Baltic Sea Cycling Cruise 2028

Welcome to Stockholm, Sweden! Spread across fourteen islands where the shimmering waters of Lake Mälaren meet the Baltic Sea, Sweden’s magnificent capital is a city that seems tailor-made for exploration. Often called the “Venice of the North,” Stockholm enchants visitors with its colorful waterfront buildings, elegant bridges, grand royal palaces, and cobblestone lanes that wind through centuries of Scandinavian history.

In the heart of the city, Gamla Stan—Stockholm’s beautifully preserved Old Town—invites you to wander narrow medieval streets, discover charming cafés, and admire architecture that has watched over the harbor for hundreds of years. Beyond its historic center, leafy parks, fashionable neighborhoods, and spectacular waterfront promenades reveal a capital that effortlessly blends Old World charm with contemporary Scandinavian sophistication. With its pristine waterways, inviting outdoor cafés, and endless summer daylight, Stockholm provides a spectacular setting for the beginning of our Baltic Sea adventure.

Want to make your arrival even more memorable? Join our optional Stockholm PreTour! Arrive two or three nights early and discover why this captivating Scandinavian capital deserves more than a passing glance. Our thoughtfully planned PreTour will provide the perfect introduction to Stockholm, combining comfortable accommodations, memorable sightseeing, and plenty of opportunities to experience the city’s distinctive culture and charm. Best of all, we’ll take care of the logistics!

From a friendly airport greeting and convenient transfers to the seamless handling of your luggage and bicycles, our PreTour makes arriving in Sweden wonderfully effortless. And when embark day arrives, while other travelers are busy navigating transfers and transporting their belongings, you’ll be enjoying another delightful day of discovery as we arrange for your luggage and bicycles to reach our awaiting ship. It’s the perfect way to ease into your vacation—and begin your Baltic Sea Cycling Cruise feeling relaxed, refreshed, and ready for adventure!

Day 2 – Our first day on two wheels is the perfect introduction to cycling in the Baltics. We’re exploring a corner of Finland that feels more Swedish than Finnish. Welcome to the Åland Islands, where the locals speak Swedish, fly their own flag, and enjoy a laid-back island lifestyle. Our quiet country roads wind through dense pine forests, rolling farmland, and tiny villages dotted with traditional red-painted barns. Around every bend, another glimpse of the sparkling Baltic Sea.

Our first stop is Kastelholm Castle, a 14th-century fortress where Swedish royalty once stayed. We’ll explore its medieval chambers and winding staircases, with time to peek into island life from centuries past at neighboring Jan Karlsgården.

A few miles farther, we’ll discover the ruins of Bomarsund Fortress, where the Russians dreamed of building an impregnable Baltic stronghold. Unfortunately for them, the British and French had other ideas. During the Crimean War, they blasted the unfinished fortress into ruins, leaving massive stone walls for us to explore.

Our return ride delivers more pine-scented forests, peaceful villages, and winding country lanes, with an extended loop for those craving extra miles. Back in Mariehamn, faster riders may have time for one final adventure aboard the Pommern, a magnificent four-masted sailing ship that once rounded Cape Horn carrying cargo between Europe and Australia. Today, she’s a remarkable survivor from the golden age of sailing ships—and a fitting finale before returning to our own floating home.

Day 3 – Of the Nordic countries, Finland may be the most overlooked. After centuries of Swedish and Russian rule, the fiercely independent Finns gained their freedom in 1917 and defended their homeland against Soviet and German forces during WWII. With their distinctive language and culture, the Finns have carved out a remarkable identity. Perhaps it’s no coincidence that Finland has topped the world’s happiness rankings for nine consecutive years.

Today’s cycling is centered on Turku. A hidden jewel largely unknown to Americans, Finland’s oldest city combines a medieval heart with bridges to forested islands and miles of peaceful cycling routes.

As we pedal through leafy neighborhoods, waterfront parks, and the surrounding islands, we’ll discover a city where cycling and nature are woven into everyday life. Perhaps we’ll uncover a few secrets behind Finland’s remarkable happiness.

Day 4 – Welcome to Estonia, where medieval towers, onion-domed Orthodox cathedrals, and an exceptionally well-preserved 13th-century street plan are hallmarks of Tallinn, one of Europe’s most glorious cities.

After decades of Soviet occupation, Tallinn reclaimed its independence in 1991, revealing a fiercely proud capital whose medieval heart had survived centuries of upheaval. Behind its ancient walls, cobblestone lanes and colorful merchant houses evoke the prosperous trading city that flourished here centuries ago.

Tallinn is nothing less than the Prague of the Baltics—a magnificent setting for today’s cycling adventure through centuries of history.

Day 5 – Our itinerary’s smallest mainland port is Ventspils, Latvia’s historic gateway to the Baltic Sea. Beyond this colorful harbor town, we’ll stretch our legs on a network of paved country lanes winding through forests and farmland, past old stone barns, fields of summer wildflowers, and patches of wild berries.

Back in town, you’ll want to explore one of Latvia’s oldest surviving medieval fortresses. Built in 1290, the Castle of the Livonian Order has guarded this Baltic port for more than seven centuries. Its thick stone walls and centuries of history offer a fascinating contrast to the peaceful countryside we’ve just explored.

The final half-mile back to our ship passes several inviting spots where you might be tempted to linger over a frothy Latvian brew.

Day 6 – Welcome to Sweden! We’ll dock at Visby, a UNESCO World Heritage Site and one of Europe’s best-preserved medieval walled cities. Beyond its ancient gates lies the island of Gotland, celebrated for its unspoiled countryside and remarkable collection of more than 90 medieval churches, many still in regular use.

Concerned about climbing mountains? The hilliest cycling on Santana’s eight-country adventure occurs right here on Gotland, where the highest point on our cycling routes is just 269 feet above sea level. A few gentle rollers are about as challenging as the climbing gets!

Those who claim Swedes are cool and reserved clearly haven’t spent time on Gotland, where friendly smiles and warm greetings are as much a part of the experience as the island’s medieval villages and peaceful landscapes.

Day 7 – Welcome to Lithuania! Our port is Klaipėda, an ancient Baltic seaport whose medieval castle dates to 1252, when German crusading knights established a fortress at the mouth of the Danė River. Known for centuries as Memel, this strategic harbor witnessed repeated struggles between competing European powers.

Today’s cycling begins with a short ferry crossing to the Curonian Spit, a UNESCO World Heritage landscape where a narrow ribbon of sand separates the Baltic Sea from the Curonian Lagoon. Cycling south through fragrant pine forests, past sweeping dunes and Baltic beaches, we’ll explore one of Europe’s most unusual coastal landscapes before returning to Klaipėda.

Stronger riders can extend their adventure with a northern loop through Lithuania’s Seaside Regional Park. Peaceful paved paths wind through fragrant pine forests, wooded dunes, and coastal meadows near the traditional fishing village of Karklė. With occasional glimpses of the Baltic Sea and a landscape of small lakes, wetlands, and protected woodlands, this scenic extension reveals another beautiful side of Lithuania’s coastline.

Day 8 – Arriving in Poland, our yacht-size cruise ship ties up at the dock where Lech Wałęsa and his fellow shipyard workers launched the Solidarity movement that helped bring down communist rule. Their historic victory in Poland’s partially free elections of 1989 set off a chain reaction that included the fall of the Berlin Wall and the eventual dissolution of the Soviet Union.

With centuries of tumultuous history, Gdańsk is a treasure trove of colorful merchant houses, ornate facades, intriguing museums, sidewalk cafés, and inviting beer gardens. Much of its magnificent historic center was painstakingly rebuilt after the devastation of World War II.

Today’s cycling reveals another side of Gdańsk, where an impressive network of bike paths connects leafy parks, inviting neighborhoods, and miles of Baltic waterfront. Our routes explore the city’s quieter corners, passing neighborhood bakeries fragrant with freshly baked pastries before following the coast toward the fashionable seaside resort of Sopot. With sandy beaches, seaside promenades, and plenty of opportunities to stop for a coffee or a Polish treat, it’s a delightful day of cycling through a city that knows how to enjoy life.

Day 9 – Welcome to Bornholm, Denmark’s enchanting “Pearl of the Baltic.” A favorite summer playground for Danes, Swedes, Germans, and Poles, this island is a cyclist’s paradise. Ambitious riders can tackle the island’s celebrated 65-mile coastal circuit, while shorter routes across the island offer equally rewarding discoveries.

One of the island’s most intriguing landmarks is the 12th-century round church at Østerlars, where local legends suggest that returning Knights Templar concealed the Ark of the Covenant beneath its ancient stone floor. Whether or not you believe the tale, the mysterious church is a fascinating reminder of Bornholm’s medieval past.

With its quiet roads, dedicated cycling paths, picturesque fishing villages, and unusually generous sunshine, Bornholm has long attracted cyclists and artists alike. It’s no wonder this Danish treasure is celebrated as the Baltic Sea’s legendary “Island of Light.”

Day 10 – Our ninth and final day of cycling begins in Sassnitz, a historic fishing port on Rügen, Germany’s largest island. Once a fashionable retreat for European aristocracy, Rügen remains one of Germany’s favorite seaside escapes, celebrated for its elegant resort towns, sandy beaches, and distinctive Baltic architecture.

Today’s routes head south along the island’s eastern coast, passing grand seaside villas, picturesque fishing villages, and stretches of Baltic shoreline. Continuing toward the coastal villages of Lobbe and Gager, we’ll discover a quieter side of Rügen before turning north for our return to Sassnitz.

Riders looking for a longer finale can continue north from Sassnitz into Jasmund National Park, where ancient beech forests give way to Rügen’s most spectacular natural landmark: the brilliant white chalk cliffs of Königsstuhl, rising dramatically above the Baltic Sea. What a magnificent setting to celebrate nine days of cycling through eight countries!

Day 11 – Our Baltic adventure concludes this morning in Copenhagen, one of Europe’s most captivating capitals. Famous for its colorful Nyhavn waterfront, royal palaces, picturesque canals, and extraordinary cycling culture, Copenhagen is a city that rewards exploration. From the enchanting Tivoli Gardens to its world-class museums, innovative Nordic cuisine, and lively pedestrian streets, Denmark’s capital offers plenty of reasons to extend your vacation by a few days.

Not ready to go home? Our spectacular Norwegian Fjords Cycling Cruise embarks aboard the very same ship just hours after our Baltic disembarkation. Combine these two extraordinary adventures for an unforgettable back-to-back voyage through Northern Europe!

Santana has chartered Windstar’s all-suite Star Legend for our Baltic Sea Cycling Cruise!

The Star Legend is an ALL-SUITES motor yacht!

The smallest suite, at 277 sq.ft., is twice as large as staterooms found on other new cruise ships.

10 different suite categories makes it easy to find one that’s right for you.

The Star Legend has a 1:1.5 crew-to-passenger ratio to provide award winning service.

A total of 5 gourmet restaurants provide a variety of fresh culinary options. Jan wants you to know that 24-hour room service is a no-cost extra!

Santana has worked with Windstar since 2010. With this win-win relationship, Santana obtains the lowest pricing and best availability. Their yacht-sized fleet allows Santana’s charters to use small ports that are better suited for cycling. We’ve now worked with Windstar to create custom-for-cycling itineraries in the Mediterranean, Tahiti, Japan, British Isles, Australia, New Zealand, Norway & the Baltic Sea.

Santana and our participants love the intimate size of Windstar’s yachts, as does the cruising public and industry critics. Year after year, Windstar wins all the major awards for small ship cruising, and scores the highest return-client loyalty.

Why is the Star Legend so special? In 2020, the Star Breeze was withdrawn from service to take part in Windstar’s “Star Initiative Project”—a quarter billion dollar stretch of their 3 motor yachts (they’re triplets). After cutting the Star Breeze into front and rear halves, a precursor to the installation of quieter new eco-friendly motors and generators, they replaced the entire ship’s decor and furnishings—Every single suite has been rebuilt better than new. Before buttoning things up, they slid in a new 84-foot midsection.

This 90 second video shows the process –
https://www.youtube.com/watch?v=OTpVxCOjmPY&feature=youtu.be

The Star Legend we’ve chartered for the Baltic Sea is essentially a new ship with larger additional public areas, a tripled-size ocean-view swimming pool, new tenders, new lifeboats, and a fleet of expedition-worthy zodiacs.

Existing suites have all been completely rebuilt, will obtain enhanced soundproofing, and feature all-new bathrooms. Added suites include new categories at both ends of the price range. Now that the Star Legend has been relaunched, you not only have a wider range of staterooms to choose from, the Star Legend now has five gourmet dining venues to provide a wider range of fresh cuisine.