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Traveling in Italy

Traveling to & from Italy

Flight Details

We will purchase your flight tickets. However, we need to have details from you about your desired travel days, airports, and personal information when we actually purchase the tickets. So, here is information to help you decide.

If you are adamant about buying your own tickets, please let us know and we will help you keep an eye out for good deals. For example, the last time we went to Italy, we paid less than $600 compared with $1,200+ normally. 

The event is at Lupaia just outside the town of Montepulciano, about a 2 hr drive north of Rome.


You will be flying into Rome, arriving no later than Friday, May 24th. (We will be at Lupaia May 24-27.) Because of the time difference (Italy is six hours ahead of EST), the best flights to Italy are typically red-eyes that leave the US in the evening and arrive early morning the next day. You are most likely to land in Rome at approximately 09:00 a.m. after an 8 hour flight. This means you will depart a major International airport, such as Atlanta or Boston, the evening before around 7:00-8:00 p.m. If you do not live near that international airport, you will need to get there via a regional flight or driving. Of course, traveling from the West coast adds that 4.5-6 hours flying into a major Eastern airport.

For return flights, it's common to fly out of Italy in the morning and arrive in the US in the evening on the same day. If you join us in Sicily for the after-party, you'd most likely fly back through Rome to return to the US.

Abbey & Dan are flying in a few days early to get things ready and get settled. You may want to fly in groups. We will ensure that at least one seasoned, international traveler is with each group. We suggest you fly in a day early, arriving in Rome Thursday morning, do some sightseeing in Rome and get accustomed to the time zone. We will have vans driving everyone from Rome to Lupaia on Friday morning.

Suggested Travel Days

More details are provided under Recommended Itinerary

The most limited schedule:

  • Depart U.S. Thu. evening, May 23, arrive Rome Fri. morning, May 24th

  • Depart Rome Mon. mid-day, May 27th, arrive U.S. late same day

Extended days of touring after the wedding (possibly joining us in Sicily):

  • Depart U.S. Wed evening, May 22, arrive Rome Thu. morning, May 23th

  • Travel to other desired destinations/Fly to Sicily, Mon. May 27th

  • Depart Sicily around Fri May 31st, traveling through Rome to the U.S. all that day

What we need from you now

We will need this information soon so that we can purchase tickets quickly when we come across good prices eliminating the need to contact you and wait for a response.

  • Desired travel days

  • Desired departure/routing airport (if it works out that there are good flights to Rome)

  • Name as it appears on your passport

  • Passport number

  • Mobile phone number

  • Desire to travel in a group or solo/as a couple

  • Other travel constraints or considerations we need to keep in mind as we purchase flights

Recommended Itinerary

Day 1- May 23 Arrive in Rome

To give yourself ample time to adjust to the time zone, we recommended arriving in Rome a day early. As most flights arrive in the morning, you will have the day to explore Rome. If you can manage to stay up until the evening, it will be an easier adjustment to the time zone. There is of course a lot to see! The Colosseum (if open) is a must. We can assist you with making a hotel reservation.

Day 2 - May 24 Arrive at Lupaia

We will have shuttles from Rome around 12pm on May 24th (pickup location TBD). That evening there will be a welcome dinner at Lupaia! You will fall in love with this quaint, luxurious renovated estate, with the infinity pool, hot tub, blooming flowers and sitting areas, fine cuisine, and much much more.

Day 3 - May 25 Wedding

All meals and events will be at Lupaia.

Day 4 - May 26 Relax

We will have a list of activities you can enjoy. Relax around the property, ride one of the bikes provided, visit a local vineyard or olive grove, or head over to tour Montepulciano shops and museums. Dinner will be provided at Lupaia. We will have more details soon.

Day 5 - Shuttle to Rome

After breakfast, a shuttle will be provided from Lupaia to Rome. You can fly directly back to the U.S. if your schedule demands it, or you're just tired of all the amazing food, wine, and social engagement!

Or you can (a) join us in Sicily, or (b) explore Italy or Europe on your own, or (c) both!

See below for some ideas.

Florence Cathedral

Travel After the Wedding

La Festa Dopo in Sicilia -

The After Party in Sicily!

You've flown all the way to Italy. Do you really want to end the party after just three days on a hill in Tuscany, even if it is a beautiful hill? Since we want to continue the celebration, and some of our friends can't join the wedding festivities due to our size-of-the-wedding constraints, we plan to head to Sicily right after the wedding on May 27th! Why Sicily? Just because we've never been there and why not?!


Sicily has amazing sun, food, wine and a world-class relaxation culture. We will fly there from Rome and then return to Rome to head home around May 31. We are leaning towards Palermo!

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Some Other Common Destinations

Traveling around Italy is best done by train. Trains run on time, are quiet, smooth and comfortable, are inexpensive, and remove the hassles of driving (and getting tickets when you don't follow Italian rules! Trust us, we know!).

Take time to search for info on these places and others you have always dreamed of visiting.

These are just some idea generators.

Visit Italia Rail to purchase tickets between any major city you wish. 

Purchase a Eurail ticket to travel all over Europe.

Castle Tower

Siena is only a short distance from Lupaia. It is an ancient city that is home to a World renowned and extremely unique horse race known as the Palio di Siena that occurs around July 2nd and August 16th. The center piazza, Piazza del Campo, is an amazing site to visit, shop and grab food.

Amalfi Coast

The Amalfi Coast is a beautiful coastline with a Mediterranean landscape known as an escape destination for Europeans since the 1700s. 

Ponte Vecchio

Florence is amazing for sculptures everywhere, especially the David from Michelangelo, the Duomo cathedral, Uffizi art museum, Leonardo Da Vinci museum, Galileo museum, leather markets, and the famous old bridge in all the photos, Ponte Vecchio (Old Bridge).

Solo Traveler

This string of 5 ancient seaside villages along the rocky northeastern coast, not far from Pisa, is full of vibrantly colored dwellings, swimming coves, amazing views from every direction, and a hiking trail between them all.


The city of 1000 waterways with the amazing St Marks Basilica cathedral has local artists, theatrical mask shops, eateries, gondola rides...and lots of tourists in the summer! But it's worth it!

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The most famous lake in Italy, home to George Clooney's villa, site of numerous movie scenes, and one of our favorite places to visit in the world, Lake Como is a place to eat, watch people and take 1500 images.

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