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2022 DATES:
May 1st - May 8th

(if you book by February 28th)
Please note the price is in Euros. When you click "book now" you will be redirected to Anna's licensed and registered travel agency, Florence and Beyond, to make your secure payment.

What's Included:

  • 3 pre-departure Zoom sessions with Ashley
  • Accommodations in a shared room with someone of the same gender
  • 3 nights in Florence, 2 nights in Tuscany (near the fame Val d’Orcia), and 2 nights in Rome
  • In-country transportation for included activities
  • Transport from Tuscany to Rome
  • Rooftop prosecco welcome toast
  • 7 breakfasts, 5 dinners
  • Private Duomo terrace tour (Florence)
  • Food history experience and tasting
  • Entrance to the Palazzo Pitti
  • Entrance to the Boboli Gardens, and Bardini Garden
  • Vintage Cinquecento and Vespa tour in Tuscany
  • Cooking class
  • Winery tour and tasting
  • Hot-air balloon ride in Tuscany (weather permitting)
  • Tour of the Colosseum underground
  • Entrance to the Roman Forum
  • Baroque art gelato crawl (Rome)
  • 24/7 Insider knowledge from Ashley (history, art, and photos) and Anna (culture, food and wine, and the art of “fare niente”)
  • ALL the epic photo ops along the way!

Traveling with Ashley and Anna

There will be no large tour operators, big groups, or standard tours. Everything will be small and bespoke, uniquely crafted by Anna and I to showcase what we love about Tuscany and Rome.

I fell in love with Italy when I studied abroad in Rome as an undergraduate. Focusing on the history of Early Modern Italy in grad school allowed me to return regularly and even call Florence home for a time. I started working with Anna nearly a decade ago while teaching and working with study abroad programs in Florence. I dreamed up the perfect Amalfi Coast trip for my students and Anna made it happen (and made it better).

Despite being complete opposites—I am a bubbly American that loves to get up early and is always on the go while Anna is a sassy Australian who does not love sunrise photoshoots (but she will tolerate them for me) —we love traveling together, and balance each other perfectly!

What's Not Included

  • Flights to and from Italy (please be sure to arrive in Florence by 3:00 pm May 1st, which means you must depart the U.S. on April 30th)
  • Airport transfers
  • Train from Rome to Florence (if flying into Rome, budget $50)
  • Mandatory trip insurance (budget approx. $75-$220)
  • Meals not mentioned (budget around $175)
  • Incidental Expenses
  • Optional activities
  • Tips and gratuities



Day 1 - Ciao Bella!

Arrive in Florence by 3 pm and make your way to the hotel. You will be able to check in and relax or have some free-time to explore Florence. At 6 pm we will welcome you with a rooftop prosecco toast overlooking Florence's famed "duomo" (means Cathedral) followed by a welcome dinner at one of our favorite restaurants.


Day 2 - Home Sweet Dome

We will start with an optional sunrise photoshoot at two of Florence's most famous sites, the duomo and Ponte Vecchio. Afterwards you will enjoy a private tour of Florence's cathedral from the unique point of view of its terraces! You will have free time for lunch and to climb the dome, bell tower, or visit the museum. We will end our day with a delicious food experience highlighting Tuscan cuisine.


Day 3 - A Pitti We Can't Stay

Our third day in Florence will begin with a photoshoot in and a tour of the beautiful Bardini gardens. Afterwards we will head to the Palazzo Pitti for a complete history of Florence's most famous family -- the Medici! After free time for lunch, we will explore the Boboli Gardens. There will also be an optional afternoon to visit the Uffizi Galleries.


Day 4 - Under the Tuscan Sun

Weather permitting, we will depart Florence early for an epic morning hot-air balloon ride over Tuscany! Next we will head to the charming city nicknamed "medieval Manhattan" for some free time to explore and grab lunch. Afterwards we will stop for a photo overlooking Tuscany's famed Val d'Orcia before enjoying a group dinner in the countryside.


Day 5 - Pasta la Vista, Baby

We will begin our second day in the countryside exploring via vintage Cinquecentos and Vespas (if you do not wish to drive you can be a passenger)! Afterwards you will have some free time to grab lunch and explore the charming town of Pienza before our farm-to-table pasta making experience at a local agriturismo.


Day 6 - If It Ain't Baroque...

Before departing for Rome, we will enjoy the morning at our gorgeous country estate (with photo ops of course). On our way to Rome we will also stop for a winery tour and tasting. After arriving in Rome and settling into our accommodations, we will end our day with a Barque Art gelato crawl!


Day 7 - Rom(e)ing Around

Our full day in Rome will begin with a sunrise photoshoot at the Trevi Fountain (always optional of course). Afterwards, we will tour the newly-opened underground of the Colosseum and the Roman Forum. You will some free time to explore a bit more of Rome before our farewell dinner.


Day 8 - Ciao for Now

Feel free to schedule your departure at any time on this day... or extend your trip and stay a while in Italy... perché no? *Please note that this itinerary is subject to change.

Flight Information

Everyone should arrive in Florence by 3 pm on Day 1, which means you will depart the US on the previous day. You can depart whenever on the last day (day 8). If you wish to arrive early or stay longer that is fine! Just let us know, we are happy to help you plan and provide advice/guidance.

The easiest way to arrive to Florence is via Rome (the Florence airport is expensive and often requires more connections). We recommend arriving and departing from Rome’s international airport in Fiumicino (FCO). From the airport in Rome, you can take the Leonardo Express train to Roma Termini (Rome’s main train station) and from there you can hop on a high-speed train to Florence (approx. 1 hour and 30 minutes).

P.S. – It is best to chat with us about your flights before booking!

The Nitty Gritty

HEALTH and COVID: You must be fully vaccinated by September 10, 2021, to join us on this trip. Both Anna and I are fully vaccinated and value every one’s health and safety. We will ask for a photocopy of your valid vaccine card prior to departure. You must also abide by any airport, airline, and /or immigration policies and procedures from both the United States and Italy (or your home country). On the off-chance Italy closes its borders, History in High Heels (Ashley) and Florence and Beyond (Anna) are not responsible for your airfare, airline fees, or related travel expenses. Individual airlines will be responsible for handling reimbursements. While we require basic travel insurance for every participant, we HIGHLY recommend that in the time of Covid, each participant selects a travel insurance with Covid coverage.

You must carry a valid passport and have obtained all of the required visas, permits, certificates, proof of vaccinations, and other travel documentation for all the countries in which you will visit during your trip. Your passport must be valid for 6 months beyond the duration of the trip. It is your responsibility to ensure that you satisfy all entry requirements and that you are in possession of the correct visas, permits and certificates for your trip and that all of the information on those documents are accurate. We are not responsible if you are refused entry to a country because you lack the correct passport, visa or other travel documentation.

Participants should check with consulates for the latest health requirements. Participants must bring their own medications, insect repellent or other recommended prescribed drugs, including but not limited to allergy medication (e.g., EpiPen).

CANCELLATIONS: This trip is subject to a minimum number of participants. If the minimum number of participants is not reached by the end of August, we reserve the right to cancel the trip. If this happens, any participant who has already registered and paid the trip deposit, or paid in full, will be fully refunded.

To register for the program and secure your spot, there is a 20 percent deposit. Payment in full for the trip is due by September 10, 2021.

We reserve the right in our sole discretion to accept, decline, or remove anyone from a trip (at or prior to departure or during the trip) if we deem their continuation of the trip to be harmful or dangerous to themselves or other trip participants.
If for some reason you need to cancel your trip, A cancellation will only be effective when we receive written confirmation of the cancellation from you by email at Cancellation by any other means, including social media comments, are not considered by us and do not constitute a cancellation. If you cancel your trip, you will be responsible for the below amounts based on the date we receive your written confirmation of cancellation.
  • 30 days or more prior to departure, full refund minus the deposit.
  • 29-16 days before departure, 50% of the trip is refunded. The rest is non-refundable.
    15-8 days before departure, 25% of the trip is refunded. The rest is non-refundable.
  • 7 days or less prior to departure NO REFUND.

No refund is due if a traveler fails to join a trip, joins it after departure, or leaves it prior to its completion for any reason. There will be no refunds for unused services after a trip has commenced.

There are no exceptions to this cancellation and refund policy, including for reasons related to weather, terrorism, civil strife, airline default, strikes, personal, family, or medical emergencies or any other circumstances beyond our control. This means that even if you cancel because of medical issues, virus, sickness, quarantine, travel restrictions/warnings, fear of traveling or any other reason, your booking will be subject to this cancellation and refund policy. This is why we require that you secure travel insurance in order to participate on a trip and, again, recommend comprehensive Covid coverage.

If a trip is full, and you are unable to book, please email Anna at info@florenceandbeyond to request to be added to the waitlist. If a spot becomes available, you will be notified by email. You will have 24 hours from when we send the email to accept the spot on the trip and pay the deposit, or it will be offered to the next person on the waitlist.

Still Have Questions?

Are you interested in this trip but still have questions before you register? Not a problem! Let us know how we can help below.