2025 Upcoming Small GroupTours:
Flavors of Sicily, a Special Departure – March 22-30, 2025. This is a wonderful introduction to Sicily with lots of variety and has a food and culture focus, with easy walks. And added plus are the festiviti es surrounding the feast of San Giuseppe with visits to private homes and an astonishing food auction. Contact us for a detailed itinerary. info@italian-connection.com
Walk & Taste Umbria – April 12-17, 2025. Enjoy beautiful walks through vineyards and olive groves and visit the exqiusite hilltowns of Orvieto, Todi, Montecastello and Assisi. Stay in a boutique hotel with an aromatic herb garden as well as 2 nights in a luxurious 5-star hotel in Assisi with an amazing spa built into ancient Roman ruins. Taste delicious Umbrian specialties and quaff the best vintages of prestigious Sagarantino wine.
Wildflowers in the Dolomites – July 10-16, 2025. Admire the rugged peaks of the Dolomite mountains during the wildflower season, and enjoy spectacular challenging hikes in this stunning alpine area. Relax in two welcoming stylish hotels with spa facilities in top locations – enjoy strolling through chic Cortina from your newly renovated hotel. Great food and wine along the trail and in gorgeous setting makes this a truly amazing trip.
Join one of these small group departures, (maximum 12 participants) or book that private family get together that you’ve thought about for so long. Don’t see the dates you want? Contact us, as we often add tours during the season.
Our prices are guaranteed in US dollars. Once you book your tour, the price is guaranteed so you are protected from exchange rate fluctuations.
Contact us if you are interested in a private tour. Our 2025 -26 calendar of Italy tours is already getting full!
Accommodation Key:
- Signature: Boutique hotels and luxurious country inns
- Homestyle: Welcoming family-run inns and farms
- Blend: A combination of Signature and Essential lodgings
- Rental: Luxury townhome
Independent Travel, Choose your Dates:
Inside Tuscany
The best time to go is May, June, September, and October
View Trip Details | Contact Us to Book Trip
Costa Rica Experience
The best time to go is in the dry season, from December to April.
View Trip Details | Contact Us to Book Trip
Scheduled Departures, Join a Trip:
2025 Tour Calendar – Email us for Scheduled Departures not yet on our website! info@italian-connection.com
Italy Private Tour Suggestions to be Tailored to your Budget and Interests. These are the best times of year to travel in Italy, depending upon the region, for weather, festivals, & seasonal specialties.
The following tours are suggested itineraries that can be booked as a private departure for 6 or more guests – we can also customize a private tour in Italy for a couple or small private group that will be tailored to your interests and budget.
January, February, March: Cuba Experience
Experience Music, Dance, Nature, and Cultural Encounters. It’s easy and legal to go to Cuba in a small group, so join us as we introduce you to our Cuban friends and immerse you in Cuban culture. Maximum 11 participants on this small group tour of Cuba. $4880. Homestyle
February: Sicily Grand Tour
A comprehensive tour of Sicily’s amazing archeological sites at a relaxed pace, interspersed with great meals and encounters with our Sicilian friends. Join us during the gorgeous season of almond blossoms and bright early wildflowers, and enjoy splendid sites without the crowds. $6380. Blend
March, including the 19th: Walking & Cooking in Eastern Sicily
Special Departure, San Giuseppe Festival. Explore the idyllic countryside in Eastern Sicily on foot, and participate in the exciting activities during the Festival of San Giuseppe. Bid on a wild variety of edible items during the San Giuseppe food auction, including fanciful breads, huge hunks of cheese, wild asparagus, and the occasional live chicken. Visit a selection of private homes with astonishing displays of homemade sweets in honor of the saint – called the Table of St. Joseph – and admire the Baroque architecture in Ragusa, and Greek ruins in Syracuse. An exciting and fun introduction to Sicily, from the folks who live there! .Signature
Late March and all of April: Splendors of Sicily Walking Tour
Travel around the island enjoying beautiful varied walks, archeological and Unesco sites, Sicily’s most beautiful towns, and great food and wine, while staying in Sicily’s best boutique hotels. Opt for dinner in a 2-star Michelin restaurant and meet Chef Ciccio Sultano, or join us for dinner in a rustic spot frequented by locals. This award-winning tour was featured in National Geographic Traveler as one of “50 Tours of a Lifetime ,” and is packed with insider experiences and a festive lunch in our home. One of our most popular tours! $56990. Signature
April & May: Western Sicily & Egadi Islands Walking Tour
Explore the little-known Egadi Islands with stunning sea views, explore fascinating archeological sites from ancient Greece, enjoy a wine-paired dinner with an acclaimed chef, and revel in the fabulous wildflowers on this unique spring trip. $5980. Signature
April & May: Aeolian Islands Walking Tour
The Aeolian Islands off the northeast coast of Sicily offer a wonderful variety of walks, and each island has its own personality. Drift past bright hibiscus flowers and a tangle of caper plants on the greenest island of Salina, or watch the natural fireworks spurting from the Stromboli volcano, and hike to a prehistoric site on the tiny island of Filicudi. $5980. Blend
May, early June, late September, early October: Amalfi Coast & Capri Adventure
Walk on rugged paths high above the coast with spectacular views, and descend through lush lemon groves to the bustling town of Amalfi. Take a ferry to the beautiful island of Capri, where we stay 2 nights in a family-run inn, and explore the island on foot. Enjoy sumptuous farm-to-table meals and heady local wine. $5250. Blend
May & June, September: Walk & Taste Umbria
Charming villages, spectacular wildflowers, and undiscovered territory greet the traveler on this walking tour in Umbria, with a guided visit to Assisi and luxurious boutique hotels. Enjoy prestigious wines & walks to lofty hilltowns. $6480. Signature
May & June, September: Southern Tuscany to the Sea
Soak in the joys of southern Tuscany with walks to exquisite hill towns, a fascinating exploration along an amazing Etruscan trail, and a stunning walk overlooking the gorgeous blue sea. Visit a tiny synagogue, taste prestigious Tuscan wines and genuine country cuisine, as well as perfectly fresh fish on the coast. An incredibly varied trip with lots of off-the beaten track sites. $6380. Signature
July: Wildflowers in the Dolomites Walking & Hiking Tour
Enjoy alpine splendor and rustic mountaintop lunches during the spectacular wildflower season, while walking in 3 different valleys. Stay at the Rosalpina, the Dolomite’s finest hotel, and dine at one of Italy’s only Michelin 3-star restaurants. $6380. Signature
July & early September: Cortina Dolomites Hike.
Splendid walks with spectacular scenery and gourmet meals await the fit walker on this luxurious hiking and walking tour in the Dolomites. Unpack once in stylish Cortina. 4-star hotel $5880. Signature
Late April, May, late September, October: Puglia Walk
Explore delightful white-washed towns, follow a trail lined with wild cyclamens, walk by the turquoise sea, shape orecchiette pasta, explore the fascinating “sassi” of Matera, sleep in a trullo, dine divinely, meet our passionate local friends on the trail and at the lunch table, hang out at the fish market or cool art studios. $6480. Signature
September & early October: Walk & Taste Umbria
Charming villages, spectacular wildflowers, and undiscovered territory greet the traveler on this walking tour in Umbria, with a guided visit to Assisi and luxurious boutique hotels. Enjoy prestigious wines & walks to lofty hilltowns. $6480. Signature
May, late September, early October: Italian Lakes Como & Iseo Walk
Enjoy the romantic scenery and lovely small towns on Lake Como and Lake Iseo, visit lush gardens and lavish villas while walking quiet trails with stunning views. Relax in luxurious lakeview rooms and taste authentic regional cuisine and great local wines in prestigious Franciacorta. If only briefly, live the life of George Clooney! $6550. Signature
October: Splendors of Sicily Walking Tour
Travel around the island enjoying beautiful varied walks, archeological and Unesco sites, Sicily’s most beautiful towns, and great food and wine, while staying in Sicily’s best boutique hotels. Opt for dinner in a 2-star Michelin restaurant and meet Chef Ciccio Sultano, or join us for dinner in a rustic spot frequented by locals. This award-winning tour was featured in National Geographic Traveler as one of “50 Tours of a Lifetime,” and is packed with insider experiences and a festive lunch in our home. One of our most popular tours! $6980. Signature
March, October, & November: Savoring Sicily Culinary Tour
Connect to Sicily through its amazing food and enjoy hands-on cooking lessons and visits to artisan producers. Taste olive oil the moment it is pressed, shape warm curds into soft cheese, and visit lovely towns as we travel east to west across the island. This unique tour includes a meal in our home and introductions to our Sicilian friends for an amazing insider experience. $6350. Signature
Don’t see the dates you want?
We often add tours during the course of the year, so contact us with your preferred dates and trip and we’ll see what we can do!