Bermuda Islands Discovery

0044 1606 720199

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  • Holiday code
    W14BM
  • Holiday type
    Self-guided walking
  • Duration
    14 nights
  • Accommodation
    single-centre
  • Activity level
  • From $4700per person, tour only
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 14 nights single-centre accommodation in a hotel
  • Room only
  • Briefing at the start of your holiday
  • Comprehensive route directions
  • Standard transfers to/from your hotel (if booking inclusive flights)
  • 14 day travel pass
  • Local taxes, resort levy and service charge
  • Optional Upgrades
  • Room upgrades and extra nights at selected hotels
  • Suitable for
  • Couples
  • Excellent choice for
  • Flora & fauna, bird spotting opportunities, art & history, swimming opportunities, coastal routes, island exploring
      from 2 reviews

Mr Hill says...
Excellent choice of destination and hotel offering a mix of history, nature and culture.
Read reviews »

Bermuda

Bermuda Islands Discovery

  • Unspoilt pocket-sized paradise, perfect for independent discovery; fabulous year-round climate
  • Sugary pink sands, secret turquoise bays, sea grottoes
  • Gentle traffic-free trails, spectacular coastal paths, lush woodland tracks
  • Colonial towns, pastel coloured villages, panoramic forts, vibrant Hamilton
  • Colourful flowers, kiskadees, tree frogs, sea turtles and humpback whales!

This self-guided walking holiday is the perfect mix of gentle walking and independent exploring allowing you to discover the quintessential island paradise of Bermuda at your own pace. Warmed by the temperate Gulf Stream, this sub-tropical gem, seemingly adrift in the North Atlantic Ocean is a stunning archipelago of 181 islands and islets, the eight largest of which form the fishhook-shaped mainland. Famed for its stunning turquoise waters in a whole rainbow of blues, incredible pink sands and coral reefs home to hundreds of colourful fish, Bermuda is a beach-lover's heaven and, as Britain's oldest colony, it is packed with history too. Beyond the postcard-worthy bays, the islands offer a lush interior alive with a multitude of birds and flowers, making it perfect to explore on foot. As Mark Twain commented, 'You go to heaven if you want. I'd rather stay here in Bermuda'.

A traffic-free trail spans Bermuda's diminutive 21-mile length and we provide detailed routes for 6 different walks, each exploring it's own diverse sections of the islands. From hidden sea grottoes to panoramic forts, lush flower-speckled fields to the sun-kissed sands of the South Shore Trail, the kaleidoscope of colour is unforgettable and the diversity of flora and fauna unbeatable. To help you get around, a 14-day travel pass is included, allowing unlimited access to the modern and efficient bus and ferry networks. Our local partner, Tim Rogers, will brief you about how everything works; he has a wealth of knowledge about Bermuda's flora, fauna and history.

You stay at either the Coco Reef Resort or the Grotto Bay Beach Resort. The Coco Reef is on the edge of the best private beach on the island and just 15 minutes from the capital, Hamilton. The Grotto Bay Beach Resort sits within a lush tropical estate, with 3 private beaches and a wealth of excellent facilities.

From either hotel, you're free to pick and choose your itinerary each day and with stunning beaches, fabulous golf courses, outstanding natural beauty and fascinating history to discover there's plenty of interest for your 'rest days'.

We also offer a 7-night itinerary on our Islands of Bermuda Walk



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Walking information

The walking is predominantly flat with no real ascents or descents. Terrain varies between asphalt, gravel, and earthen surfaces as well as some sandy trails. Walking boots are recommended.




We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Your base in Bermuda

You stay at the exclusive 64-room 3* Coco Reef Hotel in a deluxe ocean view room (with either balcony or terrace). The hotel is just 15 minutes from the capital, Hamilton and perfect for independent exploring.

Day 2: Your itinerary

Bermuda is the perfect destination for a mix of relaxation and gentle walking. We provide six detailed walking routes to help you discover the historic, cultural and natural highlights of the island, but there's no set itinerary so you're free to choose when and where to walk - you are on holiday after all!

To help you get around, a 14-day travel pass is included, allowing unlimited access to the modern and efficient bus and ferry networks. Our local partner, Tim Rogers, has a wealth of knowledge about Bermuda's flora, fauna and history, and will brief you about how everything works.

Day 3: The Walking routes

You're free to choose when and where to walk:

Somerset and Ireland Island 7km/4.5mi/2hr or 8km/5mi/3hr

Begin at Somerset Bridge, the world's smallest drawbridge, and follow the Railway Trail lined with unusual screw palm and cedar, reaching C19 Fort Scaur, with stunning views to Hamilton. Onwards to sleepy Somerset Village for lunch by pretty Mangrove Bay, you then follow a coastal track out along Ireland Island to Bermuda's most westerly end.

Exploring the East End 11km/7mi/4.5hr

You start the day in charming St George, a UNESCO World Heritage Site. There's time to explore the tangle of colourful streets and pretty harbour, before a dazzling path lined with prickly pear and casuarina leads to Gates Bay where Sir George Somers first came ashore in 1609. You continue along a herb-scented coastal track to Ferry Reach, with its C17 forts and Corsican tower.

St David's and Cooper's Island 4km/2.5mi/2hr or 5km/3mi/2.5hr

At tranquil St David's, fragrant hibiscus scents the salty ocean air as you visit Red Hole bay. Then it's on to St David's Battery, with cliff views stretching infinitely across the ocean, before heading over to Cooper's Island, Bermuda's newest nature reserve, a truly isolated and unspoilt area.

Sights of the South Shore 13km/8mi/3.5hr

From Gibbs Hill Lighthouse, balcony views span the entire west end across the azure waters of Great Sound, dotted with white sailboats. From here you descend to the sugary pink sands of the South Shore Trail, a string of nine gorgeous bays linked by a scented path of flowering morning glory and oleander. There's time for a dip at Chaplin Bay before savouring a Dark 'n' Stormy cocktail back at the hotel.

Coast and Caves 12km/7.5mi/4.5hr

Colourful prickly poppies dot the sparkling coastal route towards Flatts Village, where friendly locals cast their nets into the azure expanse of Harrington Sound, an inland lake littered with sea grottoes. It's then onwards with views over the northern shore to reach Blue Hole Park, a tiny treasure trove of caves filled with aquamarine waters. Visit the fascinating Crystal Caves perhaps, before a leisurely dip in the pool back at the hotel.

Botanical Gardens and Spittal Pond 5km/3mi/1.5hr or 4km/2.5mi/2.5hr

Alive with the noisy chatter of yellow kiskadee, a gentle allspice-scented trail brings you to Paget Marsh, a wetland oasis, home to herons and warblers. Then it's on to the Botanical Gardens - John Lennon's Double Fantasy album is named after the purple flower he spotted here - before heading to Spittal Pond; maybe spot herons, egrets and flamingos before following the coastal path, vibrant with sea lavender, looking out for humpback whales basking in the warm Atlantic waters.

Day 4: Independent exploring

There's plenty to see and do for the remainder of your stay, with the hotel's private beach an obvious attraction! The island boasts many other beautiful beaches, such as Elbow Beach and Horseshoe Bay, and several excellent golf courses too.

Pay a visit to the island's capital, Hamilton, and stroll along the harbour where pastel-coloured colonial buildings mix with high-end shops. Perhaps visit the stone Cathedral of the Most Holy Trinity and climb the tower for glorious city views befroe relaxing in one of the many harbour-side cafes for a spot of people watching.

The Royal Naval Dockyard is also well worth a visit: once the largest naval base outside the UK, the beautifully restored buildings now house a museum that offers a fascinating glimpse into the UK's and Bermuda's naval past. Nearby you'll also find the National Museum of Bermuda where you can discover more about the island's history and wildlife and pay a visit to Dolphin Quest to learn more about these fascinating animals, while the Bermuda Aquarium and Zoo on the shores of Harringston Sound, offers the chance to see seals, turtles, fish, monkeys, birds, and the first living coral reef exhibit in the world.

Where you stay

This single-centre holiday is based at the following hotel. If you'd like to extend your stay here, or upgrade your room, just let us know at the time of booking.

To find out more call our sales team on 0044 1606 720199 or email sales@headwater.com


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Grotto Bay Beach Resort Bermuda,

Swimming Pool IconHair dryer icon NEARBY:

The Grotto Bay Beach Resort sits within a lush tropical estate set along the water’s edge in Bailey’s Bay. It comprises of 3 private beaches and 11 brightly coloured cottages which overlook the turquoise Bermudian waters.

The hotel boasts fantastic facilties including tennis courts, water sports and the 'Natura Spa' which is set within the atmospheric Prospero's Cave - complete with stalactites and stalagmites - overlooking a crystal-clear ocean-fed lake.

The resort's luxurious Great House comes with dark wood floors and tropical colours, as well as stunning views of the hotel grounds and turquoise ocean beyond. It's home to the Rum House Bar - where there is regular live entertainment - and the resort's 2 restaurants: the relaxed Palm Court or the elegant Hibiscus Dining Room. The Bayside Grill is also available at lunchtime, whilst the Bayside Bar serves tropical drinks along the water's edge.

The newly renovated bedrooms at the Grotto Bay Beach Resort are spacious and contemporary with marble bathrooms and either private balcony or private patio.

As your stay at the Grotto Bay Hotel is on a room only basis, please let us know if you would like to add breakfast, breakfast and evening meal or all inclusive to your stay. Please contact us for a quote.


Room upgrades: Ocean View Deluxe and Ocean Front Superior
Ocean View Deluxe Rooms offer spectacular views from the hillside near the main clubhouse. They are on the second or third floors and come with balcony and views across the bay and beyond. Ocean Front Superior Rooms are located closest to the pool and waterfront. On the ground floor, they have a walk out patio with a partial view of the calm waters of the bay.

Extra nights: Please contact us for details.

Travel

Transfers from Bermuda airport at 18:30, and back to Bermuda airport at 17:45 are available at a supplement.

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

Reviews

Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.


Mr Hill, 03/02/2023

Excellent choice of destination and hotel offering a mix of history, nature and culture.


Mrs Marrin, 16/02/2020

Excellent holiday but very expensive destination, it would be nice to offer some self catering accommodation.



Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

This 14 night self-guided walking holiday includes:

Single-centre accommodation in a hotel

Room only

Briefing at the start of your holiday

Comprehensive route directions provided prior to departure

Standard transfers to/from your hotel (if booking inclusive flights)

14 day travel pass

Local taxes, resort levy and service charge


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

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24th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
25th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
26th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
27th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
28th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
29th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
30th Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
31st Dec 2024 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
DepartingTour only Prices   Single supplement
1st Jan 2025 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
Check availability
Check availability
2nd Jan 2025 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
3rd Jan 2025 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
4th Jan 2025 US$6200 US$3678 Tour only: US$6200
Single supp: US$3678
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Check availability
5th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
6th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
7th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
8th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
9th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
10th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
11th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
12th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
13th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
14th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
15th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
16th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
17th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
18th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
19th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
20th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
21st Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
22nd Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
23rd Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
24th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
25th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
26th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
27th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
28th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
29th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
30th Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
31st Jan 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
DepartingTour only Prices   Single supplement
1st Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
2nd Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
3rd Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
4th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
5th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
6th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
7th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
8th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
9th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
10th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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11th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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12th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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13th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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14th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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15th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
16th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
17th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
18th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
19th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
20th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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21st Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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22nd Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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23rd Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
24th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
25th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
26th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
27th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
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28th Feb 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
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DepartingTour only Prices   Single supplement
1st Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
2nd Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
3rd Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
4th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
5th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
6th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
7th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
8th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
9th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
10th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
11th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
12th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
13th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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14th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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15th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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16th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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17th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
18th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
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Check availability
19th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
20th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
21st Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
22nd Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
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23rd Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
24th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
25th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
26th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
27th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
28th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
29th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
30th Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
31st Mar 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
DepartingTour only Prices   Single supplement
1st Apr 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability
2nd Apr 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
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3rd Apr 2025 US$4700 US$2343 Tour only: US$4700
Single supp: US$2343
Check availability
Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Minimum group sizes
No minimum group size, however transfers are subject to at least 2 people (in total) booked on each departure.

Solo travellers
Please call for details and prices

Children
This holiday is unsuitable for children.

Holiday type
Self-guided walking Managed by Headwater rep.

Departures
Daily departures from 29th Apr 2024 to 3rd Apr 2025, for 14 nights. All dates are subject to availability, please contact us to check.

Meals
Room only

Tailor-made travel

This holiday does not include any flights or rail.

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.

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