British Isles Cycling Cruise 2026

Santana Adventures always dreamed of offering the perfect British Isles adventure spanning all six kingdoms. Despite the seemingly small size of the British Isles, the sheer wealth of cycling is awe-inspiring. In 2019, our first British Isles itinerary cruised the Irish Sea before circling Scotland’s North Cape to reach Edinburgh. Our second version exited the Irish Sea to pass through a different portion of the North Atlantic to reach Greenwich. Realizing the best days of both challenging tours were within the calm confines of the Irish Sea, our superior plan for 2026 is to avoid the tempestuous Atlantic while enjoying a finer collection of rides. As with Goldilocks, this third sampling of cycling through all six Kingdoms of the British Isles will be “just right.”

Embark Day – Santana’s 2026 British Isles Cycling Cruise will again start from Dublin, where everyone’s favorite English-speaking capital is also the friendliest city in Europe.

Most participants will arrive two to three nights early for our optional Dubin PreTour, which explores the heart of the Irish capital. After a walking tour through Temple Bar, a vivacious district with live music and dozens of pubs, other activities include a reserved-time viewing of the Book of Kells. After a brief introduction and route talk, a welcoming-night culinary experience awaits!

Day 2 – The following morning we’ll wake up in Northern Ireland, where our ride along one of the most spectacular coastlines in the world will take us to a clifftop castle perched over the Irish Isle’s North Channel.

Built in the 4th century to fend off Saxon raiders, hundreds of years later it protected this coast from the Vikings. You’ll feel immersed in Irish history as you pause for a photo in front of this historic fortress.

As we pedal down the coast we’ll park our bikes for a short hike to reach one of the natural wonders of the United Kingdom. Hopping across the stones of Giant’s Causeway, it’s incredible to imagine how an ancient underwater volcano created the unique honeycomb pattern of shoreline rocks.

A little further along the cliffs, we’ll use the high rope bridge at Carrick-a-Rede with phenomenal views of the Irish Sea.

Today’s longer routes include the fishing village of Ballycastle before looping inland to cycle through The Dark Hedges (one of the many spots of today’s ride where Game of Thrones was filmed).

All routes return through the colorful village of Bushmills, where participants can detour past the namesake distillery to sample a few drams of Irish Courage.

Day 3 – After sailing deep into Scotland’s Firth of Clyde, our second day of rides begin from a small port near the edge of Glasgow.

Our routes today begin by venturing into a mild section of the Scottish Highlands, where we’ll pedal alongside lochs, waterfalls, and forest glens on our way to a 13th century castle redecorated with stunning modern artwork.

After a sojourn to explore the estate, longer route options include challenging climbs. The easier choice will be a Clydeside ferry crossing to circle a small island famous among cyclists for its choice of coastal cafes. Back on the mainland, all routes hug the Scottish coast for an effortless return to the ship.

Whether you’re seeking a challenging cycling tour with long miles or a relaxing glide through nature; every day you’ll have a choice of rides and route stops. All of the rides are GPS-guided, so that you can enjoy the British Isles your way and at your own pace.

A “Late Lunch” is available every day aboard the Star Pride after returning from your ride. Additionally, many of our participants do love to stop for lunch at local restaurants and pubs for a more authentic local experience during their rides.

On each night of our cruise we’ll enjoy dinner in any one of the five restaurants aboard the Star Pride, while our floating five-star resort transports us to our next hand-selected cycling destination.

Day 4 – This morning we’ll hop on our bikes to explore the Isle of Man, a fourth country in only four days. Inhabited by Manxmen and famous for its annual TT motorcycle race, this island’s amazing routes inspired a local kid to take up cycling. Recently knighted by King Charles III, during his pro cycling career Sir Mark Cavendish (aka The Manx Missile) won 35 Tour de France stages, besting the previous record held by Eddy Merckx. This very real island with great cycling and a collection of antique railways is also the inspiration for Sodor.

Riding from the ferry port of Douglas, we’ll cycle next to a still-active steam railway to reach one of the world’s most beautiful bike shops. From there a rail trail uses the abandoned cross-island express line to reach the opposite coast for our visit to Peel Castle. Along the way we’ll weave our way through storied elm forests to reach ancient castles, Victorian churches, nature preserves, and a fabled-stone circle — one of the age-old mysteries of the British Isles.

The exact purpose of these ancient stone circles remain elusive, many speculate they were erected as tombs to great chiefs, sacrificial altars to the old gods, or even portals to another realm. Regardless of your beliefs about these enigmas, the majesty of these sacred places is palpable as you stand before them in the lush green fields.

Day 5 – Every year millions of rock music fans make a pilgrimage to Liverpool in their attempt to get closer to the birthplace of the Beatles. The best reviews are from those who explore the “World Capital of Pop” by bike—the same way four local lads discovered places such as Penny Lane and Strawberry Fields.

Today’s tourists also stop at the grave of Eleanor Rigby and enjoy visits to famous clubs, including the must-see Cavern Club which still reverberates with the sounds of over 290 Beatles gigs.

Liverpool’s still-trendy waterfront has statues, murals, and a Yellow Submarine. At a port where big ships have prevented a downtown bridge, the legendary ferry across the Mersey is not only where the boys were paid to entertain passengers, it’s also where they returned for their first performance with a new recruit named Ringo. While urban cycling isn’t typically part of our programs, we found that the upbeat atmosphere of downtown Liverpool coupled with the expertise of local guides makes cycling an exciting prospect.

Day 6 – This morning we’ll cycle a fifth country in five days. Although Wales, like Scotland and Northern Ireland are part of the UK… the Welsh are proud of their heritage, which includes their own language! Our rides from Holyhead explore the island of Anglesey, where the bike paths wind through majestic sequoia forests.

One of Jan’s favorite highlights is a short hike down the “thousand steps” and across a bridge to reach a picturesque island lighthouse nestled over the Irish Sea.

The day continues by riding along Trearddur Bay and across Four Mile Bridge to reach the last surviving windmill in Wales. Now the home of a fabulous family-run bakery, run by an eccentric Welshman, where you can try their photo-worthy donuts produced from mill-ground flour and sample the Windmill’s handcrafted gin—produced using onsite botanicals. Before getting back on your bikes, take time to discover the adjacent Iron Age archeological site with its stone-and-hide dwellings.

A slightly longer return continues north to a secluded fishing village where riders can eat lunch while looking out over a small harbor where boats rise and fall with the tide.

Stronger riders can opt for a metric-century that loops past Beaumaris Castle and the iconic Menai Suspension Bridge which connects the island of Anglesey to mainland Wales. All riders will finish the day by taking in the rolling hills through a coastal forest before returning to Holyhead.

Day 7 – A second day in Wales (!) was mandated by the great cycling routes linking Milford Haven with Saint Davids; small towns at opposite ends of the Pembrokeshire Coast National Park. While Europe is famous for its Catholic cathedrals, few are as impressive as Saint Davids, a monastic community founded in the year 589.

Six centuries later Pope Callixtus II decided that a Cathedral would be sited here, and per his Papal Decree two pilgrimages to Saint Davids are equivalent to a trip to Rome, and three would equal a journey to Jerusalem. Converted to an Anglican Cathedral by King Henry VIII, his Tudor grandfather was entombed at the foot of the high altar. The adjacent Bishop’s Palace is nearly as impressive as the Cathedral.

After using coastal routes to reach Saint Davids, our inland return uses tiny lanes and stops at a stream-side woolen mill where craftsmen use the ancient machinery to produce fine textiles.

After exploring the looms of the mill’s busy work floor, we recommend a restful interlude in the Solva Mills tea shop. In addition to indoor seating, there are tables at the water wheel.

Day 8 – After a cruise across the Irish Sea, we’ll awake in Cork’s seaport for a memorable day of Irish cycling. Although the biggest tourist draw in Cork County is a lipstick-stained stone at Blarney Castle, a better set of cycling routes avoids city traffic to tour Camden Fort Meagher, the historic site preferred by locals.

Routes continue past this coastal fortress and former prison situated perfectly to protect the largest natural harbor in the world.

Medium and long riders will have the chance to find lunch in Kinsale, a historic fishing village that has re-imagined itself to become one of Ireland’s leading get-away destinations as well as the country’s most colorful town.

The longest loop on our tour’s final day of cycling continues past Kinsale to reach the Lusitania memorial at Old Head.

Do you desire the Gift of Gab? This day’s non-cycling options include Blarney Castle, where you can kiss the stone and tour the gardens.

After 8 nights aboard, and 7 days of rides in 6 countries, disembark will occur in Dublin. Dublin’s DUB Airport is served by all 3 airline alliances. If you wish to spend additional time in the British Isles or Europe, DUB airport offers convenient train service across Ireland and short flights to all parts of Europe.

Santana has chartered Windstar’s all-suite Star Pride for our 2026 British Isles Cycling Cruise!

The Star Pride 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, all with an exterior view, makes it easy to find one that’s right for you.

The Star Pride 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 Adventures always dreamed of offering a British Isles adventure spanning all six kingdoms. In 2019, we chartered the Star Breeze for a cycling cruise of Northern Ireland and the Northern Coast of Scotland. In 2024, our second version exited the Irish Sea to pass through a different portion of the North Atlantic to reach Greenwich. The cycling was spectacular, but our vision was not yet fully realized. Realizing the best days of both challenging tours were within the calm confines of the Irish Sea, our superior plan for 2026 is to avoid the tempestuous Atlantic while enjoying a finer collection of rides. As with Goldilocks, this third sampling of cycling through all six Kingdoms of the British Isles will be “just right.”

Santana’s latest British Isles itinerary is a culmination of over a dozen years of planning, scouting, and touring in order to offer you the ultimate British Isles cycling experience with rides in all six countries! Listening to the invaluable feedback of our participants, we have designed a true highlight reel of the best cycling destinations along the idyllic Irish 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 Pride so special? In late 2020, the Star Pride 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 Pride 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!

The Star Pride we’ve chartered for the British Isles 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, now have enhanced soundproofing, and feature all-new bathrooms. Added suites include new categories at both ends of the price range. Now that the ship has relaunched, you not only have a wider range of staterooms to choose from, the Star Pride has five gourmet dining venues to provide a wider range of fresh cuisine.