17 days in Italy, Santorini & Mykonos Town Itinerary

17 days in Italy, Santorini & Mykonos Town Itinerary

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Route & dates

17 days in Italy, Santorini & Mykonos Town Itinerary

Start: San Juan, Puerto Rico
Fly:  15 h 30 min
1
Florence, Italy
— 3 nights
Train:  1 h 45 min
2
Rome, Italy
— 3 nights
Fly:  6 h 45 min
3
Oia, Greece
— 3 nights
Drive:  6 h 30 min
4
Mykonos Town, Greece
— 5 nights
Drive + Fly:  25 h
End: San Juan, Puerto Rico

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your day-by-day itinerary now includes Pitti Palace as well as Tuscany Bike Tours. Do some cultural sightseeing at Piazzale Michelangelo and Cathedral of Santa Maria del Fiore. Get out of town with these interesting Florence side-trips: Radda in Chianti (Fattoria di Montemaggio & Castello di Monterinaldi). There's still lots to do: admire the masterpieces at Academy Of Florence Art Gallery, snap pictures at Ponte Vecchio, get to know the fascinating history of Piazza della Signoria, and take in panoramic vistas at Campanile di Giotto.

To see photos, other places to visit, where to stay, and tourist information, read our Florence trip maker.

San Juan, Puerto Rico to Florence is an approximately 15.5-hour flight. You can also do a combination of flight and train. Due to the time zone difference, you'll lose 5 hours traveling from San Juan to Florence. Traveling from San Juan in October, expect nights in Florence to be colder, around 14°C, while days are slightly colder, around 25°C. Finish your sightseeing early on the 5th (Mon) so you can take a train to Rome.

Things to do in Florence

Historic Sites Museums Outdoors

Side Trip

Radda in Chianti
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Piazzale Michelangelo ©
Piazzale Michelangelo

3
nights
Rome, Italy

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
On the 5th (Mon), take in the architecture and atmosphere at Santa Maria in Trastevere. Here are some ideas for day two: delve into the distant past at Catacombe di San Callisto, steep yourself in history at Colosseum, delve into the distant past at Palatine Hill, then appreciate the extensive heritage of Piazza Navona, then delve into the distant past at Pantheon, and finally contemplate the long history of St. Peter's Basilica.

To find more things to do, traveler tips, other places to visit, and tourist information, go to the Rome trip itinerary tool .

Traveling by train from Florence to Rome takes 2 hours. Alternatively, you can drive; or fly. In October, daytime highs in Rome are 26°C, while nighttime lows are 15°C. Finish your sightseeing early on the 8th (Thu) to allow enough time to travel to Oia.

Things to do in Rome

Historic Sites Parks Outdoors

Side Trip

St. Peter's Basilica
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

3
nights
Oia, Greece

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Do some cultural sightseeing at Akrotiri and Domaine Sigalas. You'll enjoy a bit of beach vacationing at Red Beach and Perissa Black Sand Beach. Explore Oia's surroundings by going to Kamari (Kamari Beach & Ancient Thera) and Santo Horse Riding (in Akrotiri). There's lots more to do: explore the striking landscape at Skaros Rock, take in the exciting artwork at Oria Gallery, do a tasting at Santo Winery, and indulge your senses at some of the top wineries in the area.

To see maps, topicsMoreInfo.option.ratings, more things to do, and more tourist information, go to the Oia online road trip planner .

You can fly from Rome to Oia in 7 hours. Other options are to do a combination of train and flight; or do a combination of flight and ferry. Traveling from Rome to Oia, you'll lose 1 hour due to the time zone difference. Traveling from Rome in October, Oia is a bit warmer at night with lows of 20°C. Wrap up your sightseeing on the 11th (Sun) to allow time to drive to Mykonos Town.

Things to do in Oia

Parks Outdoors Tours

Side Trips

Akrotiri, Kamari, Perissa Black Sand Beach, Santo Winery, Wine Tours & Tastings
Highlights from your plan
Santo Horse Riding ©
Santo Horse Riding
Akrotiri ©
Akrotiri
Red Beach ©
Red Beach

5
nights
Mykonos Town, Greece

Mykonos Town ©
A holiday in Mykonos Town offers a chance to relax on picturesque beaches and explore a labyrinth of charming streets lined with traditional white houses.
Get in touch with nature at Panormos Beach and Platis Gialos Beach. Relax by the water at Paradise Beach and Agios Stefanos Beach. Change things up with these side-trips from Mykonos Town: Old Town (in Naxos Town), Agios Prokopios Beach (in Agios Prokopios) and Archaeological Site of Delos (in Delos). The adventure continues: stop by Little Venice, stroll through Agrari Beach, and enjoy the sand and surf at Agios Sostis Beach.

Discover how to plan a Mykonos Town trip in just a few steps with Inspirock's itinerary builder.

You can drive from Oia to Mykonos Town in 6.5 hours. In October in Mykonos Town, expect temperatures between 25°C during the day and 20°C at night. Finish up your sightseeing early on the 16th (Fri) so you can travel back home.

Things to do in Mykonos Town

Parks Outdoors Beaches

Side Trips

Paradise Beach, Mykonos, Platis Gialos Beach, Plaka Beach, Paraga Beach
Highlights from your plan
Little Venice ©
Little Venice
Panormos Beach ©
Panormos Beach
Paradise Beach ©
Paradise Beach

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