There are few places in the world where one can explore a pristinely preserved medieval old town before taking a few steps and being thrust into a modern city where autonomous robots deliver groceries, but Tallinn is one of those privileged few. The capital of Estonia, a country of 1.3 million people nestled between Russia to the East and Finland to the north is something of a megalopolis, at least by Estonian standards. Today, more than a third of the population lives in the city and surrounding suburbs, although most travel frequently to countryside cabins and homes on one of Estonia’s more than 2,000 islands to escape the hustle and bustle of city life.

The city is home to most of Estonia’s bustling tech scene, which took the world’s top spot in venture investment relative to GDP, just ahead of Sweden according to the VC firm Atomico. Estonian engineers were the driving force behind Skype and today global startups like Bolt and Starship Robotics all call Tallinn home. Many of the newer generation of startups are birthed in Telliskivi, Tallinn’s hipster neighborhood home to artists workshops, galleries, and more than a few late night haunts catering to starving artists, entrepreneurs, and tourists. 

To visit Tallinn is a chance to visit both the future and the past, with ample opportunities to see how technology and e-government services can simplify everyday life while still being able to embrace a rich culture centered around nature. While visiting, don’t forget to pick up a reflector – there is no easier way to spot a foreigner than seeing someone traverse the city without one attached to their coat, especially in the dark winter months when there are only a few hours of natural light a day.

1:15pm: Late Lunch at Mimosa Pizza

4pm: Combine the Old with the Hip

Recommendations 

Key Stops:

• The Tallinn Old Town, a UNESCO World Heritage Site, is the crown jewel of the city having principally been built during the 13th-16th centuries. Within its well preserved streets lie the Estonian parliament building, churches, ancient (and not so ancient) restaurants and watering holes, and picturesque views overlooking the rest of the city.

• Vabamu, opened after the country regained its independence in ‘91 from the Soviet Union, the museum details the bleak picture of life under Communist rule with an emphasis on telling the personal stories of those affected.

• Telliskivi Creative City, Tallinn’s hipster community home to numerous craft shops, concept stores, hip restaurants and bars, and ample opportunities for people watching.

Museums and attractions:

• Estonian Museum of Architecture, housed in the historic Rotermann Salt Storage facility, the museum showcases the history of local architecture and includes archives dating back to the first independence period in the ‘20s and ‘30s through the Soviet occupation. 

• PoCo (Pop & Contemporary Art Museum), is a rapid romp through modern pop art in one of Tallinn’s newest neighborhoods with a collection that includes Warhol, Banksy, Koons, Basquiat, and others. 

• Linnahall, a decaying architectural gem once used to host sailing events for the widely boycotted 1980 Moscow Summer Olympics. 

• Pikakari Beach, the starting point for a walk along the Paljassaare peninsula of northern Tallinn sporting seaside views.

• Iglupark, a sauna facility with private rentals and daily public access that provides visitors and locals with a taste of that classic Nordic tradition of sauna. 

  Restaurants and Bars:

• NOA, boasting pristine views of the Tallinn old town and a robust yet reasonably priced menu relative to its quality, is one of the top restaurants in Tallinn. 

• Mimosa Brooklyn Pizza, located in the old town, Mimosa Tallinn is the sister restaurant of Mimosa Kyiv, home to pizza that puts most NYC establishments to shame.

• Restoran Salt, a true locals joint, Salt is a hidden gem in Tallinn with top tier seafood offerings and a grilled octopus worth straying off of the beaten path.

• Pohjala Tap Room, skip the Texas BBQ and stay for the Estonian craft beer specials in the trendy new Noblessner neighborhood.

• Whisper Sister, for those in dire need of a high quality cocktail, Whisper Sister is Tallinn’s finest speakeasy. It’s located at the edge of the old town but beware that it is easy to miss (look for a small plaque on the door with a number to call to be let in). 

• Tops, a retro cafe and bar in Kalamaja, the residential neighborhood adjacent to hip Telliskivi. Its unassuming exterior belies the endearing nature of the bar and its mostly local clientele.
  

  Shopping:

• Telliskivi Creative City, the hipster hangout, has two buildings packed with rotating and permanent artist shops and concept stores stocked with Estonian fashion finds.

• A Galerii, located in the heart of the old town, A Galerii is a pearl in a sea of tourist traps with an eclectic collection of jewelry from Estonian artists.

• Rotermann Quarter, one of the newer neighborhoods in Tallinn is home to a number of local design shops including Aegon Watches and the Tallinn Design House which stocks fashion finds from a number of Estonian designers.

• Hyrv, a local gem run by designer Kateryna Pishon specializing in high end and custom jewelry with a unique Estonian flavor.

• Autonomous Grocery Delivery, The Estonian startups Bolt and Starship Robotics have teamed up to offer grocery delivery services via adorable autonomous robots. Users of the Bolt Food app can hail these automatons and have food staples brought directly to their door in most parts of town.
  

  Where to Stay:

• Schlössle Hotel, tucked away in a quiet corner of the old town, the boutique 5 star hotel, replete with medieval ornamentation and cozy accessories is a member of The Small luxury Hotels of the World. 

• Bob W, for those who want to truly embrace the Estonian culture of isolation, this edgy sustainable apart-hotel chain has contactless properties so you don’t have to talk to a human unless you really want to.

  Getting Around:

• Public transportation around much of Tallinn is excellent with easily accessible tram lines zigzagging across the city and encircling the old town. However, Bolt, a local rideshare company is an excellent reasonably priced alternative. As an Estonian startup, supporting the business is something of a patriotic duty and the company has a monopoly on the local transportation market for both rideshares and scooters.

Reading Recommendations:

• Estonia, The Digital Republic, Nathan Heller’s ineffable New Yorker piece on how Estonia became a digital society and some of the colorful cast of characters behind its history is absolutely required reading for those interested in the country’s modern history.

• Baltic: The Future of Europe, for those unfamiliar with the region, The Times Berlin bureau chief Oliver Moody’s 2025 book presents an enlightening overview of the region while providing context on the cultural drivers and current events affecting the Baltics.

• Silverwhite, The Journey to the Fallen Sun, translated from Estonian in 2025 by Adam Cullen, Silverwhite is one of the definitive works of nonfiction by the Estonian founding father, writer, filmmaker, and President Lennart Meri (1929 - 2006). Written during the depths of Soviet Occupation, this epic work is an exploration of the early history of the Baltics created in an inimitable literary style by a prescient statesman who warned of the threat of Russia to the West more than thirty years ago at a 1994 speech in Hamburg that led then St. Petersburg Deputy Mayor Vladimir Putin to storm out of the meeting.

Itinerary

8am: Walk the Bog

The Paaskula Bog, a fifteen minute drive from the Tallinn city center, is a pristine example of one of the staples of Estonian nature which cover one fifth of the nation’s landmass. The Raba ring route is a 4km journey through the heart of the bog that traverses springs and various types of forestlands (but is well maintained and easy to walk). In the early morning mists one can wake up along with local fauna and enjoy birdsong before the rest of the city rises, making it the optimal time to visit (although saving the trip for later and having a bog day afternoon is very much acceptable). For those who prefer to be caffeinated on early morning excursions, consider a stop at a local Reval coffee shop before heading out.

11am: Old Town Tour

Every day at 11am, walking tours depart from the Old Town Information Centre at Niguliste 2. While often crowded, the tours provide an excellent introduction to the old town and make later independent exploration through the old town’s winding roads and alleys much more manageable. The tour takes visitors to some of the high points of the old town including Vabaduse väljak (Freedom Square) and Toompea Castle, the home of the Riigikogu (parliament) which is housed in a stately pink painted complex adjacent to the Alexander Nevsky Cathedral of Tallinn catering to mostly Russian speaking Orthodox parishioners. The cathedral, built in the late 1800s during one of the repeated periods of occupation by regional powers, serves as a poignant reminder of Russia’s continued influence on the country. The walking tour is also sure to take visitors to one of a few scenic overlooks before depositing ending in the town square, which during the winter is home to an idyllic Germanic Christmas market.

After hours of walking, one deserves a hearty meal. Skip the tourist fare endemic to much of the Old Town (if the waiters are wearing medieval garb, it’s a trap) and visit Mimosa Pizza. A Ukrainian pizza joint which has since expanded to Tallinn, Mimosa serves Brooklyn style pizzas (starting at €13.50) that give anything in New York a run for its money. The Friedman pizza with salami, fried eggplant, and pecorino cheese is an absolute delight with a tasty crunch. For those with a sweet tooth, the Four Cheese pizza features a blend of goat’s milk cheese, fig confiture, and wild arugula that when dipped in the accompanying spicy honey sauce forms a perfect flavor profile.

2pm: Understanding the Soviet Occupation

It is hard to overstate how impactful the decades of Soviet Occupation were on the nation of Estonia. From mass deportations to the collectivization of farmland and the attempted decimation of a fledgling national identity, the Soviet Occupation left indelible scars on Estonian society. It is Vabamu, the Museum of Occupations and Freedom, (standard tickets are €15) which endeavors to share the trials of the Estonian people due to the Soviet and Nazi occupations with a focus on how the Estonian people persevered, preserved their culture, and eventually won their independence (or more accurately, their re-independence as the country was briefly independent from 1918 to 1941). Be prepared to leave with a heavy heart, but one full of hope for the future of Estonia and all peoples who fight against tyranny.

7pm: Dinner with a View

After learning about Estonia’s rather bleak modern history, explore the city with fresh eyes and a newfound appreciation for freedom. The best way to do so is with a rambling sojourn through the Old Town streets, with no specific destination in mind. Walking down unknown alleys and getting lost intentionally is unusual travel advice, but wandering through Tallinn’s old town is sure to expose one to far more historical sites and breathtaking views than any tour ever could. But make sure to stop by Hyrv, a jewelry studio run by Kateryna Pishon specializing in breathtaking design in a unique style that combines Estonian and Scandinavian aesthetics.

Continue on to Telliskivi, Tallinn’s hipster neighborhood. Home to numerous startups, restaurants, shops, and bars, there is no paucity of options for an evening. However, any day of exploration deserves a sweet pick me up, and La Muu, a local ice cream chain (€5 for two scoops), is the perfect indulgence. Take your cone a few yards away to the Telliskivi Creative City shops which house a number of local art and concept stores.

Come for the steak au poivre (€45) but stay for the sunset view. The steak is a tender cut paired with a succulent sauce and comes with handmade roasted potatoes buried under truffles. Situated across a small inlet from downtown and old town Tallinn, NOA Restoran boasts immaculate views and better dishes with a Chef’s Tasting Menu (€80) that includes smoked eel, beef tartare, and a tasty halibut. The restaurant, like many in Estonia, is heavy on meat, fish, and bread, the staples of local cuisine.

10:30am: e-Estonia Briefing

2pm: Enjoy a Seaside Stroll

8pm: Nature on Tap

The e-Estonia Briefing Center is the central nervous system of the government’s efforts to educate global audiences about the country’s unique history, digitalization journey, and the people behind the country’s rise as a global e-government and tech leader. A nontraditional stop for tourists, the briefing center is well worth a visit to learn more about what makes the country tick and how it has brought 100% of government services online, including e-voting (which has been in use since 2007), marriage, and divorce. Just make sure to book your visit ahead of time.

12:30pm: Restoran Salt

It’s a short Bolt ride away to get to a preferred locals destination for a meal. Salt is a fusion restaurant boasting phenomenal seafood offerings with ample portion sizes including spicy tiger prawns with a sriracha aioli (€9) that leave diners licking their fingers and a grilled octopus dish (€28) cooked to perfection.

Pikakari Beach in northern Tallinn is a sandy spot to start a slow seaside stroll. Beginning at the beach, follow the trail up to the tip of the peninsula through the nature preserve to enjoy pristine views, brisk sea air (Estonia is one of only 7 countries whose air is clean enough to meet WHO guidelines), and ever present birdsong.

4pm: Shopping and Soviet Sightseeing

Originally the Lenin Palace of Culture and Sports, the now decaying Linnahall (Tallinn City Hall) was created for the 1980 Moscow Summer Olympics sailing events. Today, locals frequently bring lunch or an ice cream and climb to the top of the building to enjoy the seaside view. Next door is Kultuurikatel, a creating hub in the former city power plant which now hosts various maker labs, events, and artists in residence. Nearby is the Rotermann Quarter, home to both chic local design shops like Aegon and the Tallinn Design House and Kalev, the local (and delicious) Estonian chocolate brand which has been serving up confectioneries since 1806. Happen to have time to spare? Check out the Estonian Museum of Architecture (regular tickets €12) for a fascinating look at the country’s urban design history.

6pm: Eat Some Meat

Pull is owned and operated by two local grill masters, one of whom was granted a lifetime achievement award for his contributions towards developing Estonian BBQ culture. The deer (€33) is to die for, as is the seafood, always an Estonian culinary mainstay. However, it’s their sides, like chunky chips (€7) and charcoal potatoes (€7) which make the restaurant a must visit.

The Põhjala Brewery Taproom in Noblessner is the perfect place for a nightcap (or two). The local craft brewery focuses on creating beers like the Forest Series of lagers, stouts, and IPAs inspired by nature. At the taproom, visitors can imbibe one of the 24 Põhjala and guest beers on tap, but also enjoy a private sauna available for rent (€80/hr for the first hour and €60/hr for each consecutive hour). Naturally, sauna sommeliers can help recommend a beer to match the temperature.