Baltic Sea Sailing Island Explorer: Estonia to Copenhagen

An Estonia Sailing Holiday — Westbound Across the Baltic to Copenhagen

Tallinn → Swedish Archipelago → Gotland → Kalmar Strait → Bornholm / Danish Islands → Copenhagen

This Estonia sailing holiday begins in Tallinn, where the medieval towers of the old town rise above one of the Baltic’s most storied harbours. Estonia’s capital has always looked outward across the sea, and it sits at a natural crossroads between Scandinavia and the east, and leaving it by sail feels like stepping into a much older tradition of Baltic seafaring.

From Tallinn, Iris heads west across the open Baltic, guided by wind, waves, and the rhythm of the ship. This is a longer passage as Iris will average around 50 nautical miles a day with longer hours at sea on some days, and some nights under sail. Night watches, sunrises at sea, and the particular peace of sailing through the dark hours are woven into a voyage like this, and they are among the things that make it genuinely unforgettable.

The exact route will always shift with the conditions, but the general course will sail west through the Swedish archipelago, south along the Swedish coast, and on through the Danish islands to Copenhagen. 

Gotland and the Kalmar Strait – The Heart of the Passage

The centrepiece of this Estonia sailing holiday is Gotland, Sweden’s largest island, sitting out in the middle of the Baltic. The UNESCO-listed town of Visby is home to medieval walls, cobbled streets, and the ruins of ancient churches softened by rose gardens. Its dramatic limestone sea stacks, long sandy beaches, and peaceful anchorages tucked into sheltered bays are certainly best explored under sail.

From Gotland, Iris may continue south through the Kalmar Strait. A narrow, sheltered waterway that runs between the Swedish mainland and the island of Öland. After the open Baltic crossing, the strait offers a calmer sailing experience, with historic towns on one shore and Öland’s flat limestone plains on the other. 

• Visby, Gotland – a walled medieval city, cobblestone lanes, and anchorages on a dramatic Baltic island
• Gotland’s sea stacks – distinctive limestone formations rising from the clear Baltic water
• Kalmar Strait – sheltered sailing between the Swedish mainland and the UNESCO landscape of Öland
• Kalmar Castle – one of Scandinavia’s best-preserved Renaissance fortresses, sitting directly on the waterfront

The Danish Islands – The Final Leg to Copenhagen

As Iris crosses into Danish waters, the character of the coastline shifts. Depending on wind and timing, possible stops on this final leg include Bornholm – Denmark’s most easterly island, with granite cliffs, sandy beaches, and the dramatic ruins of Hammershus Castle. The historic port of Ystad on the Swedish south coast, or the sheltered waters of the Danish South Sea, with its scattering of quiet islands and unhurried harbour towns. Each potential stop adds its own character to the passage. Bornholm feels remote, while Ystad has a quiet working harbour that welcomes arriving sailors. 

The voyage ends in Copenhagen. After days of open Baltic sailing, island anchorages, and night watches under a northern sky, arriving in one of Europe’s great capital cities by tall ship is the perfect finale.

Copenhagen repays time spent exploring after the voyage – whether that’s a long lunch on the waterfront, a wander through the old town, or simply sitting by the water and letting the miles sink in.

Tall Ship Iris – a Traditional Ketch

Built in 1916 as a herring drifter and converted into a charter vessel, Iris is a boat with real character and a hull that was built to handle the Baltic. Her traditional ketch rig and sturdy steel construction make her well-suited to longer passages, and life below decks is comfortable and considered. She sleeps 12 guests in 6 private twin cabins, with a generous saloon that includes a dining area, sofa corner, and a small onboard library.

• Sleeping: 6 private twin cabins, sleeping up to 12 guests
• Below decks: Spacious saloon with dining area, sofa space, and library
• Food & service: Full board, prepared by the crew
• Experience: Hands-on passage sailing with skippers Jans and Liv
• Suitable for: Solo travellers, couples, those seeking a genuine sailing challenge

Things to note

Sailing vs Shoretime

Night-watches?

Travel insurance notes

As this is an active adventure holiday, we advise that everyone has the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.

Please read more information on our Insurance guidelines page.

This voyage will be more than 12 miles offshore.