View Travel Dates for Our Guided Tours of Italy, Cuba & Costa Rica

Join one of our small group departures, 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.

Accommodation Key:

  • Signature: Boutique hotels and luxurious country inns
  • Essential: Welcoming family-run inns and farms
  • Blend: A combination of Signature and Essential lodgings
  • Rental: Luxury townhome

Private Departures, 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:

2018 Tour Calendar

Sept 16-21: Amalfi & Capri Adventure
Walk on rugged paths high above the Amalfi 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.  $3280.  Essential

View Trip Details | Book Trip

Oct 8-16: Splendors of Sicily Walking Tour
Travel around the island enjoying beautiful varied walks, archeological sites, fascinating towns, and great food and wine, while staying in Sicily’s nicest boutique hotels. Enjoy dinner in a 2-star Michelin restaurant and meet Chef Ciccio Sultano. This award-winning tour was featured in National Geographic Traveler as one of “50 Tours of a Lifetime ,”  and is packed with insider experiences including a festive lunch in our home.  One of our most popular tours!  $5680. Signature

View Trip Details | Book Trip

Oct 18-24: 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. $4880. Signature

View Trip Details | Book Trip

Oct 26-Nov 2: 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. $4980.  Signature

View Trip Details | Book Trip

2019 Tour Calendar

Jan 14-22: 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. $3680. Essential

View Trip Details | Book Trip

Feb 18-26: 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. $4690. Signature

View Trip Details | Book Trip

March 15-21: 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, 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! $4290. Signature

View Trip Details | Book Trip

April 15-20: 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. $3970. Signature

View Trip Details | Book Trip

May 12-19: 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. $4880. Blend

View Trip Details | Book Trip

May 24-29:  Umbria Hilltowns
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.  $4980.  Signature

View Trip Details | Book Trip

June 2-7: Amalfi & 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. $3280.  Essential

View Trip Details | Book Trip

June 15-22: 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. Signature

View Trip Details | Book Trip

Sept  16-22: 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. $4880.  Signature

View Trip Details | Book Trip

Oct 1-7: 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.  If only briefly, live the life of George Clooney!  Signature

View Trip Details | Book Trip

Oct 14-21: Splendors of Sicily Walking Tour
Travel around the island enjoying beautiful varied walks, archeological sites, fascinating towns, and great food and wine, while staying in Sicily’s nicest boutique hotels. Enjoy dinner in a 2-star Michelin restaurant and meet Chef Ciccio Sultano. 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!  $5270.  Signature

View Trip Details | Book Trip

Oct 26-Nov 2: 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. $4980.  Signature

View Trip Details | Book Trip

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!

Italian Connection

Italian Connection