Italy
What makes this different from the other itineraries
This is the only road trip in the group — one rental car, total freedom, no ferry schedules or fixed departures. It's also two genuinely different Italys in one trip: the world's most famous Renaissance region, followed immediately by its most underrated one. Le Marche has Tuscany-quality scenery, food, and art history with a fraction of the tourists. September also marks the start of white truffle season — one of Italy's greatest culinary events.
Budget snapshot — per person
Dublin → Pisa (roundtrip)
~$150–300
Ryanair direct DUB→PSA, 2hr 45min
Boise → Pisa (roundtrip)
~$900–1,100
via European hub, book by May
Rental car (split 3 ways)
~$80–90pp
9-day rental ~$700–800 total, including fuel
Day-by-day itinerary
Fly into Pisa — pick up rental car — drive to Florence
Travis: BOI → hub (LHR/FRA/AMS) → PSA. Dublin couple: Ryanair direct DUB→PSA. Pick up the rental car at Pisa airport — do not attempt to drive into Florence's historic centre, park at Piazzale Michelangelo or a fringe hotel with parking. Evening: first Negroni in the Oltrarno neighbourhood.
Florence — Uffizi & Oltrarno
Book Uffizi tickets months in advance (€25pp, mandatory). Go at opening. Botticelli's Birth of Venus and Primavera, Leonardo's Adoration of the Magi, Raphael's portraits — plan 3 hours minimum. Afternoon: Oltrarno neighbourhood for lunch, Boboli Gardens walk, Ponte Vecchio at golden hour. Dinner in San Frediano — the most local-feeling quarter.
Florence — Duomo, Accademia & Fiesole
Morning: Duomo complex — climb the dome for Florence's best view (book online, €30pp). Accademia for Michelangelo's David (also book ahead). Afternoon: drive 20 minutes up the hill to Fiesole — a Roman amphitheatre, Etruscan ruins, and the view of Florence laid out below. Quieter and cooler than the city in September.
Drive to Siena via Chianti — check into agriturismo
The drive through the Chianti Classico wine zone is half the experience: vineyards in harvest, cypress-lined driveways, hilltop castles. Stop at a winery for a tasting en route (Badia a Coltibuono or Castello di Brolio). Arrive Siena afternoon — Piazza del Campo is one of Italy's great public spaces, especially at dusk. Stay outside the ZTL zone in an agriturismo for the true Tuscan experience.
San Gimignano, Volterra & hill town loop
Drive the Val d'Elsa — San Gimignano's medieval towers at 9am before the tour buses, then Volterra (Etruscan museum, alabaster workshops, vertiginous views). These are two of Europe's best preserved medieval hill towns and they're 30 minutes apart by car. Lunch in the countryside: wild boar ragù, pecorino, local Vernaccia white wine. Return to agriturismo base for one more night.
Cross the Apennines — arrive Urbino
The drive from Siena to Urbino takes 3–3.5 hours over the Apennine Mountains — genuinely beautiful, almost no traffic. Urbino is a UNESCO World Heritage Site that most Americans have never heard of. "Every bit as lovely as Siena or Florence, yet there were so few tourists." The Ducal Palace is one of the finest Renaissance buildings in Europe. Raphael was born here. Check into a small hotel in the old town. No queues anywhere.
Urbino + Marche countryside
Full day in and around Urbino. Morning: Galleria Nazionale delle Marche inside the Ducal Palace — Piero della Francesca's strange, brilliant Flagellation hangs here, one of the most discussed paintings in art history. Afternoon: drive the rolling Marche hills through borghi (medieval villages) — the scenery rivals Tuscany but is completely deserted. Pick up local Verdicchio wine and Ciauscolo sausage from a farm shop.
Drive to Conero Riviera — beach day
Drive 90 minutes east to Portonovo on the Conero Peninsula — white limestone cliffs dropping into impossibly clear Adriatic water, a protected nature reserve with almost no development. One of the best beaches on Italy's Adriatic coast. Many coves reachable only by hiking 15 minutes through oak forest, which keeps crowds minimal. Fresh fish lunch at one of the small restaurants right on the beach. Stay the night in Sirolo or Numana.
Drive south to Ascoli Piceno
Two hours south from the Conero coast. Ascoli Piceno is "the city of a hundred towers, built entirely of travertine, with a piazza considered one of Italy's most beautiful." Have an aperitivo at the historic Caffè Meletti on Piazza del Popolo — Ernest Hemingway's regular table. Eat olive all'ascolana (fried meat-stuffed olives) and crema fritta — Ascoli's signature dishes, found nowhere else quite like this. September truffle dishes on every menu.
Drive back to Pisa — fly home
Ascoli Piceno to Pisa: 3.5 hours, mostly motorway. Leave by 7am for afternoon flights. Alternative: fly from Ancona (AOI) — small airport, limited connections but closer. Or take the train from Ascoli to Ancona, then Bologna Marconi Airport for more international options. Drop car at Pisa airport, goodbye Italy.
Food & drink — the real reason to choose this itinerary
White truffles September timing
White truffle season opens in early September in Le Marche. Truffle pasta with shaved fungus is a once-in-a-decade experience. Order tagliatelle al tartufo everywhere in Urbino and Ascoli.
Olive all'ascolana
Whole green olives stuffed with seasoned veal, breadcrumbed and fried. The Ascoli Piceno version is in a different league from anything you've tasted elsewhere. Eat them standing at a bar for €2.
Chianti Classico & Verdicchio
September is harvest month in Chianti — you may see vendemmia (grape-picking) happening roadside. In Le Marche, switch to Verdicchio dei Castelli di Jesi white with fish and Rosso Conero red with meat.
Agriturismo meals
The best meals of the trip will be at agriturismi — farm stays that serve their own produce. A full set dinner with wine, antipasti, pasta, secondi costs €25–35pp. Book ahead, these are often fixed-menu only.
Bistecca Fiorentina
A T-bone steak from Chianina cattle, sold by weight, cooked rare over charcoal. Florence's signature dish and a candidate for the best piece of meat in Europe. Budget €25–35 per person for this one.
Portonovo mussels
The Conero coast is famous for its Portonovo mussels — cozze, usually served steamed with white wine and lemon in a beach restaurant. Best eaten at a picnic table 10 metres from the sea.
Full budget — per person
Le Marche vs Tuscany — what to expect
Tuscany (Days 1–5)
The world's most famous countryside, and it deserves the reputation — but September still brings crowds to Florence and Siena. Book the Uffizi, Accademia, and Duomo dome months ahead. The Chianti and Val d'Elsa countryside is genuinely magical, especially during grape harvest. Higher prices than Le Marche.
Le Marche (Days 6–10) hidden gem
"Le Marche is perhaps the most picturesque region of Italy." The same quality of art, scenery, and food as Tuscany, with almost no tourist infrastructure. Prices are 20–30% lower. Locals are genuinely delighted to see foreign visitors. September and October are the best months to visit — warm, uncrowded, and truffle season.