Tallinn Highlights: The Complete Experience

It almost seems impossible to cover such incredible contrasts in a mere half a day's time, but thanks to the compact size and incredibly rich and varied history of Tallinn, we're somehow actually able to pull it off. If you have the few extra hours of time then there really is no better way to soak in everything that Tallinn has to offer. This tour includes, and starts with, the full medieval Old Town walking tour, also available as a stand-alone walking tour, and then proceeds with drives and shorter strolls through the many incredibly different faces and facets of Tallinn, illustrating manifold periods of occupation and liberation, eras and stories of both thriving and barely surviving.
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To begin with, step then into the enchanting storybook streets of North Europe's best-preserved medieval Old Town and let us fill its scenic streets with real tales spanning centuries of joys and sorrows, triumphs and tragedies. Our private tours juggle the storylines with timelines while balancing on the tightrope between historical depth and approachable, fun narrative style – all delivered by a knowledgeable local Estonian guide with a spark in his or her eye. Our passionate local guides know this city and country inside out, combining deep historical knowledge with honest personal anecdotes. We'll take you beyond the simple postcard views of this picturesque Old Town, connecting its iconic landmarks and past events with present day realities, future plans and aspirations.
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After the Old Town we will proceed with a drive to Kadriorg, a spacious leafy suburb that houses one of the biggest and most beautiful historical parks in Northern Europe, with an exquisite 18th century royal palace in the middle—consequently also the most beautiful example of historical baroque architecture in Estonia. The historical palace, now housing Estonia's Art Museum, is actually aligned with another palace, that of Estonia's current presidential residence, or our equivalent of the 'White House'. You'll furthermore get to catch a glimpse of the architecturally bold Estonia's Contemporary Art Museum, awarded as European Museum of the Year upon its completion and opening.

We'll make a stop overlooking the one-of-a-kind Tallinn Song Festival Grounds, which is home to by far the biggest mass event in the country, the Estonian Song Festival held only once every five years and known for featuring the biggest choirs in the world made up of 25 000 people and more! Not only are these song festivals now featured in UNESCO's worldwide Intangible Cultural Heritage list, but they're an absolutely integral part of Estonia's national awakening that first brought us independence in 1918 and then saw as survive the Soviet annexation until its eventual collapse in 1991 and Estonia's re-emergence after half a century of illegal occupation. It's an emotional and inspiring story that we can't wait to share with you!

Speaking of fifty years under foreign oppression, nearby we'll visit and walk through the incredibly minimalistic yet architecturally and emotionally striking Memorial to the Victims of Communism dedicated to the victims of the communist terror regime, which saw Estonia lose every fifth person of its population—murdered, imprisoned and deported. It is an evocatively solemn site yet emerges on the other side back to daylight, poetically symbolizing our eventual liberation and 'homecoming'. Interestingly enough, the contemporary Estonian memorial has been deliberately built next to a sprawling and decaying Soviet totalitarian memorial, itself built over a bulldozed former cemetery, but that's a story best left for our actual walk. It's a fascinating physical and visual juxtaposition of different political regimes, all leaving a tangible architectural mark, telling their own stories in their own signature style.

Driving further away from downtown along Tallinn's coastal road will take us past old Olympics' facilities, and ruins of the medieval St Bridget's Convent, once a major point on an age-old pilgrimage route. We will briefly even leave Tallinn behind, for a scenic stroll through the quaint Viimsi Open Air Museum along the seashore, with old log cabins representing a very different era and pace of life in Estonia. Honestly, with waves lapping against the shore next to us, you might as well feel as if transported a few centuries back in time in the heart of remote rural countryside. Yet the famous Tallinn skyline beckons to us from right across the bay, with the medieval Gothic church spires making for a striking visual contrast with the new sleek glass and steel high-rises next door that former the heart of Tallinn's small, but budding business district.

Our drive will also take us past several former industrial areas that stood as neglected and derelict eyesores until less than than a two decades ago, having now been, or still in the process of being rejuvenated as the new vibrant creative and community hubs of the city, full of cafes, galleries and boutiques, street art and outdoor recreational spaces. Port Noblessner, which we will see as well, is now in fact considered one of the most successful examples of revitalisation of abandoned industrial spaces in Europe, hosting a lively pedestrian-only marina in what used to be the Russian Empire's largest submarine shipyard.
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And incredibly enough, by the time we finish this whirlwind tour of Tallinn's seemingly endless different faces, the day will still be young due to Estonia's geographical latitude and daylight that just doesn't seem to run out in summer. We'll be more than happy to leave you with some of our top recommendations, be it for elegant wining and dining, a casual drink or an interactive family-friendly museum visit.
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Specifically, this tour will usually cover and explain the following sights (and much more in-between, of course):

WITHIN the OLD TOWN:

• The medieval town wall, towers and fortifications
• Freedom Square & the Cross of Liberty
• Iconic medieval churches, including St Mary's, St Olaf's, St Nicholas' & the Church of Holy Spirit
• The Danish King's Garden & stunning Old Town viewing platforms
• Toompea Fortress, Tall Hermann Tower, Estonian parliament
• Alexander Nevsky Cathedral, the Prime Minister's Office & the historical noble residences
• Long Leg passageway & St Catherine's Passage
• Great Guild Hall & the Guild Houses
• Medieval Town Hall, Town Hall Square & Town Hall Pharmacy

ELSEWHERE in TALLINN:
• Kadriorg Park with the Kadriorg Palace, the Presidential Palace, and the Contemporary Art Museum of Estonia
• Tallinn Song Festival Grounds
• Memorial to the Victims of Communism, juxtaposed with the Soviet totalitarian memorial next door
• Drives through starkly different suburbs of Tallinn, spanning Soviet brutalism to leafy forested suburbs
• The ruins of the medieval St Bridget's Convent and Tallinn's former Olympic facilities
• The Viimsi Open Air Museum recreating traditional rural village look and lifestyle
• Views back across the bay towards the famous Tallinn skyline juxtaposing medieval spires with modern high-rises

​• Former industrial districts rejuvenated as the new buzzing hubs, such as Rotermanni, Telliskivi and Noblessneri​
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If there’s a specific place or sight you’re curious about and not listed here, do let us know, and we’ll do our best to weave it into the tour and the story. Book your personalized journey through Tallinn today and let us guide you through the heart of Tallinn's real history for a personal and unforgettable experience!​