and she always came in clutch.The itinerary was put together very fast, as we approached this travel company six weeks before our desired travel dates. We had an amazing time and all the activities were tailored to our interests. We would highly recommend them for any Italy travel.

Reviewed By Brad B.

Italy Tour Review: 9 Nights

It was very good and lived up to our expectations.

Reviewed By Sarpreet B.

Italy Honeymoon Review: Venice, Amalfi Coast, Florence,...

Zicasso’s travel agent did an exceptional job planning our honeymoon. The experience was well thought out, properly paced, and was truly the trip of a lifetime. The travel agent was always accessible and ready to help. Her organization ensured we had access to helpful phone numbers and information, yet she was always available if we needed to reach out (which we really didn’t because the trip was so well planned). I highly recommend this tour operator!

Reviewed By Presley S.

Greece, Italy Vacation Review: Athens, Private Tour, 18-Night...

Zicasso’s travel consultant and his entire team from Zicasso's travel agency were truly spectacular. We spent a long time planning a very involved trip and had many discussions with the travel consultant about very specific needs, wants, and desires long before we stepped on a plane.

We went to Greece and Italy, and all of the hotels, transports, and adventures were as good or better than we imagined. As a family, we were hoping for a trip of a lifetime and that is exactly what we got. He went above and beyond each step of the way. He even joined us one evening in Athens and took us on a private tour of some of his favorite places there!

I cannot thank and recommend him and his team enough. It’s a bit of a gamble planning such an intricate and expensive trip long distance. It was a magical time and all of it was due to the professionalism of the travel consultant. We are forever grateful!

Reviewed By Woody W.