• Italy With Pleasure tailor-made custom tours
  • Italy With Pleasure tailor-made custom tours
  • Italy With Pleasure tailor-made custom tours

Travel Packages

Italy with Pleasure | Flexible Italy Tours

If you are looking for a travel package to a specific area in Italy at a time that suits you, try one of these vacation package tours.

This is a safe and secure way to see Italy. For these private tours travel you will travel with a professional driver and the vehicle is solely for your party (no other passengers). Vehicles are sanitised daily.

We provide on-call local support in English, both before and during the trip.


This five day package allows you to see the best of Puglia.

You will be driven to see trulli in Alberobello.

Visit the fascinating town of Matera, with houses carved into the rock wall and cave churches covered with Byzantine frescoes.

See the famous baroque centre of Lecce, and the whitewashed hilltown of Ostuni. You will visit the stunning town of Polignano a Mare, perched over the Adriatic.

Discover how the range of civilisations that have settled in Puglia have all left their mark. For example, within walking distance you can find a Spanish palazzo, a Byzantine church and a Roman amphitheatre.


There are 3 accommodation options for this tour itinerary:


A) Stay in the vibrant coastal town of Monopoli.
Cost €1550 pp (twin share basis)

B) Stay at the historic estate Masseria Salamina, enjoying their pool and homegrown produce.
Cost €1750 pp (twin share basis)

C) Stay at the 5 star resort Masseria Il Melograno, with their private beach facilities nearby.
Cost €1950 pp (twin share basis)

Talk to us about extending your stay a few more days to relax and enjoy the numerous beaches in the area.

Click here to Book or for more details about this tour.



Puglia Highlights private tour Southern Italy

Puglia Highlights Private Tour Southern Italy

This five day package allows you to uncover the food and wine that Puglia is famous for, as well as seeing the key sights of the region.

A culinary focus - try recipes handed down through the generations that allow you to connect with this ancient wisdom. Match this with Puglia’s wonderful burrata cheese and wines found only in this part of Italy – this is a food-lovers’ dream.

You will visit an olive grove with ancient olive trees, an underground oil mill thousands of years old, and will taste a range of different olive oils. You will taste wines that are specific to Puglia.

You will have a cooking lesson with a chef, where the focus will be on cooking typical Puglia dishes, first taking you through the types of ingredients used and their provenance.

Also visit the highlights of the area – including the trulli of Alberobello, the cave town of Matera , the hill town of Ostuni, the beautiful village of Locorotondo.


There are 3 accommodation options for this tour itinerary:


A) Stay in the vibrant coastal town of Monopoli.
Cost €1700 pp (twin share basis)

B) Stay at the historic estate Masseria Salamina, enjoying their pool and homegrown produce.
Cost €1900 pp (twin share basis)

C) Stay at the 5 star resort Masseria Il Melograno, with their private beach facilities nearby.
Cost €2100 pp (twin share basis)

Contact Us to Book or for more tour details.



Puglia Food and Wine Private Tour Italy

Puglia Food and Wine Private Tour Italy


A six day discovery of Sicily. You'll do so in a safe and secure way - a private tour, your own driver with a sanitised vehicle, on call support.

See key locations such as Palermo, Agrigento, Siracusa, Taormina, Monreale, Ragusa and Modica.

The tour includes three UNESCO World Heritage sites: the Valley of the Temples in Agrigento (see picture), the late baroque towns of Ragusa and Modica, and the Arab-Norman architecture in Palermo.

Mix and mingle with the locals going about their normal daily lives, in particular the markets of Ballarò in Palermo, and in Siracusa. In these places all of your senses are stimulated; curious foods on sale, the aromas of ‘panelle’ frying, the vendors calling and chatting.

We organise the itinerary, accommodation, a driver to take you to all the destinations, and guided visits in Palermo and Agrigento.

The accommodation we use for this tour is 4 star hotels and all are centrally located in Palermo, Ragusa and Taormina. This makes it easy for you to spend time independently discovering these wonderful places.

There are three different accommodation options for this itinerary:

Cost €2200 pp (twin share basis).

Talk to us about extending your stay a few more days to relax and enjoy the numerous beaches in the area.

Click here to Book or for more details about this tour.



Puglia Culinary small group tour Matera Italy

Palermo Sicily private tour Italy