Italy · Planned start to finish
At Traveland, we plan personal journeys to Italy, from Rome and Sicily to the islands of Ischia, Capri and Procida. We take care of the research, bookings and logistics, from the first conversation to your flight home, so your time goes into enjoying the trip, not planning it. We are a family-owned travel agency in Connecticut, planning trips since 1978 as a member of the Signature Travel Network.
Since 1978Family-owned and operated
Signature Travel NetworkMember agency
Orange & BridgeportTwo Connecticut offices
Every detail handledSo you can simply enjoy the trip
Destinations
Italy rewards those who choose well. Mountain villages, sun-warmed beaches, ancient cities and quiet corners each have their own pace, cuisine and character. We help you decide where to go, how long to stay, and how to move between places with ease.
A walk through Rome is a walk through living history, where every street, monument and stone has a story. It is also two capitals in one: the heart of Italy and, within it, Vatican City, the spiritual center of the Catholic Church. Ancient ruins sit beside modern life, and there is always another layer to discover.
On the largest island in the Mediterranean, rugged mountains meet clear seas.
A volcano, a chocolate town and a farmhouse kitchen
If you’ve already seen Rome and Florence, Sicily is where we’d send you next. Spend a morning on Mount Etna, on foot or by 4x4, among craters and lava caves, then taste wine from vines grown on its slopes. In Modica, chocolate is still made by cold processing, a method traced back to the Aztecs, which gives it a texture all its own. In the countryside around Scicli and Palazzolo Acreide, farmhouse cooking classes begin with gathering wild herbs and end at the table. Palermo’s churches and markets show Greek, Arab, Norman and Spanish layers in a single walk. Tell us when you’d like to go, and we’ll build the week around what you enjoy most.
Three islands in the Bay of Naples, each with its own mood. Ischia for thermal springs and gardens, Capri for dramatic cliffs and a lively piazzetta, Procida for pastel harbors and a slower rhythm. Together they capture the essence of Italian coastal life.
More than 60 UNESCO World Heritage Sites.
One advisor to help you choose among them.
Experiences
Every journey begins with what matters most to you.
Handmade pasta, regional wines and meals that carry centuries of tradition and regional pride.
Ancient ruins, Renaissance masterpieces and more than 60 UNESCO World Heritage Sites.
Mountain trails and coastal routes for travelers who like to move.
Local festivals and evening performances, where each city becomes a stage.
Thermal waters and quiet spas set against remarkable landscapes.
Pilgrimage routes and sacred places, for travelers seeking reflection and connection.
Fashion boutiques, artisan workshops and local markets, each rooted in centuries of craftsmanship.
Generations of mastery in fashion and design, and the easy elegance of the Riviera.
Country roads, mountain trails and lesser-known villages, where the journey is the point.
Food and wine
A week in Italy works best with two bases and one hands-on meal in each. In Rome, join a small-group pizza class: make the dough, top it, then eat it with Italian wine. From Florence, spend a day in Chianti, walking a historic estate’s cellars before the tasting. Or cook a four-course Tuscan meal with a local chef, fresh pasta always included. For a slower start, a two-hour coffee and gelato walk through Rome ends with tiramisu. Tell us when you’d like to go, and we’ll build the week around the table.
When: Spring is our favorite time for this trip; the experiences run year-round.
Working with us
01
Tell us how you like to travel, who is coming, and what you hope to feel. There is no charge to begin.
02
We design the route, hotels, transfers and experiences, then refine them with you, so you skip the hours of research and comparison.
03
We book the flights, stays, cruises and tours and keep track of every confirmation, so all you have to do is enjoy the journey.
Film courtesy of Signature Travel Network.
Timing
Spring (April to June) and early autumn (September to October) offer mild weather and fewer crowds than midsummer.
Wildflowers, comfortable weather for walking the cities, and the start of the coastal season.
Peak heat and crowds in July and August. Many Italians take their holidays around Ferragosto on August 15. A good time for the islands and the mountains.
Harvest season, warm seas into early October, and softer light in the cities.
Quieter museums, festive traditions, and skiing in the Alps and Dolomites.
Questions
April to June and September to October bring mild weather and fewer crowds. July and August are the hottest and busiest months, especially along the coast. Winter suits cities, museums and skiing in the Alps and Dolomites.
Ten to fourteen days allows time for Rome plus one or two other regions without rushing. With a week, we suggest one or two bases rather than many stops.
Not for tourist stays of up to 90 days within any 180-day period in the Schengen Area. The European Union plans to introduce ETIAS, an online travel authorization for visa-exempt visitors, scheduled for the last quarter of 2026. We will confirm current entry requirements before you travel.
It depends on your pace. Rome suits lovers of history and art, Sicily combines culture, food and nature, and Ischia, Capri and Procida are ideal for time by the sea. Many travelers combine two.
Yes. We plan cruises as well as land journeys, and many Mediterranean cruise itineraries call at Italian ports. We can combine time ashore with days at sea.
There is no charge for an initial consultation. Share your ideas through the form on this page or schedule a call, and an advisor will follow up.
Planning a trip like this can take many hours of research, comparison and booking. We do that work for you, draw on decades of experience to get the details right, and keep every confirmation in one place, so you can spend that time looking forward to the journey.
We are a family-owned travel agency in Connecticut, with offices at 564 Racebrook Road in Orange (203-929-6000) and 4270 Main Street in Bridgeport (203-371-1114).
Inquire
Tell us a little about the Italy you have in mind. One of our advisors will reply personally.
Choose a time for a call with one of our advisors.
Orange
564 Racebrook Road, Orange, CT 06477
203-929-6000
Bridgeport
4270 Main Street, Bridgeport, CT 06606
203-371-1114
Monday to Friday, 9am to 6pm
info@traveland.net
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