In the luminescent twilight of a midsummer evening in Tallinn, Old Thomas – the city’s much loved mascot – stares down from the Gothic Town Hall upon an ancient, cobbled market square. The original weather vane, now protected inside the Town Hall, was presented to Tallinn in 1530 by the city’s Baltic German elite and is a relic of the Hanseatic League, a wealthy trading federation that from the 12th to the 17th century dominated commerce in the Baltic Sea.

During the Dark Ages, the Baltic was a lawless no-go zone dominated by pirates and hostile pagan tribes. Intrepid Vikings managed to brave these obstacles and brought back furs and amber from the region that is now Russia, which they traded in Western Europe. The riches of this mysterious land became so well known that in the second half of the 12th Century, merchants from Lübeck began clubbing together with neighbouring towns to send armed flotillas out into the Baltic in search of new trading opportunities. The formula of pooling resources proved so successful that during the next century fortified mercantile ports sprang up throughout the Baltic. They became the Manhattans of the Middle Ages, attracting entrepreneurs and artisans from all over Europe. Nouveau riche merchants filled these new boom towns with sumptuously decorated Gothic buildings and churches whose soaring spires became the tallest structures in the world.

During its heyday the Hanseatic League boasted over 200 member cities, but it was never a cohesive political entity. During the 16th century, England and Holland began muscling in on the lucrative Baltic trade; unable to compete with these rising maritime superpowers, the Hanseatic League slowly petered out. However, its legacy of mercantile dynamism and architectural innovation lived on, transforming the region.

In 1980 the Hanseatic League was resurrected as the HANSE, the main objective of which is to rekindle the spirit of cooperation and cultural exchange that characterised the original. Following the fall of Communism in 1989, the HANSE rapidly expanded into eastern Europe. It is now the largest voluntary association of towns and cities in the world. Its heritage projects and tourism initiatives have helped inject new pride into the Baltic’s historic seaports, where the beautifully restored, traffic-free old towns are now some of the loveliest urban spaces in Europe.

For travellers interested in exploring the history of the Hanseatic League, the six beautiful cities of Visby, Lübeck, Rostock, Gdansk, Riga and Tallinn not only have the greatest wealth of architectural Hanseatic treasures, they also take visitors on a fascinating chronological journey through the origins, expansion and legacy of this mighty trading empire.

Visby, Sweden (Shutterstock)

Visby, on the Swedish island of Gotland, was a key Viking trading hub during the Dark Ages. Its strategic position in the heart of the Baltic made it a prime destination for Hanseatic traders and it became one of the League’s earliest members. By the early 14th century, Visby had become the richest city in Scandinavia and was endowed with wealthy monasteries and mighty fortifications. Unfortunately, Visby’s prosperity was short lived and, as trade moved further east, it slipped into obscurity. The town was left as a time capsule and is today the most perfectly preserved medieval town in Scandinavia and one of Sweden’s most popular summer holiday destinations.

Don’t miss: There are 12 hauntingly beautiful ruined churches tucked away in Visby’s labyrinth of medieval lanes; St Nicolai plays host to atmospheric summer concerts performed beneath a striking contemporary wooden awning strewn across the nave.

Strandgatan was the main thoroughfare of Viking Visby and is lined with colourful houses from the Hanseatic era. Look out for the Old Pharmacy, a well-preserved merchant’s house, and the Gotlands Museum, which is packed with Viking treasures and mysterious rune stones. Saffron was a lucrative commodity for Hanseatic traders and is still used in saffranspannkaka, a delicious local pancake served with dewberry compote. You can find them on menus in many of the cafes in and around Strandgatan.

Visby’s Medieval Week, held in the second week of August, is Sweden’s largest medieval festival. Highlights include rowdy jousting tournaments held outside the City Walls, converts and street performances, and a medieval craft market that takes place along Strandtgatan.

Lubeck, Germany (Shutterstock)

As the founding member of the Hanseatic League, Lübeck quickly became its de facto capital. As wealth poured in, the city fathers invited French architects to adorn the city with the latest Gothic architectural fashions. Stone deposits are rare in northern Germany, so the architects were forced to improvise: a flamboyant new architectural style known as Brick Gothic emerged, characterised by stepped gables and ornately patterned brickwork. The legacy of Lübeck’s Hanseatic golden age is Germany’s largest medieval old town, famous for its seven church spires that form a Gothic coronet on the skyline and the twin-towered Holstentor city gate, straight out of a Brothers Grimm fairytale.

Don’t miss: Living space was at a real premium in Hanseatic Lübeck. To solve the problem, 180 alleys leading to tucked-away residential courtyards were built. About half of these courtyards still survive; their picturesque cottages and cobbled patios filled with hollyhocks and roses are now the most desirable properties in the city.

The history of marzipan is shrouded in mystery, but a plausible theory is that Hanseatic merchants introduced it to Lübeck from Moorish Spain. Whatever its origins, Lübeck is now the marzipan capital of the world and, after a wander around Lübeck’s enchanting Old Town, a coffee break in the 200-year-old Café Niederegger for a marzipan-festooned torte is the icing on the cake.

Tallinn, Estonia (Shutterstock)

In Tallinn all the elements of Hanseatic heritage come together in a walled city packed with well preserved medieval, Renaissance and 19th century architectural gems. In the 30 years since Estonian independence, Tallinn has rediscovered its entrepreneurial flair to become a world leader in digital technology, with the highest successful start-up rate in Europe. New creative hubs built upon Tallinn’s decaying industrial heritage have injected life back into the city. Full of buzzing bars, innovative restaurants and exciting fresh cultural spaces, the city oozes an upbeat newfound confidence.

Don’t miss: The Seaplane Harbour is a unique maritime museum housed within the concrete domes of a 1930s seaplane hangar complex. Built on three levels to reflect the Baltic’s air, sea and underwater maritime heritage, highlights include the Lembit (a 1930s submarine) and a fine collection of vintage ships moored outside.

Telliskivi Creative City is Estonia’s most dynamic cultural space. This totally transformed Soviet-era locomotive repair yard is now home to sustainable community cafes, artists workshops, shops, galleries, pop-up exhibitions, a wealth of events and an air of creative energy.

Gdansk, Poland (Shutterstock)

Pagan Prussians in the southern Baltic were a thorn in the side of Catholic Europe and, in 1230, a crusade was launched to Christianise the region. This was led by the Teutonic Knights, a German order of crusaders who carved out a vast empire that stretched from Poland to Estonia. With trade routes stabilised, Gdansk, at the estuary of the Vistula River, quickly expanded into a major port and centre of the amber trade. As Hanseatic influence waned, a growing Dutch mercantile community transformed the city with dazzling Renaissance buildings characterised by ornate gables and whimsical sculptured facades. During the Second World War, over 90% of Gdansk was destroyed but, in a remarkable feat of civic pride, the Old Town was entirely rebuilt and is once again the Renaissance jewel of the Baltic.

Don’t miss: A sizeable English community lived in Gdansk in the early 17th century and the city became a key stop for travelling players, who performed at the Fencing School – the only Shakespearian theatre built outside England during the Bard’s lifetime. The venue was destroyed, but its original location was later discovered from an old engraving and, in 2014, a new Shakespearian playhouse was built within a striking arts centre. Performances by visiting troupes are a highlight of Gdansk’s cultural calendar.

Malbork Castle, 45 minutes by train from Gdansk, was built in the 13th century by the Teutonic Knights and is the largest castle ever constructed. Made from terracotta-hued bricks, it is a regal ensemble of turrets and towers, widely regarded as one of the most beautiful medieval castles in eastern Europe.

Rostock, Germany (Shutterstock)

As the Hanseatic League expanded, its need for ships rose exponentially and Rostock rapidly became its main ship builder. The workhorse for the League’s maritime trade was the cog, a flat-bottomed, high-sided ship that evolved from Viking long boats. Rostock’s shipbuilding tradition continues to this day; over the second weekend in August, the city hosts the annual Hanse Sail, one of the world’s largest classic ship festivals, which attracts over 250 vessels and a million visitors to this historic German port city.

Don’t miss: The Astronomical Clock in St Mary’s Church, constructed in 1472, is the oldest in the world still operating on its original mechanism. The complex zodiac and lunar clock faces plus an hourly procession of dancing apostles are marvels of medieval engineering.

The Doberan Minster in Bad Doberan, a 30-minute train journey west of Rostock, is widely considered to be the apogee of medieval Brick Gothic. Unusually for a German protestant church, the interior is a treasure trove of medieval furnishings and decorations. Also in Bad Doberan you can hop aboard a steam locomotive and ride the Molli, a delightful narrow-gauge railway that dates from 1886 and trundles 15km to the seaside resort of Heiligendamn.

Riga, Latvia (Shutterstock)

Tapping into the riches of Russia was always the primary goal of the Hanseatic League and when the Latvian tribes were conquered by the Teutonic Knights, Riga, at the mouth of the Daugava River, became the most important Hanseatic city in the eastern Baltic. A large colony of German merchants emigrated to the city and their descendants remained Riga’s wealthiest community long into the 20th century. Powerful mercantile dynasties looked to Germany and France for the latest architectural trends and embellished the city with ostentatious new buildings. The result is an unparalleled architectural legacy, most notably the largest concentration of Art Nouveau buildings in the world.

Don’t miss: The 14th century House of the Blackheads is regarded as one of the most beautiful Hanseatic-era guild house. The step-gabled facade is decorated with swirling Dutch Mannerist ornamentation added in the 17th century. The first recorded public Christmas tree was erected here in 1510 and the house still serves as a magical backdrop to one of Europe’s most beautiful Christmas trees.

The banks of the Daugava River are still home to a vibrant trading community in Riga’s Central Market. Housed in five Art Deco Zeppelin hangars, the market has more than 3,000 stalls and is one of the largest in Europe. Four of the hangars are devoted to fresh produce while in the fifth you can sample prepared local dishes such as smoked eel, a meal Viking traders would have enjoyed long before Hanseatic merchants arrived in Riga.

Visby, Sweden There are no direct flights from the UK to Gotland island; fly to Stockholm (2hrs 10mins) and then on to Visby Airport from there (40mins). Alternatively, for a more leisurely multi-day route, take the train to Stockholm – via the Eurostar or Stena Line Rail & Sail – and then board a ferry from there.

Lübeck, Germany There are no direct flights from the UK to Lübeck; fly to Hamburg (1hr 25mins) and then connect at Hamburg Hbf to get the train on to Lübeck (40mins). Alternatively, take the Eurostar to Lübeck via Brussels, Cologne and Hamburg.

Tallinn, Estonia International flights land at Lennart Meri Tallinn Airport; direct flights from the UK take around 2hrs 50mins. Alternatively, for a more adventurous three-four day alternative, either travel by train and ferry via Copenhagen and Stockholm; or by Eurostar with connecting trains to Rostock in Germany, and from there take a ferry to Tallinn via Helsinki.

Gdańsk, Poland International flights land at Gdańsk Lech Wałęsa Airport; direct flights from the UK take around 2hrs 10mins. Alternatively, take the train, via Brussels, Cologne and Berlin; or take the ragged two-day northern route via a ferry and then a bus from Rotterdam through Lübeck and Szczecin.

Rostock, Germany There are no direct flights from the UK to Rostock; fly to Hamburg (1hr 25mins) and then connect at Hamburg Hbf to get the train on to Lübeck (40mins). Alternatively, take the Eurostar to Rostock via Brussels, Cologne and Berlin. Try this:

Riga, Latvia International flights land at Riga International Airport; direct flights from the UK take around 2hrs 30mins. Alternatively, take the train via Brussels, Warsaw and Vilnius, or the Eurostar to Stockholm and an overnight ferry from there.