Baltic Sea Sailing Island Explorer: Sweden & Estonia

An Estonian Sailing Holiday Across the Baltic — Karlskrona to Tallinn

Karlskrona → Kalmar Strait → Öland → Gotland → Saaremaa → Tallinn

This Estonia sailing holiday begins in Karlskrona – a UNESCO World Heritage city built across a series of islands on Sweden’s southern coast. It is a great starting point for a voyage that will take Iris east across open water, through some of the most historically rich and scenically varied sailing in northern Europe.

The Western Baltic at this time of year typically offers low swell and moderate winds, making for comfortable passages even for those new to sailing. To cover the distance comfortably, Iris will aim to average around 50 nautical miles a day, which means longer hours under sail. Iris will aim to be in port every second day, weather allowing, giving plenty of opportunity to go ashore and explore.

Get to grips with life on board as you help set the sails, take the helm, and learn some basic rope-work under the guidance of Jans and Liv, Iris’s owners and skippers. 

The Kalmar Strait and Öland — Sweden’s Historic Eastern Coast

The first leg of this estonia sailing holiday takes Iris north along the Kalmar Strait – the narrow body of water that runs between the Swedish mainland and the long, flat island of Öland. Historic towns line the mainland shore, picturesque coastlines open up on both sides, and the strait itself offers sheltered sailing as Iris heads northeast.

Öland – a UNESCO World Heritage landscape – stretches alongside for much of this leg with its flat limestone plains and traditional windmills visible from the water. The mainland city of Kalmar is one of the finest historic towns on the Swedish coast, with a beautifully preserved Renaissance castle sitting directly on the waterfront. 

• Kalmar Castle – one of Scandinavia’s best-preserved Renaissance castles, sitting directly on the waterfront
• Öland’s limestone plains – a UNESCO World Heritage landscape of windmills, wildflowers, and ancient ruins
• Sheltered sailing – the strait offers some of the best sheltered sailing on the Swedish coast
• Historic coastal towns – a string of well-preserved settlements with deep seafaring traditions

Gotland and Saaremaa – Two Islands at the Heart of the Baltic

From the Kalmar Strait, Iris heads out into the open Baltic towards Gotland – Sweden’s largest island. The medieval city of Visby, encircled by some of the best-preserved city walls in northern Europe, is a UNESCO World Heritage site. Beyond Visby, Gotland’s interior opens up into limestone cliffs, sandy beaches, and quiet forests – a landscape unlike anything on the Swedish mainland.

From Gotland, the course continues east to the Estonian island of Saaremaa. Dense forests, traditional windmills and the small town of Kuressaare are dominated by the remarkably well-preserved walls of a medieval bishop’s castle.

• Visby, Gotland – medieval city walls, cobbled streets, and rose gardens in the ruins of ancient churches
• Gotland’s coastline – limestone sea stacks, sandy beaches, and clear Baltic water
• Saaremaa’s forests and windmills – unhurried countryside at a pace entirely its own
• Kuressaare Castle – a medieval bishop’s fortress in near-perfect condition, right on the waterfront

Arriving in Tallinn – A Baltic Capital Like No Other

The voyage ends in Tallinn, the Estonian capital and the finale of this Baltic passage. Arriving by sail into Tallinn’s harbour, with the towers and spires of the old town rising above the waterfront, is one of those moments that stays with you. The old town – another UNESCO World Heritage site – is one of the best-preserved medieval city centres in Europe, with winding cobbled alleys, merchant houses, and a unique atmosphere that sits comfortably between history and the modern city that has grown up around it.

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.