The enchanting Old Town of Estonia’s capital city could well be described as a Sleeping Beauty, having emerged from years of Soviet occupation unkempt and therefore untouched, now to be celebrated as one of Europe’s most captivating destinations.

People arrive in their droves from giant cruise ships, and on the two days we were in Tallinn 10 different liners arrived and departed, jettisoning a million people between them into the busy port.

We know this as we parked for two nights in a thin white line of motorhomes acting as a bastion between the Baltic-crossing ferries’ dock and the giant cruisers’ terminal.

Cruising all over the Baltic

Tallinn’s position on a deep bay meant its natural establishment as a trading port and defensive fortress in the 1200s, when conquering Danes overran the settled Estonians.

The first stone fort was built on the hilltop of Toompea in 1227, which today remains the site of the city’s government and the seat of the country’s parliament.

The Danes sold their northern Estonian lands to the Teutonic Order in the mid 1300’s, causing a clash between the knights and their bishop, ensconced in the palace on the hill, against the mainly German merchants and artisans in the lower town.

Their colourful three storey houses and grain stores still wind along cobbled streets and into shady courtyards. A fortified wall was built between Toompea and the town and a long section is still in place today.

We meandered along its walls admiring the conical rooves of the nine towers, which are all that are left of the original 45.

Lower town defensive walls

Tallinn’s photogenic skyline is dominated by towers, including those of churches and guild halls.

We climbed up the steep stone spiral staircase inside the Town Hall and perched precariously at the narrow windows of the delicate minaret for lovely views of the central square and market place, below.

Above Old Town Main Square

One of us also gamely bounded up the claustrophobic and cramped 124 meters of St Olaf’s tower, taking photographs of Toompea and the port before the first of the day’s jostling crowds created turmoil on the belfry ladders by climbing up whilst others were heading down.

Back at ground level, Simon relayed that people were slipping on the narrow stone steps, and many were starting to panic in the extremely confined and already overheated space.

View of Toompea from St Olaf’s tower

It did cause us to think about the easy money that the city makes from the sheer numbers of visitors, with seeming little regard for their comfort or safety.

Other examples of this include deteriorating stone walkways around the ramparts of the Old Town and the unsupervised dereliction of the gigantic site of the Soviet’s Olympic hall, both of which are freely accessible but hazardous to walk around, especially in large crowds.

Derelict Soviet Olympic Hall

Like Riga, Tallinn has embraced the dusk till dawn party crowds and until recently had sold itself heavily to hordes of young men looking for cheap beer and flagrant prostitution.

Some sex clubs still line the cobbled back streets, but the city has shifted gear towards designer eateries and music venues for the evening’s entertainment.

When night falls at Tallinn Port

The Rotermann Quarter of old warehouses by the port is now a trendy space of studio apartments, art galleries and eye-wateringly expensive bars. Many new apartments are being built, alongside sparkling new shopping centres to lure in the newly arrived and almost departed.

We took shelter in a rainstorm on our way back to Bertha in Kochi Aidad craft brewery, another example of the ale-drinking entrepreneurism that we had seen a lot of in the Baltic states.

Modern Tallinn

Outside of the Old Town walls the modern city is immediately glass and steel skyscrapers. Tallinn’s population is relatively young and its economy outside of tourism is digitally-driven business. We enjoyed the mix of history and modernity that we experienced in our short stay, before stormy skies threatened our sailing to Helsinki.

In the event the crossing of the Gulf of Finland, although calm, was windswept and battered with rains. We realised that just over the course of two short sailing hours we were leaving East Europe behind, and heading into Scandinavia.