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Road Trip Suggestions…

  • Best for: first-time Italy visitors, culture + countryside balance

    Link to Google Map

    Thurs: Arrive in Florence
    Settle in, Dinner in Oltrarno.

    Fri: Florence → Cortona
    Sightseeing, sunset at Piazzale Michelangelo. Pick up car, 1.5 hour drive to Cortona

    Sat: Wedding Day 💍
    Slow morning, town coffee, get ready. Celebrations begin!!

    Sun: Vineyard day
    Tuscan vineyard lunch near Montepulciano or Chianti area

    Mon: Tuscany → San Gimignano → Sienna → Pisa
    San Gimignano (2–3 hours), lunch + gelato. Continue to Pisa via Sienna for a wander

    Tues: Pisa → Home
    Optional stop in Lucca.
    Pisa sightseeing, fly home.

  • Best for: repeat Italy visitors, food & wine lovers, relaxed pace

    Link to Google Map

    Tues: Arrive Pisa → Lucca
    Short transfer. Evening walk on Lucca’s city walls.

    Wed: Day Trip to Cinque Terre
    Pick 1 or 2 of the villages max to spend either a beach day, boat trip or street wander.

    Thurs: Lucca → San Miniato → Volterra
    Lunch stop in San Miniato. Afternoon in Volterra.

    Fri: Volterra → San Gimignano → Monteriggioni → Siena → Cortona
    San Gimignano early morning to beat the crowds. Lunch and a stroll in Monteriggioni
    Dinner in Siena, late check in in Cortona

    Sat: Wedding Day 💍
    Slow morning, town coffee, get ready. Celebrations begin!!

    Sun: Cortona → Montepulciano → Orvieto
    Wine tasting in Montepulciano. Evening in Orvieto.

    Mon: Orvieto → Perugia → Home
    Morning in Perugia. Fly home :(

  • Best for: quieter travel, fewer crowds

    Link to Google Map

    Thurs: Arrive Perugia
    Old town wander, dinner.

    Fri: Perugia → Cortona
    Scenic drive. Afternoon exploring Cortona.

    Sat: Wedding Day 💍
    Slow morning, town coffee, get ready. Celebrations begin!!

    Sun: Cortona → Perugia → Home
    Stop at some scenic spots around the lake

  • Best for: short stays, no rushing

    Link to Google Map

    Thurs: Arrive Florence
    Drop bags, wander, dinner.

    Fri: Florence → Cortona
    Day exploring Florence. Drive to Cortona late afternoon. Optional Stop off at Siena

    Sat: Wedding Day 💍
    Slow morning, town coffee, get ready. Celebrations begin!!

    Day 4 (Sun) – Cortona → Pisa → Home
    Optional stop in Lucca depending on flight time.
    Pisa sightseeing, fly home.

  • Best for: short stays, no rushing

    Link to Google Map

    Wed: Arrive in Pisa
    Travel to Cinque Terre

    Thurs: Beach Day!
    Grab the iconic parasol and get a tan before the wedding.

    Fri: Cinque Terre → Lucca → Cortona
    Start the drive to Cortona via Lucca for food (or Florence if you are full of energy!)

    Sat: Wedding Day 💍
    Get ready, Collect car and travel towards Cortona in your suits and dresses. Quickly check in before the celebrations.

    Sun: Cortona → Pisa → Home
    Optional stop in Lucca depending on flight time.
    Pisa sightseeing, fly home.

 2. Lucca

Best for: slow wanderers, cyclists, food lovers, relaxed city breaks
Minimum time: half a day (3–5 hours)
Pairs well with: Pisa, Florence, San Miniato, Cinque Terre

The capital of Tuscany in medieval times, it’s best known for its well-preserved Renaissance city walls, cobbled streets and relaxed, local rhythm of life. With fewer than 90,000 residents, Lucca feels intimate and lived-in rather than showy.

It’s also home to the second-largest comic book festival in the world, which takes over the city each autumn and attracts nearly 300,000 visitors over four days.

Things to See/Do:

  • Walk or cycle the Renaissance city walls
     Tree-lined and completely encircling the old town, the walls are one of Lucca’s defining features and offer lovely elevated views over rooftops and gardens.

  • Rent a bike
     Bikes can be hired from the Tourist Information Centre:
    City bikes (€10 / 3 hours, €15 / day), hybrids (€12 / 3 hours, €18 / day), or electric bikes (€20 / 3 hours, €35 / day). Cycling the walls is flat, easy and very popular.

  • Piazza dell’Anfiteatro
    An oval-shaped plaza built on the remains of an ancient Roman amphitheatre.

  • Duomo di San Martino
     A striking Romanesque cathedral with intricate marble details.

  • Climb Torre Guinigi (approx. €8)
    One of Lucca’s most recognisable landmarks, topped with oak trees. Built in the 1300s as a symbol of the Guinigi family’s wealth and power, it stands 44 metres high and offers great views.

  • Via Fillungo
     Lucca’s main shopping street, ideal for browsing local treats, souvenirs and artisan shops.

  • Browse antique & artisan shops

Things To Eat/Drink:

  • Osteria da Pasquale
    A small, curated menu that changes with the seasons, focusing on regional ingredients.

 3. Pisa

Best for: first-time Italy visitors, iconic sights, flying to/from

Minimum time: half day (ideally with one overnight stay)

Pairs well with: Lucca, Florence, Cortona, Cinque Terre


Compact, walkable and easy to navigate, the city works perfectly as one final stop before flying home, and is more than just the leaning tower!

Things to See/Do:

  • Get the photo at the Leaning Tower of Pisa
    The classic stop…whether you’re holding it up, pushing it over, or doing your own version, we’d love to see it afterwards!

  • Climb the Leaning Tower (approx. €20, or €27 combo ticket)
    Only 30 people are allowed up at a time, so booking ahead is essential.
    The climb involves 294 steps and you’re given 35 minutes total for the climb and views at the top.
    Note:No bags, purses, jackets or bulky items allowed (free lockers available nearby)

  • Pisa Cathedral (Duomo di Pisa)
    If you have a tower ticket, the cathedral ticket is included and untimed.
    This is the oldest building in the Square of Miracles and worth stepping inside to see the artwork, frescoes and marble interior.

  • Square of Miracles (Piazza dei Miracoli)
    Home to the Leaning Tower, Cathedral and Baptistery, and the reason Pisa is UNESCO-listed. Take time to walk around the whole square, not just the tower side.

  • Walk along the Arno River
    Cross Ponte di Mezzo for classic views back across the city.

  • Chiesa di Santa Maria della Spina
    A beautiful Gothic church right on the river, around a 15-minute walk from the Tower through more local neighbourhoods. You can’t enter, but legend says it once safeguarded a thorn from Jesus’s crown.

  • Tuttomondo by Keith Haring

  • Palazzo Blu (approx. €5)
    A small museum along the river showcasing temporary exhibitions and modern art, including works by artists such as Picasso and Chagall.

  • Borgo Stretto
    One of Pisa’s prettiest pedestrian streets, ideal for wandering between sights, shopping, coffee stops and soaking up local life.

  • For the curious: Museum of Human Anatomy (€2.50)
    Assembled by Pisa’s 700-year-old university, with over 1,600 specimens. booking ahead by email is recommended.

  • Museo di Anatomia ed Istologia Patologica
    A museum dedicated to what happens when nature goes wrong e.g. a cat with two legs in a jar

Things To Eat/Drink:

  • La Grotta
    A long-standing, family-run restaurant serving classic Tuscan dishes with warm hospitality and homemade pasta

  • La Pergoletta
    Cozy, unfussy and consistently good: a reliable choice for lunch or dinner.

  • Trattoria Da Stelio
    Local feel, smiley owners and big portions!

  • Bombolove
    High rated cake shop!

  • Bombolo:
    A local speciality pastry: sweet and brioche-like, often enjoyed warm with coffee or as an after-dinner treat.

  • Gelato stops

  • La Stafetta
    Pisa’s leading craft brewery, founded by three local students. A bit out of town.

  • Locus Food & Drink
    Top choice for cheap cocktails (€6 long island iced tea anyone?) or add a couple more euros for a sharing plate of Italian classics

  • Jeffer Cocktail Bar
    Ranked in the top 500 bars in the world. Creative and classic cocktails in a stylish setting

4.Florence

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 5. San Miniato

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 6. Volterra

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 7. San Gimignano

Best for: history lovers, architecture nerds, food & wine fans
Minimum time: 2–3 hours
Pairs well with: Siena, Volterra, Chianti countryside

small hill town of around 7,000 people, best known for its medieval walls. Its historic centre is a UNESCO World Heritage Site, recognised for the towers that once symbolised wealth and power. While 72 towers originally stood here, 14 remain today.

San Gimignano’s old town is largely focused on tourism rather than daily local life, which makes it perfect for a short, immersive stop rather than an overnight base. Early mornings or golden hour are noticeably calmer.

Things to See/Do:

  • Wander the medieval streets

  • Climb Torre Grossa (approx. €9)
    The tallest surviving tower at 53 metres, with panoramic views over rooftops and rolling Tuscan countryside.

  • Piazza della Cisterna
    The heart of the old town: ideal for a coffee, people-watching, and soaking up the medieval setting.

  • Walk sections of the town walls

  • Golden hour at Parco della Rocca
     Just beyond Piazza Duomo, this small park is one of the best sunset viewpoints in San Gimignano.

  • Browse local shops
     Ceramics, saffron products, olive oil and wine 

  • Hands-on food experiences

Things To Eat/Drink:

  • Pecorino tastings
     Often served with honey or jams 

  • Vernaccia di San Gimignano
     The town’s signature white wine; crisp, refreshing, and perfect for a lunchtime glass.

  • Wild boar pasta
    Look out for pappardelle al cinghiale (thick ribbons of pasta in a rich wild boar ragù)

  • Gelateria Dondoli
     Award-winning and very popular. Expect a queue (15 minutes or more in summer), and interesting flavours e.g. saffron & pine nuts, pink grapefruit with sparkling wine, cheese & olive or chestnut & rosemary.

 8. Monteriggioni

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 9. Cortona

Best for: romantics, photographers, history lovers, slow wandering, sunset views
Minimum time: ideally 1–2 nights)
Pairs well with: THE WEDDING! Perugia, Lake Trasimeno, Umbria countryside

Cortona is the hilltop town that will host our wedding! The streets are steep (brace your legs), but the reward is a town with some of the most beautiful views in Tuscany.

Founded by the Etruscans, later shaped by the Romans and Florentines, Cortona gained its global attention after Under the Tuscan Sun. Add in photography festivals, artisan workshops and views over the Val di Chiana, and Cortona feels quietly special rather than showy.

Things to See/Do:

  • Wander the historic centre
    Cobbled streets, flower-filled balconies and sudden viewpoints opening out over the valley 

  • Fortezza del Girifalco
    The highest point in town, offering sweeping panoramic views across Tuscany and Umbria. 

  • Piazza della Repubblica
    Once the Etruscan-Roman forum, now the social heart of town. On Saturday mornings it hosts the local market.

  • Museo dell’Accademia Etrusca
    Home to a 5th-century BC Etruscan chandelier adorned with dolphins, gorgons and stylised waves.

  • Parco Archeologico del Sodo (Etruscan Tombs)
    Just outside town, this archaeological site showcases Etruscan tombs, including sculpted sacrificial altars. Many artefacts now sit in the museum, but seeing the original sites adds important context.

  • Diocesan Museum
    A quieter stop for sacred art and local religious history.

  • Artisan boutiques & ceramics

  • Lake Trasimeno (short drive)
    Italy’s fourth-largest lake, just over the border in Umbria. Calm, shallow waters popular for swimming and boating — with a dramatic history dating back to Hannibal’s defeat of the Romans in 217 BC 

  • Cortona On The Move
     An international contemporary photography festival held each summer, bringing exhibitions into streets, palazzi and public spaces. Starts 16th July this year, just in time for your stay!

Things To Eat/Drink:

  • Tuscan classics: Look for pici, wild boar dishes and classic Tuscan steak.

 10. Perugia

Best for: Chocolate and truffle obsessives, people who like cities with real local life, airport!
Minimum time: half a day (ideal as a base for 1–2 nights)
Pairs well with: Cortona, Orvieto, Montepulciano, Umbria countryside

Perugia is one of the best airport options for the wedding: the closest to the venue and an easy choice if you’re flying from London .

Built high on a hilltop, it is the historic capital of Umbria and thanks to its large student population and crowd drawn to the Umbria Jazz Festival, feels creative and youthful and slightly off the tourist trail compared to Florence or Siena.

Things to See/Do:

  • Rocca Paolina (Underground Fortress)
    Built in a rebellion, the fortress required the destruction of entire medieval neighbourhoods.
    What remains today is a huge underground maze of vaults, arches and old streets, now often used as a commuter shortcut, complete with escalators.

  • Markets inside Rocca Paolina
    Often hosting local food stalls, craft markets and pop-ups within the underground spaces.

  • Via della Viola
    An artistic street filled with murals, galleries and street art. 

  • Walk the Medieval Aqueduct

  • Panoramic viewpoints (Porta Sole)

  • Chocolate shops & museums
    Perugia’s sweet legacy comes from Perugina, creators of the famous Baci chocolates (dark chocolate “kisses” with hazelnut centres and love notes inside, now sadly owned by Nestle). 

  • Chiesa di Gesù
    Unassuming church known for its three oratories stacked vertically like a tower.

  • Augusta Library (Biblioteca Augusta)
    One of the oldest public libraries in Italy

  • Etruscan Arch (Arco Etrusco)
    One of five ancient gates still piercing the city walls, dating back to between 600–300 BC

  • Etruscan Well (Pozzo Etrusco)
     Dating back to the 3rd century BCE, this underground well offers insight into ancient engineering beneath the city.

Things To Eat/Drink:

  • Umbrian classics to look out for

  • Pane al testo: flatbread filled with cured meats and cheeses

  • Truffle pasta

  • Torcolo di San Costanzo: traditional ring-shaped cake

  • Perugina chocolate: at every possible opportunity

  • Ristorante Al Tartufo
    Just steps from the Cathedral; reliable Umbrian cooking with a truffle focus.

  • Lo Moglie Ubriaca
    A charming wine bar perfect for pre-dinner plates and local wines, guided by a friendly and knowledgeable owner.

  • Fontanella da Ginetto
    A true local favourite run by a single chef. 

  • Vineria La Fraschetta (Via Antonio Gramsci)
    Authentic and full of character. Excellent home-style cooking with wine to match.

  • Sandri dal 1860 (Coffee & Pastry)
    An iconic Perugian café with chandeliers, faded frescoes and uniformed waiters…feels like stepping into another era.

  • Trattoria Oberdan
    Traditional Umbrian flavours in a relaxed setting.

  • Il Gelato di Mastro Cianuri
     A local favourite in Piazza Giacomo Matteotti.

  • Lick Gelato
    Modern gelateria using steel tins and creative flavours

 11. Siena

Best for: history lovers, architecture fans, slow wanderers
Minimum time: (2–3 hours)
Pairs well with: San Gimignano, Monteriggioni, Chianti countryside

Siena’s preserved medieval centre is recognised as a UNESCO World Heritage Site. The city unfolds in layers of brick, stone and sloping streets that all lead back to its famous central square.

Siena is best known for the Palio, a twice-yearly horse race held in summer, where the city’s neighbourhoods compete in a fast, chaotic lap around the main piazza.

Things to See/Do:

  • Piazza del Campo
     Siena’s iconic heart of the city. Perfect for people-watching 

  • Duomo di Siena
    One of Italy’s most impressive cathedrals, known for its striped marble façade and richly decorated interior. 

  • Climb Torre del Mangia (approx. €10)

  • Santa Maria della Scala Museum (approx. €9)
    To learn more about Sienna’s history. A former hospital dating back to the late 12th century, opposite the Duomo, once caring for pilgrims, the poor and orphaned children.

  • Fonte di Fontebranda
     One of Siena’s historic fountains and former city gates, located just outside the western edge of the old town — a quieter, more atmospheric corner to explore.

  • Wander the medieval streets & contrade
     Siena is divided into 17 contrade (neighbourhoods), each with its own symbol, from the Unicorn to the Seashell. Look out for flags, plaques and fountains as you move through the city.

  • Palio Museum
     A great stop if you want deeper context on the race, the rivalries and the traditions that still shape Siena today.

Things To Eat/Drink:

  • Ricciarelli (soft almond biscuits)

  • Chianti & local reds

  • Salefino (book ahead )

  • Antica Osteria da Divo
     Set across multiple cave-like levels beneath the city, very atmospheric and ideal for a longer dinner.

  • Mugolone
     Creative and slightly adventurous — Italian traditions with a Japanese influence from the head chef.

  • Torrefazione Fiorella
     One of the best coffee spots in Siena. Great pastries too from Italian croissants to rice pudding tartlets.

  • Liberamente Osteria
    Cocktail bar with a prime view over the square. Try the seasonal spritz specials and watch the world go by.

  • Permalico
    Reliable and good-value choice.

  • Gelateria Nìce

  • Where not to eat
     Avoid restaurants directly on Piazza del Campo unless the view is the priority. It’s a wonderful place for a drink but less so for food. And DalVitti despite it’s high rating, we had our menus snatched off us and told the kitchen was closed…despite others ordering around us!

 12. Montepulciano

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13. Orvieto

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14. Viterbo

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