The Heart of Tuscany

October 6 through 12

This fall, join a group of like-minded travelers to explore Tuscany and its central hill towns. We’ll stay for the week in Siena, historic rival of Florence, with its spectacular Duomo, winding narrow streets and gracious central Campo, perfect for an evening drink and people-watching. Outside of Siena is Tuscany’s agricultural heart, with its familiar rolling hills studded on the ridges by lines of dark cypresses.


Because agriculture lies at the heart of Tuscany’s history and culture, we’ll visit a working farm, and we’ll enjoy tastings of some of Tuscany’s most notable products: wines and cheeses. All our travels out of the city will be in comfortable minivans, not a big bus.

Siena’s city motto is, “Cor magis tibi Seni pandit,” (“Siena opens its heart even wider to you”), and you’ll feel its welcome and walkable scale immediately. We’ll stroll to historic sites from both the Middle Ages and the Renaissance, with many of the facades in the soft yellow-brown color we call “burnt Siena.”

On other days, we’ll visit several of the most characteristic of Tuscany’s hill towns – each quite different in character. From an authentic working farm, we’ll observe San Gimignano’s distinctive skyline of 14 towers. In the city, we’ll have plenty of time to explore its museums, churches, shops – and its world famous gelato.

The drive east to Cortona offers spectacular views of Lake Trasimeno, Italy’s 4th largest lake. The town – made famous by the books of writer Frances Mayes -- has a charming Etruscan museum, a Diocesan Museum featuring the ‘Annunciation’ by Beato Angelico and streets of small shops featuring artisan products. We’ll also visit ‘Le Celle’, St. Francis of Assisi’s first monastery built just outside the town in 1211, a beautiful, and suitably peaceful, place.

Pienza is a graceful and harmonious small town – completely rebuilt and designed to humanistic principles by Pope Pius II during the Renaissance. We’ll visit the Pope’s Palace there, as well as taste the varieties of the famous Pecorino cheese the city is known for.

In Siena, we’ll stay for the week at the Hotel Athena. Located in a quiet neighborhood right up against the old city walls, it has a terrace with spectacular views of the countryside. And if you’d like to include Florence as well, there’s an optional extension to Florence at the end of the week.

On many days, you’ll have a choice of which activities interest you most – although you’ll have plenty of free time to do even more. In the mornings, we’ll go in small groups to visit a special site, and then you’ll have the afternoons to explore on your own. But you’ll always have our trip leaders to help you decide what to do and how to do it. And they’re constantly available by phone or text.

We’ll get together every evening before dinner to talk about our days and some of the books we’ve read. Afterwards, we’ll break into small groups to walk to nearby restaurants. You have a choice about where to eat and who to eat with. You’ll never dine alone unless you choose to.

Fall is a beautiful time to visit Tuscany. The days are usually cool, crisp and sunny, and most of the tourists have headed home. We’ll wander along the narrow streets in every town, letting our imaginations run away with us as we soak in the history…and, of course, savor the food and wine.


Who should come on this trip?
Do I have to pay a single supplement?
I’m coming with a spouse or partner and we want to share a room. Do we both have to pay the full rate?
How many people will be on the trip?
How do I get from the Florence airport to Siena?
Why do you call this a “trip” and not a “tour”?
Tell me about the trip leaders.
Why are we staying in Siena all week instead of Florence?
What is the Hotel Athena like?
Is there internet access at the hotel?
What will the weather be like?
What to wear?
Why aren’t lunches and dinners included in the price?
I don’t speak Italian. Can you help me figure out what to eat?
Is it safe to walk around by myself at night?
Do you require us to buy travel insurance?
I’d love to come on this trip, but I already have a favorite hotel in Tuscany. Can I stay there?
Some friends are going to be in Tuscany while I’m there. Can they come along with us?
When do I need to sign up by?
If I want to stay longer than six days, can you arrange that?

Q. Who should come on this trip?
This is the perfect trip to take by yourself; you’ll make new friends and will always have people to do things with if you like. Or come with a friend or spouse or partner. We’ve often had mothers and daughters come together. You can spend time with each other and also have time to pursue your separate interests. The trip is also perfect for any small group that wants to travel together but doesn’t want the hassle of planning it all in advance.

Do note, though, that the hill towns of Tuscany are…well…hilly. Siena in particular has low hills in the center of town. So you must be able to walk on uneven and occasionally steep pavement for at least half a mile. (See the Terms and Conditions for more details on fitness requirements.) That said, most reasonably fit people can easily manage this trip.

Q. Do I have to pay a single supplement?
No. This trip is priced based on each person having his or her own hotel room.

Q. I’m coming with a spouse or partner and we want to share a room. Do we both have to pay the full rate?
For people who share a room, we offer a discount of $150 each. We’ve priced the trip primarily for people to have their own rooms, because Italian hotel rooms just aren’t as large as those in the U.S. But of course you can share a room if you prefer.

Q. How many people will be on the trip?
The maximum number of people is 18, so you won’t feel like you’re part of a huge group. There’s a 12-person minimum group size. So please don’t buy your plane tickets until we confirm to you that we have reached the minimum group size.

Q. How do I get from the Florence airport to Siena?
There are several options, and we’ll provide more detail to everyone who’s registered for the trip. The least expensive way is via bus from downtown Florence, a trip that takes about an hour and fifteen minutes. You’d need a taxi to the bus station in Florence, and a taxi from the station to the hotel in Siena.

The Hotel Athena can also arrange for you to be picked up at the Florence airport for a fee (at this writing, about €150). Once we have everyone’s arrival times, we’ll let you know if you’re arriving at the same time as someone else, so you might be able to share this transportation option and save money.

If you’re not using frequent flier miles for your trip, we can advise you on a recommended flight that others might also be using. Please note that we are not a travel agency, so we can’t book your flights for you.

Q. Why do you call this a “trip” and not a “tour”?
We’ve included the things we like best about group travel, including the convenience of having someone plan daily itineraries. But there are lots of things we dislike about tours, so here’s how this trip is different:
- You’ll never board a big tour bus.
- You won’t follow a tour guide, trying to keep up through crowded museums, except for the private tour in the Florence extension.
- You won’t be seated at long tables for big group meals at “We accept bus tours” restaurants. Instead, we’ll suggest authentic places for you to eat in small groups.
- You won’t have early morning calls to leave the hotel.
- There’s almost always a choice of how you’ll spend your days, so you can focus on what interests you most.
- You’ll pay only for the things you actually do. You won’t be dragged to places you don’t care about.
- You only unpack and pack once. We’ll use Siena as our base for drives out into countryside.

Q. Tell me about the trip leaders.
Sheila Campbell of Wild Blue Yonder has been organizing informal groups of travelers for years – often on hiking trips in France, England, Italy and Spain, as well as for Politics & Prose. In her day-to-day work, she’s a group retreat leader who understands how to ensure everyone is involved and having a memorable experience. She lives in Washington, DC, where she was a docent at the National Gallery of Art for many years – but she spends about four months a year in France and Italy.

JoAnn Warren has worked in Italian tourism for many years, and she’s fluent in Italian. She lives part of the year in Tuscany. She’s extremely knowledge about the local customs, history, traditions and…yes…food. She, too, has been involved with Politics & Prose trips for several years.

Q. Why are we staying in Siena all week instead of Florence?
Siena is closer in distance to the hill towns we’ll be visiting, so we’ll spend less time driving from place to place. But we also like the size of Siena for a group like ours; you’ll feel like you’ve really gotten to know the neighborhood. And – even though Siena has plenty of tourists – it’s not as crowded with them as Florence is.

If you haven’t been to Florence, or not in a long time, then we’d love to have you on the optional extension to Florence.

Q. What is the Hotel Athena like?

Our first impression of the Hotel Athena was the friendliness of the staff – and of course they all speak English. The rooms are spacious for a European hotel, and very well-appointed, with bidets in all the bathrooms. Hair dryers are provided, and every room also has a small fridge.

We particularly like the location, a few blocks out of the busy center of town, in a very quiet neighborhood, but with lots of local restaurants and shops nearby.

There’s an outdoor terrace where, weather permitting, you can sip a late afternoon drink or coffee and enjoy the view over the Tuscan landscape.

The Athena does have some rooms with walk-in showers rather than shower/tub combinations, so please let us know if you require one.

Q. Is there internet access at the hotel?
Yes, free wifi comes with your room.

Q. What will the weather be like?
It’s impossible to predict accurately these days, but generally October weather in Tuscany is fabulous – cool and sunny during the day, a bit cooler at night. Rain is always a possibility, of course. It may cool off abruptly when the sun goes down, especially since we’ll be in hill towns at a higher altitude.

Q. What to wear?
Wear what’s most comfortable, and pack lots of layers. Jeans are acceptable almost anywhere, except for the very nicest restaurants. It’s considered polite to cover your shoulders in many churches, but you probably won’t be going sleeveless in the late fall.

Don’t forget your raincoat or umbrella, just in case. You’ll need a warm jacket and maybe a scarf for evening. Most important: comfortable walking shoes.

Q. Why aren’t lunches and dinners included in the price?
Restaurants that accept tour groups are usually the last places we want to eat. And there are just so many delicious choices for meals in Tuscany that we want everyone to be free to eat where and when they want. One day you might eat a sandwich for lunch, sitting out on a piazza; or you might choose to browse the local food markets.

Alternatively, we often make lunch the biggest meal of the day, maybe even eating at a restaurant that would be too pricey at night. You’ll choose where you’ll eat, and with whom and how much you want to spend.

Q. I don’t speak Italian. Can you help me figure out what to eat?
Absolutely. The waiters in most restaurants speak English, and many menus are also translated into English. But we’ll also provide you a list of common menu terms, and let you know how to do things like ask for the check.

Q. Is it safe to walk around by myself at night?

Yes. Of course, as in any city, it makes sense to be aware of your surroundings after dark. But in both Siena and Florence it’s usually quite safe to be out on your own or with a friend in the evenings.

The most prevalent crime is pickpocketing, which mostly happens in areas where there are crowds of tourists. Pickpockets are wily, so we recommend that you leave most of your money, credit cards and passport in the safe in your room, just taking with you what you need for one day. A handbag that you can sling over your shoulder and tuck high under your arm (with a good zipper) works better than bags with long straps that dangle below your waist.

Q. Do you require us to buy travel insurance?
We strongly recommend it. Please read our Terms and Conditions carefully to see our cancellation policy. Also be aware that trip insurance companies are very strict about what they will and won’t reimburse you for, so read their policies closely.

You’ll want to be insured for both trip cancellation and medical evacuation. Many insurers require you to enroll as soon as you pay your deposit, so don’t wait. There are many websites which offer comparison information about trip insurance.

Q. I’d love to come on this trip, but I already have a favorite hotel in Tuscany. Can I stay there?
Because we’ll be doing so much coordination from our hotels, and all our walking and transportation directions start there, we don’t think it’s practical to stay in another hotel. Plus, staying elsewhere would make getting to the evening wine and planning meetings difficult. Of course you can stay somewhere else, but the price of the trip wouldn’t change, so it wouldn’t be a good value.

Q. Some friends are going to be in Tuscany while I’m there. Can they come along with us?
Because we want to keep our groups small, we can’t invite your friends to come with us on our daily excursions. But you can bring them to our evening get-togethers. Please give us a day’s notice, and there’s a €10 per person charge for the wine and snacks.

Q. When do I need to sign up by?
The sooner you put down your deposit, the better. We’re limiting the size of the group, so it’s best to reserve as soon as you think you’d like to come.

Q. If I want to stay longer than six days, can you arrange that?
Yes. We can arrange for you to stay on at the hotel at your own cost, although our trip will be over. If you’d like to arrive early, we can also make those reservations for you. We may not be there to greet you if you come early, but it’s okay if you want a day or two on your own before the official trip starts.

Please read this information carefully, as payment of a deposit represents your acceptance of the following Terms and Conditions. 

Trip Prices
The price of the trip is $4,100, based on single occupancy. There are no single supplements to pay.

For the extension to Florence, the price is $2,200. It includes three nights at the 4-star Hotel Degli Orafi in central Florence, breakfast included, and all admission fees to group activities listed in the itinerary, including a Florence museum pass.

Trip prices include hotel accommodations on a single or double occupancy basis, breakfast at the hotel, daily transportation as mentioned in the itinerary, entrance fees to museums if with the group as listed in the itinerary, tasting events, evening socials to plan the next day’s activities, and the services of the trip leaders as outlined in the trip description.

Not included in the trip price are entrance fees to museums and other attractions not expressly included; taxis or other forms of city transportation; airfare and airline baggage fees; lunches and dinners; hotel, restaurant or airport tips; costs of passports and visas; personal expenses such as beverages, laundry or room service; internet wifi except as established in the trip description; airport transfers or any other services not specified in the trip description.

Please note that we cannot guarantee any special requests for hotel rooms.

Registration and Payment
Changes to Your Reservation

If you would like to stay on for longer than the official days of the trip, we will make reservations for you at the hotel. We will not charge you for any changes to your reservation outside of 90 days before the trip start date. From 30 – 89 days before the trip start date, if you make any changes to your reservation, a $100 per person administrative fee will apply. Changes are subject to availability and cannot be guaranteed. If your reservation changes from double occupancy to single occupancy, you will be charged the single occupancy rate.

Final payment for this trip is due June 12, 2019.

Travel Documents
You are responsible for securing your own passport, valid for at least six months after the completion of your trip.

Health and Medical Issues
We welcome all travelers, but you must be in good health to participate in our trips. Our trips require a reasonable amount of walking, possibly several hours a day, uphill or on uneven streets or streets without curb cuts. You must be able to climb stairs and board trains and buses on your own. We regret that we cannot provide individual assistance if you require the use of a wheelchair or have other personal needs; in such cases you must be accompanied by a companion who will assist you.

If you are unable to navigate this amount of walking, you will not be able to participate fully in the trip, and we suggest you choose another type of trip. We cannot provide individual alternatives to the planned group activities. If your fitness level does not allow you to keep up with the group and/or travel on public transportation, you will be responsible for planning your own activities and for any additional costs incurred (for instance, but not limited to, personal taxis, train tickets, and entrance fees).

Trip Insurance
We strongly recommend that you purchase both trip cancellation insurance and traveler’s medical and evacuation insurance for your trip. Should you have to cancel your trip after you have paid in full, we cannot offer refunds other than specified above, because we will have already paid the costs of your trip to our vendors.

Arrival and Departure Dates
It is your responsibility to make sure you arrive in Siena on the specified trip start date. We cannot refund part of your trip if you arrive late or leave early, unless you have notified us of your different start or end date 90 days before the trip start date.

The liability of Wild Blue Yonder and Politics & Prose, individually or jointly (referred to hereafter as Trip Planners), is strictly limited. In no event will the Trip Planners be liable for amounts in excess of the amounts payable to the Trip Planners in accordance with the terms hereunder, nor will Trip Planners be liable for any consequential indirect or incidental damages arising from this agreement. Trip Planners purchase accommodations, transportation and other services from independent suppliers not under our control. We serve only as agents for these suppliers in securing trip arrangements, and therefore will not accept responsibility and liability for wrongful, negligent or arbitrary acts or omissions of these independent contractors, their employees, agents or representatives.

Trip Planners are not liable for injury, damage, loss, accident, or delay that may be caused by events not within our control, including but not limited to, without limitation, acts of terrorism, war, strikes, defects of any vehicle, adverse weather conditions, natural disasters or the negligence or default of any third party.

Trip Planners reserve the right to correct errors in advertised prices. We reserve the right to cancel an advertised trip, decline to accept a reservation or remove a person from a trip if it is determined by us to be in the best interests of the health, safety or general well-being of other trip participants. We will make every effort to conduct our trip as planned, but we reserve the right to make itinerary and other changes as necessary. If unforeseen circumstances require us to change a hotel, we will make every effort to select alternative accommodations of the same quality. The forgoing terms and conditions and all aspects of the relationship between Trip Planners and you shall be governed by the laws of the State of Maryland.