Italy from North to South — Self-Launched Version
11 days · Italy
Wingbuddy charges £2,070
No-markup version: ~£1,245 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched take on Wingbuddy's 11-day coach loop from Rome to Rome via Assisi, Siena, Florence, Bologna, Venice, Montepulciano, the Vatican, Pompeii, Sorrento and Capri. Instead of a 40-person coach you'll use Italy's excellent (and cheap) high-speed and regional trains, sleep in hostels and family-run guesthouses, and book the same skip-the-line Vatican, Colosseum and Pompeii entries directly through official sites or GetYourGuide. Expect a fast-paced, city-hopping run through Italy's greatest hits — with full freedom over your evenings and meals.
Day-by-day
Arrive in Rome — Trastevere evening
Rome
Land at Fiumicino and take the Leonardo Express train straight to Termini (~€14 / £12, 32 mins). Check into a hostel or budget guesthouse near Termini or Monti (dorms from ~£18, private doubles from ~£45). Spend the late afternoon wandering Monti's cobbled lanes, then cross the river to Trastevere for cheap pizza bianca, supplì and a spritz by the fountain. Buy a 48-hour ATAC transport pass if you plan lots of buses (~€12.50).
🚌Leonardo Express Fiumicino–Termini ~£12
🛏Hostel or budget guesthouse near Termini/Monti (dorm ~£18, private ~£45)
- →Monti neighbourhood wander
- →Trastevere evening food stroll
Rome → Assisi → Siena → Florence
Florence
Catch an early regional train Rome Termini → Assisi (~1h45, ~€13) and self-guide the medieval hill town: Basilica of St Francis, Piazza del Comune and the steep lanes. Then train Assisi → Terontola → Siena (~2h, ~€18) for the afternoon — Piazza del Campo, the Duomo exterior and a wander through the contrade. Finish with a regional train Siena → Florence (~1h30, ~€10) and check into a hostel in Santa Maria Novella or San Lorenzo (~£25 dorm, ~£55 private). It's a long day — if you'd rather slow it down, cut Assisi and go straight Rome → Siena → Florence.
🚌Regional trains Rome–Assisi–Siena–Florence ~£30 total
🛏Hostel near Santa Maria Novella, Florence (dorm ~£25)
- →Basilica of St Francis, Assisi
- →Piazza del Campo & Duomo exterior, Siena
- →Tuscan countryside views from the regional train
Florence highlights + optional Pisa
Florence
Morning walk of the historic centre on a self-guided route: Santa Maria del Fiore and its free-standing campanile, Piazza della Signoria, Palazzo Vecchio exterior and Santa Croce. Book a 1-hour guided Duomo complex skip-the-line entry via GetYourGuide (~£25) or just buy the Brunelleschi Pass directly from the Opera del Duomo (~€30) if you want to climb the dome. Afternoon option: regional train Florence → Pisa Centrale (~1h, ~€9 each way), 20-minute walk to Piazza dei Miracoli for the Duomo, Baptistery and Leaning Tower exterior — book a tower slot directly in advance if you want to climb (~€20). Dinner at a Mercato Centrale food stall (~£12).
🚌Optional return train to Pisa ~£16
🛏Hostel near Santa Maria Novella, Florence (dorm ~£25)
- →Duomo complex (skip-the-line pass)
- →Piazza della Signoria & Palazzo Vecchio
- →Basilica di Santa Croce
- →Optional Pisa & Leaning Tower
Florence → Bologna → Venice
Venice
High-speed train Florence → Bologna (~35 mins, ~€10, book on Italo or Trenitalia ahead). Drop bags and walk the porticoes: Piazza Maggiore, Palazzo Re Enzo, Piazza del Nettuno, Basilica di San Petronio, plus a stop at the Quadrilatero food market for a piadina or tortellini in brodo (~£8). Mid-afternoon regional train Bologna → Venezia Santa Lucia (~1h30, ~€10). Check into a hostel on the mainland (Mestre, dorm ~£18) or splurge on a Cannaregio guesthouse (~£50). Buy a 48-hour ACTV vaporetto pass (~€35) if you'll ride boats more than twice.
🚌High-speed Firenze–Bologna ~£9, regional Bologna–Venezia ~£9
🛏Hostel in Mestre or budget guesthouse in Cannaregio (dorm ~£18)
- →Bologna porticoes & Piazza Maggiore
- →Quadrilatero food market stop
- →First evening stroll along the Grand Canal
Venice — Rialto, San Marco and cicchetti
Venice
Early start to beat the crowds: walk the Rialto Bridge, then cross to San Marco for the Basilica (free entry, ~€3 for the golden altar; book a timed slot online) and the Doge's Palace — buy a combined ticket directly from the Fondazione Musei Civici (~€30) or via GetYourGuide for a short guided tour (~£35). Free time to get lost in Dorsoduro and Castello. Late afternoon do a self-guided cicchetti crawl in Cannaregio along the Ruga do Spade — five small plates plus an ombra of prosecco comes to roughly £18.
🚌Vaporetto day pass ~£9 (or walk everywhere)
🛏Hostel in Mestre or budget guesthouse in Cannaregio (dorm ~£18)
- →Rialto Bridge & San Marco Basilica
- →Doge's Palace & Bridge of Sighs
- →Cannaregio cicchetti crawl
Venice → Montepulciano → Rome
Rome
Train Venice → Florence (high-speed ~2h, ~€25) then regional Florence → Chiusi-Chianciano Terme (~1h30, ~€10), where a local bus or the short taxi hop takes you up to Montepulciano (~£5). Spend three hours in the medieval town: Piazza Grande, the Vino Nobile cellars in the tufa caves and a long lunch at a trattoria (~£15 for a full lunch with a glass of wine). Return by bus and train to Rome (~2h30, ~€25), arriving in time for a late supper near Termini.
🚌Trains Venice–Florence–Chiusi and Chiusi–Rome ~£50 total plus local bus
🛏Hostel or budget guesthouse near Termini/Monti (dorm ~£18)
- →Montepulciano old town & Piazza Grande
- →Vino Nobile wine cellar tasting
- →Trattoria lunch
Vatican Museums & Colosseum day
Rome
Pre-book Vatican Museums entry on the official site (~€20 + €5 booking) or a GetYourGuide small-group tour with skip-the-line (~£45, 3h) — go for the 8am slot. You'll see the Tapestries and Maps galleries, Raphael's Rooms and the Sistine Chapel, then exit into St Peter's Square. Lunch nearby (~£10). Afternoon: book the official Colosseum + Roman Forum + Palatine Hill 24-hour ticket directly from Coopculture (~€18) or a GetYourGuide guided version (~£35, 3h). Climb the Palatine for the best Forum view, then finish with a cheap pasta dinner in Testaccio (~£12).
🚌Metro day ticket ~£1.50
🛏Hostel or budget guesthouse near Termini/Monti (dorm ~£18)
- →Vatican Museums & Sistine Chapel
- →St Peter's Square
- →Colosseum, Roman Forum & Palatine Hill
Rome → Pompeii → Sorrento
Sorrento
High-speed train Rome Termini → Napoli Centrale (~1h10, ~€20), then the local Circumvesuviana line to Pompeii Scavi (~35 mins, ~€4) — the ruins entrance is directly across the road. Book Pompeii entry directly from the Parco Archeologico (€18) or a GetYourGuide guided tour (~£30, 2h) with an archaeologist — worth it for context. Grab a proper Neapolitan pizza near Napoli Centrale (~£8) before or after. Then train Pompeii → Sorrento (~30 mins, ~€3) along the coast. Accommodation: a guesthouse in Sorrento or cheaper in Sant'Agnello (~£45 double, ~£22 dorm).
🚌Frecciarossa Rome–Naples ~£18, Circumvesuviana Naples–Pompeii–Sorrento ~£6
🛏Guesthouse in Sorrento or Sant'Agnello (double ~£45, dorm ~£22)
- →Pompeii archaeological site with guide
- →Naples pizza stop
- →Circumvesuviana coastal ride
Capri day trip from Sorrento
Sorrento
Ferry Sorrento → Marina Grande, Capri with Caremar or NLG (~40 mins, ~€22 each way — book the early 8am crossing to dodge queue). From Marina Grande take the funicular up to Capri town, walk the Via Camerelle and Gardens of Augustus, then hop the local bus to Anacapri (~€2) for the scenic views and the chairlift up Monte Solaro (~€14). The Blue Grotto is best reached by taking a small rowboat from Marina Grande (~€20 including entry) — weather permitting. Catch a late-afternoon ferry back and eat in Sorrento (~£15). Bring water and snacks; Capri is expensive.
🚌Return ferry Sorrento–Capri ~£38, local buses ~£4
🛏Guesthouse in Sorrento or Sant'Agnello (double ~£45, dorm ~£22)
- →Funicular & Capri town
- →Anacapri & Monte Solaro chairlift
- →Blue Grotto rowboat
Sorrento → Rome
Rome
Morning free in Sorrento — swim at Marina Grande, browse the inlaid-wood shops on Via San Cesareo and have a limoncello gelato. Midday Circumvesuviana back to Naples (~1h, ~€5) then high-speed train to Rome (~1h10, ~€20; book ahead for the cheapest fares). Check back into your Termini-area hostel and spend the evening on a final wander — Pantheon, Piazza Navona and a late cone of gelato (~£3).
🚌Circumvesuviana ~£4 + Frecciarossa Naples–Rome ~£18
🛏Hostel or budget guesthouse near Termini/Monti (dorm ~£18)
- →Marina Grande swim
- →Sorrento old town
- →Pantheon & Piazza Navona evening walk
Depart Rome
Rome
Breakfast and a last coffee at a local bar (standing, ~€1.20). If your flight is later, squeeze in the Borghese Gardens or a final market stop at Campo de' Fiori before taking the Leonardo Express back to Fiumicino (~£12). Note: Wingbuddy's itinerary lists the tour as ending in Vatican City, but in practice the departure airport is Rome FCO — book your flight home accordingly.
🚌Leonardo Express Termini–Fiumicino ~£12
🛏None (departure day)
- →Campo de' Fiori market
- →Borghese Gardens stroll (time permitting)
Self-launched vs. Wingbuddy
| This itinerary (self-launched) | Wingbuddy | |
|---|---|---|
| Price per person | ~£1,245 | £2,070 |
| Duration | 11 days | 11 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £825 per person (40%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Wingbuddy-style trips? Check them out here.~£1,245
estimated per person
You never pay Travel Crew for this — you pay hostels, transport, and activity providers directly, the same as if you'd booked it all yourself.
This publishes your dates so other travellers can find and join you — no tour operator needed.
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Frequently asked questions
How much does Italy from North to South — Self-Launched Version cost?+
Doing it yourself with this self-launched itinerary costs an estimated £1,245 per person for 11 days in Italy. This is an AI-generated estimate based on typical budget-traveller prices — actual costs will vary by season and how you book.
Is this cheaper than booking with Wingbuddy?+
Yes — Wingbuddy charges around £2,070 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £1,245 — a saving of roughly £825 (40%) per person.
How long is the Italy trip?+
This itinerary runs 11 days, covering 11 day-by-day stops through Italy.
How do I join this trip?+
You can join an existing open departure using this itinerary if one is scheduled, or launch your own departure with your own dates and invite other travellers to join you — no tour operator required.
Isn't it easier to just use a tour operator?+
Well, yes, a tour operator will book all the individual parts of your travel for you and provide a guide. That's obvious, but doing this has the potential to save the group thousands, which can in turn improve your itinerary substantially or save you huge amounts of money. Also, when you launch a departure, Travel Crew has tools in place to help you book the individual sections of the trip or make it easier for you to do this as a group. Really, you do not need a middle man. If you are more comfortable paying more and using a middle man, then you should certainly do this.
Is it safer to book through a tour operator?+
Arguably, there isn't much difference. A self-launched trip runs on the same principle as a group travel crew: collective responsibility, everyone looking out for each other, the same way it would if a group of friends organised the trip themselves — because that's exactly what's happening. You should always take out travel insurance before you go, self-launched or not; that doesn't change either way. Every open departure is published publicly with real dates and a real trip organiser, so it's never an anonymous arrangement, and our support team is reachable any time you need help, including in an emergency while you're away. Longer-term, we're building direct relationships with ground DMCs in popular destinations, offered as an optional paid add-on for extra on-the-ground support. Ultimately, though, the group is responsible for its own conduct and safety on a self-launched trip, same as on any trip you plan yourself.
What kind of trip is this?+
This is a culture, foodie, city-breaks trip through Italy, self-launched rather than run by a tour operator — you organise it with a group you find or bring yourself.
Would you like to name the operator, name the trip, or have any suggestions about how to improve this itinerary?
Drop your comment below — if you've done a similar route, tell us what worked, what you'd add, or what you'd skip.
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