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escortOff-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.


Siena (3 nights)

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.


Monterosso al Mare (3 nights)

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.


Genoa (6 nights)

Enjoy a week on Italy’s enchanting Northwestern coast, where quaint fishing villages, gracious old-world harbors, and the fascinating city of Genoa have enticed travelers for centuries.

With the alluring city of Genoa as your home base, discover its elegant palaces and the fascinating labyrinth of caruggi (alleyways) that make up Genoa’s historic center and are packed with historical shops, offering treasures from spices to chocolates, fine linens, tableware, clothing, and beauty products.

Plus, venture out to the surrounding gems including splendid Portofino, charming Santa Margherita village, the medieval San Fruttuoso Abbey and Cinque Terre, five small colorful fishing villages carved out of the rocky mountainside above the sea.

Birthplace of Christopher Columbus, pesto and focaccia bread, Genoa is a city full of surprises. Named ‘the City of Palaces’ for its splendid gold-leaf halls of the Unesco-listed Palazzi dei Rolli and ‘the Superba’ for its glorious past and impressive landmarks, Genoa is arguably Italy’s most unjustly unknown city. As Charles Dickens rightly said: ‘It is a place that grows upon you every day! I will part from Genova with anything but a glad heart.’

Genoa and its region, Liguria, are perfect for marvelous outdoor activities, ranging from hiking to sailing to visiting tiny villages. It’s a territory that offers authentic experiences that are far from the more crowded and popular destinations in Italy.

Santa Margherita Ligure (3 nights), Como (3)

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 on a public ferry boat to admire the Alpine mountains and some of the most elegant villas from the water.

Enjoy a day 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.


Stresa (3 nights)

The Borromean Islands are the highlight of a stay at Lago Maggiore. Isola Bella will surprise you: its sumptuous baroque palace is completely furnished and its elegant rooms are full of paintings and works of arts. On Isola Madre the atmosphere is even more authentic: you will learn how the Borromeo family created a luxuriant English-style botanical garden full of tropical and rare plants. Isola Pescatori is the most lively, with its many little shops and cafés. On another day you will visit the gem of Lake Orta and the small town of Orta San Giulio with its 20 chapels whose frescoes tell the story of St. Francis of Assisi.

This is a great Add-On Package for anyone visiting Milan, Cinque Terre, or any part of Italy. 

Urbino (4 nights), Ascoli Piceno (3), Rome (1)

Experience an off the beaten path tour of one of Italy’s most underrated regions, Le Marche! You will be based in both Urbino and Ascoli Piceno. This region has been described as “all of Italy in one region”. On this 7 night adventure you will be delighted by the Apennine Mountains, rolling hills, beautiful beaches and rocky cliffs. At the same time being marveled by the Renaissance culture and medieval architecture of this region. This is an exclusive private tour including winery visits, local tastings and cooking experiences as well as most meals. 

Santa Margherita Ligure (7 nights)

Indulge in a week-long vacation on the enchanting Italian Riviera, famous for its rugged cliffs, turquoise coves and pastel seaside towns, including the colorful Cinque Terre fishing villages and the stylish resort areas of Portofino and Santa Margherita Ligure.

From your base in the lovely seaside town of Santa Margherita Ligure, you will explore surrounding gems: splendid Portofino, the medieval San Fruttuoso Abbey and fascinating Genoa. Your day in the Cinque Terre will be a sensory feast of breathtaking views and sea-scented air mixed with fragrant hillside gardens.
Top your stay with some culinary and artisan experiences: taste the most delicious olive oil, learn how to make the greenest pesto sauce and shop at the artisan studios in Chiavari.

The Italian Riviera and its region, Liguria, are perfect for marvelous outdoor activities, ranging from hiking to sailing to visiting tiny villages. It’s a territory that offers authentic experiences that are far from the more crowded and popular destinations in Italy.