Travel Guide: Tuscany + Cinque Terre, Italy

Travel Guide Tuscany and Cinque Terre Italy

There’s a special place in our heart for Italy… Particularly Siena (our first daughter’s namesake!) + the region of Tuscany — but there’s a reason why so many people get *starry-eyed* when talking about the gorgeous country on the Mediterranean. From lush countryside and charming towns, to the lively culture, decadent meals, the overall feeling that you get from Italy is nothing short of dreamy.

One of our darling GWS Vendors, Mandee Johnson, took a tour of Italy this summer and the moment she shared these stunning images with us we immediately gasped, started to plan our next trip to Italy, and then knew we had to share all the delights she captured with you! Focusing on two regions, Tuscany + Cinque Terre (located on the western coast, under Milan and above Pisa), we’re sharing all of Mandee’s personal tips, places to sip wine, eat, dine, and stay! Whether you’re about to start planning your honeymoon or maybe you + your love are looking to jet off on a bit of adventure, we’re pretty darn sure you’ll find what you’re looking for in Italy. :)


Pasta. Wine. Repeat. The beautiful countryside of Tuscany is pure relaxation filled with fairytale-like scenery of vineyards and wheat fields.

Places to See + Things to Do 


Montepulciano a bustling renaissance hill town sitting atop a limestone ridge. Grab a pre-lunch gelato and explore the city — with spectacular vistas of Val d’Orcia and beautiful narrow streets filled with shops, it’s a perfect place to send a few hours.

San Quirico d’Orcia

On the road to Montalcino is the walled village of San Quirico d’Orcia; it’s a perfect halfway point between Pienza and Montalcino. Walk through the San Quirico d’Orcia garden, get lost in the narrow streets, try the local wine, breath in the views of Val d’Orcia and discover the church that dates back to 714.


Montalcino is completely encircled by fortified walls (with a walking path to match) and is the home of the world-famous wine, Brunello di Montalcino. Stroll through the streets, take in the Duomo and gaze at the views of the valley.

Abbey of Monte Oliveto Maggiore

Tucked in the hills of the Crete Senesi, the Abbey is a place of serenity + open to anyone. The monks encourage silence while on the grounds, but also have a pretty good winery tucked in the cellar of the Abbey. Explore the grounds, enjoy the quiet, and take home a bottle of rosé.

Where: Monte Oliveto Maggiore, 53041 Asciano SI, Ital

Tips: Paid parking and small café on-site.



Boscarell is a small family-run winery producing the best Nobile di Montepulciano since 1968.

Where: Via di Montenero, 24, 53045 Montepulciano SI

What to buy: Rosso De Ferrari and Nobile de Montepulciano

Tips: Reservations required

Máté Winery

Máté Winery is a family-run winery with the best Brunello di Montalcino, plus some killer Syrah and Cabernet. They offer private tastings in their 13th century cellar, tours with their cellar master, plus a great family story of following your dreams, even if it means rebuilding a winery in Tuscany.

Where: Località Santa Restituta, 53024 Montalcino SI, Italy

What to buy: Brunello di Montalcino, Syrah + Cabernet Sauvignon

Tips: They ship it for free it you get a whole case of their amazing Brunello. (FREE SHIPPING!!) Reservations required.

Podere Le Ripi

South of Montalcino is Podere Le Ripi. Take a tour of their beautiful grounds, check out the ancient olive trees and then taste the amazing olive oil.

Where: Località Le Ripi, 53024 Montalcino SI, Italy

What to buy: Olive Oil

Tips: Take the tour. Reservations required.


Dopolavoro La Foce

This amazing roadside café is nestled between Riserva Naturale Lucciolabella and Riserva Naturale Pietraporciana — around the corner from La Foce. Open all day, serving traditional Tuscan fair with fresh vegetables from their garden. If you’re passing through at off meal hours you can still get a pressed sandwich and relax in a hammock with a wine in hand.

Where: Strada provinciale 40 Amiata Chianciano, 90, 53026 Pienza SI, Italy

Tips: The hammocks and lounge chairs are out back.

Good to Know: Plenty of parking across the street.

La Taverna del Pecorino, Cheese shop in Pienza

Nothing will prepare you for the fresh pecorino cheese in Pienza. Wander the gorgeous streets filled with greenery, Vespas, and bask in the immense beauty of The Duomo that dominates the Piazza Pio II. Around the corner for the Piazza is the best place to sample and buy cheese: La Taverna del Pecorino. The wonderful proprietor will offer you cheese upon entry and encourage to sample until you find one you love. Make sure to pick some up for later.

Where: Via Condotti, 1, 53026 Pienza SI, Italy

Tip: Try them all, buy the one you love. Good luck picking just one.

Locanda Demetra

Make time for a 3-hour lunch in Montalcino at Locanda Demetra. Sit in their garden with sweeping fairytale views of Val d’Orcia and enjoy lunch with several bottles of amazing local wine. Eat every course (we promise it’s worth it).

Where: Podere La Buca, 221, 53024 Montalcino SI, Italy

Tips: You can bring in a bottle from a winery you’ve visited, but they also have an amazing local selection. They also teach cooking classes!

Future Tips: The farm restaurant is opening up boutique rooms starting in March 2018. We can’t wait to come back and wake up to the view!

Antica Macelleria Cecchini

Upon entry expect a flurry of activity at this meat counter + café. A moment after entering, you’ll notice a glass of wine in your hand and a beautiful spread of meat and cheese. Ask for a table and they’ll bring you upstairs to their patio with long family-style tables. Order from one of their preset menus (vegetarian option available) and snack on crudité + delicious olive oil while you wait for what will be a meal to remember.

Where: Via XX Luglio, 11, 50022 Panzano In Chianti, Greve in Chianti FI, Italy

Tips: Menu offers a three prix fixe selections with a veggie prix fixe upon request. Ask to try the Grappa back downstairs on the way out.


Querceto di Castellina

With several rooms of all different shapes and sizes Querceto di Castellina is the perfect place to call home in Tuscany. Added bonuses: the view is breathtaking, the wine phenomenal and the owners will treat you like family!

Where: Via di Fronzano, 9, 53011 Castellina in Chianti SI, Italy

Tips: Get the tour + tasting

Abbey of San Glagono

Dating back to 1220, this monastery took six decades to be completed and was the first gothic church in Italy. Famine and the plague hit the monastery in the mid-1300s and it never fully recovered. Today, it remains a beautiful shell in the valley. A short walk away is the Hermitage of Monte Siepi that was built after San Galgano’s death. Here you can see his sword that was placed in stone – giving up a life of fighting to move towards a life of faith.

Where: Località San Galgano, 53012 Chiusdino SI, Italy

Tips: Parking is free, entrance is 3€. Stay at Farmhouse San Galgano and enjoy the silence.

La Foce

The historical La Foce is about 20 minutes south of Montepulciano and is the perfect place to end your day. Benedetta will greet you upon your arrival and take care of everything you need. Spend your afternoon hanging out by the pool, wandering through the gardens or take a scenic drive through the stunning Riserva Naturale Lucciolabella.

Where: Strada della Vittoria, 61, 53042 Chianciano Terme SI, Italy

Fun Facts: English architect Cecil Pinsent designed the gardens for Iris Origo

Cinque Terre

This grouping of five cities along the coast of Italy is a well-known wanderlust location. Each city brings its own personality to the area, but all are filled with local white wine by the liter and hiking trails with vistas that literally take your breath away.

HIKE: Manarola to Corniglia

While this hike may be one of the shorter ones between the cities, be aware that it is still a steep climb to the city of Volastra before a captivating hike through the vineyards. Head out to the trail after breakfast – timing it so you can grab lunch at L’Arcobaleno in Volastra before continuing to Corniglia. Once in Corniglia make sure to grab a few gelatos for all your efforts and enjoy the walk down to the station.

Sunset at Riomaggiore

Grab a bottle of wine at any local shop. They’ll be happy to open it for you and offer you a few plastic cups. Wander to the rocks, find a cozy spot and enjoy the sunset. If you’re feeling adventurous, there is a small cliff nearby on the other side of the dock you can climb up for a better sunset view.

HIKE: Monterosso to Vernazza

This is a must do hike. We prefer to go from Monterossa to Vernazza so you can eat lunch in Vernazza at La Torre.

Lunch in Vernazza at Ristorante La Torre

After you finish the hike from Monterosso and take in the city, make your way back on the trail toward Corniglia. Don’t worry, you’re not hiking far – it’s just a short climb to one of the most amazing restaurants and a view to end all views.

Where: Via M. Carattino, 64, 19018 Loc. Preteccia. Vernazza SP, Italy

Tips: If you can pick your table, keep walking through the patio until you get the furthest table out. Then bask in the view and eat the olive oil cake.

Boat trip from Vernazza to Manarola

After you’ve hiked, stuff your face and drink a liter of wine. Head down to the docks and snag a boat to Manarola for sunset. Manarola is the best city to jump into the water, sit on the rocks and watch the sunset. Bring some wine or champagne to drink on the 30-minute ride.

After sunset make your way to Enoteca Cantina Zio Bramante, a small basement bar, for some local limoncello and live music.

Tips: Hire your boat from Nordest. There are a lot of options in the harbor but these guys are amazing. You can use them as a taxi between cities or rent a boat for the day!


The beach city. Head to the water and rent a lounge chair for the day. Sleep, drink, swim, eat + repeat. Once you’ve had your fill, wander through the shops and collect your gifts for those back home.

Dinner in Vernazza

Make sure to take in a long dinner at Ristorante Belforte. The amazing seafood will leave you dreaming of it for days on end making it a perfect last meal.

Where: Via G. Guidoni, 42, 19018 Vernazza SP, Italy

Tips: Make a reservation + ask for the patio overlooking the water.

Thinking about Italy for your holiday getaway or as a honeymoon destination? We’d love to hear your suggestions + all about your plans/trip below!

Once again, a huge thank you to Mandee Johnson for all these photos + wonderful tips.