From the Colosseum's ancient echoes to Venice's whispered canals — your once-in-a-lifetime Italian journey, expertly crafted from the United States.
Italy is a boot-shaped peninsula reaching into the Mediterranean — a country where every cobblestone carries a story stretching back over 2,500 years. From the snow-dusted Dolomites in the north to the sun-baked shores of Sicily in the south, it blends history, art, cuisine, and natural beauty like nowhere else.
Home to the birthplace of the Roman Empire, the masterpieces of the Renaissance, and the world's best-loved cuisine, Italy welcomes over 65 million visitors a year. Whether you're after the ancient ruins of Rome, the romantic canals of Venice, the artistic treasures of Florence, or the dramatic Amalfi Coast, Italy rewards every kind of traveler.
Italians don't just live — they savor. From three-hour lunches to the evening passeggiata, Italian culture is a celebration of food, family, fashion, and the art of doing nothing exceptionally well.
From Neapolitan pizza to Bolognese ragù, gelato to espresso, every region has its own culinary identity. Eat like a local — slowly, and with reverence.
Warm, expressive, and family-minded. Italians talk with their hands, greet with a kiss on each cheek, and treat guests like extended family.
Birthplace of Michelangelo, Leonardo, Versace, and Armani. From Renaissance masterpieces to Milan's runways, beauty is a way of life here.
Venice Carnival, Siena's Palio, the Verona Opera Festival — Italians mark everything with pageantry, music, and fireworks.
Walk through 2,000 years of history in a single afternoon — from the Roman Forum to Renaissance Florence.
Regional dishes you won't find in any Italian restaurant abroad — authentic, fresh, and unforgettable.
Rome, Venice, Florence, Milan, Naples — each is a destination in its own right, each with its own soul.
Alpine peaks, Tuscan vineyards, Amalfi cliffs, Sicilian beaches — Italy fits every landscape into one country.
Visa-free entry, English widely spoken in tourist zones, easy conversion from USD, and direct flights from 15+ US cities.
Spring blooms, summer beaches, autumn vineyards, winter Christmas markets — Italy never really has an off-season.
Three thoughtfully built tiers. One journey to remember. Every package sets off from the USA with round-trip flights, top-tier hotels, knowledgeable guides, and effortless transfers — all managed by us.
The classic Italian highlights
Italy beyond the obvious
Italy without compromise
All prices are per person based on twin sharing, and exclude visa fees and personal spending. Bespoke itineraries available on request.
Our best-loved Premium itinerary, laid out tab by tab.
Skip-the-line entry with an expert archaeologist guide.
An early-access tour before the crowds arrive at 8 AM.
A private gondola at sunset with a serenading gondolier.
See Michelangelo's David and Botticelli's Birth of Venus.
Positano, Ravello, and a boat ride beneath the cliffs.
Visit Chianti estates for a sommelier-led tasting.
A photo stop at Italy's most iconic viewpoint.
Learn to make fresh pasta and tiramisu from a Tuscan chef.
Depart USA on your international flight to Rome, with meals and entertainment onboard.
Arrival at Fiumicino Airport. A private transfer to your 4-star hotel in central Rome, with a welcome dinner that evening.
Full-day Rome city tour spanning 2,000 years of history with a licensed archaeologist guide.
Early-access Vatican tour — get in before the crowds at 8 AM.
Frecciarossa first-class train to Florence (1h 30m).
Renaissance Florence with a hands-on cooking class.
Full-day Tuscany excursion by private coach.
By train to the floating city — Venice awaits.
A lagoon tour by private boat out to the colorful outer islands.
Domestic flight to Naples, then a scenic drive.
Morning at leisure before your return flight.
Rome — Near Termini
Rooftop terrace · Spa · Free Wi-Fi · Buffet breakfast
Florence — steps from the Duomo
Byzantine tower · Michelin dining · Concierge
Venice — near San Marco
Canal-view rooms · Wellness centre · Local dining
Amalfi — Clifftop
Private beach · Infinity pool · Suites over the sea
Tuscany — Wine Estate
A medieval castle · Thermal pools · Private vineyard
Ravello — Luxury
Clifftop infinity pool · An 11th-century palazzo
Hotels shown are representative. The final choice may change with availability — any alternative will match on star rating and location quality.
Roll fresh tagliatelle with a Tuscan nonna. Lunch and wine included.
A day trip from Amalfi with snorkeling and lunch at Marina Grande.
Visit 3 estates across the Tuscan hills, tasting 9+ wines.
Open-air opera in a 2,000-year-old Roman amphitheater.
A personal stylist plus access to the Quadrilatero della Moda boutiques.
The Sistine Chapel to yourselves — just 12 guests, with exclusive evening access.
A crystal-clear alpine lake, celebrity villas, and ferries between Bellagio and Varenna.
Five colorful cliff villages linked by hiking trails along the Ligurian coast.
Mount Etna, baroque Ragusa, and the Greek temples at Agrigento.
Caribbean-blue water, Costa Smeralda beaches, and Nuragic archaeology.
UNESCO-listed mountains in northeast Italy — hiking, cable cars, and alpine villages.
2,000-year-old Roman cities frozen in time by the eruption of Vesuvius.
Every Holidaysmakers Italy itinerary touches the cities that define the country's magic. Mix and match the cities to suit your interests.
The Eternal City — 2,500 years of it
A city of canals, gondolas, and masquerades
Birthplace of the Renaissance
Fashion capital, home of La Scala
Pizza's birthplace and the gateway to Pompeii
Cliffside villages and an azure Mediterranean
Vineyards, hilltop towns, and San Gimignano
Ancient ruins, Mount Etna, and seafood
The iconic Roman amphitheater where gladiators once fought — a UNESCO World Heritage Site.
Michelangelo's ceiling masterpiece — book a private after-hours tour for the full magic.
Toss a coin — right hand over your left shoulder! — to guarantee your return to Rome.
Venice's spiritual heart — Byzantine mosaics, pigeons, and the Doge's Palace right beside it.
Brunelleschi's terracotta dome — climb all 463 steps for the best view of Florence.
The world's finest Renaissance collection — Botticelli's Venus, Caravaggio, and Da Vinci.
The classic photo op — climb it, or nail the perfect 'holding up the tower' shot.
An ancient Roman city preserved by volcanic ash for nearly 2,000 years.
One of the world's most scenic drives — Positano, Ravello, and Amalfi town.
The alpine lake of emperors and celebrities — Bellagio, Varenna, and George Clooney's villa.
Five pastel fishing villages clinging to the Ligurian cliffs.
A glamorous island with a glowing sea cave reachable only by tiny rowboats.
From the second you say yes to the day you're back home, our specialists look after every last detail.
The best fares on leading airlines — Economy through Business — on direct & one-stop routes from any US gateway.
Handpicked 3- to 5-star properties & villas, personally vetted by our team, with the best rates secured directly.
Skip-the-line tickets & private guided visits to every major monument & museum.
Licensed, English-speaking guides — historians, art buffs, and food experts. Never robots reciting a script.
A private chauffeur waiting at arrivals — no haggling with taxis, no language barriers.
First-class trains, private cars, and domestic flights — smooth transitions from one city to the next.
Curated restaurant bookings — from trattorias to Michelin stars — wherever you go.
One number, one team, every time zone. We're with you from your first inquiry until you're safely home.
No call centers. No pressure. No phony deals. Just a straightforward 4-step path that takes you from "I want to go" to "I'm here, and it's perfect."
Tell us about your ideal Italian trip — dates, travelers, budget, and the places you can't miss. Two minutes, tops.
Within 24 hours, our Italy specialists put together a personalized itinerary built around you — never a template.
We fine-tune until every detail is right — flights, hotels, and the day-by-day plan. Then you lock it in with a deposit.
From airport pickup to the farewell dinner, we work behind the scenes to keep it seamless. You just soak it in.
Rome, Vatican City
Rome, Florence, Venice
Florence, Tuscany, Amalfi
Milan, Venice, Florence, Rome, and Amalfi
Palermo, Taormina, Catania
Holidaysmakers made our 25th-anniversary trip to Italy beyond perfect. The Amalfi Coast villa they booked had a private clifftop pool — and the Florence cooking class was the highlight of our lives.
Booking our honeymoon was effortless. Their team replied within hours to every change we asked for, and got us upgraded to business class on Lufthansa for the return. Worth every penny.
As a family of five with two teenagers and a 70-year-old grandma, we needed flexibility. They tailored the itinerary perfectly — easy walks for grandma, gondolas for the kids, wine tasting for us. Brilliant.
Our 7 AM private Vatican tour, with no crowds, was magical — the guide had us in tears of awe. We've now used Holidaysmakers three times: Italy, Greece, and Iceland. Never disappointed.
The best price I found anywhere for a 4-star Italy package. I checked six different sites, and Holidaysmakers beat them all by $400 per person. The hotels were better than expected, too.
When our Venice flight was canceled at 11 PM, their 24/7 line picked up in 90 seconds. They had us rebooked on a morning flight with a free hotel night inside 30 minutes. That alone justified the booking.
45 of the questions we hear most from US travelers planning an Italy trip. Don't see yours? Reach out — we're happy to get into specifics.
Tell us your dream trip. We'll craft it. You'll love it — guaranteed.
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