Tallinn Old Town
2-3H PRIVATE WALKING TOUR
See the medieval heart of Tallinn through the eyes of a native. No fluff, no time-waste – just real stories, fresh humour and honest insight. This is the essential timeless classic, covering all the highlights of North Europe's best-preserved medieval Old Town, plus a few hidden gems. Choose between a shorter or longer experience.
Confirm your booking now, risk-free — change or cancel up to 48 hours before for a 100% refund.
TOUR DETAILS
2h / 3h
English
Pet friendly
Accessible
Walking tour
Multi-tour discounts
2h+ COST PER GROUP SIZE:
1 person
140€ p/p
2 people
75€ p/p
3 people
55€ p/p
4 people
45€ p/p
5 people
40€ p/p
6 people
35€ p/p
7 people
32€ p/p
8 people
30€ p/p
9+ people
3h+ COST PER GROUP SIZE:
1 person
165€ p/p
2 people
90€ p/p
3 people
65€ p/p
4 people
55€ p/p
5 people
45€ p/p
6 people
40€ p/p
7 people
37€ p/p
8 people
35€ p/p
9+ people
EARLY BIRD LAUNCH PRICES !
🌍 NATIVE GUIDE
Personal stories & family history
🗨️ NO SCRIPTED LINES
Tours adapt to your interests
🔎 NUANCED INSIGHT
Honest, memorable storytelling
INCLUDES:
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Attentive & professional native Estonian guide
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2–3 hour private guided tour, depending on your chosen tour length and the pace
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2.5–3km walk in both the Lower and Upper Old Town
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Entry fees to St Mary's Cathedral (Tue–Sun, 10–16)
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Default starting point: Tourist Information Centre (Niguliste 2), in the center of Old Town
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Free alternative start point anywhere in the Old Town
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English-only tours (ask for other language availability)
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Discounts: 10% off for two tours, 15% off for three! (request a custom quote to avail your discount)
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Discounts for groups of 9+ people (request a quote)
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Discounts for children (request a quote)
EXCLUDES:
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Optional gratuities
HIGHLIGHTS:
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See all the famous sights and iconic landmarks in both the lower and the upper Old Town
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Learn the overall history, culture, and politics of Tallinn and Estonia in an easy conversational storytelling style
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Explore cobblestoned alleys lined with medieval fort walls and Gothic churches that have stood since before Columbus discovered America
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Visit the city's top viewpoint for sweeping panoramas of both old and modern Tallinn
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Experience the transformation along the tour route with a curated visual portfolio of archival photos and videos, offering fascinating historical glimpses of the sights we visit
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Receive honest advice and unbiased local tips on where to dine, wine, shop, and stroll on your own
FULL TOUR ITINERARY
Our private tours skillfully walk the line between rich historical depth and an engaging, fun narrative style – led by a knowledgeable and passionate native Estonian guide who knows this city inside out. We weave honest personal anecdotes into our grand narratives, connecting Tallinn's picturesque landmarks with centuries of triumphs and tragedies, present-day realities, and future aspirations. Real stories, real history, no fluff. We respect your time.
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Did you know that for most of history, the Upper and Lower Old Towns were two separate cities with their own laws and governments?
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Or what has made Tallinn a prized target through many eras, what once caused it to prosper as one of the wealthiest ports in the region, and what subsequently caused its fall from grace, becoming frozen in time?
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And what a close call it was that the Old Town narrowly escaped total destruction at the hands of the brutal Soviet army, which tragically left much of Tallinn in burning ruins in WW2?
These are just some of the tales we will explore, grounding facts and history in memorable chapters that connect and build up to every next story – all part of a bigger, cohesive narrative that makes this city come alive for you.
The usual tour route will specifically show and tell you about the following sights:
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Medieval town walls, towers, and fortifications
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Freedom Square & the Cross of Liberty
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Iconic medieval churches: St Mary's, St Olaf's, St Nicholas', and the Church of the Holy Spirit
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Danish King's Garden & panoramic Old Town viewpoint that shows much of Tallinn
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Toompea Fortress, Tall Hermann Tower & the Estonian parliament
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Alexander Nevsky Cathedral & historical noble residences
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Long Leg Street & St Catherine's Passage
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Great Guild Hall & medieval Guild Houses
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Town Hall Square, Medieval Town Hall, and the 15th-century pharmacy
If there’s a place you’re curious about that's not listed, just let us know. We’ll do our best to weave it into your tour and our story. Book your own journey through the Old Town today, and let's turn your Tallinn visit into a personal and meaningful experience, full of stories and emotions that you'll actually remember!
Photo credits: Thank you to Kaupo Kalda; Rasmus Jurkatam; Rene Altrov; Aleksandr Snitovskii; Sam Mcallister; Kadi-Liis Koppel; Thomas Lotter; Mark Harisson; Jorden Tually; Vivian Velle; VisitTallinn.ee
Confirm your booking now, risk-free — change or cancel up to 48 hours before for a 100% refund.
CUSTOMIZE YOUR TOUR | GET A QUOTE
Want to modify an existing tour?
Propose a unique one-off route or have us create one just for your interests?
Have a big group (9+ people) or a mix of adults & children?
Please include any details & context that would help us give you the best experience. We'll send you a personalized quote or a custom route designed to fit your exact preferences within 24 hours.
"Easily one of the best history and architecture tours I've ever taken (and I've been on many!)"
"I take the time to write a review only when I think something is extra special and deserves to be shared, and our tour with Tallinn InSight founder and lead guide Kristjan-Jaak Tammsaar (Chris) easily qualifies. Being led through a beautiful, historic city by a guide who is curious, experienced, professional, engaged, and a great communicator was truly a treat. There is so much about the Baltics leading up to WW2 and during the Soviet occupation that I didn't know. As Chris put it, the eyes of the world were elsewhere..."
Patricia. Davenport, Iowa