The Italian Dream — Self-Launched Edition
8 days · Italy
Wingbuddy charges £1,285
No-markup version: ~£1,124 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched version of Wingbuddy's 8-day coach tour of Rome, Assisi, Siena, Florence, Bologna, Venice and Montepulciano. Instead of a 40-person motorcoach and fixed hotel blocks, you'll string the same cities together with Italy's excellent (and cheap) high-speed trains and regional buses, stay in hostels and family-run guesthouses in each city centre, and book the same headline experiences — Vatican Museums & Sistine Chapel, Colosseum & Roman Forum, a Florence walking tour, a Venice cicchetti crawl — directly via GetYourGuide or the official museum sites. Same highlights, roughly half the price, and total freedom over your own pace.
Day-by-day
Arrive in Rome — Trastevere orientation
Rome
Land at Fiumicino and take the Leonardo Express train into Termini (~£12, 32 mins) or the slower FL1 regional to Trastevere (~£7). Check into a hostel or budget guesthouse around Termini or Trastevere (dorms from ~£25, private twin from ~£55). Spend the afternoon on a free self-guided wander: Pantheon (free), Piazza Navona, Campo de' Fiori, then cross the river into Trastevere for a cheap dinner of supplì and pizza al taglio (~£12). Pick up a Roma Pass or just buy individual tickets as you go — most of Day 7's sights are booked separately.
🚌Leonardo Express train Fiumicino → Termini, ~£12 one way (or FL1 regional ~£7 to Trastevere). City buses/metro £1.50 per 100-minute ticket.
🛏Hostel or budget guesthouse near Termini / Trastevere — dorm bed ~£25–30, budget double ~£55–70
- →Leonardo Express airport transfer
- →Self-guided Pantheon & Piazza Navona walk
- →Trastevere evening food wander
Rome → Assisi → Siena → Florence by train
Florence
The coach tour crams three towns into one day; you can do the same by rail, or (better) drop one. Fastest version: regional train Rome Termini → Assisi (~£8, 2h), store bags at the station, walk up to the Basilica di San Francesco, grab a slice of torta al testo for lunch (~£5), then train Assisi → Siena via Foligno/Chiusi (~£12, 2h). Wander Piazza del Campo and the old town for an hour, then regional train Siena → Florence (~£8, 1.5h). Arrive Florence early evening and check into a hostel near Santa Maria Novella (dorms ~£28, private ~£60). Honestly, skipping Siena here and coming back as a day trip from Florence is the calmer option — Siena deserves more than 90 minutes.
🚌Regional trains Rome → Assisi (~£8), Assisi → Siena (~£12), Siena → Florence (~£8). Book on Trenitalia app; regional fares are fixed and cheap. Total ~£28.
🛏Hostel or guesthouse near Santa Maria Novella, Florence — dorm ~£28–35, budget double ~£60–80
- →Basilica di San Francesco, Assisi
- →Piazza del Campo, Siena
- →Evening arrival walk in Florence
Florence — Duomo, Signoria, Santa Croce (+ optional Pisa)
Florence
Book a small-group Florence walking tour on GetYourGuide (~£25–30, 2–3h) covering Piazza della Signoria, Palazzo Vecchio (exterior), the Duomo exterior and Santa Croce. Climb Giotto's Campanile or Brunelleschi's Dome with a direct-booked timed ticket via the Opera del Duomo official site (~£15–25; the dome needs booking weeks ahead). Lunch at a Mercato Centrale stall (~£8). If you want Pisa, take a regional train from Firenze S.M.N. (~£9 each way, 1h) and buy the Leaning Tower climb ticket direct on the Opera della Primaziale Pisana site (~£20) — the tour version famously doesn't include going up. Back in Florence for an aperitivo in Santo Spirito (~£6).
🚌All on foot in Florence. Optional return train Florence → Pisa ~£18. Local bus £1.50.
🛏Same Florence hostel/guesthouse
- →Small-group Florence walking tour (GetYourGuide)
- →Brunelleschi's Dome or Giotto's Campanile timed ticket
- →Optional self-launched Pisa day trip incl. Leaning Tower climb
Florence → Bologna food walk → Venice
Venice
High-speed Frecciarossa Florence → Bologna (~£10–15 with advance fare, 37 mins). Drop bags at Bologna Centrale lockers (~£4), then self-guide the portico walk: Piazza Maggiore, Piazza del Nettuno, Palazzo Podestà, Basilica di San Petronio (free entry to the church). Lunch the way locals do — a plate of tagliatelle al ragù or a crescentina from a Quadrilatero deli (~£10). Then regional train Bologna → Venezia Santa Lucia (~£9–12, 1h50). Stay on the mainland in Mestre for cheapness (hostel/budget hotel ~£30 dorm / ~£55 double) or pay a premium for a Venice island hostel (~£40 dorm). Evening stroll to the Rialto Bridge after the day-trippers leave.
🚌Frecciarossa Florence → Bologna ~£12; regional Bologna → Venice ~£10. Total ~£22.
🛏Hostel or budget hotel in Mestre (budget double ~£55–65) or Venice island hostel (dorm ~£40)
- →Self-guided Bologna portico & piazza walk
- →Quadrilatero street food lunch
- →Evening Rialto Bridge & Grand Canal wander
Venice — San Marco, Doge's Palace, cicchetti crawl
Venice
Buy a vaporetto day pass (~£18 for 24h, or single rides £8) and ride Line 1 down the Grand Canal to San Marco. Book a Doge's Palace skip-the-line ticket direct via the official Palazzo Ducale site or GetYourGuide (~£22–28) and pre-book a free-timed entry to St Mark's Basilica (~£3 online booking fee; the terrace/museum is extra). In the afternoon join a small-group Venice walking tour or a cicchetti food tour on GetYourGuide (~£28–35) that includes a glass of spritz or prosecco — this replaces the tour's included tapas stop. A shared gondola ride (30 min, ~£30 per person booked online) is the budget way to tick that box rather than a private £80+ gondola.
🚌24h vaporetto pass ~£18; otherwise £8 per single ride. Walk everywhere in between.
🛏Same Venice/Mestre base
- →Vaporetto Grand Canal ride
- →Doge's Palace skip-the-line ticket
- →St Mark's Basilica timed entry
- →Cicchetti & spritz small-group food tour
- →Optional shared gondola ride
Venice → Montepulciano wine country → Rome
Rome
This is the trickiest leg of the original itinerary by public transport — plan it early. Take a regional train Venice → Montepulciano station (~£15–18, 3h, change at Chiusi or Firenze). From Montepulciano station, the LFI bus or a shared taxi runs up to the hill town (~£2–3, 20 mins). Wander the Corso, taste Vino Nobile at a small enoteca (~£8 for a flight), have a long Tuscan lunch (~£15). Then bus back down and take the train Montepulciano → Rome Termini (~£15–20, 2.5h via Chiusi). Arrive Rome late evening; three nights in a hostel or budget guesthouse near Termini (dorm ~£28, double ~£60). If this feels too rushed, alternative: skip Montepulciano and do direct Venice → Rome high-speed (~£35, 4h), using the saved day to explore Rome.
🚌Regional trains Venice → Montepulciano (~£16) and Montepulciano → Rome (~£18); LFI bus up to the town ~£3. Total ~£37.
🛏Hostel or budget guesthouse near Termini, Rome — dorm ~£28–32, budget double ~£60–75
- →Montepulciano old town & Corso walk
- →Vino Nobile tasting in a local enoteca
- →Tuscan trattoria lunch
Rome — Vatican Museums & Colosseum + Forum
Rome
Book both headline experiences online in advance. Vatican Museums with skip-the-line entry direct via the official Musei Vaticani site (~£17 plus £5 booking fee) or a GetYourGuide small-group tour (~£40) — the official ticket is far cheaper and you can follow the Sistine Chapel at your own pace. Metro A to Ottaviano, walk to the entrance. Lunch near the Vatican (~£10). In the afternoon, book the Colosseum + Roman Forum + Palatine Hill combined ticket direct via the official Coopculture site (~£16, timed entry) and add an audio guide or a small-group tour if you want the storytelling (~£30–40 via GetYourGuide). Finish at Circo Massimo, then cheap dinner in Monti (~£14).
🚌Metro and bus day pass ~£6 (or two single tickets £3). Rome's centro storico is walkable.
🛏Same Rome base
- →Vatican Museums & Sistine Chapel (official timed ticket)
- →Colosseum + Roman Forum + Palatine Hill combined ticket
- →Monti neighbourhood evening
Trastevere morning & departure
Rome
Slow breakfast at a neighbourhood bar (cornetto + cappuccino ~£4), a last wander through the Pantheon area or up to the Aventine Keyhole (free, queue-free early), then Leonardo Express back to Fiumicino (~£12). If your flight is late, add the Borghese Gallery (official site, ~£13, timed entry — book ahead) or a free walking tour of the Jewish Ghetto (tip-based, ~£5–10).
🚌Leonardo Express Termini → Fiumicino ~£12; metro/bus £1.50.
🛏—
- →Early Trastevere & Aventine Keyhole walk
- →Optional Borghese Gallery timed entry
- →Optional tip-based free walking tour
Self-launched vs. Wingbuddy
| This itinerary (self-launched) | Wingbuddy | |
|---|---|---|
| Price per person | ~£1,124 | £1,285 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £161 per person (13%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Wingbuddy-style trips? Check them out here.~£1,124
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 The Italian Dream — Self-Launched Edition cost?+
Doing it yourself with this self-launched itinerary costs an estimated £1,124 per person for 8 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 £1,285 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £1,124 — a saving of roughly £161 (13%) per person.
How long is the Italy trip?+
This itinerary runs 8 days, covering 8 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?
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