Fresh & NUANCED STORIES
Passionate local guideS
INSIGHTFUL PRIVATE TOURS IN TALLINN AND ESTONIA FOR THE SOPHISTICATED TRAVELLER
Our every tour is an immersive story crafted for You and adapted to your particular interests—authentic, personal, and full of meaningful connections you won’t easily forget. Our narratives fit together like puzzle pieces, forming a memorable big picture rather than leave you with a clutter of disjointed names and numbers. Make the most of your time here and let us take You around, so You can really come to understand what it means to think, feel, and live like an Estonian.
OUR TOP TALLINN TOURS
Tallinn Old Town
2-3H WALKING TOUR
This is the timeless classic, like your favorite granny's fresh apple pie, covering all of the must-see highlights of the UNESCO World Heritage listed medieval Old Town, plus a few of our own favorite detours and hidden gems if you're up for a bit of extra exploration!
Tallinn Highlights: The Complete Experience
CA 5-6H DRIVING + WALKING TOUR
This tour includes the Old Town walking tour, and then proceeds with drives and walks through Tallinn's distinctly different districts. This is like your grand old 12-course Christmas feast at granny's that leaves you full for days! No better way to absorb Tallinn in its infinite different faces.
200€ P/P IN A GROUP OF 2
TO 90€ P/P IN A GROUP OF 8
Tallinn behind Iron Curtain: Cold War & Soviet occupation
CA 5-6H DRIVING + WALKING TOUR
Since Estonia's liberation from Soviet occupation in 1991, Tallinn has thrived, overcoming its painful past. This tour explores life, both bleak but also absurd, trapped on the wrong side of the Iron Curtain. This one is grandpa's old war tales, full of resistance and resilience in the face of evil.
200€ P/P IN A GROUP OF 2
TO 90€ P/P IN A GROUP OF 8
TOP DAY TOURS
AROUND ESTONIA
Lahemaa National Park & the North Coast
CA 8-9H DAY TOUR IN THE LAP OF NATURE
With some of the cleanest air in the world and nearly a quarter of its area under nature protection, Estonia was recognized as the most environmentally friendly country in the world in 2024. Come for a wholesome full-day tour, visiting both the natural and historical highlights of the biggest and oldest National Park in Estonia.
Eclectic Estonia: Coastal cliffs to Nuclear reactors
CA 6-7H DRIVING + WALKING TOUR
This trip is a true whirlwind cocktail of the explosion of contrasts in Estonian history. From Teutonic crusaders and medieval monasteries, through feudal foreign landlords in decadent manors, all the way to secret military installations of two different imperial occupations, plus the surreal alien landscape of a submerged prison quarry. All served with the dramatic coastal cliffs crumbling into the Baltic Sea.
Ancient Revalia: Pagan tribes & Crusader era
CA 8-9H DAY TOUR OFF THE BEATEN PATH
Estonia is a tiny land, yet with a deep and multi-layered history. Tallinn Old Town is well-known for its medieval heritage, yet a mere stone's throw from Tallinn, you can still find some fascinating and secluded sights dating back thousands of years, with hardly a single soul around.
COMING SOON! Inquire for details if interested.
Your Perfect Dream Day
YOU SET THE COURSE, WE'LL STEER THE WHEEL
Everything and everywhere in Estonia is easily accessible from Tallinn. We love putting together exclusive, one-of-a-kind routes for You, as it’s an adventure for us as well! We have hunted for obscure lighthouses on deserted coasts, sought out forgotten World War ruins in remote wilderness, arranged both home-cooked lunches and Michelin-starred dining experiences. Whatever it is that You might be wandering about, let us brainstorm together to come up with a genuinely unique and unforgettable day for you.
TRANSFER TOURs
Transfer tours between Tallinn and Riga
YOU SET THE TIME, WE'LL WATCH THE CLOCK
Are you on a tight schedule — got a flight to catch, a ferry to board? Or do you simply want to see the sights on the way, rather than simply commute from point A to B? Tell us Your schedule and we'll ensure You'll be on time, while filling a day or a half with sightseeing stops en route. This tour can be conducted both ways, either from Tallinn to Riga or Riga to Tallinn, as per your needs and preferences.
Kristjan-Jaak Tammsaar
Founder / Lead guide
After a decade of guiding for various companies, I realized the only way to deliver truly authentic and personalized tours without having to cut any corners was to do it my way. Welcome to Tallinn InSight.
As a documentary photographer by my first profession, I've been fortunate to travel far and wide, from remote mountain communities to sensitive political hotspots. Yet, everywhere I’ve been, I’ve encountered the same universal welcome, curiosity, and kindness from locals eager to share their lives and dreams.
With Tallinn InSight, my mission is to bring that same spirit of genuine connection to every tour. It's not about growing and scaling—it's about connecting and sharing, because that's what keeps me fuelled for tomorrow.
ANY QUESTIONS, DOUBTS, CLARIFICATIONS, IDEAS ?
Whatever it is, reach out and start the conversation!
Catherine, Germany
Our tour was very good for us because we all know a bit of history and we like to learn about the place. Our Guide, Christian, gave us enough background information so we could have a better understanding of the Tallinn of today. Very knowlegdable and intesting. Christian was well prepared and could answer all relevant questions.
andycJ7219ZB
My partner and I loved this tour with Kris. We spent over 2hrs wandering the streets and Kris's knowledge was first class. He told us a lot about the history of Tallinn, its buildings (uses and architecture) and lots more. Our group also asked lots of questions which kept up the interest for everyone, including Kris!
name, country
Chris for the Old Town Walking tour was funny, fast talking, sarcastic, and incredibly well versed on his topic. He ensured our time was enjoyable and Informative.
IGNORE THE FOLLOWING.
OLD PLACEHOLDER ASSETS
kengwee,
Singapore
"Kris was really humorous and entertaining and at the same time knowledgeable - not only about Estonia, but also about other cultures and places such as India - and was very enthusiastic about sharing his knowledge. On top of that, Kris is also an amazing photographer! Great trip, definitely a highlight of our time in Estonia."
KareninCalabria,
Las Vegas, Canada
"Although this tour focused on the northeastern coast of Estonia, I can say that it was a journey into the "heart" of Estonia as that is where our wonderful, slightly eccentric guide Kris took us by way of his abundant knowledge and personal insights regarding the land, its people and its history"
JagmoN,
Toronto, Ontario, Canada
"Our family of 5 people enjoyed this wonderful trip to the National Park and other attractions. This is our first trip in the Baltic region and is well worth. Kris you ROCK dude!!"
OUR TOP TALLINN TOURS
Tallinn Old Town
2-3H WALKING TOUR
This is the classic, covering all the must-see highlights of the Unesco World Heritage listed medieval Old Town plus few of our own favorite detours and hidden glimpses if you’re up for it!
READ MORE for itinerary & to BOOK
OUR TOP TALLINN TOURS
Tallinn Highlights
CA 6H WALKING + DRIVING TOUR
This tour starts with the walk in the Old Town, then continues with drives and walks through Tallinn's unique districts. Enjoy an 18th-century royal park with a baroque palace, witness the transformation of old industrial areas into ultramodern happening spaces, and explore Soviet-era neighborhoods alongside lush & leafy private suburbs.
Tallinn Old Town
2-3H WALKING TOUR
This is the classic, covering all the must-see highlights of the Unesco World Heritage listed medieval Old Town plus few of our own favorite detours and hidden glimpses if you’re up for it!
Tallinn Highlights
CA 6H WALKING & DRIVING TOUR
This tour starts with the walk in the Old Town, then continues with drives and walks through Tallinn's unique districts. Enjoy an 18th-century royal park with a baroque palace, witness the transformation of old industrial areas into ultramodern happening spaces, and explore Soviet-era neighborhoods alongside lush & leafy private suburbs.
OUR TOP TALLINN TOURS
TALLINN OLD TOWN WALKING TOUR
2-3H WALKING TOUR
This is the classic, covering all the must-see highlights of the Unesco World Heritage listed medieval Old Town plus few of our own favorite detours and hidden glimpses if you’re up for it!
CLICK FOR FULL ITINERARY & DETAILS !
BEST OF TALLINN HIGHLIGHTS
CA 6H WALKING + DRIVING TOUR
This tour starts with the walking tour around Old Town and proceeds by car through and past different districts and neighborhoods of Tallinn with their own distinct looks. We’ll take a lovely stroll through a centuries-old former royal park, where we’ll see both the 18th century baroque palace dating to the Russian Empire and the current presidential residence. You’ll see old industrial districts and massive factories now fused with sleek modern architecture, rejuvenated as new thriving hubs of creative life and entertainment. But you’ll also walk down the striking memorial for tens of thousands victims of Soviet era atrocities and genocide against not only the native Estonians but many other ethnic minorities, getting to know the stories of heartbreak, but also resistance, and eventual liberation from the Soviet totalitarian empire.
CLICK FOR FULL ITINERARY & DETAILS !
TALLINN BEHIND IRON CURTAIN - SOVIET OCCUPATION & DARK HISTORY
CA 6H WALKING + DRIVING TOUR
Since the collapse of Soviet occupation of Estonia in 1991, Tallinn has been a quite capable little overachiever, shaking off the shackles of its darkest times. But 30+ years is still only a single generation away. This tour will visit many places that shed light to both the horrors and lies, but also ridiculousness and impotence of the Soviet totalitarian regime in and around Tallinn. As a bonus, we’ll get to visit some of the last remaining accessible Soviet military ruins around Tallinn. This tour doesn’t beat around the bush and will show you the true extent of Soviet crimes and deceit, but we can of course tone down the narrative if you’d like to join this tour with children.
CLICK FOR FULL ITINERARY & DETAILS !
DAY TOURS IN ESTONIA
LAHEMAA NATIONAL PARK & THE NORTH COAST
CA 8-9H NATURE FOCUSED DAY TRIP
Estonia has some of the cleanest air in the world and ca 1/5th of the country is under degrees of nature protection, recognized as the most environmentally friendly country in the world in 2024. We love and respect our nature and couldn’t be prouder for it. Come for a full day trip in the lap of greenery, criss-crossing both the natural and historical highlights of the biggest and oldest National Park in Estonia.
CLICK FOR FULL ITINERARY & DETAILS !
LAYERS OF ESTONIA - MEDIEVAL MONASTERY. TOP-SECRET NUCLEAR REACTORS. PRISTINE COASTAL CLIFFS
7H WALKING + DRIVING TOUR
This trip is a true whirlwind tour through a ridiculous contrast of various facets of Estonian history, from the times of Teutonic knights and medieval monasteries conquering and converting the ancient pagan lands, through feudal eras of Baltic German landlords ruling the countryside from their decadent manors, all the way to former top secret Soviet military installations of strategic importance that vanished off the maps or were never known to have existed in the first place.
CLICK FOR FULL ITINERARY & DETAILS !
YOUR PERFECT DREAM DAY
ACCORDING TO YOUR PREFERENCE
The unique feature of Estonia is how accessible everything and everywhere is from Tallinn itself. We love putting together and leading one-off custom routes, as it’ll be adventure for us as well! We have hunted for obscure lighthouses on remote peninsulas, sought out forgotten World War era ruins, and arranged everything from home-cooked lunches to Michelin starred dining experiences. Whatever it is You might be curious about, let us know, regardless if you know exactly where you want to go and what to see or experience, or whether it’s just a vague theme, a yet fully unformed idea you have in mind. Let us feed on your excitement and brainstorm together to come up with a genuinely unique and unforgettable day.
CLICK FOR MORE IDEAS & DETAILS !
UnScripted Tours offers highly personalized and refined tours in Tallinn and Estonia. Our tours emphasize authenticity and honesty, with real-time adaptation to the client’s interests, character, and background.
