Traveling Through Tuscany Destination Guide | Willow & Oak Events

Traveling Through Tuscany

Destination Guide

Ciao, bella! If a honeymoon traveling through Tuscany is on the horizon for you, you’ll be living la dolce vita from the moment you begin daydreaming about the cypress lanes and 17th c villas to the second you take that first bite of pear and cheese tortellini at Enoteca Coquinarius. Italy is where Alexis, Ben and I met for the first time nearly a decade ago, and it holds special significance in our hearts. We’ve returned many times, and I even convinced myself I should live in Rome for a summer last year! And live I did. In our book, you couldn’t choose a more romantic destination to spend your first few weeks as newlyweds than traversing the Tuscan countryside and all its hidden treasures. Read on to discover some of our favorite places to stay, restaurants to eat, attractions to see and experiences not to be missed throughout Tuscany. 

Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany

Tuscan weddings have a more relaxed feeling about them. Imagine yourself dining al fresco with twinkle lights and rustic greenery (throw in some Norah Jones tunes in the background) and you’ve got yourself a scenario much like the Italian fetes that happen all year long across the countryside. The venues we’re about to share are often the perfect situation if you envision an intimate getaway with your guests across a whole week or weekend. Many of these villas or resorts can help you organize group activities like cooking classes, horseback rides, hot air balloon excursions and more… we certainly can’t imagine a better way to spend this time with your loved ones! Except perhaps with the addition of wood-burned pizza to cap off every night.

Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany

Where to stay

Belmond Villa San Michele
No hotelier does hospitality quite like Belmond. Their boutique, luxury properties peppered across the globe are seeped in beauty, quality and experience. Honestly, peruse their hotels everywhere in the world here to get a feel for the level of excellence + personalization they boast. And no this is not an ad! We just really love Belmond. This property in particular sits regally above the city of Florence, offering sprawling views of the landscape and historic city below. As a guest, you can receive complimentary shuttles to and from the city center (about 15 minutes long) and admire the picturesque views every step of the way. The rooms are sumptuous, the pool is breathtaking and the al fresco meals overlooking all of Florence are something that can’t be beat. During your stay, you can also indulge in their on site cooking school, take a fresco class and take a day trip to Chianti to learn the process of cashmere-making.

Borgo San Pietro
A renowned Relais & Chateaux property, Borgo San Pietro is a Tuscan farm estate with character for days. Encompassing Michelin-starred restaurants, an organic skincare range, a bespoke yacht and holistic spa, this boutique estate is rated 5 stars for a reason. An incomparable oasis for those seeking a tranquil Tuscan escape with relaxation at the core, Borgo San Pietro places great importance on the feeling of sanctuary – a concept embedded in their luxury farmhouse aesthetic and 300 acre gardens growing herbs, nuts and market vegetables. A must visit!

Borgo Pignano
Located in the heart of the Tuscan countryside near the towns of Volterra and San Gimignano, Borgo Pignano is almost like it’s own little village – complete with honey lab, vegetable garden, horseback riding, spa, orchard, restaurants, cocktail bar and yes… an infinity pool. Truly, a country estate has never looked so good! Not only do they have a 13th c Romanesque parish church, but a darling 18th c villa just around the corner. The Tuscan chic ambiance is perfect for couples who want to indulge across a number of days and experience unique activities during their stay, since the resort offers many on site and is just a short drive from Florence and Siena.

Rosewood Castiglion Del Bosco
You’ll want to bookmark this scenic hamlet set along the same path that pilgrims and merchants used to travel in medieval times from Canterbury to Rome. Rosewood Castiglion Del Bosco is a historic 800 year old estate that comprises ancient castle ruins, a medieval church and a historic village, which now plays a central role in the resort. Rustic stone exteriors give this space a classic Etruscan vibe, and the 11 private luxury villas (in addition to the 23 rooms in the main estate) are overflowing with a blend of curated antiques, bespoke furnishings, inspiring textiles and modern comforts – hello home theater! 5,000 acres of beauty make this diverse, yet intimate hideaway a coveted spot for destination weddings and honeymoons every year.

Monteverdi Tuscany
If Goop and Architectural Digest had a baby, it would look like Monteverdi Tuscany. Tranquil is their middle name, and their style is nothing less than refined, yet comfortable. It’s hard to imagine a retreat more relaxing than this secluded piece of heaven with exposed beams, stone walls, and “found” pieces from all over Europe. This Tuscan escape offers delicious views, calming energy and serenity at every turn, so be sure to visit the next time you’re near the Val d’Orcia region of Tuscany.

Villa Montanare 
Straight out of Letters to Juliet? Or is that just me? Villa Montanare is one of those visual treasures you just never want to forget – good thing photographers are always at the ready to shoot at this gorgeous Tuscan property in Cortona! A 1640-built farmhouse overlooking a happy mix of cypresses, pines, figs, fruit trees, rosemary bushes, lavender and cacti, the timeworn facade and subtle olive hues blend exquisitely with the surroundings. The villa is reserved for weddings, but can accommodate up to 6 guests for overnight stays. It’s easy to see why some might never want to leave (talking to you Frances from Under the Tuscan Sun)… Cortona is where she started her new life!

Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany

Where to eat

Da Delfina – The best Italian comfort food in and old stone farmhouse overlooking a Medici villa? Count us all aboard the Da Delfina train, just a few miles from Florence.

Il Canto Del Maggio – A garden setting with a seasonal menu, this charming hamlet boasts central Italy cuisine like no other, using local ingredients straight from their backyard!

Antica Osteria Da Divo – Siena dining at its finest, this restaurant’s interiors date back to the ultimate Middle Ages… 1000 bc! Lauded for its culinary masterpieces and over 300 wines to choose from, you can dine beneath ancient medieval faults for the experience of a lifetime.

Il Faconiere – Dine on the panoramic terrace overlooking the Tuscan countryside at this Relais & Chateaux property in Cortona where you can also book a stay. Boasting a Michelin star, the Etruscan menu changes seasonally and never disappoints!

La Tana Degli Orsi – A fantastic little spot in Pratoveccio that serves traditional Casentino dishes cooked to perfection with local produce. This chalet-style restaurant is extremely popular, so advance reservations are a must!

Restaurant Al Fresco – A Tuscan garden ambiance for an al fresco meal? Count us in for a stop by this Borgo Pignano treasure on every visit to Tuscany. Here you’ll find authentic Tuscan recipes, such as grilled meat, Mediterranean seafood rotating daily and wood-fired pizza to name a few. Other favorites of ours include the artichokes with pecorino and Spaghetti Martelli. Bellissimo!

La Bucaccia – If you’re a fan of recipes passed down for generations (hello, Pasta Nannies!), you’ll find yourself inevitably drawn to this hot spot inside a 13 c palazzo. Wander slowly up the ancient Roman road during your visit to Cortona, and enjoy the exceptional regional dishes that await you. Pro tip: When you book, ask the owner if they can make you a cheese making demonstration as well!

Alla Vecchia Bettola – The old-fashioned Italy ambiance is just what the doctor ordered at this sweet osteria beloved by locals and visitors. Sit family-style at marble-topped tables and indulge in the authentic Florentine menu that changes daily – I’m talking pasta made in house, traditional antipasti from local producers and amazing house wines, people! Don’t miss this one.

Enoteca Coquinarius – No exaggeration, this was one of the most transformative meals of my life. From the honey and almond brie starter to the iconic pear & cheese tortellini, this unassuming restaurant will forever be one I return to on each visit to Florence. Be sure to book a reservation in advance! While still a secret from the tourists, it’s definitely a hot spot for locals. 

Cibreo – Another star restaurant in Florence, Cibreo has been around for over 30 years now. The menu focuses on ultra traditional Tuscan cuisine (before pasta!, so you’ll find everything from polenta and minestra di pane to polpetti di vitella. To pay about half the price for food from the same kitchen, you can opt to dine at Il Cibreo Trattoria next door as opposed to the formal ristorante which has a more limited menu, but is still amazing!

Enoteca Pinchiorri – If you’re looking for an exceptionally formal dinner in Florence, this ristorante is one to bookmark. Awarded two Michelin stars, Enoteca Pinchiorri specializes in innovative gastronomy. You’ll find dishes like Saffron Fusillo, Lamb of the Lucanian Dolomites and Pigeon cooked in a cocoa beans crust to name a few!

Osteria di Castelvecchio – A kingpin of creative cuisine, this intimate + affordable Siena restaurant with Chef Mauro Lombardini at the helm has a menu that changes daily (always at least 1 vegetarian option) and features delights like risotto with artichokes and herbs, picci with ragu and pennette in tomato sauce sprinkled with crunchy cream.

Osteria Le Logge – Top level Tuscan cuisine with a twist in a gorgeous setting, you won’t find this Siena restaurant just off Il Campo unless you’re looking for it. Inside, you’ll find a display of glass-fronted bookcases and white truffle dishes that will blow your mind. A little on the pricier side, but well worth it in our opinion. Grab a bottle of the local Morelljno di Scansano to drink with your meal!

La Grotta – Two 16th-century vaulted rooms play host to this fabulous gourmet restaurant in Montepulciano facing one of the Tuscan renaissance’s most stunning buildings, Tempio di San Biagio. The elegant setting lends itself to dishes of equal glamour, such as the renowned malfatti (gnocchi-like balls of sheep’s-milk ricotta and basil, served with a taleggio sauce) and hand-rolled pasta with guinea-fowl sauce and dry prunes. They’re closed on Wednesdays, so plan accordingly!

Latte di Luna – A Pienza favorite, Latte di Luna is a laidback trattoria with a relaxed ambiance and quality food at fair prices. It’s the perfect spot to take your time with the courses, from the superb crostini starter to the original pasta of this region, pici (hand-rolled spaghetti). End with a delicious hazelnut flavored gelato if you know what’s good for you! If the weather is nice, be sure to aim for a post on the terrace and regardless, make reservations well in advance. You wouldn’t believe how popular this place is!

Osteria da Gagliano – Located 15 min from the town of Chianciano Terme, this petite family-owned osteria (and I mean petite with only a couple dozen seats inside the entire place!) feels like coming home. The owner, Giuliano, greets you warmly as you walk through the door and you’re overcome with sense of familiarity as if you’ve known him your whole life. From the golden saffron torte to the hand cut duck ragu to the world-class panna cotta, you might never want to leave.

Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany
Traveling through Tuscany has become increasingly popular for modern romantics, whether it’s for honeymooning or multi-day destination weddings. Having lived in multiple Italian cities, we’re sharing our go-to spots for places to stay, restaurants to dine, activities to indulge in and other insider tips on the Willow & Oak journal with couples in mind. Read on to discover some of Italy’s best kept secrets and begin your Tuscan daydreams now! #destinationwedding #honeymoondestinations #tuscany

What to experience

  1. Wander the leather market in Florence and search for the perfect leather jacket, bag, loafers, coasters or beyond! Take it a step further and visit Scuola del Cuoio to see how leather is prepared and purchase the most quality pieces.
  2. Marvel at all things Renaissance as you peruse one of the most important collections of paintings in the world at the Uffizi Gallery in Florence. Be sure to book tickets online via the museum’s official website well in advance so you can skip the crazy lines when you visit!
  3. Admire some of the best bird’s eye views of Florence from the Piazzale Michelangelo, located on a hill on the south bank of the Arno River. Grab a bottle of wine, an assortment of formaggio from a cheese shop in the city and park yourself here an hour before sunset to enjoy charcuterie with unparalleled Magic Hour views.
  4. Window shop for jewelry along the iconic Ponte Vecchio, Florence’s oldest bridge built in 1345, to start your day. During WWII, it was the only bridge across the Arno the Germans did not destroy, and it boasts a history of merchant shops filling its stalls since the 13th century! Of course, no more butchers or fishmongers dwell here – but the history behind this bridge is truly incredible.
  5. Wander the cobblestoned streets of Florence after a classic Tuscan dinner. There’s nothing like the romance of this city at twilight, and the street musicians peppered throughout the city are the cherry on top to this idyllic ambiance. Our favorite spot to stumble upon live musicians just might be surrounding the famous Duomo.
  6. Visit the world renowned Italian megastore, Eataly. Whether you’re searching for gifts + souvenirs, attending a cooking or wine-tasting course, grocery shopping for your stay in Florence, or stopping by for a coffee, lunch or dinner, Eataly is a one-stop shop for Italian cuisine that can’t be beat. I always end up with a backpack full of their unique pastas, truffles and a few bottles of the 600 Italian wines on display to bring home after my visits!
  7. Stand in awe of Michelangelo’s David, carved from a single piece of marble in 1504. The original sculpture is located inside the Accademia Gallery, though you can spot a replica in the Piazza della Signoria for free. We’d recommend purchasing tickets in advance via the museum’s website, as its an incredibly popular gallery at all times of year – and rightfully so!
  8. Pay homage to the first basilica in Florence: Basilica of Santa Maria Novella. Built between 1279 and 1357 by Domenican friars, its green and white marble facade beckons you closer and you can’t help but explore the treasure trove of medieval artwork within (including Giotto’s Crucifix from 1290!).
  9. Take a day trip to Pienza and utterly melt in their famous pecorino cheese. The family-owned Marusco e Maria in town is an absolute oasis for cheese lovers near and far, overflowing with a wide selection of regional cheeses, wine and spices too!
  10. Head to Lucca to stroll their famous medieval city walls at Golden Hour, just after sunrise or before sunset
  11. Laze the day away in the thermal springs of Saturnia, a hidden gem that’s existed for since the Etruscan times and once believed to be a gift from the gods for their healing powers
  12. Take a cooking class in the Tuscan countryside and have local chefs guide you through the markets and their gardens, then show you how to prepare a signature Tuscan dish!
  13. Taste the best gelato on the planet at Gelateria Dondoli and experience crazy flavors like eggnog, pine nuts, saffron and black olives. It’s located in San Gimignano
  14. Rent a vintage Fiat and take a scenic drive through the countryside with this playlist
  15. Go truffle hunting in San Miniato, then learn how to prepare them. You can combine this activity with a winery tour, tasting or even a private lunch/dinner!
  16. Enjoy a pottery making class in Colle di Val d’Elsa at Ceramiche Manufactum
  17. Rent the quintessentially Italian villa from Under the Tuscan Sun in Cortona and head into town to wander the cobblestoned alleyways and maybe dance in the fountain like Sylvia (though it wasn’t us who told you to)
  18. Explore the Vespa Museum in the province of Pisa and see some of the earliest scooters all the way up to modern day Vespas!
  19. Take a picturesque stroll in Monteriggioni and window-shop for handmade ceramics. End the day with a cheery gelato break at sunset!
  20. Head to Siena, and park yourself in Piazza del Campo with a good book or people-watching game face. Don’t leave before grabbing aperitivo amidst the red-bricked facades!
  21. Indulge in the ultimate luxury of an olive oil tasing, and don’t count the calories *wink, wink*
  22. Take a romantic hot air balloon ride above the vineyards and admire the Tuscan landscape from a bird’s eye view.

Just about ready to book your flight? Yep. I knew we were kindred spirits! Whether you’re looking for inspiration to guide your honeymoon plans or interested in a destination wedding in Italy, I hope this curated guide on traveling through Tuscany gave you some insights into the most charming places to stay, the hidden gem ristorantes festooned throughout the countryside and once-in-a-lifetime activities to indulge in during your visit.

Arrivaderci!
Haley

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