Sample Itinerary · Italy

Self Drive Tour
of Italy

Rome · Umbria · Tuscany · Cinque Terre

Duration
10 Days · 9 Nights
Accommodations
4-Star or Higher
Transport
Self-Drive (Rental Car)
Best For
Independent Travelers · Road Trip Enthusiasts

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This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients travel a very similar route — if this resonates, book a free consultation and an Italy specialist will build something just like it (or better) specifically for your travel style, dates, and group.

1
Day One

Arrive in Rome

Rome

Your Italian road trip begins in Rome — but you won’t need a car here. A private transfer from the airport delivers you to your hotel near the historic center. Rome’s cobblestone streets, pedestrian zones, and restricted traffic areas make walking the only way to explore.

Spend the afternoon orienting yourself: the Trevi Fountain, the Spanish Steps, the Pantheon. Find a trattoria in Trastevere for your first Roman meal — cacio e pepe, supplì, a carafe of house wine. Tomorrow you’ll explore the ancient city properly before picking up the car and heading into the countryside.

Private airport transfer
No car needed in Rome
Orientation walk

Overnight: Rome

2
Day Two

Ancient Rome

Rome

A full day exploring Rome on foot. Your pre-arranged skip-the-line entry takes you into the Colosseum, through the Roman Forum, and up the Palatine Hill. A private guide brings the ruins to life — gladiators, emperors, the fall of a civilisation described while standing on the exact ground where it happened.

Afternoon, the Vatican Museums and Sistine Chapel — Michelangelo’s ceiling, the Raphael Rooms, St. Peter’s Basilica. Your specialist has timed the entry to avoid peak crowds. Evening free for dinner in the Campo de’ Fiori neighborhood, where the restaurants serve locals, not tourists.

Colosseum skip-the-line
Vatican Museums
Private guide

Overnight: Rome

3
Day Three

Pick Up Car & Drive to Umbria

Orvieto & Umbria

Morning, pick up your rental car at a location near your hotel. Your specialist has arranged a vehicle suited to Italian roads — compact enough for village streets, comfortable enough for long drives. Your curated route avoids the motorway entirely, taking you north through the Roman campagna into Umbria.

First stop: Orvieto, a hilltop town perched on volcanic rock with a cathedral whose facade is one of the great masterpieces of Italian Gothic architecture. Walk the underground caves, taste Orvieto Classico wine at a local enoteca. Continue to your agriturismo in the Umbrian countryside — rolling green hills, olive groves, and the kind of silence that makes you realize how noisy the rest of the world is.

Car pickup
Orvieto cathedral
Scenic drive to Umbria

Overnight: Umbria

4
Day Four

Assisi & the Umbrian Countryside

Assisi & Umbria

Drive to Assisi, the pink-stone hilltop town where St. Francis was born. The Basilica of San Francesco contains Giotto’s extraordinary fresco cycle — 28 scenes from the life of Francis painted on the walls of the lower church. The art alone justifies the visit, but the town itself is equally rewarding: medieval streets, panoramic views across the Valle Umbra, and a pace of life that hasn’t changed in centuries.

Afternoon, explore the Umbrian countryside at your own pace. Drive through Spello (the flower-covered village), Bevagna (the medieval market town), or Montefalco (the “balcony of Umbria” famous for Sagrantino wine). This is the Italy that most tourists miss — quieter, greener, and arguably more beautiful than Tuscany.

Assisi & Basilica
Umbrian hill towns
Wine tasting option

Overnight: Umbria

5
Day Five

Umbria to Tuscany

Drive to Siena

After breakfast, drive northwest into Tuscany. The landscape shifts from Umbria’s green valleys to Tuscany’s golden hills — cypress-lined roads, vineyards on every slope, medieval towers on distant ridgelines. Your route passes through Cortona (the hilltop town from Under the Tuscan Sun) and Montepulciano (home of Vino Nobile).

Arrive in the Siena area and check into your Tuscan accommodation — perhaps a converted farmhouse in the Chianti hills or a boutique hotel near Siena’s medieval center. Afternoon at leisure: swim in the pool, walk through vineyards, or drive to a nearby town for aperitivo. This evening, dinner at a local osteria — pici with wild boar, pecorino, and a bottle of Chianti Classico.

Scenic drive Umbria to Tuscany
Cortona or Montepulciano stop
Chianti check-in

Overnight: Tuscany

6
Day Six

Chianti Driving Day

Chianti & Siena

Today is the day the self-drive format shines. Take the Chiantigiana — the wine road between Florence and Siena that winds through the heart of Chianti Classico. Stop at any vineyard that catches your eye; most offer tastings without reservation. Pull over for hilltop villages, roadside chapels, and views that belong on postcards.

Visit Siena: the Piazza del Campo, the striped marble cathedral, the narrow lanes that seem to lead nowhere and everywhere at once. Your specialist has pre-arranged a wine tasting at a small-production estate — the kind of place that doesn’t appear in guidebooks but produces exceptional wine. Return to your accommodation as the Tuscan light turns everything gold.

Chiantigiana wine road
Siena exploration
Private wine tasting

Overnight: Tuscany

7
Day Seven

Tuscany to La Spezia

Drive & Arrive Cinque Terre

Drive north from Tuscany, through the marble mountains around Carrara (where Michelangelo sourced his stone), and into the Ligurian hills. Your destination is La Spezia, the gateway town to the Cinque Terre — and crucially, the place to park your car. The five villages of the Cinque Terre are car-free; everything from here is by train or foot.

Park at the La Spezia station garage, check into your accommodation (either in La Spezia or in one of the five villages, reached by a 5-minute train), and spend the afternoon exploring whichever village you’re based in. Riomaggiore and Manarola are closest to La Spezia; Vernazza and Monterosso are further north and equally charming. Fresh pesto, focaccia, and Vermentino wine — Liguria’s cuisine is lighter and more coastal than Tuscany’s.

Scenic drive north
Park car in La Spezia
Cinque Terre by train

Overnight: Cinque Terre area

8
Day Eight

Cinque Terre — Day One

Cinque Terre Villages

A full day in the Cinque Terre by train and on foot. The five villages — Riomaggiore, Manarola, Corniglia, Vernazza, Monterosso — are connected by both a coastal train (5 minutes between stops) and hiking paths carved into the cliffs. Your specialist has recommended the best sequence based on your fitness level and interests.

Walk the Sentiero Azzurro between villages if conditions allow — the path between Vernazza and Monterosso offers some of the most dramatic coastal scenery in the Mediterranean. Swim at Monterosso’s beach, the only sand beach in the Cinque Terre. Lunch on the harbor in Vernazza: trofie al pesto, fried anchovies, a glass of Sciacchetra dessert wine. This is the Italy of postcards made real.

Village hopping by train
Coastal hiking path
Vernazza harbor lunch

Overnight: Cinque Terre area

9
Day Nine

Cinque Terre — Day Two

Cinque Terre & Portovenere

A second, more relaxed day. Visit the villages you missed yesterday, or return to your favorite for a longer stay. Take the ferry from Riomaggiore to Portovenere — a stunning harbor town at the tip of the peninsula, with a 6th-century church perched on the rocks above the sea. Lord Byron swam from here to the next bay; the water is still that inviting.

Afternoon at leisure: kayak along the coast, join a cooking class in one of the villages, or simply sit on a terrace with a book and a glass of wine, watching the fishing boats come and go. This evening, farewell dinner at a restaurant built into the cliff face, the Mediterranean stretching to the horizon beneath your table.

Ferry to Portovenere
Kayak or cooking class option
Farewell dinner

Overnight: Cinque Terre area

10
Day Ten

Departure

Pisa Airport

Collect your car from La Spezia and drive south to Pisa Airport — about an hour along the Ligurian coast. If time allows, stop in Pisa itself for the obligatory photo with the Leaning Tower; the Piazza dei Miracoli is genuinely impressive beyond the famous tilt.

Return the rental car at the airport and depart. You leave Italy with the memory of open roads through Umbria’s green valleys, the golden light of Chianti at sunset, and the vertigo of the Cinque Terre cliffs dropping into blue water. The self-drive tour gives you something no chauffeured trip can: the freedom of a country discovered on your own terms.

Drive to Pisa
Return rental car
Depart Pisa Airport

Overnight: Depart from Pisa

Love this itinerary? Make it yours.

This is a sample luxury custom route — a starting point, not a fixed package. Many clients travel something very close to this, customized for their travel style, group, and dates. Book a free consultation and a specialist will build from here.

Accommodations
Hand-picked hotels with parking, agriturismos, or countryside villas — chosen based on your preferences and travel style.
Transportation
Full self-drive, or hybrid with private driver for specific legs — all confirmed before you travel.
Experiences
Pre-arranged tours and activities built around your interests — entrance tickets sorted, no queuing.

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Activities on this itinerary

Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.

Colosseum & Forum TourRome

Vernazza Harbour LunchCinque Terre

Orvieto CathedralUmbria

Assisi BasilicaUmbria

Chianti Wine TastingTuscany

Siena Walking TourTuscany

Cinque Terre HikingLiguria

Vernazza Harbour LunchCinque Terre

Portovenere FerryLiguria

Cortona VisitTuscany

Montepulciano WineTuscany

Pisa Tower StopPisa

Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.

The people who will design your Italy trip

You work directly with a specialist who knows Italy deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Italy · Switzerland · Portugal · Spain

Lexi Blade

Florence and Austria-based, Lexi brings on-the-ground expertise across Southern Europe’s most sought-after destinations. Every recommendation comes from personal experience.

Book a Consultation




Ireland · Scotland · UK · Iceland

Taryn Harrison

25 years designing European trips, with a deep network across Italy’s regions. CMSC certified and former Peace Corps. Ideal for multi-country trips combining Italy with Ireland, Scotland, or beyond.

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About this itinerary

Is a self-drive tour of Italy a good idea?


Yes — a self-drive tour is excellent for independent travelers who enjoy the freedom of the open road to the country. The route covers Italy’s most iconic regions in a logical sequence: Venice’s canals, Florence’s Renaissance art, Tuscany’s rolling countryside, Rome’s ancient monuments, and the Amalfi Coast’s dramatic cliffs. It’s Juniper’s most popular Italy itinerary precisely because it works well for first-time visitors without feeling rushed.

Can I customise this itinerary?


Yes — this is a sample for inspiration. Every Juniper trip is designed from scratch. You can add regions (the Amalfi Coast, Sicily, the Dolomites), swap cities, extend stays, change the type of transport, and adjust the pace entirely. Your specialist builds the actual itinerary around your group’s preferences during the free consultation.

Is it safe to drive in Italy?


Driving in rural Tuscany and Umbria is straightforward and genuinely enjoyable — quiet roads, beautiful scenery, and well-signposted routes. City centers like Rome and Florence have restricted traffic zones (ZTL) that your specialist will help you navigate. The itinerary is designed so you never need a car in cities — Rome is explored on foot, and the Cinque Terre by train.

Is this itinerary good for a honeymoon?


This route works well as a honeymoon base — the freedom of the open road, Tuscan hilltop villages, and the Cinque Terre coast are all genuinely well-suited to couples. That said, our dedicated Amalfi Coast with Capri itinerary (7 days) is specifically designed for honeymoons and couples and covers the most romantic coastal regions and properties in more detail.

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“Juniper Tours did an amazing job booking our vacation to Italy. Lexi Blade helped us schedule our dream vacation from Venice all the way to Sorrento on the Amalfi coast, with stops in Florence and Rome. Lexi was phenomenal and made changes for us many times to assure we got the most out of our trip.”

Nikki Walls  ·  Verified Google Review

Build your luxury custom self-drive Italy tour with one of our top travel specialists.

30 minutes, completely free. Walk away with a clear picture of what your luxury custom self-drive tour could look like — dates, route, 4 and 5-star accommodations, and all.

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