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Most scenic Tuscan drive? Any suggestions?

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We will be in Italy in August and are planning to drive through Tuscany starting from La Spezia (after visiting Cinque Terre) and going down to Rome. We plan to stop in small towns along the way and stay a few nights in the area. While we are excited to explore these Tuscan cities, we really are looking most forward to the actual drive through the country side. Does anyone have any suggestions for the most scenic route, like which cities to pass by/through? I've glanced through a bunch of guidebooks, but its hard to find the best route that would end in Rome. Thanks!

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    The Chiantigiana (SS 222) from Florence to Siena is very scenic, as is SP 146 after Siena through the Val d'Orcia. SS 222 will take you through Greve and Castellina in Chianti, and SP 146 through San Quirico d'Orcia, Pienza and Montepulciano. Many of the picture postcards of the Tuscan countryside are taken in the Val d'Orcia.

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    Hi Zerlina,

    Just looked up your recommendation of Val d'Orcia. It is wonderful! What a great recommendation!

    If one were to use public transportation to get there. How/what can one do that?

    Thank you so much!

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    Here is something I've posted a couple of times in the past:

    Tuscany – Val d’Orcia
    My wife & I first visited the Val d’Orcia (around Pienza) in the late ‘80s when we were doing the typical “once over lightly” tour of Italy. On an old map I used at the time, I had scribbled the comment “pretty” on the road running between San Quirico d’Orcia and Montepulciano. We passed though this area again on several subsequent visits – usually staying 1 or 2 days each time. In September ’94, we stayed 4 days at the 5-room Hotel La Saracina near Pienza, and explored the area a little more (using up a lot of film) and then moved on to the Chianti area for 3 days, San Gimignano for 2, Lucca for 2, etc. In September ’96 we met 3 other couples (old college friends celebrating our 25th anniversaries together) for a 4 day stay in La Saracina. One of the couples liked the area so much that they booked a 3 week stay at La Saracina the next year, and then bought a 2nd home in the town of San Quirico the year after that (after exploring Chianti & Umbria to make sure they were buying in the area they liked the most). In ’99 when we retired early so we could travel more, we stayed in their apartment for 3 weeks - taking day trips to other areas in Tuscany & Umbria, exploring the Val d’Orcia, and enjoying Italian village life in San Quirico. That same year we had spent a considerable amount of time in Provence (7 weeks), and when we arrived in the Val d’Orcia, we both commented that this area was the prettiest countryside we had seen anywhere in Europe. I have various books & posters showing the Val d’Orcia in early spring when everything is green. It looks quite different in these spring pictures than it does in September when we had always been there. In March of ‘04 when the airfares were low and our friends were living in their apartment in San Quirico for 5 months, we visited the Val d’Orcia again. We thought that in September the countryside looked remarkable with the fields freshly plowed, exposing the soil with colors ranging from dark rust to light tan, with the cypress trees dancing up hills or running along the crest of a ridge, farmhouses tucked here & there, medieval villages everywhere, castles, vineyards, olive groves, and virtually no ugly commerce to spoil the scene (like elsewhere in Tuscany). Well, March is even prettier. The winter wheat that is planted almost everywhere is bright green and when it catches the late day sun, it is really spectacular with all the rolling hills, cypresses, farmhouses, etc. Our friends in San Quirico say it’s even more scenic in late May or early June when it’s still green, but the wheat is taller and blows in the wind. Since our 3 week stay in ’99, we have visited Vermont during leaf season, Provence several more times (including poppy, lavender & sunflower seasons), the Dordogne, Alsace, Pays Basque, Scotland, Bavaria, the Cotswolds, and many places in between – but we both feel that the Val d’Orcia is the prettiest open countryside we have seen anywhere. When we were there in March, we took several day trips to other sections of Tuscany, and when we returned “home” we always commented “why do we travel anywhere else in Italy – there’s nothing prettier than where we are staying”. So, for the remainder of our 2 week trip, we didn’t travel anywhere else – we spent all our time finding more nooks & crannies in the Val d’Orcia.

    The following is a 1 day driving itinerary through this area, with stops at various villages and sites. If you have more time to spend in this vicinity, by all means drive down some of the dirt roads and even take some walks.

    The best times of day to see this area are in the early morning or late afternoon when the sun is lower in the sky. When the shadows are long, the cypress trees & umbrella pines look more pronounced as they “dance up the hill” (my wife’s term). The farmhouses sprinkled throughout the landscape take on a special look in the early morning and at sunset. Budget at least two rolls of film for this area. The Val d’Orcia can get some morning fog. If so, spend the morning in a village & start your drive when the fog lifts.

    In my opinion, the countryside is the “star” in this part of Tuscany. You “must see” Pienza and there are other interesting villages too, but don’t shortchange the drive through the countryside. If you are behind schedule, skip some villages – not the countryside. You might think that this itinerary seems out of order in places & I’m often taking you down roads that you have already driven. Sometimes, I’m considering the position of the sun when you drive on a road, and other times I’m just trying to extend the time to enjoy the countryside.

    You will need the Touring Club Italiano map of Tuscany to follow this route. Also, obtain the Michelin Green Guide to Tuscany. If anyone wants to take walks in this area, get the Carta Turistica e Stradale – Val di Chiana, Val d’Orcia map. They have it at the bookstore in Pienza.

    If you are doing this tour as a day trip from Siena, leave Siena going south on the N2 (marked SS2 also). It’s actually a pretty drive. Just past the second turnoff to Montalcino and past the bridge, look for a beautiful grove of cypress trees to your right. At San Quirico, take the N146 east to Montepulciano. This is an easy drive. If you leave Siena by 7:00 you should get to Montepulcano by 8:30 or earlier.

    Do not visit Montepulciano at this time, unless it is foggy in which case you should wait until the fog lifts before proceeding on this drive. Take the N146 west to Pienza. The sun will be at your back. When you pass the large domed church of San Biagio (on your right/north) just after leaving Montepulciano, look back towards Montepulciano & you will be rewarded with a spectacular site – the Church of San Biagio in the foreground with Montepulciano cascading down the hillside behind it. This is one of the most photographed sites in Tuscany. Before I retired, I had a giant poster of this view in my office – reminding me why I wanted to retire & spend more time traveling. Don’t take a picture just yet – you will be back over this route later in the day and the sun will be in a better position to shine on the church and the perched village behind it.

    Continue on the N146 to Pienza. This road has some wonderful scenery. You should get to Pienza by 9:00.

    As you approach the “old” part of Pienza and the N146 turns right towards San Quirico, make a sharp left turn and you will find some parking spaces. If these parking spots are filled, continue down this road & look for the blue parking (P) to your left. During tourist season, you have to pay to park in this lot. You can also park south of Pienza below the village, but you will have a slight climb uphill to the center of town.

    Explore Pienza by entering through the Porta al Murello, at the west end of Pienza. Just as you enter Pienza, there is a nice pottery/gift shop on your left (in the large square) which has had a significant impact on my wallet. Most stores open at 9:30 & close for a 1 ½ to 3 hr lunch at 1:00 (typical in Italy). You can obtain a self guided 1 hour audio tour of the town (in English) by renting a head set from the tourist office (closed at lunch time, but open on Sunday). If you want to have a picnic lunch at Sant’ Antimo abbey, pick up some lunch provisions while in Pienza. There is a pizza shop just outside of the Porta al Murello (next to the book store/news stand) where you can pick up a slice of pizza. There is a walking path next to the town walls on the south side of Pienza – don’t miss this. It’s a great place to just sit in the sun & admire the views. Plan on spending 1 ½ hrs in Pienza if you take the audio tour or you’re a big shopper, 1 hr if not. It’s one of the few villages in Tuscany that has most of it’s stores open on Sunday, & Monday mornings.

    Leave Pienza on the N146 toward San Quirico. This is another stretch of road with fantastic views – perhaps our favorite. Just 2K from San Quirico, there is a splendid view to the south of a very small church and another building with cypress trees & umbrella pines surrounding these buildings. This site is on the crest of a hill. If you have been in Tuscany for any length of time, you will have seen this view on many postcards & calendars. You will pass this church again later in this drive when the late afternoon sun makes this scene perfect for picture taking. As you approach San Quirico, drive into the parking lot behind the Taverna del Barbarossa restaurant (which is associated with the Casanova hotel). The parking lot is at the south end of the complex. Park the car, get out & you will see another of the most photographed sites in Tuscany. In fact, the very first picture that appears in my ’95 Michelin Green Guide to Tuscany, is a photograph of this scene – a farmhouse sitting on top of a hill, surrounded by cypress trees. A “coffee table” book I have has photographs of this site at different times of the year – it’s quite remarkable. This site is even on the cover of that book. I also have a poster (yes, it was hanging in my office too).

    You should get to San Quirico by 11:00 if you stopped for some picture taking along the way. Don’t visit San Quirico now – do so later in the itinerary if you have time (it’s worth a visit).

    Follow the signs at San Quirico and get on the N2 toward Siena (north). Just after you leave San Quirico on the N2, you will be on a bridge. If you look back, there is a nice view of the village of San Quirico from the bridge. Unfortunately, I have never been brave enough to get out of the car & take a picture from this bridge. Further along the N2 there is a pretty grove of cypress trees on your left (west). This grove can be seen better traveling south, however. On your right, you will see several cypress trees and umbrella pines dotting the ridge of a hill. You might recognize this site from postcards & calendars you have seen. Turn off the N2 & go to Montalcino.

    As you approach Montalcino, you will get some good views of this perched village. The road will turn a few times & will take you to the south entrance of town, which will be marked with a large “Montalcino” painted on a white background on the stone wall of town, and a “centro” sign will be pointing into town . Do not enter through this entrance - instead turn a very sharp left when you see this town sign and follow the road uphill. Very shortly you will see a round-about. Exit to the right off the round-about to find a place to park. There is a rather large car parking lot near the old fortress (Rocca). Note – When you arrive into Montalcino and encounter the round-about, note the sign to Sant’ Antimo Abbey (marked “S. Antimo”), where you will go next on this itinerary (it’s marked on the round-about). The road to this abbey is a very sharp left (almost a full circle around the round-about).

    Visit Montalcino. You should get there by 11:00. Many shops will close by 1:00. You can visit the fortress, but I found it only OK. Budget about 1 hour or less in Montalcino. It has some nice outdoor lunch spots if you want a sit down lunch (I’m pushing the picnic at Sant’ Antimo).

    Follow the signs (and your map) to Sant’ Antimo Abbey. The Abbey is quite lovely, but what I like best about it, is the setting – we’ve used up a lot of film there. It’s located in a valley surrounded by hills, cypress trees dancing up these hills, and a lawn around of the Abbey (where you can picnic). It’s also a good place for a little snooze in the sun. There are Gregorian chants inside the church at various times of the day (posted on the entrance to the church – one chant is at 12:45). See for a full chant schedule and a description of Sant Antimo.

    Continue on your drive through the countryside. You should leave Sant’ Antimo about 1:30. Take the road south-east of the abbey, toward Monte Amiata on your Touring Club map. Pass through Monte Amiata, and at Ost. Ansidonia, turn left (north-east) to Castiglione d’ Orcia. This is pretty countryside. Pass through Castiglion & get on the N2 & head north toward San Quirico. You should get to San Quirico about 2:00 or so.

    Continue past San Quirico toward Siena. You will have another chance to see the cypress grove to your left, and the cypresses & umbrella pines running along the ridge to your right. Get off the N2 at Torrenieri. There is a road that runs from Torrenieri to San Quirico, just east of the N2. Find it on the Touring Club map. You want to head south on this road from Torrenieri to the “phantom” village of Bellaria on the map (there really isn’t any village there). When driving through Torrenieri just after leaving the N2, you need to turn right at the first stop sign (in front of a small church) and you will immediately cross a railroad track. As you approach Bellari, look to your right and you will see more umbrella pines & cypress trees dotting the top of a ridge. These are the same trees you saw from the N2 on your drive to Montalcino and to Torrenieri. When you get to Bellaria, turn left (east) to Cosona (it’s marked at the turn). You will be on a dirt road. It is one of our favorite drives in this area. Continue & go slowly on this dirt road. Lots of pretty sites here. This dirt road will kind of dead-end onto another road (see it on your map). Turn right toward Pienza and continue on toward Pienza. When you get to the N146, turn west (right) toward San Quirico. You should get here around 3:00.

    About half way to San Quirico, there is a dirt road that heads south of N146 – find it on the map (it’s the only one on the map between Pienza & San Quirico). There is a sign for this road on the N146 and the turn is marked by a direction sign to the “Agriturismo il Rigo”, and before a “watch for deer” sign. Turn south on this road. We have often driven down this road, parked the car, & started on a hike from here. Continue on this road until it connects with the N2.

    Continue south on the N2, and after about 2K, head east on the paved road (marked yellow on the touring club map) toward Chianciano & Pienza (well marked). This road passes through another “phantom” town called Spedaletto – find it on the map to make sure you turned at the right place off the N2. This road goes trough the heart of the Val d’Orcia and is quite picturesque. Continue on this road toward Chianciano Terme. You will have a nice view of Pienza perched on top of a ridge, off in the distance to the left (north). There is an “interchange” on this road – pay attention & keep heading to Chianciano Terme. Just before La Foce, you will see a lovely double set of cypress trees to the north, dancing (again) up the hill (another much photographed site). Continue on this road, and shortly you will see a parking lot opposite the Restaurant Oasi la Foce. Pull into this lot & you will get another view of this double set of cypress trees. Continue toward Chianciano, and about 1/2K after the parking lot, take the first left (north) on a dirt road toward Montepulciano (well marked). This will be a dirt road and will pass around a lovely castle. When the dirt road becomes a paved road, turn left towards Monticchiello (well marked). As you approach Monticciello, this road becomes particularly scenic.

    Monticchiello is a very cute village – it’s where my father-in-law says he wants to live. Park the car in the lot outside this village near the refreshment stand (do you need any) & wander around. It’s a 30 min wander. There is a nice restaurant in town called La Porta.

    Look at Monticchiello on the Touring Club map. You will see lots of roads radiating from this small village like spokes on a bicycle wheel. All these roads have fantastic views of the countryside – in my opinion, they offer the prettiest drives in the Val d’Orcia. If you have time to spare, by all means drive down all these roads. We’ve done this quite often at various times of the day when the sun casts different shadow patterns on the rolling hills and from the cypress trees. My favorite drive is the one branching out at 8:00 from Monticchiello. It connects to the road heading directly north to Pienza. Turn right towards Pienza on this road & you will get a fantastic view of Pienza. Just a little south of Pienza, there is a dirt road that heads south-west. Take this road and it will connect with the N2/Chianciano road running east/west. From here you can retrace the drive east towards La Foce where you will head to Montepulciano (by-passing the turn to Monticchiello). When this road hits the N146, turn left to Montepulciano.

    If you don’t have extra time available for this side trip, after visiting Monticchiello head back down hill from the parking lot. Immediately after leaving the lot, go straight at the fork (just after the first house on the right) instead of turning right the way you entered the lot. This will lead to Montepulciano on a paved road that shortly becomes a dirt road and later paved again. There is a nice view of Montepulciano from this road. When this road dead-ends at the N146, turn left towards Pienza, or right to Montepulciano if you want to visit this town (one of my favorites).

    Visit Montpulciano, if you like (1 hr visit). Use the Michelin Green Guide to find the sites you want to visit. Hike all the way up to the Piazza Grande. It’s a somewhat steep walk through town, however, but the village is very pretty. You can taste some excellent wine at the Avignonesi estate (you will see it – just opposite the tall column in the middle of the main street, just after you enter town). If you need a snack, find a place where you can get pizza by the slice & have a mushroom (fungi) and truffle (tartufi) pizza (only in Italy!!!).

    Leave Montepulciano towards Pienza on the N146 again. Now you get a better view with the remarkable San Biagio Church in the foreground and Montepulciano in the background (you may have to drive a little west on the N146 to get the view). Hopefully you are at this spot about 5:00 or so. Without any further stops, you are less than 1 ½ hrs from Siena.

    Drive along the N146 toward Pienza & San Quirico again (30 min drive). The sun will be in your face, but now the little church with the cypress trees around it will look quite different, as will other sites you photographed when you drove this route in the morning.

    If time allows, visit San Quirico (it’s 45 mins to Siena from SQ). San Quirico is kind of a poor man’s Pienza – but they like it that way. It’s a town where people really live. In fact, I’ve told friends that San Quirico is the type of town we wish our small towns in the US would be like – kind of a River City, Iowa (Music Man). Everyone knows everyone else, people are out strolling, there are stores where locals shop for their everyday stuff, etc. Families congregate at the Bar Centrale (closed Thurs) in the evening, where the men play cards in one room, the younger children are in the video room, and the older children are outside playing soccer in the town square or just hanging out. If you visit San Quirico, have a coffee latte at the Bar Centrale & “people watch”. SQ is a 30-45 min visit. Some stores may be closed Wednesday afternoon.

    Further reading suggestions:
    War in the Val d’Orcia by Iris Origo
    This is a woman’s diary of happenings in this area during WWII. “Non-political, it is an elegantly simple chronicle of daily life at La Foce, a manor in Tuscan no-man’s land bracketed by foreign invasion and civil war. The Marchesa Origo’s faithful record is one of those rare and precious accounts that give the truth of history with the art of a gifted writer, that bear witness nobly to ignoble times.” The preceding was lifted from the back cover of the book. While we were there in ’02, they were celebrating the 100th anniversary of her birth.

    Stu Dudley

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    i would recommend the drive up to the natural thermal water near saturnia. it's a beautiful drive-- with the payoff being cascading hot water in a gorgeous setting-- for free! when we were there, soaking in the water, the hills around it were covered with sunflowers. beautiful.

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    I'd say it's the Laurentina Road in le Crete Senese, running from Siena-Asicano-San Giovanni d'Asso), and from there you can head down through Montalcino to the Val d'Orcia, and on to Rome. Here's a description:

    (By the way, roads in Italy are not marked with numbers, so you should plot a route knowing which towns the roads run through.)

    Crete Senese Drive

    "South of Siena, the hilly area known as the "Sienese Crests" is full of colorful fields and curvy, scenic roads. You'll see an endless parade of classic Tuscan scenes, rolling hills topped with medieval towns, olive groves, rustic stone farmhouses, and a skyline punctuated with cypress trees. You won't find many wineries here, since the clay soil is better for wheat and sunflowers, but you will find the pristine, panoramic Tuscan countryside that you find on calendars and postcards.

    During the spring, the fields are painted in yellow and green with fava beans and broom, dotted by red poppies on the fringes. Sunflowers decorate the area during July and August, and expanses of wind-blown grass fill the landscape almost all year.

    Most roads to the southeast of Siena will give you a taste of this area, but one of the most scenic stretches is the Laurentina road (Siena–Asciano–San Giovanni d'Asso, #438 on road maps; you can also take S-2 — Via Cassia — toward Rome and turn off at Asciano sign; either way allows you to easily continue to Montalcino). You'll come across plenty of turnouts for panoramic photo opportunities on this road, as well as a few roadside picnic areas.

    For a break from the winding road, about 15 miles from Siena, you'll find the quaint and non-touristy village of Asciano. With a medieval town center and several interesting churches and museums, this town offers a rare look at everyday Tuscan living, and a great place for lunch (TI at Corso Matteotti 78, open Mon–Fri 10:30–13:00 & 15:00–18:00, Sat–Sun 10:30–13:00, tel. 0577-719-510). If you're in town on Saturday, gather a picnic at the outdoor market (Via Amendola, 8:00–13:00).

    Five miles south of Asciano, the Abbey of Monte Oliveto Maggiore houses a famous fresco cycle of the life of St. Benedict, painted by Renaissance masters Sodoma and Luca Signorelli (free, daily April–Oct 9:45–12:00 & 15:15–18:00, Nov–March closes at 17:00, Gregorian chanting Sun at 11:00 and Mon–Sat at 18:15, call to confirm, tel. 0577-707-611). Once you reach the town of San Giovanni d'Asso, it's only another 12 miles southwest to Montalcino.

    Another scenic drive is the lovely stretch between Montalcino and Montepulciano (S-146 on road maps). This route alternates between the grassy hills of the Crete Senese and sun-bathed vineyards of the Orcia River valley. Stop by Pienza en route."

    Since you are coming from La Spezia, you might find that the most scenic route is to through San Gimignano-Volterra-Monteriggioni. Without stops, that's about a 4 hour drive. A base somewhere just south of Siena would enable you to both enjoy the Crete Senese drive and loop back to see the Chiantigiana as well. You'd also be able to explore the val d'Orcia, and again as you headed south to Rome.

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    Only a fraction of the val d'Orcia can be seen by public transportation, although it is a very pretty fraction and the area of most historic interest. You can take a train to Chiusi and catch a bus at the train station that goes through scenic country to the hill town of Montepulciano, a 30 minute ride. From Montepulciano, it is a 10-minute bus ride to Pienza.

    From Pienza, there is limited bus service from to Buonconvento, which goes through San Quirico. Buonconvento has several small museums of interest and is a lovely, undertouristed valley town.

    From Buonconvento it is possible to take a bus to Montalcino (or a train to Siena). However, you would need to be very careful about timing and making the return bus home.

    If you are interested in Etruscan history, a visit to Chiusi for its fine Etruscan museum is very rewarding, and the hilltown itself is pleasant and charming.

    So from a base in Pienza, you would have a number of options to take buses through scenic countryside to interesting destinations. But "Tuscany" has become a tourist destination mainly for drivers, either ones with very fixed scenic itineraries or people who like to explore independently, without a map.

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    Wow, thanks for all the input guys! StuDudley - that is a crazy detailed driving plan, I love it! Zeppole, your answers are very helpful as well, especially the part about the roads not being marked by numbers - thats definitely a good thing to know, lol! Your answers have made me even more excited for this trip, thanks so much!!

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    Zeppole--is the link you have above for a bus line? We are staying for two nights in Montepulciano and my plan was to take train to Chiusi and then bus. This looks like a different bus system. I am interested in the Siena to Montepulciano line.

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    This is for bird watchers.

    Both this year and last year, in April/May we have driven along the S438 between Siena and Asciano. Near a farm called Fontanelle, we saw see bee eaters (, very colourful birds, which were nesting in the soft sandy hillocks and perching on the telephone wires. For anyone from northern Europe, they are a real reminder that you are in the warm south. We also saw kites in the same location.

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    Head out of Pienza towards San Quirico, turn right at the sign post for Sant Anna en Camprena/Montisi. After about a mile turn left onto a very small road without a sign post (it is the first turn). The road takes you the long way to Montisi and through the most stunning countryside around. If you get lost, don't worry knock on the door of the nearest rambling farm and usually a batty 90 year old aristocrat will take you in for lunch and rabbit on about the Nazis (WW2).

    The other road that stands out (other than the usual cheesy ones near Monticello is between Buonconvento and Murlo - long ranging views over to Siena.

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    Did you scroll down the list? I see buses listed there for Chiusi to Montepulciano. If that isn't what you have in mind, I always have good luck with the most obvious google searches (i.e., "bus from Chiusi station to Montepulicano timetable" etc.)

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    By the way, I meant to add that a daytrip loop though scenic Tuscany can be made by taking a bus from Florence to Panzano (one hour) and then catching the bus there to Siena (one hour.) The stretch from Panzano to Siena travels the scenic Chiantigiana, mentioned by Zerlina above.

    From Siena, you can take a bus back to Florence.

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    Hi Adoc86--I am planning for the exact same drive through Tuscany (from La Spezia to Rome), and am wondering what you ended up doing?? I would love to hear how it went.

    Thank you!

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