Best of Italy — Self-Launched: Rome, Florence, Venice, Assisi, Sorrento & Capri in 14 Days
14 days · Italy
Insight Vacations charges £3,300
No-markup version: ~£970 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched version of Insight Vacations' 14-day "Best of Italy" coach tour, rebuilt for independent travellers using trains, buses and ferries instead of a private coach. Same route — Rome's Vatican and Colosseum, Florence and a Chianti day trip, Pisa, Venice, Assisi, Sorrento with Capri and Pompeii — but booked yourself: Trenitalia high-speed trains between cities, a Leaning Tower stop en route to Venice, a shared boat and funicular on Capri, and a self-booked opera dinner in Rome. Expect hostels/guesthouses and 2–3 star budget hotels, self-guided museum entries timed in advance, and supermarket or trattoria eating. Costs are rough backpacker/mid-budget estimates in GBP excluding international flights.
Day-by-day
Arrive Rome — evening in Monti
Rome
Land at Fiumicino and take the Leonardo Express train into Termini (~€14, 32 mins) or the FL1 regional for under €10 if your hostel is further out. Settle into a hostel or budget guesthouse near Termini, Monti or the Vatican. In the evening wander Monti's lanes, grab a plate of cacio e pepe or a pizza bianca from a bakery, and do a free (tip-based) evening walking tour if you want an orientation. Book tomorrow's Vatican Museums ticket online tonight — timed entry slots sell out.
🚌Leonardo Express Fiumicino→Termini ~£12
🛏Hostel or budget guesthouse near Termini/Monti — dorm ~£25–35, private double ~£55–75
- →Free Rome orientation walk (Monti, Trevi Fountain, Pantheon exterior)
- →Book Vatican Museums timed entry online
Vatican Museums, Sistine Chapel & Ancient Rome
Rome
Beat the crowds with an 8am Vatican Museums slot (book direct at museivaticani.va, ~€20 plus €5 booking — far cheaper than a resold 'VIP entry'). The Bramante Staircase's behind-the-scenes access is tour-only, but the standard route covers the Sistine Chapel and Raphael Rooms; St Peter's Basilica is free to enter (dress code: knees and shoulders covered). After lunch walk the Circus Maximus and Arch of Constantine and view the Colosseum exterior — or pay ~€18 to go inside with a timed ticket. Evening: Pantheon (€5), Trevi Fountain and Piazza Navona with a cone of gelato.
🚌Metro A/B hops ~£1.30 each, or walk
🛏Same hostel/guesthouse in Rome
- →Vatican Museums & Sistine Chapel self-guided (~£22)
- →St Peter's Basilica (free)
- →Colosseum exterior or timed-entry ticket (~£16)
- →Pantheon, Trevi Fountain, Piazza Navona
Rome → Florence via Chianti wine country
Florence
Take a morning Frecciarossa high-speed train Rome→Florence (~1h35, book ahead for as little as £20–30). Dump bags at your hostel near Santa Maria Novella. In the afternoon, replace the coach's private Tuscan-estate picnic with a small-group Chianti wine-tasting day trip from Florence booked on GetYourGuide or Klook (~£45–65, half-day, includes tastings) — or DIY by bus to Greve in Chianti and lunch at a village enoteca. Evening: aperitivo in Santo Spirito and a bistecca or ribollita dinner.
🚌Frecciarossa Rome→Florence ~£20–35
🛏Hostel or budget B&B in central Florence — dorm ~£28–38, private ~£60–85
- →Chianti wine tasting day trip or DIY Greve in Chianti
- →Santo Spirito aperitivo
Florence — leather, markets & Oltrarno
Florence
Do the leatherwork experience independently: the Scuola del Cuoio at Santa Croce and the San Lorenzo leather market both let you watch artisans at work for free, with short workshops bookable direct (~£40–70) if you want to make something. Browse the Mercato Centrale food hall for lunch. Cross to Oltrarno for artisan workshops and a free visit to the Brancacci Chapel (small entry fee, book ahead). Evening walk up to Piazzale Michelangelo for sunset over the Duomo.
🚌Walkable city, tram/bus ~£1.50
🛏Same hostel/B&B in Florence
- →Scuola del Cuoio visit / optional leather workshop
- →Mercato Centrale food hall
- →Oltrarno artisan streets
- →Piazzale Michelangelo sunset
Accademia, Duomo & Piazza della Signoria
Florence
Pre-book a timed Accademia ticket for Michelangelo's David (~€16 + booking, official site or GetYourGuide skip-the-line ~£25). Then take the combined Brunelleschi Pass for the Duomo, Giotto's Campanile and the Baptistery (~€30, book a climb slot for the dome) — the Baptistery's Ghiberti 'Gates of Paradise' doors are outside and free to see. Stroll Piazza della Signoria and the Palazzo Vecchio courtyard, then a cheap trattina dinner in San Frediano.
🚌Walk
🛏Same hostel/B&B in Florence
- →Accademia & Michelangelo's David (~£20)
- →Duomo + Campanile + Baptistery Brunelleschi Pass (~£26)
- →Piazza della Signoria & Palazzo Vecchio courtyard
Florence → Pisa → Venice
Pisa & Venice
Take an early regional train Florence→Pisa Centrale (~1h, ~£8). Walk 20 minutes to Piazza dei Miracoli to see the Leaning Tower, Cathedral and Baptistery — the square is free, and climbing the tower is ~€20 if booked ahead. Lunch near the station, then train Pisa→Florence and a Frecciarossa Florence→Venice Santa Lucia (~2h10, ~£25–40 booked early). Stay in Mestre or a hostel near the station on Venice island for cheaper beds.
🚌Regionale Florence→Pisa ~£7; Frecciarossa Florence→Venice ~£15–30
🛏Hostel in Mestre or Cannaregio — dorm ~£25–35, private ~£60–80
- →Piazza dei Miracoli: Leaning Tower, Duomo, Baptistery
- →Optional tower climb (~£17)
Venice — canals, cicchetti & islands
Venice
Buy a 24-hour ACTV vaporetto pass (~€25) and use it like a local — line 1 down the Grand Canal is the cheapest sightseeing boat in town. Explore San Marco square, the Rialto market, and the quieter Cannaregio and Dorsoduro quarters. Do the 'glassblowing centre' vibe on Murano: vaporetto line 3/4.1, free furnace demonstrations at several furnaces, or a small paid demo (~£10–15). Evening cicchetti crawl with a glass of wine house wine for under £20.
🚌ACTV vaporetto 24h pass included above
🛏Same Venice/Mestre base
- →Grand Canal vaporetto ride (24h pass ~£21)
- →Murano glassblowing demonstration
- →Rialto market & cicchetti crawl
Venice — St Mark's, Doge's Palace & gondola
Venice
Book St Mark's Basilica entry (~€3–6) and the Doge's Palace (~€30, or the combined Museums ticket) online to skip the queue — the Bridge of Sighs is visible from the palace interior and from the Ponte della Paglia. Rather than the tour's gondola serenade, join a shared 30-minute gondola ride booked via GetYourGuide/Klook (~£30–35 instead of €80+ private). Afternoon: Libreria Acqua Alta and the Accademia bridge for photos.
🚌Walk/vaporetto
🛏Same Venice/Mestre base
- →St Mark's Basilica (~£5)
- →Doge's Palace (~£26)
- →Shared gondola ride (~£30)
Venice → Assisi
Assisi
Train Venice Santa Lucia→Foligno/Assisi (~4h with a change at Foligno or Florence, ~£25–40 booked early), then the local bus or a short walk up to the old town. Check into a small family-run guesthouse inside the walls. Late afternoon: the Basilica of St Francis (free entry; Giotto's frescoes in the Upper Basilica) and the Church of St Mary of the Angels down on the plain. Dinner of Umbrian strangozzi pasta and Sagrantino wine.
🚌Regional/high-speed train Venice→Assisi ~£25–40
🛏Family-run guesthouse inside Assisi's walls — ~£35–50 double, dorm ~£22
- →Basilica of St Francis & Giotto frescoes (free)
- →Church of St Mary of the Angels
Assisi — Mount Subasio & Umbrian hill towns
Assisi
A slower day: hike up to the Eremo delle Carceri hermitage on the slopes of Mount Subasio (~1h each way on marked trails, free) or take a local bus to Spello, a gorgeous flower-lined hill town 15 minutes away. Back in Assisi, visit the Basilica of Santa Chiara and Rocca Maggiore for valley views (~€6). Cheap dinner from a bakery (torta al testo) plus local wine.
🚌Walk/local bus ~£2
🛏Same Assisi guesthouse
- →Eremo delle Carceri hike
- →Optional Spello by local bus
- →Rocca Maggiore viewpoint
Assisi → Sorrento via Naples
Sorrento
Train Assisi→Naples (~4h via Foligno/Rome, ~£30–45), then the Circumvesuviana local train Naples→Sorrento (~1h, €5) — cheap and frequent. Swap the coach's Mount Vesuvius viewpoint for the ferry view: from Sorrento's Marina Piccola you look straight across the Bay of Naples. Settle into a hostel or budget hotel a few minutes from the centre and eat at a pizzeria (fried pizza or a margherita for under £10). Buy a SITA bus or ferry ticket for Capri for tomorrow.
🚌Train Assisi→Naples ~£30–45; Circumvesuviana Naples→Sorrento ~£4.50
🛏Hostel/budget hotel in Sorrento — dorm ~£28–40, private ~£65–90
- →Bay of Naples views from Sorrento
- →Marina Piccola sunset
Capri day trip
Capri & Sorrento
Take the morning ferry from Sorrento Marina Piccola to Capri (~20 min, ~€20–25 each way, buy at the port or online with NLG/SNAV). On the island, ride the open-top convertible taxi up to Capri town (~€20 shared) or the funicular from Marina Grande (~€2.20), wander the alleyways to the Gardens of Augustus and the Faraglioni viewpoint, and take the funicular back down. Optional boat trip around the island or the Blue Grotto if seas are calm (~£15–25). Return for dinner in Sorrento.
🚌Ferry Sorrento↔Capri + funicular
🛏Same Sorrento base
- →Ferry to Capri (~£40 return)
- →Funicular & Capri town alleyways
- →Faraglioni viewpoint / Gardens of Augustus
Pompeii ruins → Rome (opera dinner)
Pompeii & Rome
Circumvesuviana from Sorrento to Pompeii Scavi (~30 min, €3), then a self-guided walk through the excavations with an audio guide or a small-group archaeology tour booked via GetYourGuide (~£20–30, skip-the-line entry ~€18; the tour's 'Local Expert' equivalent). See the Forum, shops and patrician villas. Train Pompeii→Naples→Rome (~2h total, ~£25–35). Evening: swap the Celebration Dinner for a self-booked dinner-and-opera experience in Rome (e.g. a small concert in a church or a trattoria with live arias, ~£45–70) or a cheap Roman dinner plus a €15 church concert.
🚌Circumvesuviana ~£2.50; trains Pompeii→Rome ~£25–35
🛏Hostel/guesthouse near Termini or Monti — dorm ~£25–35
- →Pompeii excavations with audio guide or small-group tour (~£35)
- →Dinner & live opera evening in Rome (~£55)
Rome — slow morning & departure
Rome
Last morning: a proper Italian breakfast at a bar (cappuccino + cornetto ~£4), a final wander through Campo de' Fiori market, or climb the Aventine keyhole for a St Peter's view (free). Train to Fiumicino for your flight — Leonardo Express ~€14 — leaving buffer time for the airport.
🚌Leonardo Express to Fiumicino ~£12
🛏—
- →Campo de' Fiori market
- →Aventine keyhole viewpoint
Self-launched vs. Insight Vacations
| This itinerary (self-launched) | Insight Vacations | |
|---|---|---|
| Price per person | ~£970 | £3,300 |
| Duration | 14 days | 14 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £2,330 per person (71%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Insight Vacations-style trips? Check them out here.~£970
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 Best of Italy — Self-Launched: Rome, Florence, Venice, Assisi, Sorrento & Capri in 14 Days cost?+
Doing it yourself with this self-launched itinerary costs an estimated £970 per person for 14 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 Insight Vacations?+
Yes — Insight Vacations charges around £3,300 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £970 — a saving of roughly £2,330 (71%) per person.
How long is the Italy trip?+
This itinerary runs 14 days, covering 14 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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