PRIVATE TOURS IN TALLINN AND ESTONIA — CANDID & PERSONAL
Tallinn InSight is for curious travellers seeking 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 built around meaningful connections on what matters most to you. No fluff, no pretense, no filler. Just an honest, nuanced conversation to help you truly understand our land. Come for a deep dive into Estonia that leaves you with a clear, lasting sense of place.
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 cherry on top with a few of our own favorite detours and hidden gems. You bring the curiosity. We bring the insight.​
Complete Tallinn: Legends, Layers & Liberation
5-6H DRIVING + WALKING TOUR
This tour includes the Old Town walking tour, then continues with drives and strolls through Tallinn's notably different districts. This is like your 12-course Christmas feast at granny's, leaving you full for days — a real deep dive into Tallinn's past, present, and future in one go.
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 a painful past. This tour uncovers what life was really like, absurdities and all, on the wrong side of the Iron Curtain. Think grandpa's old war stories: true tales of resilience and resistance against overwhelming odds, trapped under a totalitarian regime.
ITINERARY COMING SHORTLY, INQUIRE IF INTERESTED!
OUR TOP ESTONIA DAY TOURS
Lahemaa National Park & the Coastal Heritage
8-9H DAY TOUR IN THE NATURE
With some of the cleanest air and one of the fastest energy transitions in the world, Estonia was named the most environmentally friendly country in 2024. Come for a wholesome full-day tour exploring both natural wonders and historic highlights in our biggest, oldest National Park.
Eclectic Estonia: Stone, Steel & Silence
7-8H DRIVING + WALKING TOUR
A true whirlwind cocktail of Estonia's wild contrasts — medieval monasteries, opulent feudal manors, secret Soviet and Tsarist imperial military installations, and a surreal alien landscape of a sunken prison quarry. All this served with dramatic coastal cliffs crumbling into the Baltic Sea. Enjoy your drink with an umbrella on top!
Ancient Revalia: Pagan tribes & Crusader era
8-9H DAY TOUR OFF THE BEATEN PATH
Estonia is a tiny country, yet with a deep and multi-layered history. Tallinn Old Town is famed for its medieval heritage, but just a short drive from the city will take you to some fascinating, secluded sights — some thousands of years old, and often with no one in sight.
ITINERARY COMING SHORTLY, INQUIRE IF INTERESTED!
Make Your Own Tour
YOU SET THE COURSE, WE'LL STEER THE WHEEL
In Estonia, everything is within reach from Tallinn — and we love crafting exclusive, one-of-a-kind routes just for you. From tracking down forgotten World War I & II ruins on deserted coasts to arranging home-cooked meals or Michelin-star dining, it'll be an adventure for us too. Let's design a genuinely unforgettable day just for you.
Transfer tours between Tallinn - Riga - Tallinn
YOU SET THE TIME, WE'LL WATCH THE CLOCK
On a tight schedule with a flight or ferry to catch? Or just want to turn a direct bus ride into a scenic adventure? Tell us your timing — we’ll get you there on time, with varied stops along the way. This tour can run in either direction: Tallinn to Riga or Riga to Tallinn. Your timing, your pace.
"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
Kristjan-Jaak Tammsaar
Founder / Lead guide
After a decade of guiding for others, I realized the only way to offer truly authentic, personalized tours, without having to cut any corners, was to do it my way. Welcome to Tallinn InSight.
As a photographer, I've been fortunate to travel far and wide, from remote Himalayan villages to bustling Middle Eastern bazaars. And everywhere I’ve found the same universal welcome, warmth, and curiosity from locals eager to share their own lives and dreams.
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That's the same spirit of genuine connection that fuels my every tour. Tallinn InSight is not about growing and scaling — it's about connecting and sharing, because that's what keeps me coming back every day.​​
FREQUENTLY ASKED QUESTIONS
WHAT? WHERE? WHY?
Q: WHAT SETS YOUR TOURS APART?
Glad you asked! We know our stories inside out, but never blindly follow a script. Every tour is personal, candid, and simply human — full of nuanced insight, spontaneous humor, honest perspectives, and opportune detours tailored to and reflecting your own interests and communication style. Travel has changed me for the better, thanks to all the people across the world who have unlocked countless doors for me — both physical and metaphorical — to new and different cultures and ideas. I feel a genuine responsibility to be the best Estonian ambassador I can — not just showing you its pretty side, but sharing candid, nuanced, and unbiased stories. With us, you’ll always get accurate, balanced info so you can draw your own conclusions about Estonia.
Q: HOW CAN YOU BE SO COMPETITIVELY PRICED?
Small size and laser-focus can be an advantage — just like with the country itself, as you’ll learn on our tours :) We have honed in on our core offering and cut any and all non-critical, recurrent expenses. As a result, you get a much higher degree of personalization at minimal extra cost, if any. Do we really need our own cars or a physical office? Of course not, if we can tap into our local partners with their wide range of rental vehicles, or use portable tech to stay flexible and available around the clock, whether in town or deep in the forest.
Q: ARE YOUR TOURS SUITABLE FOR VIP, MICE & B2B CLIENTS?
Absolutely. We regularly host high-level political delegations, conference guests, and business investors exploring Estonia. From first idea to final detail, we design every experience around your exact schedule and needs. Please see our dedicated B2B / MICE page for details. I personally lead all VIP and business tours, drawing on a decade of professional guiding and personal travel experience, two postgraduate degrees, and a love for big-picture conversations. I am bound to find common language and themes with your guests — whether it’s a reserved political delegation from Tokyo or a straight-shooting entrepreneur from New York.
Q: YOUR COMPANY IS NEW— WHAT’S YOUR EXPERIENCE?
The brand may be new, but you’re in experienced hands. In a decade of experience guiding thousands of travelers in Estonia and abroad, I’ve learned what works, what doesn’t, and what makes a tour truly memorable. As uncomfortable as it might be for an Estonian to highlight their own achievements, my guiding record speaks for itself, with excellent feedback, reviews, and top ratings across leading local tour companies. That’s why I take your trust seriously — and will do everything to make your tour a highlight of your trip.
Q: WHO EXACTLY WILL BE OUR GUIDE ?
Usually me — hi :) I’m Kristjan, Tallinn InSight’s founder, a native Estonian, born and bred in Tallinn, and I personally lead every tour I can — not because I have to, but because I truly enjoy the job. If I’m unavailable, I’ll hand-pick a trusted colleague who’s just as personable, knowledgeable, and genuinely loves sharing Estonia. For custom deep-dive tours outside my expertise, I may bring in an external expert to ensure sufficient know-how.
Photo credits: Kaupo Kalda; Kadi-Liis Koppel; Giulio Gröbert; Simon Snopek; Rivo Veber; Priidu Saart; Annika Metsla; Rene Altrov. Courtesy to VisitTallinn.ee & VisitEstonia.com
Q: HOW DO I BOOK? WHAT IF I NEED TO CANCEL OR CHANGE?
We’ve tried to keep everything as simple and transparent as possible. For standard bookings, simply pick your tour, date, and time, fill in your details, and pay securely after we confirm availability. You’ll get a quick response, often within hours. We accept many modes of payment, such as Visa, Mastercard, Apple Pay, Google Pay, Revolut, N26, and Estonian bank links. For custom or unique tours, just send us your wishlist and preferences — we’ll reply within 24 hours with specific options and a quote. Plans change and life happens, especially when you’re traveling — we get it. You can easily cancel for a full refund up to 48 hours before your booked tour, no questions asked. We always strive to accommodate any necessary changes until the very last minute, when and where possible, but can’t always guarantee full refunds for cancellations within 48 hours, due to our own preparations and expenses. Please see our full Booking & Cancellation Policy in the footer of this page for all details.
Q: CAN WE ADJUST THE TOUR, SKIP OR ADD STOPS?
100%! Private tours are fully flexible — your timetable, your passions, your preferences. Share your interests before or during the tour, and we’ll tailor the experience to match. We can always linger longer, skip what doesn’t excite you, or detour on a whim. If changes require extra time or costs, we’ll always be upfront. Minor tweaks and running a bit over time? No problem. If we’re all enjoying ourselves together, that’s a win-win in our books :)
Q: I HAVE MOBILITY ISSUES, SPECIAL DIET, PETS... CAN YOU ACCOMMODATE?
In most cases, it’s a wholehearted yes. We gladly adapt routes and pacing to your needs — no rushing; it’s all about your comfort, enjoyment, and safety. Just let us know in advance so we can plan the route, transport, and timings ahead, and work out the best possible experience for you. Tallinn’s Old Town does have some slopes, stairs, and cobblestoned streets, but we can design even wheelchair-friendly routes when needed. Similarly, we can adjust driving tours to show you as much as possible from the vehicle itself, cutting down on the length or nature of walks in between. Pet friendly? Absolutely — as we’ve grown up with various furry fellows ourselves! The more the merrier, or should I say (forgive the obvious pun) — the terrier (apologies)! If it weighs more than a ton (literally), just let us know in advance, as special rules may apply when it comes to navigating full-grown elephants within downtown during working hours :)
Q: WHAT IS THE TONE OF THE TOUR — FORMAL OR CASUAL?
Professional and informed in content, casual in tone and delivery. Expect a friendly, conversational vibe — not a dry lecture. Think: hanging out with a local friend who knows Tallinn inside out, plus plenty of insider tips (and which tourist traps to avoid). Please pick our brains about whatever interests or intrigues you — from politics to religion. Any questions are encouraged and welcome, and no topic is too personal or off-bounds!
Q: WHAT TOURS DO YOU OFFER — WALKING? DRIVING? TRANSFER?
All of the above and more, exactly according to your preferences and needs. We run walking tours in Tallinn Old Town, combined driving and walking tours around Tallinn, half-day to full-day explorations around Estonia, and scenic transfer tours between Estonia and Latvia. All the standard tours are listed on the website, but everything’s flexible, so make it your own! Or propose something completely off-beat — want to explore Tallinn while getting your regular run in? We’re absolutely game for any distance up to a half-marathon :)
Q: CAN WE JOIN A GROUP TOUR? DO YOU DO FIXED DEPARTURES?
Our focus and strength lie in personalization, depth, and integrity — not volume. We give you our full, undivided attention, so your experience is never compromised by having to accommodate strangers with different interests or travel styles. That said, you’re always welcome to form your own group with family, friends, colleagues, or fellow travelers you’ve met along the way, and book together to split the costs. As long as you know you’re all on the same wavelength, we’re more than happy to take you surfing :) There are no hidden fees or surprise extra costs. Each tour page lists the final per-person price based on group size, with all inclusions and exclusions clearly stated. Transparency is key, because it’s what I expect and value myself — so you’ll always know exactly how much, and what, you’re paying for.
QUESTIONS? IDEAS? PLANS? REQUESTS?
Reach out and start a conversation!
