Discovering Tallinn's Old Town: Places To See And Things To Do

Nestled on the Baltic coast and steeped in pristine medieval charm, the Old Town of Tallinn, Estonia, transports me to a timeless world.Tallinn tempts me to its shores on a vibrant European summer day, following a packed work week in Finland.Sailing on a cruise from Helsinki across the kaleidoscopic Baltic waters, I am already in a mood for exploration. The scent of the sea drifts through the air, blending into the soft murmur of voices onboard.The cruise is quite full—multiple nationalities, both tourists and locals. I step out from the cabin onto the deck, entranced by the surrounding vastness and the sight of distant shorelines. I am in the company of a dear friend and colleague from South Africa, both of us on our maiden voyage to Tallinn.The couple of hours on the cruise pass quickly—feasting on the view, engaging in “girlie” conversations, and enjoying snacks purchased onboard.Five Amazing Experiences In TallinnTallinn’s enchanting coastline appears kissed by the light of an unsetting sun. It is past 8 p.m., yet the Nordic sky shines in soft pearlescent hues.A fantasy grips me. "Beyond what looks like towering walls, is Hans Christian Andersen’s ‘Little Mermaid’ singing to sailors in the dark?" I quickly return to the present.We ditch the idea of taking a taxi and choose to walk instead. My friend leads the way with her deft command of Google Maps, while I trail behind with my trolley. Modern-day travelers on the road to a very old world.An Evening of Revelry and Medieval CharmThe Old Town, brimming with Friday evening revelry, beckons. A cobblestone haven alive with music and laughter, the streets are an intricate tapestry woven from centuries past. The warm glow of lanterns dances along the paths, and as we approach, the architecture whispers of another time—a medieval splendor untouched by modernity.Of Light & Songs In Estonia: Exploring The Underrated European GemUpon reaching the hotel, a moment of confusion overtakes us. The heavy, ornate door is locked! “Have we stumbled upon some mystery and are about to unlock the secret door of Enid Blyton?” We spot a telephone on the door. My friend picks up the receiver. The voice on the other end gives us instructions to take the adjacent lane and navigate to the other side of the hotel. Lo and behold! We arrive at a most artistic porch leading to a beautiful lobby.We set out for a stroll to soak in the ‘atmosphere’ of Friday night in Old Town. At the square, the cafés are adorned with delicate lanterns. The servers, dressed in traditional costumes and accessories, are seamlessly woven into the landscape. We linger, savoring a moment that feels stolen from the pages of a storybook.Morning Magic and Timeless StoriesThe following morning, Tallinn is transformed. Gone is the pulse of revelry; instead, a quiet dawn light bathes the streets in an ethereal glow. The buildings stand tall, their grey stone walls softened by morning rain, shimmering as though painted by the hand of a gentle master. This looks surreal. I feel the pull of history and beauty all around.I see a horse-drawn carriage rumbling around the narrow cobblestone street. “Will Cinderella step out from this carriage?” wonders the romantic in me. Every shopfront is a window into a story, an artifact of a memory long preserved. We stop in a small, exquisite shop where a young woman speaks of her wares with quiet pride. She tells me about the artisans and their crafts, her voice as tender as the treasures she holds. I select an aquamarine scarf.Wandering through the labyrinth of ancient streets, I wonder if there might be a ‘Sleeping Beauty’ waiting to be woken up by her prince in any of these beautiful houses.I marvel at the magnificent architecture. One finds a blend of styles—Hanseatic, medieval Europe, Nordic, and Russian. In the 14th and 15th centuries, Tallinn thrived as a port city, attracting merchants and craftsmen from across Europe. This shaped its unique mix of Gothic spires, Nordic wooden buildings, and medieval structures.The Old Town of Tallinn is recognized as a UNESCO World Heritage Site. It stands unfazed by the passage of time.I am particularly charmed by its fairytale appeal. The narrow lanes lined with quaint shops, cosy cafés, and pastel houses make my imagination run wild. “Is that a ‘Goldilocks’ I see looking out of that window?”I come out of my reverie. “There is a lot of ground to cover still…” First on the list is the Town Hall Pharmacy, among the most ancient medicine retail outlets in the world. “The kind of place Rapunzel might visit for a magic potion to grow her hair,” I muse once again.I find it hard to escape the spell that the Old Town has cast on me. Throughout the tour, I constantly slip into the fairy tales, somewhat forgotten to me.I feel a bewilderment within, which is so precious, yet rare in a world that has drifted away from fairy tales. On the cruise back to Helsinki, I reflect upon this wonderful personal discovery. It fills me with gratitude. Places to See in TallinnAlexander Nevsky CathedralThis stunning Orthodox cathedral, located on Toompea Hill, is one of Tallinn’s most iconic landmarks. Its onion-domed towers and intricate mosaics reflect Russian Revival architecture, making it a must-visit site. Inside, visitors can admire beautiful religious iconography and experience a sense of tranquility amidst its ornate design.Tallinn Town HallDating back to the 13th century, Tallinn Town Hall is the oldest surviving Gothic-style town hall in Northern Europe. Situated in the heart of the Old Town, its slender spire offers breathtaking views of the city. Inside, the building houses exhibitions that provide insight into medieval Tallinn.St. Olaf's ChurchOnce the tallest building in the world, St. Olaf’s Church boasts an impressive spire that dominates Tallinn’s skyline. Visitors can climb to the top for panoramic views of the city and the Baltic Sea. The church’s Gothic interior and history as a place of worship and defense make it a fascinating stop.Kohtuotsa Viewing PlatformSituated on Toompea Hill, the Kohtuotsa viewing platform offers one of the best panoramic views of Tallinn. From here, you can see the city’s red-roofed buildings, medieval walls, and modern high-rises blending seamlessly into the Baltic coastline. It’s a photographer’s paradise!Viru GateA medieval gateway that once guarded the entrance to Tallinn’s Old Town, Viru Gate is now a picturesque landmark. The charming towers are surrounded by flower stalls and cobblestone streets, welcoming visitors into a vibrant area filled with shops, cafes, and history.Balti Jaama TurgThis bustling market near the main train station is a vibrant mix of old-world charm and modern trends. Balti Jaama Turg offers fresh produce, street food, antiques, and unique local crafts, making it a great spot to experience local culture and cuisine.Toompea CastleHome to the Estonian Parliament, Toompea Castle is a historic fortress with roots dating back to the 9th century. Its pink baroque façade hides centuries of history, and the castle grounds provide stunning views of the city.Estonian Art Museum (KUMU)KUMU, located in Kadriorg Park, is a contemporary art museum showcasing Estonian art from the 18th century to modern times. The museum’s striking architecture is as impressive as the exhibitions inside, which range from classical works to avant-garde installations.Town Hall PharmacyEurope’s oldest continuously operating pharmacy, the Town Hall Pharmacy, dates back to 1422. Located in the Old Town, it is both a functioning pharmacy and a museum displaying historical remedies, tools, and curiosities.Kadriorg ParkKadriorg Park is a lush green space featuring manicured gardens, fountains, and pathways. It’s home to the Kadriorg Palace, built by Peter the Great, and several museums. The park is perfect for a leisurely stroll or a family outing.Holy Spirit ChurchThis small yet stunning medieval church is known for its intricately carved woodwork and a unique 17th-century clock adorning its façade. The church played a significant role in Estonian history as the first church to conduct services in the Estonian language.Telliskivi Creative CityLocated in a former industrial area, Telliskivi Creative City is Tallinn’s hub for creativity and innovation. The area is filled with art galleries, quirky boutiques, trendy cafes, and street art. It’s a lively spot to explore modern Tallinn’s artistic and cultural side.