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Winter Cycling Holidays

Winter Cycling Holidays

Escape the cold in the best winter cycling destinations

Our winter cycling tours are the best way to take you and your bike from cold winter to new, hot summer. Explore global destinations and beautiful exotic landscapes on a winter cycling holiday with Eat Sleep Cycle.

Our trusted, local guides will help you explore new landscapes at your own pace, and trust us the views and winter heat are the perfect salve to the winter blues.

Riders can choose to join a group tour or opt for a private trip.

Our winter cycling holidays range

If you’re looking for an epic winter cycling holiday in Europe, South America or even if you’re not sure where yet, Eat Sleep Cycle has what you need. Check out our warm winter cycling tours below.

New Year in Málaga
Andalucia
|
6 days
|
Intermediate
|
Road

New Year in Málaga

2999.00
Special offer! As a special treat we’re offering free bike hire…
Next Departures
29 December 2025
28 December 2026
4
Scheduled
417 km
7,199 m
Offer
Christmas in Girona
Girona
|
6 days
|
Intermediate
|
Road

Christmas in Girona

1899.00
Welcome to cycling paradise at Christmas time! Join the Eat Sleep…
Next Departures
22 December 2025
22 December 2026
4
Scheduled
357 km
4,597 m
New
Málaga Road Camp
Andalucia
|
7 days
|
Advanced
|
Road

Málaga Road Camp

2199.00
Special offer! To help kick start your winter training, we’re offering…
Next Departures
9 February 2026
4
Scheduled
500 km
8,460 m
Offer
Girona Road Camp
Girona
|
7 days
|
Advanced
|
Road

Girona Road Camp

2199.00
If you’re looking for a block of long rides in the…
Next Departures
15 March 2026
5 April 2026
4
Scheduled
470 km
7,260 m
Tour of Gran Canaria
Canary Islands
|
7 days
|
Advanced
|
Road

Tour of Gran Canaria

3299.00
The Canary Islands are a paradise for cyclists seeking to escape…
Next Departures
3 November 2025
19 January 2026
4
Scheduled
595 km
13,065 m
Canary Islands Gravel
Canary Islands
|
8 days
|
Advanced
|
Gravel

Canary Islands Gravel

3799.00
With ideal riding conditions 365 days a year, majestic landscapes, challenging…
Next Departures
5 January 2026
4
Scheduled
423 km
9,760 m
New
Patagonia Gravel: The Great Divide
Patagonia
|
8 days
|
Advanced
|
Gravel

Patagonia Gravel: The Great Divide

4499.00
For adventure seekers, nature lovers and gravellers. Ride from Chile across…
Next Departures
23 November 2025
30 November 2025
10 December 2025
2
3
4
Scheduled
453 km
6,900 m
Top seller
The Great Lakes of Chile Road Tour
Patagonia
|
8 days
|
Intermediate
|
Road

The Great Lakes of Chile Road Tour

4599.00
Patagonia on Two Wheels: A Road Cycling Adventure Embark on an…
Next Departures
2 December 2025
15 December 2025
23 February 2026
3
4
Scheduled
418 km
5,042 m
New
Classic Climbs of Medellín
Colombia
|
6 days
|
Advanced
|
Road

Classic Climbs of Medellín

3899.00
This is a tour designed for road cyclists looking to experience…
Next Departures
26 January 2026
4
Scheduled
393 km
7,570 m
New
Classic Climbs of Málaga
Andalucia
|
6 days
|
Intermediate
|
Road

Classic Climbs of Málaga

2999.00
Discover some of the most beautiful corners of Malaga guided by…
Next Departures
17 November 2025
13 April 2026
12 October 2026
4
Scheduled
417 km
7,199 m
Beyond Medellín
Colombia
|
7 days
|
Advanced
|
Road

Beyond Medellín

4199.00
Welcome to the coffee-scented mountains of the Western Colombian Andes. Filled…
Next Departures
8 December 2025
14 December 2026
4
Scheduled
430 km
7,850 m
New
Colombia Gravel Adventure
Colombia
|
8 days
|
Advanced
|
Gravel

Colombia Gravel Adventure

3899.00
Welcome to the coffee-scented mountains of the Western Colombian Andes. Filled…
Next Departures
10 November 2025
2 February 2026
2 November 2026
3
4
5
Scheduled
386 km
8,880 m
Top seller
Andalucia Gravel Adventure: Badlands Official Tour
Andalucia
|
7 days
|
Intermediate
|
Gravel

Andalucia Gravel Adventure: Badlands Official Tour

3999
Discover the iconic Badlands region with Eat Sleep Cycle on our…
Next Departures
16 February 2026
16 November 2026
3
4
5
Scheduled
405 km
5,783 m
Top seller
Patagonia Lakes & Volcanos: Chile to Argentina
Patagonia
|
7 days
|
Advanced
|
Gravel

Patagonia Lakes & Volcanos: Chile to Argentina

4799.00
Experience the unending beauty of Patagonia on our ultimate experience for…
Next Departures
16 February 2026
16 November 2026
4
5
Custom tours
340 km
6,550 m
Algarve Gravel
Portugal
|
6 days
|
Advanced
|
Gravel

Algarve Gravel

2899.00
Algarve is a hidden gem of cycling in Europe. With over…
Next Departures
17 November 2025
9 November 2026
4
5
Scheduled
300 km
3,604 m
New
Tour of Mallorca Self-Guided
Mallorca
|
7 days
|
Advanced
|
Road

Tour of Mallorca Self-Guided

1899.00
Ride the scenic landscapes of Mallorca on our 6 night self-guided…
4
Self Guided
540 km
10,191 m
New
Patagonia: Self-Guided Tour
Patagonia
|
7 days
|
Advanced
|
Gravel

Patagonia: Self-Guided Tour

2399.00
For adventure seekers, nature lovers and gravellers. Ride across the Argentinian…
2
3
4
Self Guided
327 km
4,010 m
New
Off-Grid Girona Micro-Adventure
Girona
|
4 days
|
Intermediate
|
Road

Off-Grid Girona Micro-Adventure

899
Escape the buzz of the city and go Off Grid on…
4
Self Guided
320 km
4,000 m
New
The Costa Del Sol Self-Guided
Andalucia
|
6 days
|
Intermediate
|
Road

The Costa Del Sol Self-Guided

1699.00
Ride from the beachside city of Málaga to the historic city…
4
Self Guided
310 km
4,690 m
New
Classic Andalucia Self-Guided
Andalucia
|
7 days
|
Intermediate
|
Road

Classic Andalucia Self-Guided

1799.00
This seven-day tour of Andalucia is an unmissable opportunity to visit…
4
Self Guided
396 km
7,610 m
Top seller
Andalucia Gravel Adventure: Badlands Self-Guided
Andalucia
|
7 days
|
Epic
|
Gravel

Andalucia Gravel Adventure: Badlands Self-Guided

1999.00
Discover the iconic Badlands region with Eat Sleep Cycle. The adventure…
3
4
5
Self Guided
467 km
8,300 m
Top seller
Custom Tours
Custom
|
Custom
|
Custom
|
Custom

100% CUSTOM TOUR

1723
Custom hotels
Self Guided
Custom kms
Custom m
Custom

UNSURE WHERE TO START?

In need of a warm winter cycling experience?

It goes without saying that winters can be bleak when you live in northern Europe or Northern America. Maybe you’ve never been on a warm winter cycling holiday before, or you’ve experienced this pleasure a thousand times – at Eat Sleep Cycle, we do our utmost to deliver winter cycling holidays you’ll never forget.

Escape the cold at home and discover a new world of winter warmth. With cycling tours to fit any skill or fitness level across multiple continents, we’re confident you’ll find a trip to suit your situation.

I keep coming back for the combination of excellent service and support, fantastic routes (including some wonderful, lesser known climbs and villages), and great choices of accommodations and dining!

Rich

A wide range of bikes are available to hire on your journey, and we’ll help you match the bike to you and your cycling holiday. Regardless of your location, our team of cycling experts will have you covered.

What you can expect to experience

VARIETY & ROUTES FOR ALL LEVELS

When you join an Eat Sleep Cycle winter cycling holiday, you can expect fantastic routes, quality accommodation and great support from the team. Our itineraries and routes are designed for riders with different skill levels and comfort zones, but with pleasure at the forefront of our minds.

TAILORED RECOMMENDATIONS

We’ll recommend the best roads, journeys, food, drink and more for you. Plus, check out our self-guided cycling & group cycling tour pages to understand the different support levels available.

winter cycling guides

Will Harper

Will Harper

As a coach Will’s primary concern is forging a comprehensive understanding of exactly what makes his athletes tick- everyone is different! His academic background in Law has encouraged him to analyse every aspect of training with great detail and precision. In recent years Will has ridden for some of the UK’s biggest pro teams including ONE Pro Cycling and Swift Carbon Pro Cycling, competing across Europe in some of the world’s most prestigious races. Will is Performance Director at Duchy Cycle Coaching.

Mario
GUID

Mario

During the past 10 years, Mario has lived in different countries, but now he’s back home in Conegliano to ride every steep hill in the area! Despite his focus on road cycling, he’s had some amazing moments with his beloved steel gravel bike! Mario has been a member of the ESC Team since 2019 and couldn’t be happier! He looks forward to seeing you on the road soon!

Josep
GUID

Josep

Josep is from a small city in Catalunya called Reus. He loves cycling and has a passion for sharing cycling experiences with others. He’s a guide for Eat Sleep Cycle all over Europe & leads our Morocco tours.

Fernando
GUID

Fernando

Fernando lives in the Montes de Málaga! He’s spent a career travelling extensively and working with the UN. A Malagueñan, Fernando rides MTB and road and continues to love to travel.

Laura
GUID

Laura

Laura is a guide, professional cycling coach and endurance cyclist who has completed some of the coolest ultradistance gravel events (which she absolutely loved!). Laura loves guiding as she really enjoys empowering people to ride their bikes and discover new places, help their cycling adventures come true, and share unforgettable moments together.

Emanuela
GUID

Emanuela

Emanuela is Italian and after many years living in Barcelona relocated to Mallorca. She started triathlon 10 years ago and has made it her life! Alongside guiding Emanuela hosts guests from all over the world in her Airbnb.

DOUBTS?
CONTACT US

Our winter cycling holiday services

custom trip design

custom trip design

We are experts in designing trips with you, the rider, in mind. We love to learn about you and your cycling dreams to create a trip of a lifetime!

ride support

ride support

We provide professional ride support and in 2023 we welcomed our first fully electric support van to our vehicle fleet! Choose your support level, from on call phone support on our self-guided packages to full vehicle & mechanical back up on our supported tours.

local guides

local guides

Our network of local guides spans across Europe and into Morocco. We work with guides who are the type of people you can’t wait to go on a ride with. Expect a professional, friendly service and deep local knowledge. Our guides are trained to keep you safe & enjoying every pedal stroke.

food & culture

food & culture

The perfect paring with any good cycling holiday is a dose of great local food & culture. We work with local partners who put people & the community first to bring you delicious food every day. Experiencing the local culture is an integral part of travel. Meet the people who define the place you’re riding through & learn about it’s history.

accomodation

accomodation

We seek out unique, family run, high quality places to stay which only add to the experience and guarantee a good night of rest & recuperation. Expect a warm welcome and memorable experiences.

bike hire

bike hire

Every year we select a new fleet of bikes to ensure your cycling tour of a lifetime is enjoyed on one of the best bikes in the world. Our brand partners include Basso, Colnago, Cannondale & Giant.

TRANSFERS

TRANSFERS

We arrange private transfers for our guests. We’ll ask you for your travel details and take care of the rest.

special requests!

special requests!

We love to celebrate special occasions with our guests, let us know the special moment you’ll be celebrating on tour & we’ll make some magic happen.