TUSCANY ITINERARIES
FOR ROMANTICS, FOODIES AND WINE LOVERS.
Below are several different Tuscany itineraries, ranging from 3 days to 10 days. Choose the itinerary that best fits your time frame and travel styles.
3 day Itinerary
DAY 1 FLORENCE
Morning
Uffizi Gallery (“RESERVE”)
Piazza del Duomo (Florence Cathedral)
Afternoon
Ponte Vecchio
Palazzo Pitti and Boboli Gardens
Evening
Piazza Michelangelo Panoramic View
Rooftop Bar
Dinner Authentic Tuscan Cuisine
Stay in FLORENCE
DAY 2 SIENA AND SAN GIMIGNANO
Morning
Travel to Siena: Drive or take a train to Siena, Approximately 1.5hours from Florence
Piazza del Campo
Afternoon
Siena Catherdral
Travel to San Gimignano (45 minute drive)
San Gimignano: Wander through it’s charming streets
Diner:
Enjoy a local meal with a Vernaccia di San Gimignano wine
-Stay in SAN GIMIGNANO
DAY 3 Chianti and Val d’ Orcia
Morning
Chianti Wine Region ( at a vineyard for a wine tasting and tour)
Afternoon
Val d’Orcia (Visit picturesque towns of Pienza and Montepulciano)
Evening
Enjoy a diner at a countryside Agriturismo Farm Stay
This itinerary balances city sightseeing with country relaxation, offering a rich taste of Tuscany’s diverse attractions.
5 DAY ITINERARY
A five-day tour of Tuscany allows you to explore the region’s rich cultural heritage, stunning landscape, and exquisite cuisine more deeply.
DAY 1 FLORENCE
MORNING
Uffizi Gallery (Reserve ticket in Advance)
Piazza del Duomo (Florence Cathedral)
AFTERNOON
Ponte Vecchio
Palazzo Pitti and Boboli Gardens
EVENING
Piazzale Michelanglo (Panaromic view)
Rooftop Bar
Dinner authentic Tuscan cuisine
Stay in Florence
DAY 2 SIENA AND SAN GIMIGNANO
MORNING
Travel to Siena – Drive or take the train (about 1.5hours from Florence)
Piazza del Campo
AFTERNOON
Siena Catherdral
Travel to San Gimignano (45 minute drive)
EVENING
San Gimignano (wander its charming streets)
Diner : Enjoy a local meal with a Vernaccia di San Gimignano
Stay in SAN GIMIGNANO
Day 3 Chianti Wine Region
MORNING
Drive to Chianti (visit a vineyard for a wine tasting and tour)
AFTERNOON
Greve in Chianti (visit the charming town)
Castellina in Chainti (another picturesque town)
EVENING
Dinner: Enjoy diner at a countryside Agriturssmo Farm stay
DAY 4 PISA AND LUCCA
MORNING
Travel to Pisa (1.5hours from Florence)
Piazza dei Miracoli : Visit the iconic leaning tower
AFTERNOON:
Travel to LUCCA: 30 Minutes from Pisa (Lucca is a charming walled city)
Lucca walls: Walk or Bike along the city walls
Historical Centre: Explore Lucca’s narrow streets and enjoy the atmosphere of Piazza del Anfiteatro
EVENING
Diner: Dine in Lucca at a local trattoria, enjoying the city’s relaxed ambiance stay in LUCCA you like us may not want to leave.
DAY 5 VAL d’ORCIA
MORNING
Drive to Vald’orca: head to this UNESCO World Heritage Site, known for its stunning landscape
PIENZA Explore this beautiful town, and sample some (Pecorino Cheese)
AFTERNOON
Montepulciano : Visit this hilltop town famous for its vino nobile wine
Bagno Vignoni: This enchanting village with its unique thermal baths in the main square.
EVENING
Dinner enjoy dinner at a countryside AGRITUAISMO Farm stay
This 5 day itinerary offers a balanced mix of Tuscany major cities charming towns and scenic country rides, providing a comprehensive and unforgettable experience.
BEST 7 DAY ITINERARY
A seven-day tour of Tuscany is best, it allows you plenty of time to explore the region more deeply.
DAY 1 FLORENCE
MORNING
Uffizi Gallery – link Book tickets in advanace
Piazza del Duomo – Climb to the top of the dome or bell tower for the stunning views.
AFTERNOON
Ponte Vecchio
Palazzo Pitti and Bobocci Garden
EVENING
Piazzale Michelangelo – enjoy a panoramic view of Florence sunset.
Roof top bar
Dinner : Savor Tuscan cuisine at a local trattoria
Stay in Florence for 2 nights
DAY 2 FLORENCE
MORNING
Accademia Gallery: Visit to see “ David Michelangelos”
Santa Croce Basillica: the burial place of famous Italians like Michelanglo and Galileo.
AFTERNOON
Beholi Gardens Wander theough these historic gardens and enjoy the peace and serienty.
Oltrarno District: Discover artisan workshop and the beautiful Santo Spirito Basilka.
EVENING
Dinner: Enjoy dinner in the Oltrano district, known for its authentic restaurants.
DAY 3
MORNING
Travel to Siena: Drive or take a train to Siena (about 1.5 hour from Florence)
Piazza del Campo: Visit the heart of Siena.
AFTERNOON
Siena Cathedral: Explore the Gothic Catherdral
Travel to San Gimignano (45 minutes from Siena)
EVENING
San Gimignamo: Stroll the Charming streets, enjoy local Gelato from Gelato Dondoli.
Dinner: Enjoy a meal at a local Trattoria stay in SAN GIMIGNAMO
DAY 4 CHIANTI WINE REGION
MORNING
Drive to Chianti: Explore the stunning Chianti countryside.
Greve in Chianti: Visit this enchanting town and its main square.
AFTERNOON
Castellina in Chianti: another pictureque town
Radeta in Chianti: A charming village ideal for a relaxed afternoon.
EVENING
Dinner enjoy a rustic meal at an Agriturismo (farm stay) sampling local food and wine.
DAY 5 PISA AND LUCCA
MORNING
Travel to Pisa
Piazza dei Miracoli – Visit the leaning tower
AFTERNOON
Travel to Lucca – (30 minute from Pisa)
Lucca is a charming walled city.
Lucca Walls – Walk or bike along the walls.
Histrorical centre: Explore luccas narrow streets enjoy the atmosphere of Piazza dell Anfiteatro.
EVENING
Dine in Lucca at a local Trattoria, enjoy the city’s relaxed ambience.
Stay in Lucca you like us, may not want to leave this gem of a town.
DAY 6 VAL D’ORCIA
MORNING
Drive to Val d Orcia: Breath taking hills, landscape, romantic farms, picturesque cypruss avenues.
Pienza – Explore this beautiful town, (sample the pecorino cheese)
AFTERNOON
Montepulciano: Visit the hilltop town famous for its Vino Nobile wine or tour a winery enjoy a tasting.
Bagno Vignoni: Stop by this charming village with it’s unique thermal baths in the main town.
EVENING
Dinner: Enjoy a meal at your Agriturismo Farm Stay
DAY 7 MONTALCINO AND CORTONA
MORNING
Montalcino: Visit this town known for Brunello di Montalcino wine.
AFTERNOON
Travel to Cortina – a scenic drive to this charming hilltop town. Made famous by the book and movie Under the Tuscan Sun
EVENING
Dinner: Enjoy a final meal in Cortona enjoying the flavors of this region.
Stay in Cortona
This seven-day itinerary offers a balanced mix of charming towns, breathtaking scenery, Romantic farms, and Medieval villages to conjure up a perfect vacation.
10-DAY TUSCANY ITINERARY
A 10-day tour of Tuscany allows you to explore at your own pace, gives you more time to spend in the regions richness, scenic landscapes and culinary delights.
Day 1 FLORENCE
MORNING
Uffizi Gallery. Tip “Reserve Tickets in Advance”
Piazza del Duomo – Florence Cathedral (Duomo)
AFTERNOON
Ponte Vecchio – Stroll across the historic Bridge
Pallazzo Piti and Boboli Gardens – Explore the Palace and the stunning gardens.
EVENING
Piazzale Michelangelo – Panoramic view of Florence sunset.
Dinner – Rooftop bar
Enjoy Tuscan cuisine at a local Trattoria
DAY 2 – FLORENCE
MORNING
Accademia Gallery – Visit Michelangelo’s David
Santa Croc Basilica – Explore this Gothic Church, and the tombs of many Italian Personalities including Michaelangelo.
AFTERNOON
Oltrarno District: Discover artisan studios, antique shops, and fashion boutiques.
Boboli Gardens – A lovely place to close out the day of sightseeing.
EVENING
Dinner – Enjoy dinner in the Oltrarno district, known for its local cuisine and authentic restaurant.
DAY 3 SIENA
MORNING
Travel to SIENA: Drive or take a train (About 1.5 hrs from Florence)
Piazza del Campo – Visit the heart of Siena.
AFTERNOON
Siena Cathedral: Explore the Gothic Cathedral.
Mueso dell Opera del Duomo.
EVENING
Enjoy a meal in a local restaurant.
DAY 4 SAN GIMIGNANO
MORNING
Travel to San Gimignano – a 45-minute drive from Siena. Famous for its Medieval Towers.
Piazza della Cisterna – Explore the main square and climb one of the towers.
AFTERNOON
Collegiata di San Gimignano – Visit this beautiful church famous for its Frescoes
Gelateris Dondoli: Enjoy award-wining gelato from this famous shop.
EVENING
Dinner: Enjoy dinner at a local restaurant with a view of the stunning landscape.
STAY in SAN GIMIGNANO
DAY 5 CHIANTI WINE REGION
MORNING
Drive to Chianti explore the stunning Chianti countryside and stop at a vineyard for wine tasting.
Grene in Chianti – Visit this charming old town and its main square.
AFTERNOON
Castellina in Chianti: Another picturesque town not to be missed.
Radda – A Charming village ideal for a relaxed afternoon.
EVENING
Dinner: Enjoy a rustic meal at an Agriturismo (farm stay) enjoying local food and wine, and STAY the night.
DAY 6 PISA AND LUCCA
MORNING
Travel to PISA
Piazza dei Miracoli – Visit the famous Leaning Tower of Pisa
AFTERNOON
Travel to LUCCA – (30 minutes from Pisa)
Lucca is a charming walled city.
Lucca Walls: Walk or bike along the famous walls.
Historical centre- Explore Lucca’s narrow streets. Enjoy the atmosphere of Piazza dell’Anfiteatro.
EVENING
Dinner: Dine in Lucca at a local trattoria enjoying the city’s relaxed ambiance.
STAY the night in LUCCA, if you can leave this gem of a town (We couldn’t leave)
DAY 7 VAL D’ORCIA
MORNING
Drive to Val d’Orcia – UNESCO would heritage site, famous for its stunning landscape.
PIENZA: Explore this beautiful town a real gem. (Make sure you try the famous cheese Peconino).
AFTERNOON
Montepulciano: Explore this hilltop town famous for its Vino Nobile wine. Tour a winery and enjoy a tasting.
Bagno Vignoni: Visit this charming village with its unique thermal baths in the mail square.
EVENING
Dinner: Enjoy a meal in the countryside, and STAY at a local agritourism (Farm stay).
DAY 8 MONTALCINO AND CORTONA
MORNING
Montalcino: Visit this hillside town known for Brunello di Montalcino wine.
AFTERNOON
CORTONA – Travel to this charming hilltop town made famous by the book and film Under the Tuscan Sun.
EVENING
Dinner: Enjoy a meal in Cortona, enjoying the rich Flavors of this region.
STAY the night in CORTONA
DAY 9 AREZZO
MORNING
Travel to Arezzo: Visit this lesser-known gem with its rich history, Famous for its antiques.
Piazza Grande: Explore the main square, which host the famous Giostra del Saracaro Medieval festival.
AFTERNOON
Basicalla of San Francesco – see the beautiful Frescoes by Piero della Francesca.
Antiques: Stroll through the streets filled with antique shops and artisan shops.
EVENING
Dinner: Enjoy a traditional Tuscan meal ARREZZO “STAY” the night.
DAY 10 RELAXING DAY IN TUSCANY
MORNING
Tuscan countryside: Spend a relaxing morning in the countryside, perhaps visiting a spa in Montecianti Terme
Wine tasting – Enjoy a leisurely wine tasting session.
AFTERNOON
Volterra – This medieval jewel of Tuscany is well worth visiting.
Stroll the historic centre with its countless romantic alleys and squares.
EVENING
Dinner: Have a final Tuscan meal, reflecting on the highlight of your trip. STAY the night in Volterra this jewel of Tuscany is certainly worth an overnight stay.
This 10-day itinerary offers a perfect combination of cultural history, scenic beauty, and culinary delights, providing the ideal experience in Tuscany.
WHAT WE DID:
OUR TUSCAN ITINERY
We have visited Tuscany many times our last trip was for 8 days.
DAY 1 Lucca: We always base ourselves in Lucca.
DAY 2 Volterra
DAY 3 Montalcino
DAY 3 Montalcino – Day trip to Pitigliano
DAY 4 Montepulciano
DAY 5 Cortona
Day 6 Cortona – Day trip to Arezzo
Day 7 San Gimignano
DAY 8 Florence
DAY 9 Back to Lucca
We only had the one day in Florence as it is an hour from Lucca on the train and we do visit it regularly, but I would include 2 days in Florence if you have the time.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – SKYSCANNER – we always start here and usually always finish here. They price check over 1,200 travel sites to help you find the best prices. You can also try GOING to search prices across a variety of sites.
TRAVEL OPTIONS
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.