The Nakasendo Trail or 'Road through the Central Mountains' was part of Japan's network of highways. Travellers moving between Kyoto and Tokyo took several days to travel the Nakasendo, staying overnight in Juku post towns. In the seventeenth century, the Nakasendo was crowded with travellers, including feudal lords, samurai, itinerant merchants, and pilgrims. Now largely forgotten and quiet, the road provides a pleasant trail through scenic countryside and the history of Japan.
Explore the fascinating city of Kyoto before starting the Nakasendo Trail, your trip ends in the sprawling city of Tokyo. Famous for its beautifully built Buddhist temples and traditional teahouses, Kyoto is a great introduction to your Japanese adventure. From here, you can visit the historical city of Nara, full of cultural treasures and tranquil gardens.
In Tokyo you can experience the whole breadth of Japanese arts and culture, not to mention the abundance of culinary treasures. An ever-evolving city, Tokyo is an explosion for the senses with a discovery around every corner.
Take the express train from Osaka Kansai Int. Airport to Kyoto City (approx. 70mins), then a local taxi to your first hotel. (approx. 10mins).
Overnight Kyoto (breakfast included).
Enjoy a rest day in the incredible city of Kyoto, famous for its Buddhist temples, tranquil gardens, and traditional teahouses. We recommend visiting the historical city of Nara, full of cultural treasures and expansive parks, located approx. 1hr from Kyoto city on the train.
Overnight Kyoto (breakfast included).
Take the train to the hills of northern Kyoto (included), on sacred Mount Kurama. Here, Samurai trained with mountain Buddhist practitioners in the 12th century. From Kurama Temple, walk to the Kifune Shrine, which is known for bringing good fortune to those seeking luck in love. The walk begins with a steep and long ascent up stone steps to the Kurama Temple. Stop to take in the beautiful scenery and spend some time at the shrines and smaller temples along the way. Return by local train to Kyoto (included). The remainder of your day is free for you to explore Kyoto.
Overnight Kyoto (breakfast included).
Begin with a train journey from Kyoto to Nakatsugawa, including a ride on the world-famous Shinkansen (Bullet Train) to Nagoya (included). At Nakatsugawa, you board a local bus for the short journey to Magome. When you alight from the bus at Magome, a taxi driver will be waiting to pick up your luggage to be delivered to your accommodation before dinner.
Walk over Magome Pass to Tsumago, one of the best preserved and most evocative of the Nakasendo post towns. Spend the night at a family-run Minshuku in Tsumago or the nearby hamlet of O-Tsumago, with a delicious home-cooked Japanese dinner and breakfast included.
Overnight Minshuku Guesthouse, Tsumago (breakfast and dinner included).
Today is your longest day on the trail and is a beautiful and varied hike from Tsumago or Nagiso to Nojiri. The trail travels through small valleys and past forests of bamboo and Japanese cedar, through some of the least-developed scenery on the tour. Continue by train to Kiso-Fukushima (included). Stay at a lovely hot-spring Ryokan set in a peaceful valley above the town. Complimentary transfer from the station is provided by the Ryokan if you're staying outside of the village (availability is on request).
Overnight Ryokan (traditional Japanese inn), Kiso-Fukushima (breakfast and dinner included).
If you have free time in Kiso Fukushima, you can take this optional walk from Kiso Fukushima Station to Gongentaki Waterfall. The trail combines a riverside path, a dirt trail leading up to the waterfall, and gentle descent back down through a quiet neighbourhood with good views over the town and the traditional buildings near the Nakasendo Trail.
Overnight Ryokan (traditional Japanese inn), Kiso-Fukushima (breakfast and dinner included).
The Ryokan will drive you back to Kiso-Fukushima after breakfast if you're staying outside the village. From here, you take the train to Yabuhara (included) which is the starting point for your walk over the Torii pass to Narai. Explore this atmospheric village before you continue on today's journey to the small town of Kiso-Hirasawa, famous for its lacquerware. There are many small shops selling beautifully crafted tableware and furniture. From Kiso-Hirasawa, take the train to the castle town of Matsumoto for your overnight stay. Your hosts will serve a home-cooked Japanese dinner and breakfast.
Overnight Ryokan (traditional Japanese inn), Matsumoto (breakfast and dinner included).
After breakfast, you will have free time to explore the castle town of Matsumoto. This historic town is home to the iconic artist Yayoi Kusama and the largest collection of Ukiyo-e wood blocks. With many things to see and do Matsumoto is a destination in and of itself. Be sure to visit the well-preserved Matsumoto Castle also known as the 'Black Crow Castle'. You can enter the castle and enjoy the unique architecture, hidden nooks, and panoramic views of the castle town. This afternoon head onward to Karuizawa where you will stay this evening and enjoy a natural hot spring baths before your final walk to Yokokawa.
Your included luggage transfer ends here. To continue the service from Matsumoto to Tokyo, you can arrange this locally with your inn in the morning who will liaise with the long distance courier Takkyubin; this is paid for locally (approx. £16 per bag/20kg). Using this service, you will be without your luggage from the morning of day 8, until the evening of day 9.
Overnight Ryokan (traditional Japanese inn), Karuizawa (breakfast and dinner included).
After breakfast, your final walk on the Nakasendo Trail is from Karuizawa to Yokokawa. Leaving Karuizawa, the trail takes you over the Usui-toge Pass and down a gentle descent along one of the most beautiful sections of the Nakasendo, and certainly the least-developed. From Yokokawa, take the local train to Takasaki and change there for your ride on the Shinkansen bullet train to Tokyo (approx. 3 hours - included).
Overnight Tokyo (breakfast included).
You have a full day in Tokyo to explore this vibrant city. Visit the glittering Ginza area with elegant department stores and food halls crammed with all kinds of unfamiliar delicacies. Or spend time among the skyscrapers of Shinjuku and pass-through Shinjuku station, the busiest transport hub in the world. Eat and drink in one of the myriad small bars and restaurants which cluster around most railway stations or splash out on an elegant meal in an upscale restaurant. We recommend visiting the grand Sumiyoshi Shrine, an easy 10-minute ride on the Nankai railway from Namba station. The shrine grounds have beautiful nature such as sacred trees over a thousand years old, and the main shrine buildings feature the ancient Sumiyoshi-zukuri style of architecture which pre-dates the arrival of Buddhism to Japan.
Overnight Tokyo (breakfast included).
Enjoy breakfast at your hotel before walking to Hamamatsucho station (approx. 10mins) to take the monorail directly to Tokyo Haneda Airport (approx. 15mins - paid locally).
During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.
To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com
Hotels: Modern western-style hotels are used. The rooms are generally smaller than equivalent hotels in the West. All have en-suite facilities, air-conditioning, TV, and fridges in rooms.
Extra nights: Please contact us for details.
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.
Here at Headwater we thrive on feedback and pride ourselves on our excellent customer service. Below is a small selection of reviews we've received from our satisfied customers.
I am at the beginning of the booking process. So far everything has been ok. There was some confusion about the insurance position in the event of theft or damage to the bicycle, but this was cleared up to my satisfaction. The sales and admin staff I have dealt with so far have been pleasant and helpful, and service has been good and timely. Telephone answering times are good.
Excellent and rapid response from Jo Chaplin adapting to our dates and requirements.
Excellent service and would definitely book other holidays through Headester.
Fast response and friendly service
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 10 night self-guided walking holiday includes:
Hotel-to-hotel accommodation in a mix of hotels
All breakfasts & 5 dinners
Comprehensive route directions provided prior to departure
Luggage transfers between accommodations from Magome to Matsumoto
Train from Kyoto to trail starting point and from trail end point to Tokyo
Trains as per itinerary
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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2nd Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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3rd Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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4th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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5th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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6th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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7th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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8th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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9th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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10th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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11th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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12th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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13th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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14th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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15th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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16th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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17th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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18th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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19th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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20th Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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21st Aug 2024 | US$6650 | US$1119 | Tour only: US$6650 Single supp: US$1119 |
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22nd Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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23rd Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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24th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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25th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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26th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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27th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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28th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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29th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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30th Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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31st Aug 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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1st Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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2nd Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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3rd Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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4th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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5th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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6th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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7th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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8th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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9th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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10th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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11th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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12th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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13th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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14th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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15th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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16th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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17th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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18th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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19th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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20th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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21st Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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22nd Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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23rd Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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24th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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25th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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26th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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27th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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28th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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29th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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30th Sep 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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Departing | Tour only | Prices ![]() |
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1st Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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2nd Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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3rd Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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4th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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5th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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6th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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7th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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8th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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9th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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10th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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11th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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12th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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13th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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14th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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15th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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16th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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17th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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18th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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19th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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20th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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21st Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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22nd Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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23rd Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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24th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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25th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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26th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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27th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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28th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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29th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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30th Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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31st Oct 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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Departing | Tour only | Prices ![]() |
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1st Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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2nd Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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3rd Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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4th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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5th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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6th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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7th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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8th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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9th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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10th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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11th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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12th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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13th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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14th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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15th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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16th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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17th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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18th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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19th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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20th Nov 2024 | US$5615 | US$1119 | Tour only: US$5615 Single supp: US$1119 |
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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.
Solo travellers
Please call for details and prices
Children
Please contact us for child prices.
Holiday type
Self-guided walking Managed locally by Headwater appointed agent.
Departures
Daily from 25th Mar 2024 to 20th Nov 2024, for 10 nights. All dates are subject to availability, please contact us to check.
Meals
All breakfasts & 5 dinners
This holiday does not include any flights or rail.
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.