Difficulty level
Activity (Bike)

Israel: Jerusalem & South Israel Bike Tour

Seven nights; seven days of activity in Southern Israel between Jerusalem and the Red Sea, including cycling, walking, and snorkelling.

“A day still does not go by that I do not think of my great trip to Israel.” – Larry L.


  • A well-rounded active holiday experience combined with cultural elements and historically significant sites.
  • Full days of activity, with mostly easy cycling on gravel and some roughly paved roads; little or no vehicular traffic, and challenging options available for more experienced riders.
  • A full day of walking, exploring and learning in Jerusalem with engaging and informative guides.
  • Visit Masada National Park by foot and float in the Dead Sea at 1412ft below sea-level! Spa enthusiasts should request extra service and treatment options.
  • In-depth Negev Desert experience, visiting places not easily accessible by vehicles.
  • Amazing scenery and landscapes from the fertile valleys and flatlands near Jerusalem southward into the Judean and Negev Deserts, and the mountains surrounding Eilat and the Red Sea.
  • World-class reef snorkelling in the Red Sea, and optional hiking and birdwatching near Eilat.
  • Excellent lodging and dining options throughout.



Learn about our difficulty-rating system

Expect very full days with a variety of easy to moderately challenging activities. Walks and bike rides are interspersed by brief interpretations. This adventure is best suited to people who are accustomed to several hours of continuous yet moderately paced activity.

Daily Distance:

  • DAY 1: Introductions
  • DAY 2: Variable
  • DAY 3: ~62 km
  • DAY 4: ~36 km and ~19 km
  • DAY 5: ~38 km + options
  • DAY 6: Variable
  • DAY 7: ~46 km
  • DAY 8: Snorkelling or hiking, and Farewells

Israel: Jerusalem & South Israel Bike – Elevation Profile

(Click image to enlarge)


Not sure about difficulties, and support level? Check out our What to Expect page!


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Start: Jerusalem, Inbal Jerusalem, 18:00, day one.

Finish: Eilat, Royal Beach Hotel, 18:00, day eight.

Please contact us to arrange alternate plans, if necessary.



Meet in Jerusalem, for introductions, technical briefing and dinner. D (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)

Inbal Jerusalem, or, Mamilla Hotel, Jerusalem


Walking in Jerusalem

Jerusalem is (and always was) a small town by international standards, but most humans round the globe have heard its name; people who never heard the names of New York, London, Paris, Tokyo, Rome or Beijing know something about the city that endured 87 regime changes, two thirds of them by battle. Your guided tour of Jerusalem is an essential introduction for those whose knowledge of Israel’s history is not complete. In the morning you will visit observation points round the city, then visit the old city to see the important sites that draw the attention of millions of tourists, pilgrims, poets, artists, philosophers, politicians, warriors, and media correspondents over the ages. In the afternoon you will walk the caves of the City of David. B

Same lodging


Tzur Hadassa, Beit Guvrin, Lachish, Arad, ~62km

Transfer 45-minutes to where your cycling begins. You’ll start on quiet unpaved farm tracks, gravel side roads, and easy sections of the Israel National Trail. You will descend to the “flat land” or “Eretz Pleshet, as it is named in the Bible. You will see the Judean Mountains as you bike through “Emek Ha’Ella” (The Goddess Valley) where young David defeated Goliath some 3000 years ago. Visit the Roman Amphitheatre of Eleutheropolis and wander through the famous Bell Caves of Beit Guvrin. After emerging to light again, continue cycling the trail between small villages alongside many fields and vineyards as you head south toward the edge of the desert. Finish with a 40-minute transfer to Arad. BLD

Yehelim Boutique Hotel, Arad


Masada and the Dead Sea: walking, and cycling 36km + an optional 19km challenging ride

Cycling directly from your inn, the quiet, curvy desert road leads you to the Roman Ramp at the back entrance of Masada, a fascinating archaeological site with breath-taking views and a heroic story to tell. Climbing to Masada by foot, you’ll be rewarded with spectacular views of the Dead Sea, the Moab Mountains, and Jordan across the African Rift Valley. Learn about Masada and the ideological debate it inspires, then descend on foot following the “snake path” or by cable car towards Earth’s lowest elevation on land at the Dead Sea. Continue on bikes or by van to Ein Bokek to enjoy the buoyant and healing waters of Dead Sea; best experienced using one of the resort spas where extra treatments can be booked by request. An optional challenging bike ride is available for those looking for more activity before a 40-minute transfer back to Arad at day’s end. BLD

Same lodging


Wadi Zin, Ein Akeve, Sde Boker 38km + walking and desert spring swimming

Transfer about 40 minutes to the ancient Nabataen city at Mamshit. In the heart of the Negev, Mamshit was a prosperous city of great importance to the trade route that linked Egypt and India in the 1st and 2nd centuries. You’ll begin cycling a hillier track today, first descending into Machtesh Gadol, the second largest crater in Israel, to the beautiful desert spring at Ein Akeve. Continue cycling in the canyon, the afternoon includes some challenging yet rewarding climbs before arriving directly at Sde Boker where you’ll spend two nights lodging. BLD

Kedma, Sde Boker


Zin Canyon, Ein Advat & Sde Boker; cycling & walking

Spend the day cycling and hiking amidst the desert beauty of the Zin Canyon where the flora and fauna illustrate the delicate uniqueness of this desert region. Your trail leads into the canyon at Ein Advat and onto the Ein Ma’arif observation point – a once prosperous city on the spice route linking Petra and the Mediterranean coast. There is an award wining winery at Kibbutz Sde Boker, also the home and burial place of David Ben-Gurion. BLD

Same lodging


Timna to Eilat, ~46km

Start with a long transfer across Makhtesh Ramon to Timna Valley Park where you will begin on your final bike ride through the unique geological features of the Eilat Mountains into the popular tourist city of Eilat. While the large resorts beckon many an inactive visitor, Eilat is also a gem for divers, snorkellers, hikers, birdwatchers. BLD

Royal Beach Hotel, or, Queen of Sheba Hilton, Eilat


Snorkelling or hiking, Farewells

Start early, with the option to snorkel and explore some of the most beautiful reefs of the world or to hike in the mountains to observation points overlooking Israel, Egypt, Jordan, and Saudi Arabia. Finish in time for late afternoon flights back to the center of the country, some 300km north, where your Freewheeling Adventure started. You may also opt for extra time in Eilat where you can enjoy many activities such as scuba diving, hiking, birdwatching, or excursions to Petra. B

All details and pricing are subject to change without notice.


2023 Guided:

  • Contact us

2024 Guided:

  • Contact us

New dates are also welcomed for guided or private departures.


Guided: C 5895 (per person, double occupancy)

Includes 8 days, 7 nights, 7 breakfasts, 5 lunches, 6 dinners, luggage handling, van and guide support, maps and route instructions, taxes

Small groups or private tours, fully supported with drivers/guides and vehicles, all lodging and most meals included. Choose from existing dates or request new departures. Read more on our “What to Expect” page.

Single Occupancy: 1645

Bike Rentals:

Hybrid: 235

Flat bars. Trek fx3 or similar, with rear rack/trunk bag

All details and pricing are subject to change without notice.

Please see above for accurate pricing and inclusions, unless we have proposed a customized trip for you and those details are provided in your custom proposal.

1. Choose an advertised date to join a small group, or see our Join a Group page to see where groups are already forming.

2. Pick your own dates. We will confirm quickly, and are happy to talk with you as you make your choice. If you would like a private guided date, this usually comes at a surcharge depending on the details, please get in touch for more information. If you prefer self-guided, we usually only require two participants to initiate a new date at the advertised price, and can sometimes reduce prices for you if you have four or more.

PLEASE NOTE: Trip Cancellation Insurance is highly recommended. If this is not provided by your credit card or elsewhere, please let us know and we can provide recommendations.

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