The Perfect 5-Day Itinerary Through Uruguay: Wine, Gastronomy & Unforgettable Experiences

You know those destinations that win you over at first sight? Uruguay is exactly like that. Small, charming, filled with surprising wines and a heartwarming gastronomy.

Every corner of this country has a story to tell — and this 5-day itinerary was crafted for those who love authentic experiences, savoring each glass and every dish with intention and calm.

Here, time flows at the right pace — the pace of good food, great wine, and meaningful conversations. So grab your glass and come along with me on this unforgettable journey!

Oh, and one important tip: to truly make the most of your visits to the wineries, renting a car is essential. But of course — always have a designated driver or book transportation services so everyone can enjoy the wines worry-free.

Now yes, let’s dive into the itinerary!

Day 1 – Montevideo with Open Arms

Just landed in Montevideo? Take a deep breath, feel the fresh air, and get ready for a day full of delightful discoveries.Uruguay’s capital welcomes you with warmth — like a soft embrace and a gentle invitation to slow down.

Breakfast: Café Philomène

There’s no better way to start your day than at this cozy, charming café in Pocitos.The aroma of freshly brewed coffee mingling with the scent of warm croissants is pure soul-comfort.Take your time here — order a creamy cappuccino, choose a pâtisserie, and enjoy an atmosphere that feels like it was lifted from a European film.

Morning: Stroll along the RamblaI

f there’s one thing Uruguayans know how to do well, it’s embracing their shoreline.Walk slowly along the Rambla, watch locals sipping mate, pause to feel the breeze from the Río de la Plata, and simply enjoy the moment.

Lunch: Mercado del Puerto

You simply can’t leave Montevideo without tasting an authentic parrilla. Here, cuts of meat are grilled to perfection, infused with smoky flavor, and served with the classic chimichurri.Grab a seat at the counter, order an ojo de bife or asado de tira, and pair it with a bold, velvety Uruguayan Tannat. Guaranteed success!

Afternoon: Exploring Ciudad Vieja

Stroll along the cobbled streets, discover local art shops, and stop by Librería Más Puro Verso for a coffee and a good book. It’s the kind of place that makes you want to move to the city just to become a regular.

Dinner: Francis

A Montevideo classic that balances elegance and warmth.The star of the evening? The braised lamb — tender, juicy, and unforgettable — perfectly paired with a robust Tannat.Every detail matters here: from impeccable service to a jaw-dropping wine list.

Day 2 – Unforgettable Wines: Bouza & Pizzorno

Today is wine day! Get ready for a deep dive into the world of Uruguayan winemaking.Wake up early, rent a car, and set out for a day of unforgettable experiences.

Breakfast: Sin Pretensiones

This place has soul!It’s small, intimate, and full of personality.Try the warm artisanal bread with melted cheese and honey — trust me, you’ll want seconds.

Morning & Lunch: Bodega Bouza

This winery looks like a postcard!The guided tour takes you through immaculate vineyards and into cellars that hold unforgettable vintages.The highlight? A wine-paired lunch at the winery’s restaurant, where each dish enhances the wine — and vice versa.

Pro tip: Don’t miss the Bouza Tannat Parcela Única, one of Uruguay’s finest.

Afternoon: Pizzorno Family Estates

Small, family-run, and absolutely charming.This is a truly intimate experience — it feels like visiting a friend who happens to know everything about wine.The family-led tour takes you through barrels full of stories and wines full of soul.The tasting is served with artisanal cheeses and cured meats, taking the experience to a whole new level.

Return to Montevideo & Rest.

Dinner: Fellini

A cozy Italian spot in Pocitos, perfect for ending the day with a good glass of wine and a heartwarming pasta dish.The beef lasagna is simply unbeatable!

Day 4 – High-End Wines: Bodega Deicas & Braccobosca

Breakfast: Café Gourmand

A little piece of France in Montevideo — with buttery croissants that melt in your mouth and bold, full-bodied coffee. The perfect start.

Morning & Lunch: Bodega Deicas

A journey through tradition and innovation. Here, wine is treated as a true art form, and the wine-paired lunch elevates the experience to something unforgettable.Expect refinement, bold flavors, and impeccable pairings.

Afternoon: Braccobosca

This place is not just about wine — it’s about connection.Fabi, the owner, personally hosts each visit with warmth and authenticity, making you feel like part of the family from the moment you arrive.

Small, charming, and full of soul, Braccobosca is the kind of winery that leaves a mark.The tasting takes place in a relaxed, intimate setting, accompanied by delicious bites and heartfelt stories.

The special touch? The care behind every detail and Fabi’s passion for what she does. You leave not only in love with the wines — but with the entire experience of being in such a special place.

Return to Montevideo & Rest.

Dinner: Bar Facal

The last night calls for something special. A cheese board, a velvety Tannat, and a toast to Uruguay — to its flavors, its stories, and the memories we now carry with us.

Uruguay is a country to feel, to savor, and to fall in love with.

This itinerary is an invitation to live each moment with intention and intensity.

Want to follow more unforgettable wine experiences?

Join us on Instagram: @vinholifestyle — we’d love to toast with you there!