You’re in prime Chianti wine country, surrounded by vineyards, historic estates, and some of the best reds in the world.

Very Close (10–15 minutes)

Fattoria Castello di Monteriggioni – Just outside the village walls, this estate offers wine tastings paired with local products.

Agricola Poggio ai Laghi – Known for its wines, olive oils, and balsamic vinegars; perfect for a well-rounded tasting.

Il Colombaio Winery – A historic spot with panoramic views and deep Chianti roots since 1897.

Fattoria Lornano – Family-run and charming, this Chianti Classico producer also offers vineyard tours.

Tenuta Villa Trasqua – An organic estate blending tradition and modernity.

Further Out (30-50 minutes)

Dievole Winery – Organic wines, olive oil, and sweeping vineyard views in a peaceful Chianti Classico setting.

Poggio Torselli – A historic villa near Florence with elegant wines and beautiful Renaissance gardens.

Castello di Albola –Hilltop castle with panoramic views and award-winning Chianti Classico wines.

Borgo Savignola – Family-run boutique winery offering intimate tastings of small-batch wines.

Castello di Verrazzano – Historic estate with castle tours, Chianti tastings, and incredible countryside views.

And SO many more!

A tiny medieval gem, Monteriggioni feels like stepping into a storybook. If you have a few hours to spare, it’s the perfect spot for a peaceful stroll, local wine, and incredible views.

Walk the Walls – Climb sections of the ancient stone walls for sweeping views of the Tuscan countryside.

Piazza Roma – Relax in the charming main square, home to a 13th-century church and cozy cafes.

Medieval Armor Museum – A quick and quirky stop, especially fun if you like history or want to snap a photo in medieval gear. It won’t take long.

Via I Maggio – The village’s main street, lined with shops, wine bars, and trattorias—perfect for a lazy wander.

City Gates – Two beautiful gates mark the entrances to the village: one faces Siena, the other Florence.

Restaurants

Ristorante Le Torri Monteriggioni – Set in the main piazza, offering dishes like wild boar pasta and lamb chops, with indoor and outdoor seating.

Osteria Antico Travaglio – A charming spot within the fortress walls, known for traditional Tuscan dishes and homemade gelato.

Bar dell'Orso – Just outside the walls, this rustic eatery is famed for its generous portions and lively ambiance.

Siena is one of Tuscany’s most magical cities, full of Gothic architecture, winding alleys, and local charm.

Must-Sees

Piazza del Campo – Siena’s famous fan-shaped square. Grab a gelato and people-watch!

Siena Cathedral (Duomo) – A black-and-white marble masterpiece. Step inside to see stunning frescoes, sculptures by Michelangelo, and one of the most beautiful floors in Italy.

Torre del Mangia – Climb the 300+ steps of this medieval tower for breathtaking views of the rooftops and Tuscan hills.

Palazzo Pubblico & Civic Museum – Art lovers, don’t miss Lorenzetti’s frescoes showing the effects of good vs. bad government.

Santa Maria della Scala – Once a hospital for pilgrims, now a museum complex with underground tunnels and ancient art.

Restaurants

La Taverna di San Giuseppe – Widely considered one of Siena’s best meals. Incredible food, unbeatable ambiance in an ancient cellar, and a top choice across review platforms.

Antica Osteria da Divo – Dining in Etruscan caves is a rare and romantic experience. Classic Tuscan fare with a dramatic setting—ideal for a special dinner.

Grotta Santa Caterina da Bagoga – A true local favorite with deep ties to Siena’s food culture, this family-run osteria is relaxed, welcoming, and full of soul. Known for its handmade pasta and commitment to Slow Food values, it’s a great place to experience hearty, traditional Tuscan dishes in a no-frills, authentic setting.

Vineria Tirabusciò Siena – Charming, intimate, and great for pre- or post-dinner drinks with a local feel. Excellent wine and charcuterie options.

If you’re looking for a peaceful break from wine tasting and sightseeing, this hidden gem is just 25 minutes from Borgo Stomennano. The Elsa River Trail (Sentiero lungo il fiume Elsa) is a beautiful walk along crystal-clear turquoise water, complete with small bridges, shady woods, and a waterfall at the end.

Why You’ll Love It

Diborrato Waterfall
A 15-meter waterfall you can admire, or even take a dip in since it will be hot in July!

Easy and Scenic
The full trail is about 3 miles round trip and mostly flat, making it a great option for a casual morning or afternoon outing.

Quiet and Relaxing
Not as crowded as other Tuscan spots, which makes it feel like your own little nature retreat.

Good to Know

Wear comfortable shoes (it can be a bit rocky in places).

Bring a swimsuit and towel if you want to swim.

There aren’t many shops or restrooms nearby, so pack a water bottle and maybe a snack.

San Gimignano is one of Tuscany’s most iconic hilltop towns, known for its medieval towers, cobblestone streets, and charming atmosphere.

What to See

Torre Grossa – The tallest tower in town. Climb to the top for panoramic views of the rolling Tuscan countryside.

Piazza della Cisterna – The town’s picturesque main square, surrounded by stone buildings and perfect for a relaxed coffee or gelato break.

San Gimignano Cathedral – A beautifully preserved Romanesque church filled with vibrant frescoes that line the walls and ceilings.

Palazzo Comunale & Civic Museum – A historic palace with an art museum inside, and it’s where you’ll find the entrance to Torre Grossa.

SanGimignano1300 – A quick stop if you’re interested in medieval architecture or want a visual overview of how the town looked centuries ago.

What to Taste

Gelato at Gelateria Dondoli – This world-famous gelato shop is in Piazza della Cisterna

Vernaccia di San Gimignano – A crisp, local white wine that pairs perfectly with a sunny afternoon.

Saffron & Pecorino Dishes – San Gimignano is known for saffron and sheep’s cheese. Look for it on menus if you’re staying for lunch.

There’s so much more to Tuscany than wine (though we fully support a glass or two). If you’re looking to explore beyond the vineyards and hilltop towns, here are a few ideas to round out your trip:

Take an Italian Cooking Class – Learn how to make handmade pasta, classic sauces, or even tiramisu, from a local nonna or a professional chef. A fun way to bring a bit of Tuscany back home with you.

Sample Olive Oil – Tuscany is famous for its extra virgin olive oil. Many small farms nearby offer tastings, where you can learn how to tell the difference between fresh, peppery oils and smoother blends.

Bike the Countryside – Rent a bike and ride past rolling hills, vineyards, and sunflower fields. Many nearby towns have easy rental options and mapped routes for all skill levels.

Shop Local – Love a good souvenir? Nearby towns like San Gimignano and Siena are full of artisan shops selling handmade ceramics, leather bags, olive wood kitchenware, and more.

Aperitivo Hour – Settle in with an Aperol Spritz or a glass of prosecco at golden hour. Many piazzas and small wine bars offer stunning views and a relaxed vibe. Aperitivo is a ritual in Tuscany for a reason.

Iconic Photo Ops – Tuscany’s cypress-lined roads, hilltop views, and rustic villas are made for photos. If you’re up for a mini road trip, the Val d’Orcia region has some of the most photographed landscapes in Italy.

The Duomo – Climb Brunelleschi’s dome for breathtaking city views; don’t miss the cathedral’s intricate marble facade and underground ruins.

Uffizi Gallery – See masterpieces by Botticelli, da Vinci, Caravaggio, and more! Plan ahead, it’s one of the most famous museums in the world.

Accademia Gallery – Michelangelo’s David is the star, but the unfinished Prisoners sculptures and art halls are just as moving.

Palazzo Vecchio – Florence’s historic town hall, filled with frescoes and secret passages—go up the tower for another incredible view.

Santa Croce – A stunning church that’s also the resting place of Galileo, Michelangelo, and Machiavelli.

Bargello Museum – A lesser-known gem packed with Renaissance sculptures and medieval treasures.

Scuola del Cuoio – Historic leather school in a former monastery. Handcrafted bags, wallets, and jackets, with artisans often working on-site.

San Lorenzo Market – Popular outdoor market for leather goods and souvenirs—just check quality before you buy.

Via de’ Tornabuoni – Florence’s luxury shopping street, with Gucci, Prada, Ferragamo, and more. Great for window-shopping, too.

Via dei Calzaiuoli – Pedestrian street linking the Duomo to Piazza della Signoria. Includes Zara, H&M, Sephora, and casual shops.

Oltrarno District – Across the river, this artsy area is full of vintage shops, artisan studios, and hidden gems. Check out Via di Santo Spirito and Via Romana.

The Mall Firenze – Outlet village 40 minutes outside Florence with discounts on brands like Gucci and Valentino. Shuttles available from the city.

Local Boutiques – Florence is full of stylish, family-run shops and concept stores. Wander the side streets; you’ll find treasures everywhere!

Piazzale Michelangelo – One of Florence’s best panoramic spots. A short uphill walk or drive from the city center, this terrace offers sweeping views of the Duomo, Ponte Vecchio, and Arno River; perfect for sunset photos or a scenic evening.

Divina Terrazza at Grand Hotel Cavour – A rooftop bar with 360° views, including the Duomo and Palazzo Vecchio.

SE·STO on Arno – Stylish rooftop at the Westin with panoramic views and an upscale vibe. Great for drinks or dinner. (Closed currently, but will reopen before the wedding)

B-Roof at Grand Hotel Baglioni – A terrace with garden-like settings and views of Florence's rooftops.

Angel Roofbar at Hotel Calimala – Offers a cozy setting with views of Palazzo Vecchio and a portion of the Duomo. Cool creative cocktails!

Boboli Gardens – Behind Palazzo Pitti. Grand Renaissance gardens with fountains, sculptures, and views.

Bardini Gardens – Peaceful with panoramic views. Lush in summer, though wisteria blooms in spring. The on-site café offers a scenic spot to relax.

Schiacciata 

L’Antico Vinaio – Famous and tourist-heavy, but worth trying once.

I’ Girone De’ Ghiotti– Local favorite. Truffle salami is a standout. If you only have time for once sandwich shop, choose this one!

Panetteria e Stuzzicheria De Neri – Quiet spot with fresh, simple sandwiches.

Pino’s Sandwiches – Salumeria Verdi – Friendly service and big portions. Add truffle spread.

Dinner

Vini e Vecchi Sapori – Small, traditional, and authentic. Book well in advance (you have to call).

Trattoria ZaZa – Bustling and tourist-friendly. Try the truffle gnocchi. Reservation recommended.

Osteria Pastella – Romantic and known for cheese wheel pasta. Reserve ahead.

La Giostra – Elegant, fairy-lit interior. Try the pear ravioli. Reservation highly recommended.

Gusta Pizza – Casual, good for takeaway. Expect a crowd. No reservation.

Ristorante Natalino – Classic Tuscan spot with old-world charm. Reservation helpful. Friend’s recommendation!

Osteria Santo Spirito – Expect lines out the door, but it’s worth it. The truffle gnocchi comes highly recommended. Reservations are very helpful (you have to call).

Ristorante Storico Sabatini – One of the city’s oldest restaurants, perfect for a fine dining experience. Known for Florentine steak and tableside pasta. Reservations suggested.

Trattoria Marione – A cozy Tuscan favorite known for its lasagna and ravioli. Ask if they have zuccotto cake; it’s not always on the menu. Reservations recommended.

Buca Mario – Historic, family-run restaurant renowned for its classic Tuscan dishes. Located in a 16th-century cellar! Reservations are essential.

But honestly, I’m confident you’ll have a great meal no matter where you end up!

Florence’s wine windows, or buchette del vino, are tiny arched openings in historic buildings. Originally used by noble families to sell wine directly from their homes—especially during the plague—they’ve made a charming comeback. Today, you can sip a glass passed straight through the wall for a uniquely Florentine experience.

Osteria Belle Donne
Address: Via delle Belle Donne, 16R, 50123 Firenze FI, Italy

Wine Window Highlight: A charming and floral wine window nestled into the osteria’s exterior wall, perfect for a quick glass of wine while strolling near the city center. Aesthetically pleasing and an easy stop while shopping or sightseeing.

Cafe Odeon
Address: Piazza degli Strozzi, 8R, 50123 Firenze FI, Italy

Wine Window Highlight: Located within the historic Giunti Odeon cinema-bookstore, this wine window offers a serene spot to enjoy a glass of wine or an Aperol spritz while observing the lively Piazza degli Strozzi.

BABAE
Address: Via Santo Spirito, 21R, 50125 Firenze FI, Italy

Wine Window Highlight: Perhaps the most renowned and photogenic wine window in Florence, BABAE revived this historic tradition in 2020. They serve wines, cocktails, and small bites through their charming window, attracting both locals and tourists alike.

Osteria San Fiorenzo
Address: Borgo dei Greci, 1R, 50122 Firenze FI, Italy

Wine Window Highlight: Situated near the Basilica di Santa Croce, this wine window offers more than just wine; you can even order an espresso martini through it (the bride’s favorite).

DiVin Boccone
Address: Via delle Caldaie, 20, 50125 Firenze FI, Italy

Wine Window Highlight: Nestled in the Oltrarno district, DiVin Boccone is a cozy spot that embraces the wine window tradition. They offer glasses, bottles, and even small snacks through their window; ideal for a relaxed, sit-and-sip experience.

And more!

Coffee

Melaleuca – Trendy and bright; great coffee and pastries. This spot is American/Australian-owned, so while it’s not authentically Italian, it’s a comforting taste of home, especially nice after you’ve been traveling for a while! Get the cinnamon buns!

Ditta Artigianale – Stylish and modern with top-notch espresso and creative brunch. Great for a relaxed morning or mid-day coffee break.

La Milkeria – Warm and casual, known for its waffles, crepes, and sweet drinks. A cozy stop for breakfast or an afternoon treat.

La Ménagère – A gorgeous concept space that blends a café, flower shop, and boutique. Stop by for great coffee in a stunning setting during the day. In the evening, it transforms into a fine dining restaurant with creative dishes that go beyond traditional Italian fare.

Ala Grande Caffè – Cozy spot near the Accademia, known for its pistachio croissants and great coffee. A perfect stop for a quick, delicious break while exploring Florence.

Gelato

Vivoli – One of the oldest gelaterias in Florence. A favorite for locals and tourists. Get the affogato!

Gelateria dei Neri– Rich flavors and generous scoops. Often busy, but worth it.

Perché no! – Artisanal and creamy. Try ricotta & fig or sesame and honey.

Riva Reno – Gelato is made fresh in small batches throughout the day. Try the Cremino or Pistacchio Bronte.

Gelateria La Carraia– Inventive flavors like ricotta-pear and pistachio with white chocolate sauce. Open daily until midnight, it’s perfect for a sweet treat after dinner.

Edoardo il Gelato Biologico – Organic, all-natural gelato near the Duomo. Try the salted pistachio and handmade cones!

And MANY more!