Best Season to Travel - Guided Walking Tours of Italy, Cuba & Costa Rica

We’ve added a new tour in the fall of of 2023 ! Wondrous Western Sicily, Oct 7-14, 2023.  Contact us for a detailed itinerary. Enjoy a special offer of a free arrival transfer from Palermo airport and a room upgrade.  Just 2 rooms left, so act now! info@italian-connection.com 

It’s not too soon to think about 2024 & 2025, as we have some dates already booked.  We look forward to hearing from you and welcoming you back to Italy with our unique style of travel.  A presto!

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. Our 2024 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

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Costa Rica Experience
The best time to go is in the dry season, from December to April.

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Scheduled Departures,  Join a Trip:

2024 Tour Calendar – Email us for Scheduled Departures in Sicily, Puglia, Amalfi & the Dolomites not yet on our website!  info@italian-connection.com  We have a 14 -day departure in Sicily – you can take all or part of it – that includes Easter celebrations and the San Giuseppe festival.  Email us and ask about “Spectacular Sicily!”

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. $4100. Homestyle

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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. $5600. Blend

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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! $5600. Signature

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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!  $5880.  Signature

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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. $5890. Signature

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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. $5600. Blend

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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

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May & June, September:  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.  $5980.  Signature

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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. $5980. Signature

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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. $5990. Signature

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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 $5400. Signature

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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. $5990.  Signature

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September & early October:  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.  $5990.  Signature

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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

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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!  $6550.  Signature

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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. $5890.  Signature

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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