If you find yourself staring at dreary skies and wet roads, wishing for better cycling weather—we’ve got the answer! Winter can be the ideal time to discover a new riding location and trade the bad weather in for some off-season sun. There is certainly no shortage of sunny locales to enjoy all year long, but we’re breaking down some of the best destinations in a series, offering more detail and highlighting some of the options available.

We start in the land of sun and wine—Portugal. With summer heat making cycling a challenge in many parts of the country, the off-season is the ideal time to explore this beautiful country. There are tours available for all styles and budgets, and we’ve selected 5 great tours that offer variety depending on the type of experience you’re after. All tours are available throughout the winter months.

Get to know the authentic Algarve

Offered in 8- or 5-day trips, this moderate cycling tour in the Algarve takes you all the way from the Spanish border in the east to Sagres at the southwestern tip of Portugal. You will get an authentic Algarve experience while exploring hidden inland villages, the Natural Park and lagoon of the Ria Formosa, and taking in fantastic views from the top of cliffs. A much different Algarve than the tourist-packed beaches, this tour is about enjoying nature at its finest and getting to relax in gorgeous hotels at the end of a solid day’s riding.

Level: Moderate
Distance: 260km (8-day trip)
Price: £900

Challenge yourself in Madeira

Get your legs burning while exploring the sub-tropical island of Madeira. Winding around most of the coast from Canico town to the capital, Funchal, this self-guided tour allows you to enjoy Madeira’s mild climate while passing through coastal villages, ancient grottoes, and traditional thatched houses. This tour involves a few long ascents, including a stunning cycle to Europe’s highest cape. You’ll also have plenty of time to unwind and enjoy Madeira’s famous wine.

Level: Moderate to Challenging
Distance: 121mi/195km
Price: £706 to £1124 for 7 nights

Experience relaxed cycling from a delightful farmhouse

This is a trip for those looking to experience the best of Portugal’s countryside and get acquainted with a relaxed rural way of life. Staying from four nights to a full week, you’ll be living in a typical Alentejo farmhouse from which you can venture out on daily rides. Choosing from five diverse cycle routes, you’ll have the opportunity to visit some of Europe’s largest and oldest megalithic monuments, ride past Roman ruins, discover ancient watermills and take in the views from hilltop castles. To stay fueled, you’ll have time to stop off at cheese farms, wine cellars, and traditional villages renowned for their rustic meat pies, olives, and fresh herbs.

Level: Easy to moderate
Distance: 44mi/71km
Price: 4 nights from £451 to £619

Get your ladies together for a women-only tour

If you’re looking to plan a girls-only winter vacation, Practice Bicycle Tours offers custom women’s bike trips throughout southern Portugal. They have flexible dates and routes, so all you need to do is round up a few of your favourite gals and create your ideal cycling vacation. They offer a selection of over 70 proven ride routes with a variety of terrain and distances throughout the Algarve.

Level: Easy to moderate
Distance: You choose
Price: N/A

Castles and wine by bike

Benefit from lower prices in the off-season and take advantage of this tour that certainly lives up to its name. You’ll spend most nights sleeping in a castle or an old convent that have been transformed into charming hotels. Along the way, you’ll see the ancient city of Évora, world heritage site, and small fortified hamlets that hold stories of wars with the Moors and Spain. You’ll pass the biggest artificial lake in Europe and have ample opportunities to learn for yourself why Portuguese wine is famous around the world.

Level: Moderate
Distance: 200km
Price: Self-guided from €931

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