Cycling Holidays

Showing 118 out of 337 trips

We believe that a cycling holiday is one of the best ways to get to know a new destination. Exploring places on two wheels allows you to go further faster, giving you plenty of chances to extend your time in places that interest you. Whether you want to cycle solo on one of our self-guided tours or hit the road with a group and guide, we're sure you'll find something to enjoy.

We head to some of the best cycling holiday destinations in the world, from the rolling hills of  . Wherever you choose to visit, you can expect to see breathtaking landscapes, sample local dishes and immerse yourself in the culture of your destination.

What are you waiting for? Freewheel your way to a new adventure by checking out our cycling holidays below.



Which cycling holiday destinations do you go to?

There are many incredible cycling holiday destinations you can visit with us. Each route has been carefully chosen to ensure you see the very best of the area, including popular spots and lesser-known gems along the way. Here are some of the places you can visit during our cycling holidays:

Italy

We offer both self-guided and guided cycling holidays in Italy, allowing you to experience this magnificent country in a way that suits you. Head to the north and cycle from the Dolomites to Venice, or visit the south to explore the sun-soaked region of Puglia on two wheels.

If you're keen to explore the largest island in the Mediterranean, our Secrets of Sicily tour will be right up your street. Alternatively, you could head to the vineyards of Veneto to immerse yourself in the quaint Italian countryside.

Greece

You can discover the natural beauty of Greece during one of our fantastic cycling holidays. It's one of the most popular cycling destinations thanks to its varied landscape, with incredible vineyards, mountains, coastline and villages to explore.

Get a taste of island life by navigating eastern Crete, visiting archaeological sites, relaxing on golden beaches and enjoying tasty dishes at local tavernas. Or head to the mainland to explore the beautiful Peloponnese and the historic city of Athens, with a guided tour of the Acropolis.

France

France is the perfect place for bike lovers, with a huge number of picturesque trails to enjoy throughout the country. Visit the UNESCO World Heritage area of Champagne or Beaune, the beautiful wine capital of Burgundy, for some well-deserved vino after a day of cycling.

We also have trips to the stunning Loire Valley, the hilltop villages of Provence, breathtaking Brittany and the delightful Dordogne . You can head out on your own on our self-guided tours or ride with a group of like-minded cyclists on our group holidays.

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2000


4.7 (40 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Denmark

Cycling from Copenhagen

NZ$2025


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : The Dolomites

Cycling from the Dolomites to Venice

NZ$2220


4.8 (6 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Albania

E-bike Across Southern Albania

NZ$2400

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Umbria

The Wine Trails of Umbria Cycling

NZ$2485


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Brittany

St Malo to Mont St Michel Cycling

NZ$2530

 
 

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Holland

Cycling the Highlights of Holland

NZ$2705


5.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Greece

Cycling in the Peloponnese

NZ$2730


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Belgium

Cycling from Bruges to Amsterdam

NZ$2905


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

NZ$3080


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3125

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3210


4.6 (10 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Atlantic Coast

Cycling along the Atlantic Coast

NZ$3830

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Greece

Cycling in Greece

NZ$4025

 
 

VIEW TRIP

Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4160

NEW FOR 2025

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Trentino

Brenner Pass to Venice Cycling

NZ$4180


5.0 (2 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Norway

Cycling in the Lofoten Islands

NZ$7635


5.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Provence

Hilltop Villages of Provence with e-bike

NZ$3500


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
twin centre

Level: 1+ & 2

Printed route
directions

Italy : Veneto

Heart of Veneto Cycling

NZ$2070


4.8 (72 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : Veneto

Bolzano, Verona & Venice Ride

NZ$2375


4.7 (18 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Veneto

Venetian Villas and Vineyards Cycling

NZ$2375


4.7 (57 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Italy : Sicily

Secrets of Sicily Cycling

NZ$2550


4.6 (22 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Cycling

NZ$2685


4.9 (27 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Portugal : The Algarve

Cycling in The Real Algarve

NZ$2815


4.7 (61 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Provence

Cotes du Ventoux Cycling

NZ$2840


4.8 (36 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Sicily

Cycling through Baroque Sicily

NZ$3255


4.4 (20 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France

Landscapes of the Luberon Cycling

NZ$3475


4.4 (21 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Slovenia

Julian Alps to the Adriatic Cycling

NZ$4160


4.8 (118 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Austria : Carinthia

Cycling from Vienna to Budapest

NZ$2245


4.6 (49 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Dordogne

Dordogne Valleys & Villages Cycling

NZ$2355


4.7 (42 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Spain : Catalonia

Contrasts of Catalunya Cycling

NZ$2375


4.7 (53 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

NZ$2595


4.7 (25 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

NZ$2815


4.6 (123 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

NZ$2970


4.3 (12 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

Austria : Carinthia

Lake Constance Cycling

NZ$3060


4.7 (88 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

United Kingdom : Norfolk

Contrasts of Norfolk Cycling

NZ$3190


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal : Mainland Portugal

Porto Coastal Cycling

NZ$3190


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3255


4.7 (85 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$5060


4.8 (88 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : Burgundy

Cycling in Beaune Vineyards

NZ$1630


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

Holland

Cycling from Amsterdam

NZ$1670

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

France : Champagne

Cycling the Vineyards of Champagne

NZ$1715

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

France : Provence

Tour de France - Provence

NZ$1870

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

France : Burgundy

Classic Burgundy Cycling

NZ$2000


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Italy : Italian Lakes

Cycling Lake Garda with e-bike

NZ$2045


4.5 (2 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

NZ$2110

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Austria : The Danube

Cycling along the Danube from Passau to Vienna

NZ$2090


4.9 (20 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling In The Royal Loire Valley

NZ$2110

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 1
Leisurely

Navigation App

Sweden : sweden

Cycling from Stockholm

NZ$135

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

France : Provence

Hilltop Villages of Provence Cycling - Short Break

NZ$2135


4.9 (7 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Short Break

NZ$2135


4.8 (6 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling The UNESCO Loire Valley

NZ$2135


5.0 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Germany : Bavaria

Highlights of Lake Chiemsee by Bike

NZ$2135


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

Austria : Salzburg

Cycling the Lakes and Rivers of the Salzkammergut

NZ$2180

 
 

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2
Moderate

Navigation App

France : Alsace

Cycling the Wine Route of Alsace

NZ$2265


4.8 (9 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Austria : Lake Constance

Highlights of Lake Constance by bike

NZ$2330


4.9 (26 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Spain : Catalonia

Classic Catalan Cycling

NZ$2330


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Germany : Bavaria

Cycling Bavaria’s Lake Chiemsee

NZ$2400


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

NZ$2400


4.6 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Normandy

D-Day Beaches Of Normandy Cycling

NZ$2420


4.5 (6 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

France : Burgundy

Cycling The Grand Crus of Burgundy

NZ$2465


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Greece

Cycling the Coast of Eastern Crete

NZ$2465


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

France : Champagne

Cycle The Wine Route of Champagne

NZ$2510

 
 

VIEW TRIP

Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

United Kingdom : Norfolk

Highlights of Norfolk Cycling

NZ$2510


4.3 (10 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

NZ$2530


4.5 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Belgium

Cycling from Brussels to Bruges

NZ$2575


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Loire

Tour de France - Loire

NZ$2595

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Germany : Bavaria

Lakes and Mountains of Bavaria Cycling

NZ$2595


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

NZ$2595

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Ireland

Walking and Cycling the Wild Atlantic Way

NZ$2595

 
 

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Bordeaux

Cycling The Grand Crus of Bordeaux

NZ$2620


4.5 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Loire

Cycling The UNESCO Loire Valley - Deluxe

NZ$2640


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Provence

Hilltop Villages of Provence Cycling

NZ$2660


4.8 (16 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

NZ$2685


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Burgundy

Cycling the Vineyards From Beaune to Macon

NZ$2705


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

Ireland

Unspoilt Ring of Kerry Cycling

NZ$2705


4.4 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

NZ$2730


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Germany : The Moselle

Meandering the Moselle Cycle Path

NZ$2750

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

France : The Loire

Cycling The Chateaux Of The Loire

NZ$2795


4.5 (10 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Rioja

Vineyards of La Rioja Cycling

NZ$2815


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Canal du Midi

Tour de France - Canal du Midi

NZ$2840

NEW FOR 2025

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Sweden : sweden

Cycling Stockholm's Archipelago

NZ$2840


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

NZ$2840


4.9 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Austria : The Danube

Passau to Vienna Cycling

NZ$2860


4.8 (75 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

NZ$2905


4.6 (5 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Holland

Cycling from Amsterdam to Brussels

NZ$2905


5.0 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$2990

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Portugal : The Azores

Azores By E-bike

NZ$3015


4.0 (4 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

Spain : Extremadura

Cycling Central Spain in Style

NZ$3060

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : Atlantic Coast

Tour de France - Atlantic Coast

NZ$3080

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3145


4.5 (16 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

NZ$3170


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sardinia

Undiscovered Sardinia Cycling

NZ$3430


4.7 (19 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Normandy

Paris to the Sea Along the Seine River

NZ$3520

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

NZ$3565


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

NZ$3565


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Provence

Vineyards of Vaucluse Cycling

NZ$3585


4.8 (18 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Italian Lakes

Cycling the Italian Lakes

NZ$3630


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Corsica

Corsica with Ebike

NZ$3720


4.5 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

Sweden : sweden

Stockholm to Copenhagen Cycling

NZ$3760


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal : Mainland Portugal

Porto to Coimbra Cycling

NZ$3805


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Slovenia

Secrets of Slovenia Cycling

NZ$3870


4.9 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Puglia

Highlights of Puglia Cycling

NZ$4115


4.8 (11 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Estonia

Cycle the Baltics

NZ$4245

 
 

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Guided group cycling

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

NZ$4840


4.8 (5 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Spain : Catalonia

Cycling the Mediterranean Coast in Spain

NZ$5280

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

USA : Maine

Cycling Maine's Coast & National Park

NZ$6690

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

NZ$11350

NEW FOR 2025

VIEW TRIP

Self-guided cycling

20 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

Portugal : Mainland Portugal

Porto to Lisbon Atlantic Ride

NZ$3840

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Croatia

Cycling Croatia's Dalmatian Coast

NZ$3950

 
 

VIEW TRIP

Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

South Africa

Cycling the Cape & Winelands

NZ$5940

 
 

VIEW TRIP

Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Thailand

Cycle Indochina & Angkor - Premium Adventure

NZ$9240

 
 

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Guided group cycling

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

NZ$5740

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

Austria : Salzburg

Austrian Lakes Activities

NZ$2375


4.8 (68 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Spain : Catalonia

Catalonia Activities

NZ$1850


4.5 (13 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

France : The Loire

Multi Activity in the Loire

NZ$2110

 
 

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Dordogne

Dordogne Activities

NZ$2840


4.8 (31 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Spain : Galicia

Cycling the Camino de Santiago

NZ$3255


4.5 (6 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.

Frequently asked questions

What are the best countries for cycling holidays?

There are many fantastic cycling holiday destinations across the world, each offering something different for those who love exploring on two wheels. We've carefully created a range of options in what we believe are some of the best countries for cycling holidays, including Spain, Italy, France and Greece.

The right destination for you will depend on a variety of factors, including how difficult you'd like the route to be and the time of year you want to travel.

Which country is best for cycling holidays in spring?

If you want to head on holiday in spring, you'll be happy to hear there are plenty of fantastic places to cycle! You could get a taste of the laid-back Mediterranean lifestyle by heading to the heel of Italy in March, April or May.

Another great place to explore during spring is Mallorca, where you'll find a mix of inland and coastal trails. Our coast-to-coast holiday gives you the opportunity to see the best of the island solo, from the stunning beaches to the mountain ranges.

Which country is best for cycling holidays in summer?

There are many picturesque places to pedal during the summer months. You could visit Italy to experience the dramatic scenery of the Dolomites in the north or head west to see the unspoilt Costa Smeralda in Sardinia.

France is another picture-perfect summer destination, with cycling holidays available in Provence, Dordogne, Champagne and the Loire Valley. We also offer trips to Germany, Portugal, Spain, Austria and more, so you're really spoilt for choice!  

Which country is best for cycling holidays in autumn?

If you're keen on an autumnal adventure, there are many countries you can explore on two wheels. Why not head to Spain to explore Andalucia? This exhilarating trip will take you through the countryside from Seville to Cadiz, trying tapas and Flamenco dancing between rides.

Or you could enjoy a self-guided cycle in The Azores – a region of Portugal that sits in the mid-Atlantic. It's a nature lover's dream, with tall mountain peaks, lake-filled calderas, lush green vegetation and bright-blue waters.  

Which country is best for cycling holidays in winter?

Our winter sun cycling holidays are perfect for those wanting to get away in the colder months of the year. You could head to the unspoilt western Algarve in Portugal, which is a quieter area away from the typical tourist hotspots. You can expect weather similar to spring in the UK – ideal conditions for cycling.

Want to go further afield? Why not head to the spectacular South Africa? This winter sun cycling holiday takes you through beautiful vineyards, mountain passes and along coastal trails. It's also a great time to explore Thailand, Vietnam and Cambodia with us.

Do you provide bikes?

Yes, we do! Bike hire is included in your holiday. Depending on your chosen destination, you may be able to hire an e-bike or tandem for your trip.

All our bikes are cleaned and maintained by our overseas agents so you can be confident that you're in safe hands. If anything does go wrong, they'll come out to your hotel to fix it. The bikes used on our cycling holidays have: Straight handlebars, mudguards, pannier rack & panniers, gel saddles, puncture repair kit & tyre levers, a pump, a lock and a phone holder.

You may be able to bring additional items with rep supervision, such as pedals (with or without toe clips), water bottle cages, child seats and saddles. We will fit them as long as they're safe and compatible with our bikes. Check our FAQs page for more information or get in touch with us.

How difficult are your cycling holidays?

We offer a range of trips to suit different abilities, so you don't have to be at a Tour de France level to enjoy a cycling getaway!

To help you find the right holiday for you, we provide an activity level grading. This gives you an idea of the fitness level and experience required for each of our action-packed trips.

For instance, a level 1 holiday will be suitable for first-timers, families or those who rarely cycle, because they typically follow gentle routes. Level 2 and 3 routes are more varied and will appeal to more active cyclists. Any holidays that are graded a level 4 are our most challenging and require a high level of fitness and experience on the saddle.

Do you offer both self-guided and guided cycling holidays?

Yes, we offer both self-guided and guided group holidays, so you can choose a trip that best suits you.

Our self-guided cycling holidays are ideal for those who want to set off solo using our carefully crafted itinerary. We'll provide your route each day, which you can follow using our handy Navigation App on your smartphone. One of the benefits of our self-guided trips is that you have the flexibility to go at your own pace, stopping for longer stints in certain places if you wish.

Our guided cycling holidays are the perfect choice for those who want to be led by one of our experts. Most trips also have vehicle support, giving you peace of mind that there's help if you need it. If you choose a guided trip, you'll be in a small group of like-minded travellers all keen to explore on two wheels.

Do you provide navigation instructions for my cycling trip?

Yes! Meticulous turn-by-turn directions are available in our Navigation App for most cycling holidays. This includes audio prompts for the ultimate convenience while in the saddle.

The GPS will give you detailed instructions for each day of your trip. All you need to do is pop your smartphone in the mounted holder, put your feet on the pedals and enjoy your cycling holiday – no extra maps required!

It's really easy to use and you'll even get interactive 'point of interest' information, so you don’t miss any of the sights as you cycle.

Will I need to move my luggage between hotels?

If you'll be staying in different hotels during your travels, you don't need to worry about transporting your luggage. You can set off and enjoy a great day of riding safe in the knowledge that we'll whisk your bags to your next hotel. This means you can cycle at your own pace without being weighed down by bags.

What should I pack for cycling holidays?

You'll need to bring plenty of activewear for your cycling holiday, including moisture-wicking layers, jerseys, socks, waterproofs and sunglasses. It's worth packing some bib shorts or padded shorts to keep you comfortable throughout the trip (but they aren't a necessity). You should also pack a water bottle to stay hydrated during your rides.

It's also important that you bring your own helmet and wear it for the duration of your rides. It's a legal requirement to wear a helmet in Portugal and Spain, and for children under 16 in Italy.

Why choose Headwater for cycling holidays?

Since 1985, we've been creating exceptional holidays that allow you to enjoy the best of your chosen destination. Here are some key reasons you should book your cycling holiday with us:

  • Satisfied customers: We're delighted to have an array of five-star reviews and a great overall rating on Feefo.
  • Carefully crafted itineraries: Our team use their expertise and first-hand experience to create the ultimate itineraries for your holiday.
  • Flight bookings: You can choose to book your flights through us, saving you the time and hassle of organising your travel.
  • ABTA and ATOL protection: When you book with us, you'll know your holiday is protected. Find out more about your key rights when travelling with us.
  • Award-winning holidays: We're proud that our holidays have won awards, including 3 British Travel Awards in 2022.
  • Focus on sustainability: We want to make our trips Nature Positive, which is why we have a People, Places and Planet plan focusing on sustainability.
  • We support communities: We do our bit to support communities around the world through the Exodus Travels Foundation.
If you're keen to make your dream cycling holiday a reality, book online now or get in touch with our friendly team for more information.