The Ultimate Guide to Planning an Italy Bucket List Trip from Omaha

I'm going to walk you through exactly how to plan your dream Italy trip from Omaha, from finding the best flights to crafting an itinerary that hits every must-see destination without feeling rushed. By the end of this guide, you'll know what to book, when to go, and how much to budget so you can turn that Italy bucket list into a real departure date.

Getting from Omaha to Italy: Your Flight Options

Let's start with the practical part: getting there. Omaha doesn't have direct flights to Italy, so you'll connect through a major hub. Your best bets are typically Chicago O'Hare, Denver, or Dallas/Fort Worth. From there, you'll catch a nonstop to Rome (FCO) or Milan (MXP).

Delta and United offer the most seamless connections from Omaha. Book your transatlantic leg 3–5 months out for the best fares, you're looking at $700–$1,200 roundtrip in economy during shoulder season (April–May or September–October). Summer and Christmas weeks can push that closer to $1,500+.

Pro tip: Consider flying into Rome and out of Venice (or vice versa) to skip backtracking. Open-jaw tickets usually cost the same or just slightly more, and they save you an entire travel day.

The Italy Bucket List Destinations You Can't Skip

Rome is where most first-timers start, and for good reason. You'll want 3–4 days to cover the Colosseum, Vatican City, Trevi Fountain, and the Pantheon. Don't try to cram it all into 48 hours. Rome rewards slow mornings with espresso and evening strolls through Trastevere.

Florence is your Renaissance headquarters. Allocate 2–3 days for the Uffizi Gallery, Michelangelo's David at the Accademia, and the climb up Brunelleschi's Dome. The city is walkable, so skip the car rental and just wander the cobblestones.

Venice deserves at least 2 nights. Yes, it's touristy. Yes, it's expensive. But wandering the canals at sunrise before the cruise crowds arrive? That's bucket-list magic. Hit St. Mark's Square, the Rialto Bridge, and take the vaporetto out to Burano for the colorful houses.

Amalfi Coast is where you slow down. Positano, Ravello, and Sorrento offer clifftop views, limoncello tastings, and some of the best seafood you'll ever eat. Rent a scooter or hire a driver: the coastal roads are stunning but narrow.

Cinque Terre gives you five pastel fishing villages connected by hiking trails. If you're up for it, hike village to village. If not, the trains run every 15 minutes. Either way, you're getting postcard views at every turn.

When to Go (and When to Avoid)

April through early June is your sweet spot. The weather's warm, the crowds are manageable, and the countryside is in full bloom. September and October are equally gorgeous: harvest season in Tuscany, fewer tourists, and perfect temperatures for walking tours.

Skip July and August unless you love heat and crowds. Rome in August can hit 95°F, and half the locals leave town. Christmas markets in December are charming, but expect cold, rain, and shorter daylight hours.

Your Italy travel plans should align with what you want to experience. Wine harvest? Go in September. Truffle season? Late October through November. Easter in Rome? Book a year ahead.

Budgeting Your Italy Bucket List Trip

Here's where I help you set realistic expectations. A 10-day Italy trip from Omaha typically runs between $4,000–$7,000 per person, depending on your travel style.

Budget breakdown:

• Flights: $700–$1,200

• Accommodations: $100–$250/night (boutique hotels or Airbnbs)

• Trains & transport: $200–$400 (Italy's rail system is efficient and affordable)

• Food: $50–$100/day (mix of trattorias and fine dining)

• Tours & entries: $300–$600 (skip-the-line Vatican, cooking classes, wine tours)

You can trim costs by staying in smaller towns, eating where the locals eat (look for handwritten menus), and booking train tickets in advance. Splurge on one or two experiences: a private Vespa tour of the Amalfi Coast or a truffle hunt in Tuscany: and keep the rest low-key.

A Sample 12-Day Itinerary from Omaha

Days 1–3: Rome Fly into Rome, settle in, and spend your first full day at the Colosseum and Roman Forum. Day two is Vatican City (book skip-the-line tickets). Day three, explore Trastevere, the Pantheon, and toss a coin in the Trevi Fountain.

Days 4–5: Amalfi Coast Train to Naples, then transfer to Sorrento or Positano. Spend two days soaking up the coastal views, eating fresh mozzarella, and maybe taking a boat to Capri.

Days 6–8: Florence & Tuscany Head north to Florence. Tour the Uffizi and the Duomo, then take a day trip to the Tuscan countryside: think Siena, San Gimignano, or a Chianti winery.

Days 9–10: Cinque Terre Train to La Spezia, then hop the local line to the five villages. Hike, swim, and eat pesto by the water.

Days 11–12: Venice End your trip in Venice. Explore the Doge's Palace, get lost in the alleys, and catch the sunset from the Accademia Bridge before your flight home.

How Your Omaha Travel Agent Makes This Easier

Planning a multi-city Italy trip involves a lot of moving pieces: flights, trains, hotels, transfers, and knowing which museums require advance bookings. That's where working with an Omaha-based travel agent who specializes in European itineraries comes in handy.

I help Omaha travelers: and clients nationwide: build custom Italy itineraries that fit their pace, budget, and bucket list priorities. I'll handle the logistics, recommend the best small-group tours, and make sure your connections actually work (because a 45-minute layover in Frankfurt sounds fine until you're sprinting through the terminal).

You get the dream trip. I handle the spreadsheets.

What Most People Forget to Book (But Shouldn't)

Train tickets: Italy's Trenitalia and Italo trains are fantastic, but popular routes sell out. Book your high-speed trains (Rome to Florence, Florence to Venice) a few weeks ahead for the best prices.

Museum skip-the-line passes: The Vatican, Uffizi, and Accademia all have timed-entry tickets. Without them, you're waiting 2+ hours in the sun.

Travel insurance: Flight delays, missed connections, lost luggage: it happens. Get coverage that includes trip interruption and medical emergencies.

International SIM or eSIM: Google Maps and real-time train updates are your best friends in Italy. Don't rely on spotty café Wi-Fi.

Why Now Is the Right Time to Plan

Italy isn't going anywhere, but travel costs are. Airfare and hotel prices for 2026 and 2027 are trending higher as demand rebounds. If you've been dreaming about this trip for years, locking in your dates and flights now gives you better pricing and more availability.

Plus, when you book early, you have time to budget, save, and get excited without the last-minute scramble.

Your Next Step: Get the $1000 Insider Pass

Ready to turn this guide into a real itinerary? I'm offering a limited number of my $1000 Insider Pass through our newsletter: it includes a personalized Italy planning session, insider hotel recommendations, and access to exclusive tour discounts I've negotiated for my clients.

Sign up for our email list to get the details and grab your spot. Your Omaha Travel Agent is here to help you plan the Italy bucket list trip you've been dreaming about: without the stress, guesswork, or endless Google tabs.

Let's make it happen. Together.