Off-the-Beaten Path and the Great Outdoors
These vacation packages are meant for independent travelers. A great way to see Italy including a combination of some pre-planned activities and some free time to explore on your own.
We covered the most popular and interesting itineraries you look for and selected the hotels, day tours, and transportation for you.
This way, you can check off all the must-sees and still have time to go back to your personal favorites, or explore each city as you wish. Not only does this make seeing Italy easy and fun, it's also a great value!
Take a look at our trip ideas below- these packages can be scheduled on a date of your choosing.
If they don't quite cover what you're looking for, you can create your very own custom Italy Vacation itinerary! If you have any questions at all, feel free to chat with us. Our agents are just a call away and are happy to help you plan your perfect trip.
Celebrate Perillo’s 80th Anniversary with an exclusive Italian adventure. Experience the best of Tuscany and Verona, from a farm-to-table dinner in Tuscany to an after-hours Michelangelo tour in Florence. Hunt for truffles, savor world-class wines in Montalcino, and enjoy a private sunset photo shoot. Visit the oldest family-owned acetaia and tour Verona’s historic sites, including the famed Arena for an exclusive opera experience. End your journey with a helicopter tour over Lake Garda and a Michelin-starred farewell dinner. Luxury, history, and culinary delights await!
Price starting from $80,000 in total for 2 people.
Prices, overnight accommodations and activities may vary based on seasonality and availability.
From your base in the charming medieval town of Siena, experience hilltop villages, rows of vineyards, and culinary specialties of Tuscany.
Enjoy a privately guided walk of Siena and marvel at the many sites of the city including the Palazzo Comunale (Town Hall), the majestic gothic Basilica of San Domenico and the Piazza del Campo, where the horse race (Palio di Siena) is held twice a year.
Venture to the beautiful countryside of the Orcia Valley, recognized as a UNESCO World Heritage Site in 2004; visit the quaint village of Montepulciano, the Renaissance center of Pienza and the hill town of Montalcino; savor the food and wine these towns are famous for: Pecorino cheese, Nobile and Brunello wines.
Finally, take a traditional Tuscan cooking class in Siena and learn the secrets of this delicious cuisine!
This is a great Add-On Package for anyone visiting Tuscany, Rome, or any part of Italy.
Famous the world over, five small colorful fishing villages carved out of the rocky mountainside above the sea, the Cinque Terre are a must-visit for any traveler to Italy.
The tiny towns are connected only by boat, train and hiking paths. A short and easy hike is the best way to get acclimated. Your private local guide will take you through terraced vineyards overlooking the Mediterranean. Afterwards you will experience a traditional meal in a local trattoria, tasting focaccia, anchovies, cheeses and more. The other best way to experience the Cinque Terre is by boat and you will enjoy a private tour on a comfortable motor boat, giving you a unique view of these five villages. You will have a chance to swim in the crystal-clear waters, discover the best hidden coves and indulge in a light lunch based on typical finger food and paired with some local wine and soft drinks.
This package is available from April to October.
Explore the beautiful Italian Riviera from Santa Margherita Ligure, then relax in the iconic Lake Como area.
Under the guidance of your private local expert, discover the authenticity of charming Santa Margherita Ligure with its elegant palaces and exquisite gardens, the elegance of picturesque Portofino with it colorful houses and unique boutiques, and the stunning abbey at San Fruttuoso, a tiny untouched village considered a pearl of rare beauty. Then it is off to another natural water wonder - Lake Como. Walk through the historic center of Como to visit its main sights with your knowledgeable guide and take a cruise to admire the Alpine mountains and some of the most elegant villas from the water.
Enjoy some time at your leisure in each destination and feel free to select one of our day tours that best suits your interests: from food tours and cooking classes to hiking excursions to Cinque Terre or visits to magnificent villages on Lake Como.
