Free Single-Trip Travel Insurance Offer

We want to make sure you feel safe on your next walking or cycling holiday, and we're excited to have started welcoming our guests back to our relaxed and tranquil destinations across Europe.

Through our recently updated Booking Promise and Travel Safety Charter, we're offering travellers reassurance and peace-of-mind.

What's more, when you book by 15th September 2020, we'll include FREE SINGLE TRIP TRAVEL INSURANCE with COVID-19 cover for any European departure until 31st October 2020. Simply quote INS2020 at time of booking.

Return to holidays safely today - book and travel with confidence with Headwater.

Scroll down to view the trips on offer.

 

Italy : Sicily

Walking the Highlights of Western Sicily

$1895

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

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Italy : The Bay of Naples

The Amalfi Coast Walk

$3530


4.8 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

Paths of the Amalfi Coast

$1445


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Italy : Veneto

Heart of Veneto Cycling

$1805


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

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Italy : Veneto

Walking in the Venetian Hills

$1835


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Sicily

Secrets of Sicily Cycling

$2090


4.6 (24 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Tuscany

A Taste of Tuscany Walking

$2105


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Italy : Tuscany

A Taste of Tuscany Cycling

$2180


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy

Venetian Villas and Vineyards Cycling

$2180


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Italy : The Dolomites

Walks in The Italian Dolomites

$2255


4.9 (127 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Portugal : The Algarve

Cycling in The Real Algarve

$2330


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Portugal : Madeira

Marvels of Madeira Walk

$2345


4.7 (126 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : The Dolomites

Walking the Dolomites of Alta Badia

$2570


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy : Sicily

Cycling through Baroque Sicily

$2585


4.5 (22 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

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Slovenia

Julian Alps to the Adriatic Cycling

$3545


4.8 (123 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Portugal : The Algarve

Walk the Algarve's Wild West

$1970


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Puglia

Contrasts of Puglia Cycling

$2405


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Portugal : Mainland Portugal

Porto Coastal Cycling

$2525


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

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Germany : Bavaria

Short Break in the Altmuhltal Nature Park

$1190


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Liguria

Walking in the Cinque Terre and Portofino

$1460


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

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Germany : Bavaria

Walking Bavaria's Lakes and Mountains

$1760


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Germany : Bavaria

Cycling Bavaria's Lake Chiemsee

$1865


4.8 (6 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1+
Leisurely plus

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Germany : Bavaria

Lakes and Mountains of Bavaria Cycling

$2120


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

$2495


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Portugal : The Algarve

Walking the Algarve's South West

$2885


4.9 (34 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : Mainland Portugal

Porto to Coimbra Cycling

$2945


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy

Highlights of Puglia Cycling

$3290


4.8 (13 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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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.


Terms & Conditions

  • Valid on bookings made between 21/8/20 and 15/9/20 only.
  • Valid on trips departing between 22/8/20 and 31/10/20 only.
  • Valid on selected Headwater trips only.
  • Offer excludes UK holidays.
  • Valid only on trips open for travel at the time of booking. Please click here for details.
  • Valid on new bookings only, cannot be applied to existing bookings, cannot be used to rebook the same trip.
  • This offer is not combinable with any other offers apart from Loyalty Discounts.
  • The offer is for free standard single trip insurance, additional charges may be required to cover pre-existing medical conditions. Please click here for details.
  • Travel insurance cover for certain declared medical conditions may be subject to payment of an optional additional premium.
  • Travel insurance eligibility criteria applies, for example: age and country of residence.
  • Headwater standard Booking Terms and Conditions apply.
  • If booking a Flight Inclusive trip, flight supplements may still apply.
  • This offer is subject to availability and Headwater reserves the right to change this offer at any time.
  • This offer is not transferrable, there is no cash alternative and no correspondence will be entered into.
  • This offer is not available to Headwater Staff or to their immediate families.

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