REAL STORIES. NO TIME-WASTE. NUANCED INSIGHT. BUILT FOR YOU.
PRIVATE TOURS IN TALLINN & ESTONIA — CANDID, PERSONAL, AND REFRESHINGLY UNSCRIPTED
Tallinn InSight is for informed travellers who want authentic stories, candid perspectives, and a personalized pace. Every tour is different because every guest is different. Each tour is a story. Yours. Personal, thoughtful, unscripted, and grounded in meaningful connections around what matters to you. No fluff, no pretense, no filler. Just an honest, nuanced conversation to help you understand our land. Come for a deep dive into Estonia that leaves you with a clear and lasting sense of place.
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See Frequently Asked Questions or Browse Our Tours:
OUR TOP TALLINN TOURS
Tallinn Old Town
2-3H WALKING TOUR
This is the essential timeless classic, like your favorite granny's fresh apple pie, covering all the highlights of North Europe's best-preserved medieval Old Town, plus a few of our own favorite detours and hidden gems to seal the deal. You bring the curiosity. We bring the insight.​
Tallinn Highlights: The Complete Experience
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 soak in Tallinn in its many unique faces.
FROM 200€ P/P (2 pax)
TO 90€ P/P (8 pax)
Tallinn behind Iron Curtain: Cold War & Soviet occupation
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.
FROM 200€ P/P (2 pax)
TO 90€ P/P (8 pax)
OUR TOP ESTONIA DAY TOURS
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 crazy contrasts in Estonian history. From Teutonic crusaders and medieval monasteries, through feudal estates & foreign noblemen 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 this served with the dramatic coastal cliffs crumbling into the Baltic Sea. Enjoy your drink with an umbrella on top!
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.
Make Your Own Tour
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 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.
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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.
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FREQUENTLY ASKED QUESTIONS
WHAT? WHERE? WHY? HOW?
Q: WHAT SETS YOUR TOURS APART?
A: Glad you asked! In short: we know our stories and facts inside out, but we don’t follow a script — our tours are personalized, candid, and deeply human. Expect insight, storytelling, fresh and spontaneous humor, opportune detours, and honest perspectives. We always try to go the extra mile in delivering our narratives to you in the manner that considers and reflects on your personal interests and preference. Now pardon my verbosity for a moment, but hey, can’t hold that against a professional guide, now can we! Travelling has inarguably changed me as a human being for the better, and it’s largely for the people I have met and who have introduced me to cultures & societies very different to my own, unlocking countless doors, both metaphorical and physical. At the risk of sounding cliched, I truly do feel responsibility to be the best Estonian ambassador I can for you. Not for the sake of showing the country from its best possible sides, but for providing you with the most honest, insightful, nuanced and unbiased information and stories I can. For I want you to know that you will always be left with accurate and balanced information, which in turn forms a complete whole, so that you can then draw your own final conclusions regarding what Estonia and Estonians are about.
Q: HOW CAN YOU REMAIN COMPETITIVELY PRICED?
A: Small and focused is in fact an advantage, allowing us to really hone in on our core offering and cast aside any and all non-critical and recurrent expenses. That allows us to offer you a much higher degree of personalization, while only charging a little more per person, if at all. Do we need a carpark of our own? Of course not, and why would we want to add to the rate of motorization, when we have direct access to all the local rental companies that can provide us with the exact size and type of a vehicle that's a best fit for any given tour. Do we need a physical office with all the related recurrent costs? Of course not, when a capable laptop and a charged cellphone ensure we are available pretty much around the clock, as the 5G and WiFi reach almost everywhere in Estonia, be it deep in the bog or a thick forest!
Q: ARE YOUR TOURS SUITABLE FOR VIP, MICE & B2B CLIENTS?
A: Absolutely – in fact, it is a niche segment we specifically cater to, having led tours for various high-level political delegations, conference delegates and foreign investors exploring Estonia. From concept to execution, we propose tailored options that fit your exact schedule and needs. Please see our dedicated MICE / B2B page for details. I will always personally lead tours for such segments, as my decade of guiding experience and two postgraduate degrees help me bring the required intellectual depth and vivid storytelling to every such encounter. Meanwhile, my own extensive travelling experience and long-term interests in geopolitics and foreign policy ensure that I am able to establish a common language with your foreign guests – whether they be a political delegation from Japan or a straight-shooting enterpreneur from NY.
Q: YOUR COMPANY IS NEW — WHAT’S YOUR EXPERIENCE?
While Tallinn InSight itself is a novel brand and tour operator, it’s built on a solid foundation of a decade of my personal experience guiding thousands of travelers around Tallinn and Estonia, having led many hundreds of tours of many different kinds under other programs and companies, including high level political and business delegations. These years of apprenticeship have allowed me to file away countless mental notes for the future in terms of what and how I could do differently and improve on, if I one day decided to do it myself, freed from the frameworks of bigger tour operations. As much as it makes me uncomfortable to toot my own horn, I have earned a track record of excellent feedback and consistently ranked amongst the top rated and reviewed guides across companies. So even if it might be long due, it’s time to offer these little golden stars their very own permanent home under Tallinn InSIght :) So even though the name is new, you can trust that I know my stuff and will do everything I can to make your tour the highlight of your trip. I understand that trust is earned, and I do not take it lightly. Now pardon my verbosity for a moment, but hey, can’t hold that against a professional guide, now can we! Travelling has inarguably changed me as a human being for the better, and it’s largely for the people I have met and who have introduced me to cultures & societies very different to my own, unlocking countless doors, both metaphorical and physical. At the risk of sounding cliched, I truly do feel responsibility to be the best Estonian ambassador I can for you. Not for the sake of showing the country from its best possible sides, but for providing you with the most honest, insightful, nuanced and unbiased information and stories I can. For I want you to know that you will always be left with accurate and balanced information, which in turn forms a complete whole, so that you can then draw your own final conclusions regarding what Estonia and Estonians are about.
Q: WHO EXACTLY WILL BE OUR GUIDE ?
It's usually me – hi :) I'm the founder of Tallinn InSight, a native Estonian, born and bred in Tallinn. I personally lead every tour I can, not because I have to, but because I love my job and the chance it grants me to become the eyes and the ears to Estonia for countless people from countless backgrounds. On the occasion that I'm unavailable myself, be it for clashing dates or a personal reason, I entrust the tour to one of my hand-picked fellow guides and colleagues. In any case, you'll always be in the hands of someone who is personable, deeply knowledgeable, and genuinely loves what they do. If you are highly interested in a very specific subject matter that calls for a completely customized unique tour and route, I might propose bringing aboard an external expert in the field, should I feel that my own knowledge may run too short, considering the specificity of the topic.
Photo credits: Kaupo Kalda; Rasmus Jurkatam; Rene Altrov; Aleksandr Snitovskii; Sam Mcallister; Kadi-Liis Koppel; Thomas Lotter; Mark Harisson; Jorden Tually; Vivian Velle. Courtesy to VisitTallinn.ee & brand.estonia.ee
Q: HOW DO I BOOK? WHAT IF I NEED TO CANCEL OR CHANGE?
You will find our full and transparent Booking & Cancellation Policy at the bottom of this, or any other page. But in short, it’s very straightforward: choose your preferred tour, date and time; fill in your details; and once we have confirmed availability for your selected date, proceed to pay via our secure platform. We will usually respond within hours, if not faster. If you are instead interested in an unique one-off custom tour, tailored for your specific interests, just drop us a message with your thoughts and requirements. We strive to get back to you within 24hours with the proposed itinerary and the corresponding quote. We provide many secure modes of online payment, such as Visa or Mastercard, Apple Pay, Google Pay, Revolut, N 26 and Estonian bank links. Plans change, life happens — you can easily cancel for a full refund up to 48 hours before the booked tour date, no questions asked. We’ll always try our best to accommodate necessary changes until the last minute, when and where possible, but refunds for cancellations within 48 hours of the due tour date can not be guaranteed, as our own availability has been accordingly reserved, vehicles booked and preparations made.
Q: CAN WE CUSTOMIZE THE TOUR, SKIP OR ADD STOPS?
Absolutely. One of the joys of a private tour is that it's fully flexible, and ultimately you, your timetable and your interests run the show. Be it your profession or hobby, let us know, and infect us with your own personal passions :) Be it before the tour (or even on the fly), you are always encouraged to share any particular interests – whether it's medieval history, the Soviet era and Cold War, street art, food culture, you name it – and we'll tailor the experience to match. We can linger longer at places you love, skip things that don’t grab you, or even detour if you spot something intriguing along the way. If none of my standard tour outlines perfectly fit what you're looking for, just let us know! We're happy to craft a custom route or include that special site you have in mind, as long as it's feasible. Should the required changes alter the route or the duration to the extent that it will affect the final costings, we’ll always be fully transparent and upfront about it. But as long as the changes are minor and can be figured out on the fly, we’re not going to unnecessarily bother you. Say, we’ll never going to quote you extra for going half a hour overtime – you had fun, we had fun, in our book that’s a win-win.
Q: I HAVE MOBILITY ISSUES, SPECIAL DIET, PETS. CAN YOU ACCOMMODATE?
In most cases, it’s a wholehearted yes. Everyone should be able to travel, so we’ll gladly adapt the route and pace to your needs. We can take breaks whenever you need, and you won’t be rushed – it's all about your safety, comfort and enjoyment. Just let us know in advance about any mobility concerns or other requirements, so we can take it into account when planning the route, transport and timings, and we'll do our best to work out the best possible experience for you. Tallinn’s Old Town does have some slopes, stairs and cobblestone streets, but if you or someone in your group has limited mobility or uses a wheelchair, we’ll adapt and plan a route accordingly that avoids stairs or steep climbs as much as possible. Similarly, on driving tours we can cut down on the length and/or nature of walks inbetween and try to explain and show you the corresponding parts from the car if possible. We are also absolutely pet friendly, having grown up with various furry fellows ourselves! The more the merrier, or should i say (forgive the obvious pun) – the terrier! If it weights more than a ton (literally), just let us know in advance, as Tallinn municipality does have some rules and regulations in place when it comes to navigating full grown elephants within the city boundaries :)
Q: WHAT IS THE TONE OF THE TOUR – FORMAL OR CASUAL ?
My tours are professional and highly informed in content but casual in tone. You can expect a friendly, humorous, conversational atmosphere rather than a monotonous monologue or a stiff academic lecture. In short, the vibe is informative yet laid-back: you’ll learn a lot, but you’ll also have fun and feel at ease. I’m a big believer in bringing history and culture alive with captivating storytelling, so the aim is to make you feel like you’re spending time with a patient local friend who knows the city inside and out. A friend who also leaves you later with plenty of tips and inside recommendations on where to eat, drink, walk or unwind, and perhaps even more importantly – which tourist traps you can easily avoid. Questions and discussions are absolutely encouraged throughout the tour, and no topic is too personal or off the table for me, and I mean it!
Q: WHAT TOURS DO YOU OFFER – WALKING? DRIVING? TRANSFER?
A: In short, yes to everything, and exactly according to your preferences and needs. We run walking tours in Tallinn Old Town, combination driving and walking tours in different parts of Tallinn, half- to full-day tours in different destinations around Estonia, and even transfer tours between Estonia and Latvia with interesting stops on the way. You will find all our standard tours listed on the current main page above, or navigating through the website’s menu bar. As we are mostly focused on small private tours, then there is always a lot of scope for flexibility and change even on our standard routes, and you can thus still make it your own as much as you wish.
"Best tour of our cruise"
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"Eight of us booked the 5 hour tour while we were visiting on a cruise. It was our best tour with the best guide... ...The town is beautiful, and the history is interesting and sad at times, but that of resilient people... ...We were back to the ship with an hour to spare which is how we like it. The day was wonderful. Chris was amazing. As we walked by the cruise groups with 50 people, we kept saying…. This was the way to go."
Melissa Panchley, United States. June 2, 2024
QUESTIONS, INQURIES, CLARIFICATIONS, IDEAS?
Reach out and start a conversation with us!
