Your itinerary

2027 Palio in Siena, Italy

Rome, Tuscany

About this trip

Base Cost: $4,000 pp includes:

R/T Air from NYC
In-Country transfers
10 nights lodging
Palio Horse Event
10 breakfasts, 5 lunches and 5 dinners
2 optional tours - 1 in Rome and 1 in Tuscany

Day 1

Flight

Overnight Flight to Rome

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7:30 PM JFK departure 10:10 AM Rome arrival 8 hr. 40 minutes or 5:30 PM - 8:00 AM subject to change by airline All seats economy class unless you pay for upgrade 1 personal item, 1 carry-on and 1 checked bag included

Day 2

Lodging

Rome City Center

Meals: Dinner

3 nights stay in 6 BR Home in city center

AirBnB Info

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Cute apartment in the Monti area, right in the heart of Rome.
Easily accessible by metro stop CAVOUR or Termini Station.
The structure offers 6 bedrooms, of which 4 have a bathroom and 2 have a shared bathroom, perfectly equipped for your comfort.

Dinner Provided within short walk from lodging.

Day 3

Activity

Optional Activities in Rome

Meals: Breakfast

More details · 3 options to choose

Excursion options

Hop on Hop off BusFULL DAY

1-day hop-on hop-off bus tour, Digital commentary in multiple languages, Free Wi-Fi on Board, Free VOX digital self-guided tour download , Free Gelato from "The Gelatist" OR Glass of Prosecco, Big Bus Tours app (ticket storage, live tracking and ticket activation)

Catacombs and Capuchin Crypts Group Tour3 1/2 HOURS

Expert, English-speaking guide Timed entry & audio guide tour of the Capuchin Crypts, Guided tour of the Catacombs of St. Callixtus, St. Sebastian, or Domitilla Drive past the ancient Appian Way Views of the Aurelian Walls Private, round-trip transportation

Private Golf Cart Tour with Pick Up and Drop Off Included3 HOURS

Discover Rome in total comfort with a three-hour golf cart tour, perfect for admiring all the wonders of the Eternal City effortlessly. You will cross the most iconic places, from the Colosseum to the Trevi Fountain, from Piazza Navona to the Pantheon, with a completely customizable itinerary.

Hop on Hop off Bus · FULL DAY · 1-day hop-on hop-off bus tour, Digital commentary in multiple languages, Free Wi-Fi on Board, Free VOX digital self-guided tour download , Free Gelato from "The Gelatist" OR Glass of Prosecco, Big Bus Tours app (ticket storage, live tracking and ticket activation)
Catacombs and Capuchin Crypts Group Tour · 3 1/2 HOURS · Expert, English-speaking guide Timed entry & audio guide tour of the Capuchin Crypts, Guided tour of the Catacombs of St. Callixtus, St. Sebastian, or Domitilla Drive past the ancient Appian Way Views of the Aurelian Walls Private, round-trip transportation
Private Golf Cart Tour with Pick Up and Drop Off Included · 3 HOURS · Discover Rome in total comfort with a three-hour golf cart tour, perfect for admiring all the wonders of the Eternal City effortlessly. You will cross the most iconic places, from the Colosseum to the Trevi Fountain, from Piazza Navona to the Pantheon, with a completely customizable itinerary.

Day 4

Activity

Optional Activities in Rome

Meals: Breakfast

More details · 3 options to choose

Excursion options

Colosseum Arena Floor, Roman Forum and Palatine Hill Tour2 1/2 HOURS

Official Live Guide for Roman Forum and Palatine Hill Arena, Floor restricted area and Entrance/Gladiator Door Colosseum Entrance with Audio Guide Headsets Colosseum entrance ticket with arena access

Skip-The-Line Vatican Museums,Sistine Chapel & Optional Basilica3 HOURS

A guided tour of the Vatican Museums and Sistine Chapel, Skip-the-line access at the Vatican, Headsets provided to better hear your guide's commentary, Option for a guided tour of St. Peter's Basilica

Catacombs and Capuchin Crypts Group Tour3 HOURS

Colosseum Arena Floor, Roman Forum and Palatine Hill Tour · 2 1/2 HOURS · Official Live Guide for Roman Forum and Palatine Hill Arena, Floor restricted area and Entrance/Gladiator Door Colosseum Entrance with Audio Guide Headsets Colosseum entrance ticket with arena access
Skip-The-Line Vatican Museums,Sistine Chapel & Optional Basilica · 3 HOURS · A guided tour of the Vatican Museums and Sistine Chapel, Skip-the-line access at the Vatican, Headsets provided to better hear your guide's commentary, Option for a guided tour of St. Peter's Basilica
Catacombs and Capuchin Crypts Group Tour · 3 HOURS · Expert, English-speaking guide Timed entry & audio guide tour of the Capuchin Crypts, Guided tour of the Catacombs of St. Callixtus, St. Sebastian, or Domitilla Drive past the ancient Appian Way Views of the Aurelian Walls Private, round-trip transportation

Day 5

Note

Transfer to Tuscany

Meals: Breakfast

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Bus from Rome - Siena

Lodging

True Tuscany Siena Villa

Tuscan Villa

VRBO Listing

Free day

Free Day at the villa with catered Tuscan Dinner

Meals: Dinner

At Villa

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Catered Tuscany Dinner with Wine From host: Included antipasto (Tuscan cheese, ham, crostini), primo: handmade pasta or lasagne with homemade sauce (first dish), secondo with meat and vegetables, dolce (dessert) and two glasses of wine each person.

Dinner is provided at the villa

Day 6

Activity

Optional Tuscan Activities

Meals: Breakfast, Lunch

Choose 1 to be included

More details · 5 options to choose

Excursion options

Truffle Hunting3 HOURS

Hike through the woods with a truffle hunter and dogs to dig up truffles. Typically then they are prepared for tasting.

Horse Riding1 HOUR

Horse Riding in the Tuscan countryside

E Bike RentalFULL DAY

Use of a rental E-bike for the day

Wine Tasting2 HOURS

Tour of vineyards, cellar and 4 - 5 wine tastings with light snacks

Palio Horse Assignment6 HOURS - 12 HOURS

Each horse that will compete in the Palio is selected and given by lottery to the Contrade (Sienese districts). The first trial race also takes part, with all 10 contrade taking part in three full laps of the Piazza del Campo

Truffle Hunting · 3 HOURS · Hike through the woods with a truffle hunter and dogs to dig up truffles. Typically then they are prepared for tasting.
Horse Riding · 1 HOUR · Horse Riding in the Tuscan countryside
E Bike Rental · FULL DAY · Use of a rental E-bike for the day
Wine Tasting · 2 HOURS · Tour of vineyards, cellar and 4 - 5 wine tastings with light snacks
Palio Horse Assignment · 6 HOURS - 12 HOURS · Each horse that will compete in the Palio is selected and given by lottery to the Contrade (Sienese districts). The first trial race also takes part, with all 10 contrade taking part in three full laps of the Piazza del Campo

Choose one activity and arrange your own dinner (ride share into town or get delivery/etc). Those on the Horse Lottery Tour or the Wine Tour have the option of getting dinner as part of the tour.

Dinner is on your own.

Day 7

Activity

Florence or Pisa Option

Meals: Breakfast, Lunch, Dinner

More details · 2 options to choose

Excursion options

Florence Day Trip$200 ppFULL DAY

Take a train to Florence. Benefit from timed entry to Accademia and Uffizi masterpieces Marvel at Michelangelo’s David and Renaissance art treasures Explore Florence’s highlights: Duomo, Ponte Vecchio, and Piazza del Signoria Upgrade to a private tour for a more personalized experience.

Pisa Day Trip$150 ppFULL DAY

Take a train to Pisa and have a guided, timed entry to the tower and baptistry as well as a city tour. Discover the beauties that Pisa has to offer beyond the Tower. A complete 1 hour long tour in an electric vehicle, that will take you to areas of the city that you will not find on classic tours.

Florence Day Trip · $200 pp · FULL DAY · Take a train to Florence. Benefit from timed entry to Accademia and Uffizi masterpieces Marvel at Michelangelo’s David and Renaissance art treasures Explore Florence’s highlights: Duomo, Ponte Vecchio, and Piazza del Signoria Upgrade to a private tour for a more personalized experience.
Pisa Day Trip · $150 pp · FULL DAY · Take a train to Pisa and have a guided, timed entry to the tower and baptistry as well as a city tour. Discover the beauties that Pisa has to offer beyond the Tower. A complete 1 hour long tour in an electric vehicle, that will take you to areas of the city that you will not find on classic tours.

Dinner is provided - Steak Dinner with Wine

From host: Fiorentina steak evening with use of the bbq. Antipasto, mixed meat from the bbq, vegetables, dolce and wine included.

Note - You *can* try to do both Florence and Pisa in one day but it is a ton of train travel and an extremely long day that must be very well timed. Or you could do one city this day and the other on Saturday. These are not included in optional included excursions and will require separate payment.

Day 8

Activity

Contrada Dinner in Siena

Meals: Breakfast, Lunch, Dinner

Free Day at the Villa with Dinner in Siena

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I'm thrilled to introduce you to the cena della prova generale—a contrada dinner held the night before the Siena Palio. This is an absolutely electrifying outdoor street celebration where thousands of neighborhood residents and their guests gather at long communal tables winding through medieval alleys and squares. You'll share traditional Tuscan food, join in singing the neighborhood's anthem songs, and cheer enthusiastically for your racing district. It's the kind of massive, deeply emotional experience that captures the very heart of Siena's Palio tradition.

Volunteer Cooked: The multi-course meal is entirely prepped, cooked, and served by local neighborhood volunteers. Traditional Menu: Expect simple, hearty Tuscan fare served family-style, featuring local pasta, roasted meats, seasonal vegetables, and free-flowing regional red wine.

Day 9

Tour

PALIO!!!

Meals: Breakfast, Lunch

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Transfer Lunch Horse Blessing Parade Race

Day 10

Free day

Free Day in Tuscany

Meals: Breakfast, Lunch, Dinner

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Dinner provided at villa by hosts - appetizer and various homemade pizzas from the outdoor pizza oven with wine.

Day 11

Note

Transfer to Rome

Meals: Breakfast

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Bus to Rome

Lodging

ROME TBD

Free day

Free Day in Rome

Activity

Naples/Pompeii Option

Day 12

Flight

Fly Home

Meals: Breakfast

Day 13

Note

Amalfi Coast 3-4 Day Add On Option

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An exciting tour to discover the Amalfi Coast through its history and flavors. Immerse yourself into an archaeological journey through the ancient cities of Pompeii and Ercolano. Sail to the rocky island of Capri, and wander around its tiny pedestrian alleys.

TOUR HIGHLIGHTS
Amalfi Coast: is a mixture of history and nature that offers a lot to discover: the cathedral of Amalfi, the villas in Ravello… Also, the nature reserve of the Ferreira and the marine reserve of Punta Campanella both contribute to preserving the natural balance of the environment.

Pompei: known as ‘the buried city,’ it used to be the holiday destination of wealthy ancient Romans because of its healthy weather and impressive views. Its archaeological zones, Herculano and the Annunziata tower have all been listed as World Heritage Sites by Unesco.

Capri: the most scenic and famous island in the world. Famous for exclusive hotels and shopping is a must visit when in Campania.

Day 14

Tour

7 Day Add On

R/T Rome - Greek Isles Cruise

Cruise Information

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Royal Caribbean r/t cruise - $1800 pp for interior room. Upgrades available for a fee

You would check out of villa and go straight to the ship to board. You would fly home on day of cruise return.

Tour

8 Day Add On

One Way Cruise Rome - Athens

Cruise Information

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Royal Caribbean cruise from Rome to Athens - $2200 pp for interior. Upgrades available for a fee.

You would check out of villa and spend one night in Rome then transfer the next day to cruise ship terminal. You would fly back home out of Athens.