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Siena Trips & Tours

80 trips from 600 tour companies with 45 reviews

All Siena tours, river cruises, expedition cruises, and adventure trips. Find the best guided trips and expert planned vacation and holiday packages from over 600 tour companies. Average rating of 4.8 for all Siena trips.

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Tuscany Cycle Siena & Chianti tour

Cycling & Biking, Cultural

4.6 | Excellent | 100+ Reviews
8 Days
$ 197 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Siena, Tuscany, Florence
From
$ 1,425

Highlights

  • Ride along the back roads of classic Tuscany
  • Enjoy famous Tuscan cuisine and wine
  • Explore the cultural cities of Siena and Florence
More
Self-Guided Cycle Via Francigena to Rome tour

Education / Learning

4.6 | Excellent | 65 Reviews
9 Days
$ 186 per day
Type: Self-guided / Independent Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Rome, Siena
From
$ 1,660

Highlights

  • Cycle the Via Francigena - an ancient pilgrimage trail through Tuscany and Lazio from Siena to Rome
  • Explore medieval fortresses - as well as churches, a Roman amphitheatre and ancient walled hamlets
  • Stunning views - hilltop villages, open valleys, cypress woods and olive groves
  • Visit the thermal baths of Bagno Vignoni - cycle alongside the volcanic Lake Bolsena
  • River Tevere cycle path - Follow the picturesque cycle path to reach the gates of Vatican City
More
Bravo Italia tour

Cultural

by
4.3 | Great | 30 Reviews
13 Days
$ 175 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Assisi, Cinque Terre, Colosseum, Florence, Isle of Capri, Lake Garda, Lucca, Pisa, Rome, Siena, Venice, Verona, Positano
From
$ 2,279

Highlights

  • Train day-pass for the Cinque Terre area
  • Tuscan winery tour & al fresco dinner
  • Gondola ride in Venice
  • Local guides in Assisi, Siena, Florence & Lucca
  • Welcome & farewell dinner in Rome
More
Road Cycling in Tuscany tour

Cycling & Biking

4.6 | Excellent | 100+ Reviews
8 Days
$ 206 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Siena, Florence, Tuscany
From
$ 1,645

Highlights

  • Cycle roads from the beautiful Strada Bianche bicycle race 
  • Explore the magnificent Tuscan countryside 
  • Discover Siena, Volterra and Florence
More
Italys Pilgrim Trail Italys Pilgrim Trail - CostSaver tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
12 Days
$ 165 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Assisi, Florence, Padua, Rome, Siena, Venice
From
$ 1,975

Highlights

  • Assisi
  • Florence
  • Lanciano
  • Loreto
  • Monte Cassino
  • Padua
  • Pietrelcina
  • Rome
  • Siena
  • Venice
More
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Espresso Italia tour

Cultural

by
4.3 | Great | 30 Reviews
8 Days
$ 232 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Assisi, Florence, Isle of Capri, Positano, Rome, Siena
From
$ 1,858

Highlights

  • Tuscan winery experience & al fresco dinner
  • Walking tour of Florence with local guide, Siena and Assisi
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Rome and Tuscan Highlights Summer 2018 tour

Cultural, Education / Learning

4.5 | Great | 100+ Reviews
9 Days
$ 258 per day
Type: Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Florence, Rome, Siena, Tuscany
From
$ 2,325

Highlights

  • City tour in Rome, Pisa and Florence
  • Views of the ancient sites of Rome including the Colosseum, the Leaning Tower of Pisa, Santa Croce Basilica and the Duomo in Florence
  • Visit St. Peter's Basilica, the Tuscan city of Siena, the medieval town of San Gimignano, the Leonardiano Museum in the town of Vinci, the Vatican Museums and Sistine Chapel
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Winter in Italy with Venice Carnival tour

Cultural, Festivals & Special Events

4.8 | Excellent | 100+ Reviews
9 Days
$ 189 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Florence, Pisa, Rome, Venice, Colosseum, Siena, Tuscany
From
$ 1,699

Highlights

  • Revel with the venetians through the lively streets of venice carnival
  • Explore florence's museums and markets
  • Set eyes on the leaning tower of pisa
More
Local Living Italy—Tuscany San Gimignano tour

Local Immersion & Homestays, Cultural, Nature & Wildlife, Rafting, Kayaking, Canoeing

4.8 | Excellent | 100+ Reviews
7 Days
$ 170 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Florence, Rome, Siena
From
$ 1,189

Highlights

  • Share an apartment in our local friend ugo's home
  • Eat delicious tuscan cuisine and sample regional wines
  • Stroll the lanes of medieval san gimignano
  • Walk along the beautiful tuscan countryside
  • Make new friends at your home away from home
More
Rome to Budapest Explorer tour

Cultural, Transformative

4.8 | Excellent | 100+ Reviews
21 Days
$ 177 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Austria, Hungary, Italy, Slovenia, Budapest, Cinque Terre, Florence, Lake Como, Pisa, Rome, Salzburg, Siena, Venice, Vienna, Lucca, Colosseum, Milan, Split
From
$ 3,719

Highlights

  • Discover a passion for regional wines and italian cuisine
  • Explore the elegant countryside of lake como by boat
  • Wander over the canals and bridges of venice
  • Revel in the dramatic scenery of slovenia
  • Explore the charming streets of salzburg
  • Discover big highlights and hidden gems
More
Secrets of Italy tour

Cultural

4.5 | Great | 13 Reviews
10 Days
$ 444 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Cinque Terre, Colosseum, Florence, Lucca, Pisa, Rome, Tuscany, Venice, Siena
From
$ 4,436

Highlights

  • Travel the romantic, winding waterways of venice in a traghetto and lose yourself in the town's myriad alleyways – best done with a lot of time and no map
  • Hike to one charming village after another along the picturesque cinque terre, or take the train for a more leisurely experience without missing the stunning scenery
  • Discover the abundance of art and culture in florence, italy's outdoor museum. be sure to visit the accademia, home to the famous david by michelangelo
  • Fall in love with rome, a city that makes you gasp at every turn and effortlessly combines ancient history with modern architecture
  • Nestled in the postcard-perfect vineyards of tuscany's chianti region, your feature-stay on this trip is a five-star hotel housed in a former medieval monastery
  • Join a local shop-keeper for a pesto making class in levanto. make your own pesto and enjoy it with a glass of wine afterwards
  • Relax in a local family’s garden surrounded by olive trees and vineyards and enjoy the local organic wine varieties produced by this family for centuries
More
The Italy - Florence Untour tour

Cultural, Nature & Wildlife

by
5.0 | Excellent | 23 Reviews
7 Days
$ 148 per day
Type: Self-guided / Independent Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Bologna, Pisa, Siena
From
$ 1,039

Highlights

  • Enjoy the art and architecture in Florence city
  • Visit famous Museums and Cathedrals
  • Enjoy food markets and cafes
  • Delight in the charming neighbourhoods
More
Tuscany Biking tour

Cycling & Biking

5.0 | Excellent | 25 Reviews
6 Days
$ 833 per day
Type: Small Group Tour
Lodging:
Luxury - 5 star

Luxury - 5 star Lodging LevelThe highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Florence, Siena, Tuscany
From
$ 4,995

Highlights

  • Enjoy tasting of Tuscan reds
  • Explore vine-covered hills of Chianti
  • Explore Siena
  • Visit a private wine estate for a tasting
More
Walking in Tuscany tour

Cultural

4.5 | Great | 13 Reviews
8 Days
$ 388 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Florence, Tuscany, Siena
From
$ 3,105

Highlights

  • Enjoy a wine tasting in a montepulciano wine cellar, the perfect end to a morning spent strolling in the tuscan hills
  • Discover charming villages such as monticchiello, hidden to mass tourism by their location and tiny size
  • Uncover the secrets of the hilltop village of volterra, famous for its magnificent sunsets and etruscan ruins dating back more than 2,000 years. the romans mined volterra’s alabaster for sculpting. visit a small workshop for an exclusive demonstration by an artisan who has been plying his trade for over 70 years
  • Relax by supping a glass of vernaccia on top of the city walls in the afternoon in san gimignano, when most tourists visiting the town have disappeared. vernaccia is a local grape varietal, produced in and around san gimignano.
  • Visit beautiful san quirico d’orcia, where you will check into your 'feature stay' hotel, a converted 15th century noble mansion.
More
Tuscan Hilltowns Hiking tour

Hiking & Walking

4.9 | Excellent | 7 Reviews
7 Days
$ 557 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Strenuous

Strenuous Physical LevelFull day hiking or trekking over medium to long distances. Moderate expectation of physical fitness.

Visits: Italy, Florence, Siena, Tuscany
From
$ 3,899

Highlights

  • Discover Tuscany's gorgeous landscapes, renowned wines, and warm people
  • Hike among charming, quaint hill towns, brimming with historical splendor
  • Enjoy fresh, authentic cuisine and taste regional wine
  • Walk through stunning landscapes of villages, olive groves, and poppy fields
More
The Italy - Umbria Untour tour

Cultural, Nature & Wildlife

by
5.0 | Excellent | 23 Reviews
7 Days
$ 140 per day
Type: Self-guided / Independent Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Assisi, Florence, Perugia, Rome, Siena
From
$ 979

Highlights

  • Visit Perugia and Siena
  • Explore Assisi and Spoleto
  • Discover Rome, Orvieto and Florence
  • Visit Deruta, Gubbio and Spello
More
Tuscany & Cinque Terre 2018 tour

Cultural

by
5.0 | Excellent | 3 Reviews
8 Days
$ 499 per day
Type: Small Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Florence, Siena, Cinque Terre, Lucca
From
$ 3,990

Highlights

  • Hike Cinque Terre's coastal paths
  • visit a Restoration Specialist in her studio
  • tour Carrara marble quarries
  • bicycle atop Lucca's walls
  • attend a lecture by a Florentine art historian
  • taste olive oil in the Ligurian hills
  • meet a concert pianist for a recital at a pallazzo
  • learn pasta making at a cooking class
More
Gems of Umbria & Tuscany tour

Cultural

by
4.8 | Excellent | 100+ Reviews
9 Days
$ 254 per day
Type: Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Assisi, Perugia, Rome, Siena, Tuscany, Umbria
From
$ 2,289

Highlights

  • Rome : Special welcome and farewell dinners at a local restaurant; orientation
  • Narni : Visit the Convent of San Domenico; homemade pasta demonstration with a chef, followed by lunch
  • Spoleto : Guided walking tour, visit Piazza del Duomo; dinner with wine at a local restaurant
  • Spello : Olive oil tasting
  • Assisi : Visit St. Clare’s Church and St. Francis’ Basilica
  • Perugia : Guided walking tour, visit Piazza IV Novembre
  • Lake trasimeno: Stop in Passignano
  • Siena : Guided walking tour, visit the Piazza del Campo
  • Volterra : Orientation
  • San gimignano : Orientation
  • Pienza : Visit this UNESCO World Heritage Site
  • Montalcino : Brunello wine tasting and lunch
  • Orvieto : Visit the Etruscan underground Labirinto; dinner with wine at a local restaurant; guided sightseeing, visit the cathedral
  • The name of this escorted Italy tour—Gems of Umbria & Tuscany—says it all, as you’ll visit some of the medieval hill towns and see some of the beautiful gems that call central Italy home
  • You’ll begin and end in Rome, and in between you’ll overnight in Spoleto, San Martino in Campo, Siena, and Orvieto
More
Gems of Umbria & Tuscany with Sorrento tour

Cultural

by
4.8 | Excellent | 100+ Reviews
12 Days
$ 259 per day
Type: Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Italy, Assisi, Perugia, Rome, Siena, Sorrento, Tuscany, Umbria
From
$ 3,104

Highlights

  • Rome : Special welcome and farewell dinners at a local restaurant; orientation
  • Narni : Visit the Convent of San Domenico; homemade pasta demonstration with a chef, followed by lunch
  • Spoleto : Guided walking tour, visit Piazza del Duomo; dinner with wine at a local restaurant
  • Spello : Olive oil tasting
  • Assisi : Visit St. Clare’s Church and St. Francis’ Basilica
  • Perugia : Guided walking tour, visit Piazza IV Novembre
  • Lake trasimeno: Stop in Passignano
  • Siena : Guided walking tour, visit the Piazza del Campo
  • Volterra : Orientation
  • San gimignano : Orientation
  • Pienza : Visit this UNESCO World Heritage Site
  • Montalcino : Brunello wine tasting and lunch
  • Orvieto : Visit the Etruscan underground Labirinto; dinner with wine at a local restaurant; guided sightseeing, visit the cathedral
  • Rome-sorrento: By high-speed Train
  • Sorrento: Guided walking tour through the Old Town; visit the Cloister of St. Francis & taste Limoncello
  • The name of this guided Italy tour—Gems of Umbria & Tuscany—says it all
  • You’ll visit some of the medieval hill towns and see some of the beautiful gems that call central Italy home
More
Grand Catholic Italy - Faith-Based Travel tour

Cultural

by
4.8 | Excellent | 100+ Reviews
10 Days
$ 248 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Italy, Assisi, Florence, Padua, Rome, Siena, Tuscany, Umbria, Venice, Milan
From
$ 2,479

Highlights

  • Rome : Welcome dinner at a local restaurant; guided sightseeing, visit the Vatican Museums and Sistine Chapel, St. Peter’s Square and Basilica; see the Colosseum and Roman Forum; Papal Audience (subject to availability); visit St. Paul Outside the Walls, the Catacombs, St. John Lateran Basilica, the Holy Stairs, St. Mary Major Basilica
  • Cascia : Visit the Basilica and attend [M] Mass
  • Assisi: Visit St. Mary of the Angels Basilica and the Porziuncola; celebrate [M] Mass; guided walking tour, visit the Basilicas of St. Francis and St. Clare, the Carceri Hermitage, and the Monastery of St. Damian
  • Siena : Guided walking tour, visit the Basilica of St. Dominic, the Sanctuary of St. Catherine & House, and Piazza del Campo
  • Florence: Guided walking tour, visit the Academy of Fine Arts to see Michelangelo’s David; celebrate [M] Mass at the Duomo; walk to Signoria Square, and Santa Croce Square
  • Padua : Guided visit of St. Anthony’s Basilica; farewell dinner
  • Venice : Private boat ride; guided walking tour, visit Doges’ Palace, the Bridge of Sighs, and St. Mark’s Square & Basilica
  • Home to numerous places of devotion and worship—not to mention exquisite art and architecture—Italy is the perfect destination for travelers looking to rejoice in their faith
  • On this Italy tour, you’ll overnight in Rome, the heart of Christianity; Assisi, where St
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