This 5 Day Estonia itinerary combines Tallinn’s medieval core and creative scene with slow country drives, boardwalk hikes through ancient bogs and a stay in an architectural nature villa.
It was one of the most restorative trips we’ve taken, balancing history, creativity and stillness in a way that felt distinctly Estonian.
If you love design, unique restaurants, nature, and culture, these are the spots to experience.
5 Days in Estonia
Days 1-2: Explore Tallinn’s medieval Old Town and its creative scene in Telliskivi. Days 3-4: Retreat to the countryside for ancient bog walks, picnics and a stay in an architectural nature villa. Day 5: Drive back to Tallinn and travel home |
5 Day Estonia Itinerary
Disclosure: Some of the links below are affiliate links, meaning at no additional cost to you, we will earn a commission if you click through and make a purchase. Regardless, we only recommend products or services we have used or that we believe will add value to our readers. Thank you for supporting us!Day 1: Explore Tallinn's Medieval Old Town
Shop the medieval centre, visit Estonia’s oldest cafe, enjoy an apéro in the square, dine medieval-style, and end the night at a hidden bar.
When we first arrived in Tallinn, what struck us most was how medieval the centre felt, and how well-preserved it is.
Medieval towers and ramparts fully encircle the city, and inside, the UNESCO-listed Old Town feels remarkably intact, with red rooftops rising toward church spires and cobblestone alleyways opening into courtyards.
Yet the city doesn’t feel frozen in time. Just beyond the walls, we found a strong creative scene, wellness culture and contemporary Baltic design.
Check into your stay in the medieval centre
For your two days in Tallinn, we recommend staying inside the medieval centre.
Most restaurants, cafes, bars and shops are within easy walking distance, and you can even stroll to Telliskivi Creative City from here. It keeps everything easy.
We stayed at Schlössle Hotel, tucked into a 13th century merchant’s house just off Town Hall Square. Its pastel façade and red-tiled roof looked straight out of an old European fairytale.We enjoyed using the private sauna (complimentary for guests) and drinking in the vaulted limestone cigar lounge before heading out for the evening.
🛏️ Browse more stays in Tallinn Old Town.Stop for coffee at Estonia’s oldest cafe
After checking into your hotel, walk to Cafe Maiasmokk, Estonia’s oldest cafe, operating since 1864.
Its old-world atmosphere, complete with dark wood panelling, red velvet chairs and ornate ceiling tiles, feels carefully preserved.
Order a coffee and something sweet, and settle in. It’s a nice way to ease into exploring Tallinn Old Town.
Shop in Old Town and enjoy an apero in Raekoja plats
Tallinn Old Town is compact, so the best approach is to let yourself drift through the pedestrian streets.
You'll find antique shops, small specialty stores and independent boutiques tucked into quiet alleyways.
Don’t miss A-Galerii, an artist-run gallery dedicated to contemporary Estonian jewellery with a sculptural edge. This was our favourite shop.
I bought brass and silver earrings from a collection inspired by the designer’s interpretation of the cosmos. They were minimal and very cool.
Make your way to Raekoja Plats, a 15th-century square in Old Town. Grab an outdoor table for an apero and enjoy the people-watching.
🏰 Interested in learning more about Tallinn's history and sights? Book a walking tour with a local guide.Dine at a medieval restaurant in Old Town
One thing we didn’t realize before arriving was that Tallinn has an entire medieval dining scene. It ended up being one of our favourite parts of the trip.
For dinner, book a table at Olde Hansa, right in Town Hall Square. The restaurant is lit entirely by candles, servers dress in period clothing, and the menu is built around ingredients used in the 15th century.
Wine arrives in oversized goblets, and there’s live medieval music Wednesday to Sunday from 6-9pm.
We started with the oven-baked herb and juniper cheese, Ari ordered the bear (which is strictly regulated in Estonia), and I chose the oxen sirloin in green peppercorn sauce. It was all delicious!
We didn't know if the experience would feel bit cheesy, but it was actually a ton of fun. We even fully committed to speaking in medieval-style English to each other the entire dinner.
End the night at a hidden bar in Old Town
After dinner, head to NoKu - a secret bar in the Old Town that requires a door code (2580) to enter. Once inside the door, head upstairs to the second floor to find it.
You might be surprised to find something this edgy within the medieval walls, which is exactly what makes Tallinn interesting.
Inside, it’s not fancy at all. The atmosphere is casual and a little bohemian, with a younger crowd playing board games. We ended up playing a couple rounds of Jenga.
Day 2: Explore Tallinn's Creative Side
Shop and eat in Telliskivi Creative City, see the latest exhibition at Fotografiska, and finish with cocktails at a hidden basement speakeasy.
Today you’ll step beyond the medieval walls and into a more contemporary side of Tallinn.
About a 15–20 minute walk from the Old Town, you’ll find Telliskivi Creative City, a former railway and factory complex transformed creative hub.
Raw brick warehouses now house independent fashion brands, concept stores, design studios, relaxed cafes and restaurants, while large-scale street art wraps the buildings in colour.
It draws a younger, local crowd and feels like quite the contrast to the historic centre. It's easy to spend a lot of time here.
Explore Telliskivi Creative City
Coffee and pastries at Karjase Sai bakery
First stop at Karjase Sai for coffee and their fantastic pastries. It's a local favourite known for its sourdough.
On warm days, you can sit outside on the patio overlooking the graffiti-lined courtyard.
Studios and boutiques on the Poetanav shopping street in Telliskivi Creative City
After coffee, explore Poetanav, a shopping street within Telliskivi Creative City that brings together 26 indie shops inside former warehouse buildings.
You’ll find artisan studios, vintage stores and independent design brands clustered together, making it easy to wander without a plan.
Our favourite shop was TEKE Keraamika, which carries contemporary ceramics from different local artisans.
Also, don't miss Stella Soomlais for sustainably handcrafted leather goods designed and produced locally.
See the latest exhibition at Fotografiska Tallinn
Next, pop into Fotografiska Tallinn, a contemporary photography museum set inside a converted industrial building in Telliskivi.
Part of the global Fotografiska network, it’s known for bold rotating exhibitions and a strong sustainability ethos.
When we visited, we saw SPACE - A Visual Journey, which explored humanity’s place in the cosmos through photography.
Even if you’re not a big photography person, the exhibitions feel immersive and well curated.
Eat burgers inside a Soviet-era railcar
Telliskivi’s restaurants feel very different from the Old Town - more creative, casual and locally driven, often set inside repurposed industrial spaces.
We dined at Peatus, a burger-focused restaurant set inside two restored historic railway wagons.
One is a former Soviet-era wagon that once ran the Tallinn-Moscow route in the 80s/90s, while the second has been converted into a bar carriage complete with its own DJ booth.
Finish with cocktails at a hidden basement speakeasy
For a nightcap, head just outside the historic centre to Whisper Sister, a speakeasy hidden in a basement.
The name is inspired by the women who ran Prohibition-era bars, and it’s been recognized by the World’s 50 Best Discovery list.
Reserve ahead of time - when you arrive, call the number in your booking, and someone will come up to collect you.
From there, you’re led down into a dark, moody speakeasy with multiple rooms, each with a different feel.
Service was excellent, and we loved that each cocktail had a unique concept and story behind it.
Day 3: Head into the peaceful countryside
Explore Estonia’s ancient bogs with a lakeside picnic, then unwind in an architectural nature villa.
Estonia has a population of just 1.36 million people, so once you turn off the main highway, it gets quiet fast.
Nature is deeply rooted in Estonian culture, and the ancient bogs are some of the country’s most beautiful landscapes.
These wetlands are thousands of years old - vast, moss-covered and shaped since the last Ice Age.
In most places, you’ll explore them along raised wooden boardwalks that stretch for miles, protecting the delicate ecosystem underneath.
Walk the Jalase bog trail and picnic by the lake
From Tallinn, the Jalase Nature Trail is just over an hour's drive away along peaceful country roads.
Pop into a grocery store to pick up picnic ingredients on your way.
The Jalase bog walk is an easy out-and-back hike.
It begins with a 1 km forest path, followed by a 0.3 km stretch along the edge of a field before reaching the 0.7 km-long wooden boardwalk that crosses the bog to Jalase Jarv (lake).
The trail was quiet when we visited, and we enjoyed a picnic by the lake before walking back the same way.
If you can't store your bags out of sight, we recommend dropping your bags off at Maidla Nature Resort first.
Unwind at your architectural villa at Mailda Nature Resort
Kabi villa at Maidla Nature Resort
It’s one of the best stays we’ve ever had.
The nature resort sits on the grounds of a historic manor estate dating back to the 15th century, surrounded by forests, wetlands and protected bog landscapes that feel completely untouched.It has just three architectural nature villas, spaced far apart for complete privacy and positioned to overlook the surrounding reserve.
We stayed at Kaseke one night, and at Kabi the other, and both were incredible.
- Kaseke (236 sq ft): It may be the smallest of the three, but it features a wood fireplace and floor-to-ceiling windows with one of the best views over the bog. We played board games, opened a bottle of wine and watched the sunset sink into the landscape.
- Kabi (409 sq ft): the most secluded of the three villas, designed to resemble a pine cone, with wood shake siding, a fireplace and an outdoor hot tub. The hot tub made it easy to spend time outside when it was cold.
- Poku (538 sq ft): is the largest villa, inspired by Estonia’s wetlands, with pod-like rooms, vaulted ceilings, a thatched roof, private sauna, outdoor jacuzzi and outdoor fire pit.
✔️ Top Tip: The villas are about a 5-10 minute walk from the parking area along a forest trail, so pack light and avoid heavy luggage.
Enjoy a gourmet dinner delivered by your "house fairy"
Each villa has its own “house fairy,” who can deliver drinks or dinner to your room if arranged in advance.
We booked dinner to the villa on our first night. We began the evening with champagne in the hot tub overlooking the bog, then moved inside our villa for dinner by the fireplace.
You can choose between meat-focused, pescatarian or vegetarian tasting menus.
The food exceeded our expectations. The onsite restaurant, located in the historic Yellow House, is listed in the Michelin Guide.
Day 4 - Spend another beautiful day in nature
Enjoy a slow morning with a massage, hike to Estonia’s largest bog lake, and end with a Michelin-recommended tasting menu and unexpected nighttime tour.
Enjoy a slow morning with breakfast and a massage
We began with breakfast at the hotel, where you can choose from four wholesome options like overnight oats, an omelette, or sourdough with cottage cheese and honey. We went for the banana pancakes.
After breakfast, we booked a relaxing massage through the hotel before heading out for another bog walk.
Hike to Estonia’s largest bog lake
The hike to Loosalu Jarv was our favourite of the three we did - longer and more expansive than the previous day. Loosalu is Estonia’s largest bog lake
Park at “Loosalu raba matkarada” in Google Maps. The trail begins through the forest before opening onto an impressively long 4 km boardwalk stretching across the bog.
We walked to the west edge of Loosalu Jarv for a picnic on the dock before turning back.
From the car park, it took about 40 minutes to reach our picnic spot. It was roughly 1 hour and 45 minutes in total to hike there and back, eat, and take photos.
🧺 Stop at the Co-op in Juuru to grab picnic ingredients for your hike on the way.
Spend the late afternoon relaxing at your nature villa
Spend the late afternoon back at your villa, watching the light shift over the bog - whether from the hot tub, by the fireplace during a board game, or in between sauna sessions.
Dine at SOO with an unexpected mid-meal tour
SOO Restaurant
Book dinner at SOO Restaurant, an intimate spot set inside the historic Yellow House of the Maidla Estate.
Listed in the Michelin Guide, it felt like such a treat, especially being just a short walk from our villa.
The atmosphere felt warm and intimate, and Finnish chef Karoliina Jaakkola’s surprise tasting menu was fantastic.
What made the evening truly unique, though, was what happened halfway through the meal.
Between courses, we were invited on a nighttime tour of the estate’s abandoned manor building - a haunting, partially restored relic of the historic property.
Walking through the timeworn rooms with a wine buzz was a lot of fun. We learned about its history and kept picturing how cool the space would be for a techno party. Then, we returned to the table for the remaining courses.
Day 5: Travel Day Home
After breakfast, drive back to Tallinn to drop off your rental car and catch your flight or ferry.
At just 45 minutes from Maidla Nature Resort, it’s an easy departure.
Enjoy your 5 days in Estonia!
Combine Estonia with a trip to Helsinki. It's just a 2-hour ferry away from Tallinn.
Get started on booking your trip to Estonia
- 🛏️ Book your accommodation: in Tallinn Old Town and Maidla Nature Resort.
- 🚗 Car rental: see DiscoverCars to compare car rental prices across different companies.
- 🛫 Book your flight: use Skyscanner to compare flights across different airlines (we recommend booking direct with the airline however).
Don't forget about travel insurance
👩⚕️ For affordable travel insurance: go with SafetyWing - it's budget-friendly and you can even buy it while abroad, but note the max medical coverage is $250,000 USD. 🏥 For comprehensive travel insurance: go with World Nomads - it's more expensive, but the max emergency medical coverage is $5-10 million, depending on the plan.Save and pin this 5 Day Estonia Itinerary for later:
