Autumn in Sienna and Tuscany
with Eric Denker, Senior Lecturer Emeritus at the National Gallery of Art
Saturday, October 24 - Monday, November 2, 2026
In the fall of 2026, join us to explore Siena, historic rival of Florence, with its spectacular Duomo, winding narrow streets and gracious 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.
You’ll have an even deeper appreciation for Tuscany’s artistic treasures when traveling with Eric Denker. He’ll share his knowledge of Sienese art and history, including at the majestic black and white striped Duomo, and be with our group every day, helping us see high Renaissance art in new ways.
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.
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.
On other days, we’ll visit a couple of the most characteristic of Tuscany’s hill towns – both 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 most famous gelato.
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.
We’ll end our trip in Florence for a couple of days, where we’ll visit the Uffizi Gallery, the Palazzo Vecchio and the many glories of the Pitti Palace across the Arno river. Our Florence hotel, the degli Orafi, is perfectly located near the Ponte Vecchio, so you might want to extend your stay there even longer.
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.
Itinerary
Please note that we may make changes to this itinerary in response to unexpected closings, road conditions, weather or other unforeseen events.
Saturday, October 24, 2026
Depart from home on your overnight flight to Florence.
Sunday, October 25
Arrive in Siena, after your overnight flight from home. (We’ll send you information about how to get from Florence to Siena.)
You’ll have the afternoon on your own. We suggest you stroll down to the spacious Piazza del Campo – one of the most famous plazas in the world -- for a coffee, an Aperol spritz or Negroni. Our hotel is in the pantera (panther) contrada, one of Siena’s famous – and competitive – 17 neighborhoods. It’s full of small shops and restaurants. Or, if you’re up for a longer stroll, walk down to Santuario Catarina, a shrine built at Saint Catherine’s birthplace; she’s a patron saint of both Siena and Italy. In a chapel at San Dominico is the preserved relic of her head.
6pm. We meet in the hotel for orientation.
Monday, October 26
10:15am Meet in the lobby to walk over to the Duomo with Eric. This enormous complex of religious and artistic masterpieces is defined by the 15th century cathedral with its distinctive black and white stripes on the exterior, and its floor of white line figures on blackened marble. You’ll have an audioguide to take you through the duomo, and you’ll also be able to visit the Baptistry, the recently discovered Crypt with its magnificent frescoes, and the museum of artworks from the Duomo.
2:15pm After a break for lunch we’ll reconvene at the Santa Maria Della Scala complex. From the 10th century, it was a hospital for pilgrims on the way to Rome or Santiago Compostela, as well as a home for orphans and foundlings. In the large entrance hall are a series of remarkably preserved frescoes depicting the life and activities of those who lived and worked here. Throughout the complex are an art museum, several ancient chapels and an archeological museum, as well as many stone-lined underground tunnels.6pm Meet in the hotel for drinks and conversation.
Tuesday, October 27
9:45am We’ll walk over for a private tour of the primate museum (usually closed to the public) of the Panthera contrada. Here they display their awards from winning the Palio, Siena’s celebrated horse race around the Campo, as well as history about the contrada, and displays of their colorful traditional costumes.
Afterwards, we’ll stroll to the Sienese Gothic-style Palazzo Publico on Siena’s sunlit Campo. There’s much to see of Siena’s art and history here, although the famous Lorenzetti paintings on good and bad government are currently in conservation.
2:30pm After a break for lunch, we’ll rejoin Eric at the Pinacoteca, which features art from the many Sienese painters, including the exquisite Simone Martini. Then you might explore the many backstreets of Siena, with exquisite views over the city walls, or seek out the many local artisans who produce ceramics, embroidery and handwoven textiles.6pm Wine and conversation in the hotel.
Wednesday, October 28
9:30am We’ll drive to a working farm outside of San Gimignano (on the horizon are beautiful views of the town and its many towers). We’ll tour the farm, which makes its own wines, olive oil, honey, saffron and many other products of Tuscany. We’ll get up close to the famous Chianina cattle, one of the oldest breeds in the world -- now an endangered species -- as well as to the farm’s rabbits and chickens. Then we’ll have a light lunch on the terrace, tasting of some of the varieties of wine the farm produces, among them the famous white vernaccia of San Gimignano.
1:30pm We drive on to San Gimignano, perhaps the most famous of the Tuscan hill towns. There’s much to see here. If you care to, you can climb up the tallest tower in the town at the Museo Civico. But even if you’re not interested in the climb and its views, the museum features 14th century council meeting rooms and a small art museum. Don’t miss the 11th century Collegiata church with its impressive frescoes.
Of course, there are lots of other places to visit in San Gimignano. And the city is famous for its award-winning gelato. Gelateria Dondoli in the Piazza Cisterna is not to be missed for its inventive seasonal flavors.
3:45pm Return to Siena.
6pm Wine and conversation in the hotel.
Thursday, October 29
9:30am We’ll drive to Pienza, which Pope Pius II called the ideal Renaissance city (well, actually, he was the one who designed it). There we’ll visit the Palazzo Piccolomini, the pope’s fabulous palace, with its hanging gardens overlooking the Tuscan landscape.
You can also visit the church and crypt of Santa Maria Assunta next door to the pope’s palace. Pienza is known for its wonderful little shops with exquisite hand-made or local products, so you’ll have time for a leisurely lunch and maybe a bit of shopping.
3:15pm We depart in time to visit the Abazzia di Monte Olivetto Maggiore, still a working Benedictine monastery begun in the 1300s. It’s known for its grand cloister with frescoes of the life of St. Benedict, begun by Luca Signorelli.
(No meeting this evening.)
Friday, October 30
9:30am We depart for our drive through Chianti country to the 4-star Hotel Degli Orafi in Florence, located perfectly on the River Arno, steps from the Uffizi Palace and the Ponte Vecchio.
2:30pm After you’ve had time for lunch at one of the many trattorias nearby, we’ll meet outside the Uffizi Gallery, repository of the most spectacular art treasures of Florence. You’ll have an audioguide, but Eric will also be with us to point some of the most important art treasures, like Botticelli’s Birth of Venus, Michaelangelo’s Doni Tondo, Caravaggio’s Medusa, and Raphael’s Madonna of the Goldfinch.
6pm Join us for a cocktail in the hotel’s rooftop bar.
Saturday, October 31
This is your free day in Florence. You’ll have a Firenze card, which gives you free admission to almost all the museums, including, among many others, the Accademia for Michaelangelo’s David (you must call to reserve a time), the Palazzo Vecchio, Museo Galileo, Capella Brancacci, Palazzo Davanzati and much else.
Or should you be interested in shopping in Florence, Via Tornabuoni, Via Roma and Via Strozzi are known for high-end shopping. If it’s leather you’re looking for, the San Lorenzo and Santa Croce markets are full of leather and other Florentine goods, some fabulous and some not-so-fabulous.
(No meeting this evening.)
Sunday, November 1
(Today is All Saint’s Day, a national holiday in Italy. Usually most museums are closed this day, but because it falls on a Sunday, and many museums are closed on Mondays, we expect much to be open this day.)
9:45am We’ll walk across the Ponte Vecchio to the Renaissance-era Palazzo Pitti, a huge complex once owned by the Medici family. Frankly, you could spend all day here, as there’s the Palatine Gallery, with works by artists such at Raphael and Titian, the over-the-top Royal Apartments, the stunning Museum of Costume and Fashion, and the huge Boboli Gardens. (There’s a café inside as well.)
At your leisure, you can enjoy lunch at one of the interesting restaurants in the artisan’s quarter across the street from the Pitti.
6pm We meet in the hotel for our farewells.
Monday, November 2
Depart for home or your next adventure.
Important note: This trip is not appropriate for you if you have any mobility issues. They don’t call them the hill towns of Tuscany for nothing. The city of Siena is particularly hilly, and we will do quite a bit of walking.
Ready to Pack Your Bags?
The price for the trip is $6730. You’ll have your own room without paying an additional single supplement. To reserve your space, register here: https://www.wildblueyondertrips.com/trip-registration
Before signing up, be sure to read all the Frequently Asked Questions and Terms and Conditions. If you have more questions, contact trip leader:
Sheila Campbell
301-587-4555
To secure your space, mail your deposit check, made out to Wild Blue Yonder in the amount of $660, to Sheila Campbell, Wild Blue Yonder, 1001 Spring Street, Suite 623, Silver Spring, MD 20910. If you’d prefer to pay by credit card (there’s a 3% surcharge), email Sheila at scampbell@wildblueyonder she’ll send you a Paypal invoice.
What’s Different about Traveling with Politics & Prose
Our trips never require you to pay a single supplement if traveling solo. And we avoid moving hotels every couple of days. You’ll choose where you prefer to eat lunch and dinner rather than have limited choices on large group meals. We generally leave the hotel each day around 9:30am, so you don’t have to wake up uncomfortably early. And our maximum group size is 18 people.
Here’s What’s Included
- Two trip leaders every day to help you enjoy your time in Tuscany
- All nights at the four-star Hotel Athena in Siena and the degli Orafi in Florence
- Full hot breakfast every morning
- Comfortable transport from Siena to the other towns
- Admissions to every museum or other site mentioned in the itinerary
- Lunch at the farm overlooking San Gimiagnano
- Restaurant recommendations for lunches and dinners
- Wine and conversation socials with the trip leaders on most evenings
What’s not included: lunches and dinners, tickets to museums and attractions not listed on the itinerary, your flight to Florence and back home or anything else not listed under “What’s included.”
A Few Frequently Asked Questions
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. 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 who want to travel together but don’t want the hassle of planning it all in advance.
Just please remember that there’s lots of walking on hilly streets and uneven stone surfaces, so it wouldn’t be the right trip for you if you have mobility issues.
Q. Can I come early or stay on later?
Of course. If you’d like to stay at one of our hotels, we can make the reservations for you, insuring that you wouldn’t have to change rooms once the trip officially begins or ends. You’ll have to inform us in writing of the extra dates you’d like no later than July 1, 2026. You’ll pay for your extra nights directly to the hotel.
Q. Do I need a visa to visit Italy?
You probably will. The EU has announced that they’ll start a visa program sometime in the next few months. We’re monitoring the situation closely, and as soon as the visa program opens, we’ll send you directions on how to apply.
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 European 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 – especially since there are two trip leaders to break us up into smaller sections.
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 won’t be seated at long tables for big group meals at “We accept bus tours” restaurants.
- You won’t have early morning calls to leave the hotel
- You only unpack and pack twice – we’re not touring, but staying in Siena and Florence to really get to know them well.
- If you’re traveling alone, we make sure you get to know the other people on the trip in our evening get-togethers. Because this is a trip sponsored by a bookstore, we always have the most interesting people with us – people who read!
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. In her day-to-day work, she was a group retreat leader who understands how to ensure everyone is involved and having a memorable experience. She and Donna Morris have been designing and leading trips for P&P for twelve years – to Italy, France, Spain, Morocco and England. Sheila lives in Washington, DC, where she has been a volunteer at the National Gallery of Art for many years.
Donna Morris, an American originally from North Carolina, has lived in Paris since 2006, although she winters in Washington, DC. With Sheila, she’s one of the founders of the Politics & Prose travel program. She’s fluid in French, travels frequently all over Europe and is an expert navigator of European cities and sites.
Q. What are the hotels like?
Both the hotels are four-star entities. The Athena is tucked up against the high original walls of Siena, with glorious views of the countryside from its open-air rooftop bar. The breakfast room buffet is generously laid out with not only American-type breakfast choices but also Italian specialities. It’s a short (but hilly) walk to the center of Siena.
The degli Orafi could not be more centrally located in Florence, walkable to just about everything. Its rooms are elegantly designed, as is the breakfast room with its vaulted ceiling. The hotel too has a rooftop bar – with views of the Duomo.
Q. Is there internet access at the hotel?
Yes, free wifi comes with your room.
Q. What will the weather be like?
It’s hard to predict these days. Generally fall in Tuscany is dry, cool and sunny. Our advice is to come prepared for just about anything. Bring an umbrella, a light jacket and – most important of all – very comfortable walking shoes. In previous years, we’ve been able to sit outside at restaurants even in the evening with a jacket or sweater.
Q. What to wear?
Life is casual in Tuscany. People wear just about anything during the day. Jeans are fine. At night, if you’re eating in neighborhood restaurants, you don’t need to dress up.
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 you want. One day you might eat a sandwich for lunch, sitting in a piazza and watching the passersby. 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. We’ll provide 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?
As in any city, it makes sense to be aware of your surroundings after dark, but both Siena and Florence are usually quite safe. You might have to watch out for pickpockets in the areas where there are lots of tourists. They’re 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. And remember not to sling your handbag over the back of a chair in a café; that makes it a very tempting target.
Q. Some friends are going to be in Siena 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 12 euro 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. In recent years, our trips fill up very quickly – often in just three or four weeks after we announce them.
Q. I understand that Donna and Sheila will always be available by phone, but what if I don’t have an international cell phone?
Check with your cell provider to see if you can buy an international calling package for the time you’re here. Of course, you’re not required to have a phone while in Italy; that’s up to you. If you bring a laptop, smartphone or iPad, you can always use WhatsApp over wifi; that’s one of the least expensive ways to reach people.
Q. Do you require us to buy travel insurance?
We very strongly encourage you to purchase travel insurance. Please read our Terms and Conditions carefully to see our cancellation policy. Be aware that trip insurance companies are very strict about what they will and won’t reimburse you for, so read their policies closely. If you’re on Medicare, remember that it doesn’t cover medical treatment outside of the U.S., so you’ll definitely want healthcare coverage.
Terms and Conditions
Please read this information carefully, as payment of a deposit represents your acceptance of the following Terms and Conditions.
Trip Prices
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, 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
The payment of your deposit confirms your reservation. Deposits may be paid by check made out to Wild Blue Yonder, Inc., or credit card via PayPal. There is a 3% surcharge for PayPal.
Your deposit is refundable for two weeks from the date it is received by Wild Blue Yonder, except for deposits made less than 60 days before a trip departs; those deposits are completely nonrefundable. Two weeks after the receipt of the deposit by Wild Blue Yonder, deposits are not refundable for any reason and will be forfeited if you cancel your trip reservation. Cancellations must be in writing by either letter to Wild Blue Yonder or email to scampbell@wildblueyonder.biz. Cancellations become effective on the date they are received by Wild Blue Yonder.
Please note that, should a covid pandemic recur after trip deposits have been paid, no refunds will be possible (the funds will now be in Italy), but we will reschedule the trip as soon as possible with no change in price.
We reserve the right to cancel any reservations that are not paid in full at any time after the final payment is due. If you make your reservation after the final payment due date, payment in full will be required immediately.
Full final payment is due June 20, 2026.
Cancellations and Refunds
For any cancellations made before June 20, 2026, you will forfeit your deposit but will be refunded any other payments you have made. If you must cancel your trip, the effective date of cancellation will be upon our receipt of your notification, which must be made in writing either by email or letter. No refunds are possible after June 20, 2026.
We strongly recommend that you purchase trip cancellation insurance when you pay your deposit for this trip.
Travel Documents
You are responsible for securing your own passport, valid for at least six months after the completion of the trip, as well as the European visa which should be in effect by the time of our 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.
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).
We regret that we cannot provide individual assistance if you require the use of a wheelchair or have other individual needs.
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 on the specified trip start date. We cannot refund part of your trip if you arrive late or leave early.
Responsibility
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.
Recommended Reading
We love to read about the places we’re visiting, and we suspect you do too. Here are some books meant to enhance your travel experience. Although there may be some discussion of books in our evening salons, this is NOT required reading.
Fiction:
A Room with a View, E. M. Forster
Innocence, Penelope Fitzgerald
Restoration, Olaf Olaffson
The Golden Hour, Margaret Wurtele
Breathing Room, Susan Elizabeth Phillips
Cooking with Fernet Branca, James Hamilton-Patterson
I, Mona Lisa, Jeanne Kalogridis
Romola, George Eliot
The Passion of Artemisia, Susan Vreeland
The Birth of Venus, Sarah Dunant
Nonfiction:
Siena: The Life and Afterlife of a Medieval City, Jane Stevenson
Siena: The Rise of Painting 1300 – 1350, Joanna Cannon et al.
The Collector of Lives: Giorgio Vasari and the Invention of Art, Ingrid Rowland and Noah Charney
Brunelleschi’s Dome: How a Renaissance Genius Reinvented Architecture, Ross King
Dark Water: Flood and Redemption in Florence – the City of Masterpieces, Robert Clark
Tuscan Countess: The Life and Extraordinary Times of Matilda of Canossa, Michele K. Spike
The House of Medici: Its Rise and Fall, Christopher Hibbert
The Stones of Florence by Mary McCarthy
Memoir:
War in Val D’Orcia: An Italian War Diary, 1943-1944, Iris Origo
Every Day in Tuscany: Seasons of an Italian Life, Frances Mayes
The Hills of Tuscany: A New Life in an Old Land, Ferenc Máté
A Tuscan Childhood, Kinta Beevor
Participation is limited - reserve your space
by completing the Registration Form today.
