Carrie and I are back from two remarkable weeks in Italy, and I wanted to share a few reflections before the memories start to blur together. First, thank you to everyone who shared your tips and suggestions after I posted about our plans (https://reddotblog.com/carrie-and-i-are-heading-to-florence-any-tips/). Many of your ideas shaped our itinerary, and you were right—it’s every bit as magical as you said.
Settling into the Countryside
We stayed just outside Florence in a restored farmhouse surrounded by olive groves and vineyards. Every morning, we’d step outside to rolling green hills and the faint sound of church bells in the distance. I’ve seen beautiful landscapes before, but Tuscany combines light, architecture, and rhythm in a way that makes even a simple drive feel cinematic.
We had debated splitting our time across different regions, but I’m glad we chose to stay put. There’s something grounding about waking up in the same place long enough to notice how the light shifts each day.
Art Overload (in the Best Way)
Florence lived up to its reputation for extraordinary art, and even after two weeks nearby, I felt we’d only begun to scratch the surface. At the Uffizi Gallery, I finally stood before Leonardo’s Annunciation—the very painting I studied earlier this year for this video. Seeing Botticelli’s Birth of Venus and Primavera in person was equally awe-inspiring, each room offering another masterpiece you’ve known all your life but never really seen until that moment. I love art deeply, but I’ve learned that after about four hours in any museum, I simply can’t absorb more—the mind and eyes need time to rest and let all that beauty settle in.
And then, of course, there was Michelangelo’s David. I’ve seen countless photos over the years, but standing before the real thing was sublime—an experience that words can’t quite match.
After all that visual and emotional intensity, we needed a reset. Italy provides the perfect recovery mechanism: gelato. We made it a rule to test gelato everywhere we went, and tried not to repeat a flavor.
The Joy (and Terror) of Tuscan Roads
I’m a runner, and in order to prevent myself from ballooning on the amazing Tuscan food, I ran just about every other day. The countryside was a dream to explore—until the hills reminded me how flat Phoenix really is. My usual twelve inches of elevation change on runs in Phoenix became hundreds of feet, and my leg muscles let me know I need to try to fit more hill-running into my routine back home. Add in narrow roads and fearless Italian drivers, and every run felt like both an adventure and an act of faith.
We rented a car to facilitate our mobility, and driving those same roads wasn’t much less dramatic. Many lanes were barely wide enough for a single car, yet traffic flowed with a kind of graceful chaos.
Cathedrals, Castles, and Wild Boar
Every village offered its own masterpiece—soaring cathedrals, frescoes, and stonework from centuries past. We toured a castle whose owner, a modern-day count, still lives there and runs the winery and olive press his family has operated for 800 years. The sense of continuity is humbling.
And the food—let’s just say my respect for Tuscan cuisine now borders on devotion. I even tried wild boar. It was extraordinary.
The Return Trip (and Reality’s Reentry)
Our only real misstep came at the end. A short delay in Florence snowballed into a missed connection at Charles de Gaulle Airport. We spent an unplanned night near Paris and arrived home a full day late, thoroughly jet-lagged but grateful. My body still thinks it’s on Florence time, and I’m waking up at 3 a.m. ready for new adventures.
We jumped straight back into gallery life—the day after we landed was ArtWalk night—but the energy of the trip lingers. Traveling reminded me how much art, beauty, and connection matter. You can feel it in every frescoed chapel, every family-run vineyard, every small act of care that turns raw material into something lasting.
For anyone dreaming of their own Tuscan adventure, I’ll pass along a bit of advice we were given before we left:
You’ll ask yourself two questions while you’re there—
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Why didn’t we plan to stay longer?
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What could we give up to live here?
I can confirm both are fair questions.
So happy you had a great trip. Once you’ve seen Florence and the incredible flourishing of art, you understand the pride of Italians; from Ancient Rome to the Renaissance they have contributed so much to culture, literature, and art.
Jason
We are visiting Tuscany next year so your itinerary was really compelling. As an artist what do you think are the best compositions to paint in Tuscany?
Thanks
Jim
The number one thing you did right was to go on your own and move at your own pace. All your comments of appreciation spring from that one right decision. We were with a guided tour, not the best idea. Imagine, they were going to SKIP the Uffizi! I ditched the leather factory and went to the Uffizi on my own and it was the best thing ever. .
I don’t know if it grabbed your attention, but I was blown away by all the drapery on the sculpture. Not just in Florence but throughout Italy. Next time you are there make a mental note to give it extra attention.
Having learned our lesson, we did France on our own and were able to spend four days at the Louvre. Another day at Musee D’Orsay. Absolutely the way to go.
So happy you had a lovely time. You will never forget it.
Jason,
Sounds like a wonderful trip! If you’re ever coming to Seattle, have we got hills! We’d love to host you at our Capitol Hill condo for a good look at the Space Needle and a beverage!
I smiled all the way through your shared journey, it was contagious, which brought up dear memories from several trips there, and a longing to return. I am happy you had a wonderful time, and decided to stay put, sort of!
glad you had such a memorable experience! there is truly nothing quite like it. certainly all the world is beautiful, each place in its own right, but the combination in bella Italia is unique, particularly for the artist of whichever media. buon lavorro!!!
Wonderful trip! So vibrant and full of the intense energy of Italy. Thank you for sharing photos with us! Glad that you both had a great time.
I’m so delighted to read all about your trip, and to see the photos of you and Carrie enjoying it so much, terrifying roads notwithstanding!
You both look wonderful, and I’m thinking that if you can do that kind of thing more often, you will definitely increase your longevity – it looks like this trip not only saturated your senses with some of the best that life has to offer, but also gave you a whole new energy and joy boost!
What a fantastic trip, and you two blended well under the Tuscan sun and amid the Parisian ambiance.
Who knows? If you can dream it (ex-patting to Italy), you can do it. Cin cin! Thanks for sharing!
How fabulous! Thanks for sharing your beautiful photos! We now live in Portugal and I can’t wait for my first trip to Florence! Your tips are priceless.
We leave for two weeks in Tuscany next week ! We r three senior ladies and r planning relaxing visits to Florence, Siena, San Gim and others traveling by train! Reading your lovely description wets our palates for a fab trip!❤️❤️
I’m so glad you got to see Florence and decided to focus on one locale rather than rush around to try to see highlights everywhere. Holidays that allow time to absorb history, culture, and daily life are much more meaningful and memorable in my view. Your photos and story reminded me of our 1997 solo motorcycle tour of Tuscany, to celebrate our 20th wedding anniversary. Thanks for the reminder, and welcome home.
Hello Carrie & Jason,
It was great to view all the wonderful places and food you had on such an amazing trip. One day I will go to the southern tips of Italy. I live in wine country, Santa Ynez Valley, California. If you ever come this way you have a place to stay in one of my guest rooms.
Sincerely,
Larry R. Rankin
An unforgettable trip indeed! Thank you for sharing Jason!!
This brings back memories of our trip there many years ago (we need to go again!). We spent 3 days in Milan, 1 week in Florence and 1 week in the countryside just outside of San Gimignano. Your travel notes and photos bring all of the sights, sounds and tastes of our trip rushing back. I’m glad you enjoyed it!
I enjoyed reading about your trip. It sounds fabulous. I hope to get there some day.
A well described trip. Made me feel like I’d been along/
Thanks so much for sharing, Jason. So happy that the two of you got to “take your time” as they say in Ireland, and smell the roses/coffee/whatever in Italy. I don’t think people realize how “fast” life is until they slow down. You and Carrie looked wonderful. Your photos are beautiful.
To share and not compare with your travelogue story, I will say that my husband (82) and I (79) returned on Friday night from a 4 week trip to Ireland, Denmark, and Paris. Having travelled a great deal over the years and contemplated many art museums and cathedrals, this was a different kind of expedition, focusing mainly on friends, 60th – 65th wedding anniversaries (they DO exist), and culinary excesses!
Our one big mistake, though, was renting a car and winging it on our own in Ireland. The roads are maybe 3 feet wide and they drive on the opposite side of the road from Canadians, Americans, and others. Roundabouts in this situation can cause extreme anxiety + + +, if not a shortened life.
And be cautioned that it turns out there is a reason why Hertz won’t rent a car in Dublin to anyone without documented approval of capability from both a doctor AND insurance company if one is over the age of 76. This meant scrambling to find a rental company that would (despite having a reservation with Hertz).
Fast forward a couple of days or so, which was the longest year of our lives. At this point our rental car now looked like something from a Starsky and Hutch movie set!!!! Paint scraped off the back rear bumper and scratches all along the passenger side from bushes. And despite my startled cry of “GET OVER” (the first of many), poor hubby might have managed to take off the side mirror of a parked vehicle that we passed. Unfortunately he did not realize it and I had become eerily silent (he thought he hit a post). More missing paint. We then managed to miss the turn to the famed Cliffs of Moher, but there was no way we were turning back and putting our lives at further unnecessary risk and certain death. And besides, a lady told us it was too windy to go there anyhow.
The loveliest almost incomprehensible thing in Ireland was the astonishingly wonderful peeps who guided us along our wayward journey and had a few laughs with (at?) us. They would drop whatever they were doing without complaint or irritation. Oh, and did I mention that the Guinness beer is an acquired taste if one works at it faithfully each day?? Ya gotta love the Irish!
For any of you planning to take a “vacation” to Europe in the future, be advised. You will walk more than several miles/km if you brave the airports of Dublin, Copenhagen, and/or Paris CDG. If you are not in walking shape, you will either become so quickly or ride on a people mover or wheelchair. The Metro system and RER trains of Paris (plus walking) are the best ways to get around. You will walk and climb stairs ad infinitum. And you might even fall down an escalator like I did while trying to manoeuvre a large plus small suitcase. Luckily no harm done. And if you have an adequate amount of grey hair, people will automatically help you carry your bags up and down. Seriously!!
So have a good time, enjoy the art, flora, and fauna, and be grateful for the abundance of terrific human beings wherever you may find yourself.
Stay in the Light,
Verna
My significant other and myself just got back from a month long trip to Italy. Based out of an Airbnb in Massarosa (not the greatest decision, but we made the best of it), we took in all the regional sites, sounds and smells. From the Cingue de Terre up north to riding the bullet train to Rome, we saw it all. Loved Florence, spent several days there, the square in Siena takes your breath away as you come around the corner, did all the touristy things in Rome, which you have to do, but hated the noise, the enormity of the crowds and the over all busy atmosphere. Tuscany was a definite highlight as you described. Pictures cannot do it justice! There is no bad wine in Tuscany. Lucca was a delightful surprise as was the beach in Viareggio. Heading back soon, but probably to the south and Sicily.
Beautifully written as always. We’ve traveled both ways, with a group and on our own. I enjoy the camaraderie of a group and getting to know the usually knowledgeable guides over time. But the freedom of doing it on your own, on balance, wins out for me. We’re currently in Portugal, having just finished a group trip with Backroads (hiking) and now we’re on our own in Óbidos. Cheers to all fellow adventurers.
Jason,
How fun to know we stood right there where you just returned from. Our trip was Italy for a month. The plane ride is tooooooo long to stay for a short time. Blessed to have been in Rome for 5 nights, Venice for 3, Florence for 5 and into Tuscany. Montepulciano area, Pienza area, and on the coast in Santa Marienela – just outside Rome before our return home. One very full month.
The look on David’s face – I called it “loathing” of Goliath and all he stood for. The tour guide we had used a term that I can’t recall, but I didn’t think it fit at all. Florence was by far our favorite. We were in an Apartment just off the Duomo – between Amore Gelato and the Carousel. Of all the places, we would return there…..
Our flight mess came in Dallas, TX. Flying into the sunset…. arrive in the DFW area, circled clear down here near San Angelo (wish they could have dropped us off) landing too late for the connection to San Angelo. Our flight there was canceled due to the same weather and unbeknown to us we were rebooked on to the 11pm flight arriving in San Angelo at midnight. WE were awake and on our feet for like 24 hours straight!
I Loved seeing you plein air painting! Took my stuff like the trip to France 2 years ago. If our health holds – we hope for a trip to the Holy Lands…. but it all needs to quiet down.
Your ArtSala program – Has the website capabilities been upgraded? Shopify is overwhelming me.
Debra
Hi Jason,
I am so happy you and Carrie decided to stay close to Florence and enjoyed as much as you could in that area. There is so much to experience in Tuscany, and it’s well worth taking your time.
You two look happy and relaxed, and I bet those sunglasses are Italian:-)
The Annunciation made my wife cry. To see the Birth of Venus in person, up close, words cannot describe. We were actually at the Uffizi on Easter Day several years ago. There are so many things to see there, both in Rome and Firenze. I was a designer of liturgical furnishings back then and received some not on the tourist route directions from a few monsignors back in the states. We were also able to go into the Sistine Chapel before the crowds arrived. One of the best Italian restaurants was a tiny place close to St Paul’s. Something everyone should do is take the underground in Rome. The train between Rome and Florence is also a nice trip.
Absolutely… I often ponder if a part time retirement in Italy will be in my cards.
I was just in Florence last week for the fourth time and have just begun to know this beautiful city. The Uffizi was incredible and could have taken an entire day, twice. I love Italy and have spent many months there over several trips as half my family is from Italy. I love the people, the amazing architecture, the details on the walls and doors of homes all over this sublime country. And, of course, the gelato. I’m thankful for all the long stairways, stone walkways and long treks that allow me to enjoy one almost every day! Other wonderful places to visit in the Tuscany area and surrounds are Orvieto, Arezzo, Siena, Cortona and Lucca. I have also traveled in the north and east of Italy but have only spent a short time in Rome and nothing to the South. Can’t wait to explore!
Italy is my favourite place I have visited over the years. We also went to the balsamic place in Modena, and now anything else tastes less.Glad you enjoyed it. We will try our best to go back soon.
We also enjoyed Scottsdale and visited your gallery there last year. We got a legs and lungs workout climbing Camelback.
Welcome home!
So glad you had such a wonderful time. In Italy, you can’t go wrong!
2 weeks .. not enough… better than 1 week. Where’s the Farmhouse? An Agriturismi ? Grazie
Been 3 times… always amazing.
I lived in Florence for 10 years, i love Tuscany, you can leave tuscany but tuscany will never leave you ..
WOW! Your trip made me want to go back to Florence, Siena and the Tuscany region. I’m so glad you had a great trip (except for the return). Go with the flow is always our motto when traveling abroad. Soooo much to discover, see, eat, appreciate, learn,,. takes more than1 visit as you realized. I hope you go back to take more in and stay longer. Italy is part of my heritage and would love to live there to rekindle that long lost connection.