11 days in Oia & Tuscany Itinerary

11 days in Oia & Tuscany Itinerary

Created using Inspirock Europe journey planner
Make it your trip
Fly to Santorini, Bus to Oia
Oia, Greece
— 2 nights
Bus to Santorini, Fly to Florence
Florence, Italy
— 3 nights
Siena, Italy
— 4 nights


Oia, Greece — 2 nights

Every day hundreds of visitors come to Oia just to experience its sunsets.
You'll find plenty of places to visit near Oia: Ancient Thera (in Kamari) and Akrotiri (Akrotiri & Red Beach). There's much more to do: indulge your senses at some of the top wineries in the area, relax and rejuvenate at some of the best spas, take in the exciting artwork at Mnemossyne Gallery, and trek along Ekklisia Theoskepasti hiking trail.

To see ratings, maps, traveler tips, and more tourist information, refer to the Oia route planning tool.

Pittsburgh, USA to Oia is an approximately 18-hour combination of flight and bus. Traveling from Pittsburgh to Oia, you'll lose 7 hours due to the time zone difference. Traveling from Pittsburgh in October, expect Oia to be a bit warmer, temps between 74°F and 64°F. Cap off your sightseeing on the 2nd (Wed) early enough to travel to Florence.
Tours · Outdoors · Historic Sites · Wineries
Side Trips
Find places to stay Oct 30 — Nov 2:

Florence, Italy — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, pause for some serene contemplation at Basilica of Santa Croce, and enjoy breathtaking views from Campanile di Giotto.

For maps and tourist information, read our Florence trip builder.

You can do a combination of bus and flight from Oia to Florence in 6.5 hours. Other options are to do a combination of car and ferry; or do a combination of taxi, ferry, bus, and train. Traveling from Oia to Florence, you'll gain 1 hour due to the time zone difference. Prepare for a bit cooler weather when traveling from Oia in November: high temperatures in Florence hover around 61°F and lows are around 46°F. Cap off your sightseeing on the 5th (Sat) early enough to go by car to Siena.
Historic Sites · Museums · Parks · Shopping
Find places to stay Nov 2 — 5:

Siena, Italy — 4 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore Siena's surroundings by going to Montalcino (Cantina Cordella & Winery Solaria Patrizia Cencioni), Accademia del Buon Gusto (in Panzano in Chianti) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). Next up on the itinerary: awaken your taste buds at some of the top wineries in the area, deepen your understanding at Scuola di Cucina di Lella, steep yourself in history at Centro Storico di Siena, and take in the architecture and atmosphere at Basilica Cateriniana San Domenico.

To find more things to do, where to stay, and other tourist information, read Siena itinerary planner.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In November, daily temperatures in Siena can reach 63°F, while at night they dip to 48°F. Finish your sightseeing early on the 9th (Wed) to allow enough time to fly back home.
Wineries · Tours · Historic Sites · Museums
Side Trips
Find places to stay Nov 5 — 9:

Tuscany travel guide

Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.