Two day tour in Kakheti square

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Wine, Love & Legends: The Best 2-Day Kakheti Trip

Price for one tour per person

$255

tour features

Tour Duration: 2 Days

Tour Location:Kakheti

Tour highlights:

Tour is available Whole year

Two-day Kakheti tour Overview

Picture this: You’re standing in a 1,500-year-old monastery carved into a cliff face, looking out over endless valleys that have been producing wine since 6,000 BC. In your hand is a glass of amber wine made in a clay vessel buried underground, using the exact same method your ancestors used millennia ago. This isn’t just a tour – it’s a journey through time.

Kakheti is Georgia’s wine heartland, and honestly? It’s one of the most beautiful regions you’ll ever visit. Over two incredible days, we’ll explore ancient cave monasteries that’ll make your jaw drop, wander through the cobblestone streets of Sighnaghi (Georgia’s most romantic town), taste wines that’ll spoil you forever, and soak in mountain views that look like they’ve been painted by someone who couldn’t decide if they preferred Italy or Switzerland, so just combined both.

The best part? You’ll spend the night in Sighnaghi, which means you get to experience the town at sunset when the tour buses have left and it’s just you, the locals, and the most spectacular evening light you’ve ever seen. We’ve had guests tell us this was the highlight of their entire Georgia trip.

🌟 What Makes This Tour Special:

  • Sleep in beautiful Sighnaghi – experience it after the day-trippers leave
  • Visit David Gareja, one of the most unique monasteries in the world
  • Taste authentic qvevri wine (UNESCO heritage winemaking)
  • Small groups only – no crowded buses
  • Expert local guides who actually grew up in this region
  • Perfect mix of culture, nature, wine, and Georgian hospitality
  • Available year-round (yes, even in winter – it’s magical with snow!)

Your Two-Day Adventure (Day by Day)

Day 1: Desert Monasteries & The Town of Love

09:00 – Pickup from Your Hotel in Tbilisi

We’ll pick you up right from your accommodation in a comfortable, air-conditioned vehicle. Our guide will be there with coffee (trust us, Georgian coffee is serious business) and ready to answer all your questions. The drive to our first stop takes about 1.5 hours, which gives us time to chat about Georgian history, culture, and any burning questions you have. Feel free to ask about anything – where to eat in Tbilisi, Georgian toasts, why Georgian grandmothers are unstoppable forces of nature. We’re here for it all!

10:30-13:00 – David Gareja Monastery Complex

Here’s where things get absolutely wild. David Gareja is a monastery complex that was carved into the desert cliffs starting in the 6th century. Yes, desert – Georgia has everything, including a proper desert landscape that looks like you’ve somehow ended up in Arizona or Jordan.

The main monastery, Lavra, sits at the base of the cliffs and is still functioning today. You’ll see monks going about their daily routines, ancient frescoes (some over a thousand years old), and cave dwellings that’ll blow your mind. But the real magic? The hike up to Udabno monastery.

It’s a 20-30 minute climb up the cliff face (with amazing steps cut into the rock), and when you reach the top, you’re rewarded with two things: First, caves filled with medieval frescoes that are shockingly well-preserved. Second, views that’ll make you forget you’re supposed to be taking photos because you’re too busy just staring.

On one side, you’ve got the desert valley of Georgia. Turn around, and you’re looking into Azerbaijan – the border literally runs along the ridge. It’s surreal, spiritual, and unlike anywhere else you’ve ever been.

13:30-14:30 – Lunch Break

After all that exploring, you’ll be hungry. We’ll stop at a local restaurant where you can try authentic Kakhetian cuisine. This region is famous for mtsvadi (Georgian BBQ), khinkali (soup dumplings that’ll change your life), and churchkhela (the Georgian “Snickers” – grape juice and walnuts, weirdly delicious). Lunch is not included in the tour price, which gives you flexibility to choose what you want, but expect to pay around 20-30 GEL ($8-12) for a feast.

15:00-16:00 – Bodbe Monastery

From the desert, we head to the complete opposite – a monastery surrounded by lush gardens and forests. Bodbe is one of Georgia’s most important pilgrimage sites because it’s where St. Nino, the woman who brought Christianity to Georgia in the 4th century, is buried.

The monastery itself is beautiful, but honestly, the views are what’ll get you. From here, you can see the entire Alazani Valley spreading out below you, with the Greater Caucasus mountains rising in the background. On clear days (especially in spring and autumn), it’s so beautiful it almost doesn’t look real.

There’s also a holy spring down a bunch of steps (around 3km round trip if you want to do it), which pilgrims believe has healing properties. We’ll give you time to explore at your own pace.

16:30-18:00 – Sighnaghi Town Exploration

Welcome to Georgia’s “Town of Love!” Sighnaghi is the kind of place that makes everyone’s Instagram jealous. Picture this: cobblestone streets winding up and down hills, wooden balconies overflowing with flowers, pastel-colored houses, defensive walls you can walk along with 360-degree views, and cute little wine bars everywhere.

The Italians built the defensive walls in the 18th century (they were hired by the Georgian king – long story), and you can still walk along sections of them. The views over Alazani Valley and the Caucasus mountains are absolutely spectacular, especially as the sun starts getting lower.

We’ll give you a walking tour of the main sights, tell you the stories (including why it’s called the “Town of Love” – hint: it involves a 24/7 registry office), and then give you free time to wander. There are great little shops selling local wine, honey, churchkhela, and handicrafts. It’s the perfect place to pick up gifts or just get yourself some amazing Georgian wine to take home.

18:00 onwards – Evening at Leisure

Here’s where this tour gets special. Most tours visit Sighnaghi, take a few photos, and leave. You? You get to stay. We’ll check you into your guesthouse (charming, family-run, absolutely lovely), and the rest of the evening is yours.

Watch the sunset from the town walls (pro tip: the southwest corner has the best views). Have dinner at one of the local restaurants – we’ll give you our recommendations, from fancy spots with tasting menus to family places where grandma is still cooking everything herself. Try the khachapuri (cheese bread) – in Kakheti, they make it a bit differently, and it’s amazing.

After dinner, take a stroll through the empty streets. Sighnaghi at night is magical – quiet, romantic, with street lamps casting warm light on the cobblestones. If you’re lucky and the weather’s clear, the stargazing is phenomenal (very little light pollution).

Accommodation: Traditional guesthouse in Sighnaghi with comfortable rooms, private bathrooms, Wi-Fi, and usually incredible breakfast included. Most have stunning terrace views.

Day 2: Wine, History & Mountain Monasteries

09:30 – Breakfast & Morning in Sighnaghi

Sleep in a bit (you’re on vacation!), then enjoy breakfast at your guesthouse. Georgian breakfasts are serious business – fresh bread, local cheese, tomatoes, cucumber, often some homemade pastries, and always strong tea or coffee. Take your time, maybe take a morning stroll if you want to catch different light for photos.

10:30-12:00 – Nekresi Monastery

After breakfast, we head to Nekresi, perched high on a hilltop overlooking the Alazani Valley. This place is old – we’re talking 4th century. It started as a pagan temple, became one of Georgia’s earliest Christian churches, and has been watching over the valley ever since.

The monastery complex has several churches from different periods, including a tiny basilica from the 4th century (one of the oldest churches in Georgia) and a main church from the 9th century. But honestly, people come for the views. From up here, you can see the entire Alazani Valley, vineyards stretching as far as you can see, little villages dotting the landscape, and the Caucasus mountains forming this incredible backdrop.

There’s a short shuttle ride from the parking area (included in entrance fee), and then a bit of walking around the complex, but it’s not strenuous. The setting is incredibly peaceful.

12:30-13:30 – Wine Tasting at a Traditional Winery

Now for the part you’ve been waiting for! We visit a family-run winery that still makes wine the traditional way – in qvevri (large clay vessels buried underground). This method is over 8,000 years old and is recognized by UNESCO as Intangible Cultural Heritage.

You’ll get to see the qvevri (they’re impressive – some hold 1,500+ liters), learn how the traditional method works (it’s fascinating), and taste several wines. Usually, you’ll try at least 3-4 varieties, including the famous amber/orange wines that Kakheti is known for. These are white wines made like red wines (with skin contact), and they’re unlike anything you’ve tasted.

The family will often have homemade snacks too – cheese, fresh bread, maybe some churchkhela. And you can buy wine directly from them at prices that’ll make you want to ship bottles home (which is totally possible, by the way).

14:00-15:00 – Telavi Town & Lunch

Telavi is the main city of Kakheti and has a completely different vibe from Sighnaghi. It’s bigger, more bustling, less touristy. We’ll show you the main sights – the giant plane tree (supposedly 900 years old), the statue of King Erekle II (Kakheti’s most famous king), and the old town area.

This is also a great lunch stop. There are plenty of restaurants here, or if you prefer, we can grab something quick so we have more time at the next stops. Your call!

15:30-16:30 – Gremi Architectural Complex

Gremi is like something out of a fantasy novel. This 16th-century complex was once the capital of Kakheti kingdom, but after it was destroyed by Shah Abbas (those were rough times), all that remains is this beautiful church and tower sitting on a hill.

The church is stunning, with frescoes and tilework, but the real treat is climbing the tower. From the top, you get 360-degree views of the surrounding countryside. It’s the perfect last stop before heading back – a chance to reflect on everything you’ve seen and take in the landscape one more time.

There’s also a small museum here with artifacts from the old royal residence.

17:00-17:30 – Ikalto Monastery & Academy

Our final stop is Ikalto, a 7th-century monastery that’s famous because it once housed one of Georgia’s most important medieval academies. The famous 12th-century poet Shota Rustaveli (think Georgian Shakespeare) is said to have studied here.

It’s a beautiful, peaceful place with ancient stone buildings, a wine press from centuries ago, and that special kind of quietness you only find in really old religious sites. It’s also usually pretty empty, which means you can take your time and really soak in the atmosphere.

18:00-19:30 – Return to Tbilisi

We’ll head back to Tbilisi, arriving at your hotel around 7:00-7:30 PM. The drive is about 1.5 hours, which gives you time to nap if you need, or chat with your guide about your trip, get recommendations for the rest of your stay in Georgia, or just watch the landscape roll by.

You’ll arrive back tired but happy, probably with several bottles of wine, definitely with hundreds of photos, and absolutely with memories that’ll last forever.

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