Italian Small Group Tours
Discover Italy the way it was meant to be experienced—intimately, effortlessly, and with unmistakable style. Ole Crow Tours’ Italian small group tours blend expertly curated itineraries, local insight, and personalized attention to create journeys that feel exclusive without the price tag of a private charter.
Why choose our Italian small group tours?
Carefully sized groups: We limit group sizes to preserve an intimate atmosphere, so you enjoy authentic connections with fellow travelers and the freedom to savor each moment without crowd fatigue.
Carefully chosen experiences: cellar tours in the Tuscan hills, hands-on cooking classes in Sorrento, and archaeologist-led visits to ancient sites—each stop is thoughtfully curated, authentic, and truly memorable.
Local expert guides: Knowledgeable, English-speaking guides with deep local connections bring each region to life—history, culture, and culinary secrets explained with warmth and authority.
Seamless logistics: Comfortable transportation, accommodations chosen for character and location, and thoughtful pacing mean you spend time exploring, not coordinating.
Flexibility within structure: Daily itineraries include curated highlights plus optional add-ons and free time, so you can tailor your day while still enjoying the benefits of a guided journey.
Value-focused inclusions: Many meals, wine tastings, entrance fees, and transportation are included, offering transparent pricing and excellent value compared to booking activities separately.
Small-group camaraderie: Travel with like-minded guests who appreciate culture, cuisine, and discovery — the perfect balance of social connection and personal space.
Ideal for travelers who want more than a checklist vacation—for those who seek genuine encounters, culinary depth, and expertly guided exploration without sacrificing comfort or convenience. Whether you’re celebrating a milestone, reconnecting with friends, or simply fulfilling a long-held travel dream, our Italian small group tours deliver an unforgettable, effortless experience.
Upcoming Tours
Currently, these are the tours we offer, but we are looking to broaden our choices in the very near future
Southern Italy
Our journey starts with a drive from Naples to the Cilento region, including several nights in a 900-year-old castle. We will then head to Matera, making a stop at Castelmezzano along the way. While in Matera, we’ll explore the cave dwellings and carved churches, as well as visit Alberobello. Our trip will conclude with an extended stay in Sorrento, allowing us to explore Pompeii and the stunning Amalfi Coast. The tour includes knowledgeable guides, selected accommodations, and a leisurely pace centered on culinary delights, wine, history, and beautiful views.
Northern Italy
Start with the fashion and sights of Milan. Experience the charm of Portovenere perched on cliffs with refreshing sea breezes. In Florence, admire Renaissance masterpieces, explore artisan studios, and savor local cuisine. In Tuscany, visit picturesque villages and vineyards with exclusive wine tastings. Conclude at Lake Garda, with a journey to the beautiful city of Verona. Includes knowledgeable guides, handpicked accommodations, and a leisurely approach centering on gastronomy, wine, history, and scenic views.
April 28-May 12 2026
$5,195 per traveler/without airfare
May 15-29 2026
$5,395 per traveler/without airfare
April 11-21 2026
$4,450 per traveler/without airfare
