From climbing Kilimanjaro to cycling the Tour de France route… Readers’ Favorite Organized Challenges | travel

An unforgettable bike ride on the Tour de France route

Choose events that offer strong support as you tackle large-scale cycling challenges. That makes a big difference. Riding the entire Tour de France route with Ride Le Loop was challenging, but the great staff transformed it into an unforgettable experience (riders can also tackle individual stages). Their infectious enthusiasm and constant encouragement kept me in good spirits even on the toughest climbs. Not only did they take care of the logistics, but they also created a warm and positive atmosphere that brought the riders together and amplified the enjoyment of the trip. My advice: Choose structured challenges where your team is as interested in your success as you are. The next period runs from June 27 to July 20, 2026.
neil phillips

Quiet trail running in the Swiss Alps

If you have a week to spare and want to experience a quieter part of the Alps in summer, the Swiss Peaks Trail race is for you, spanning from 10km to 643km along some of Switzerland’s most runnable mountain passes. I chose the 100km route and disappeared into a world of bracing bravado over untouched peaks, rugged slopes and turquoise lakes. raclette This dish is made by passionate aid station volunteers. The course ends in Le Bouveret, on the south-eastern shores of Lake Leman (Lake Geneva), where you can enjoy the cold. From August 25 to September 6, 2026.
Eleanor

Run from Asia to Europe in the Istanbul Marathon

Last November, I participated in the Istanbul Marathon, probably the only organized running race in the world that starts on one continent and ends on another. I booked a week there to get a feel for the city and culture, but you can do this through the race itself, passing modern and ancient landmarks on the route. The £50 entry fee includes free use of public transport, including ferries, on match day. The start was quite spectacular with runners heading west across the Martyrs’ Bridge on July 15th. The water flows down towards Besiktas and towards Dolmabahçe Palace on the coastal road hugging the banks of the Bosphorus. I found it inspiring to look up as I raced to see the city skyline, its majestic spiers sparkling in the sunlight seemingly urging us on. The Golden Horn and the beautiful Blue Mosque beckoned me to the finish line where delicious Turkish tea, mezze and figs awaited all the runners, served by race organizers and supportive spectators. The 2026 race will be held on November 1.
april

Swimming in Lord Byron’s footsteps, Italy

I was fortunate enough to live in Genoa for several years and took part in the most poetic swim of my life in many ways. Coppa Byron is an annual swim across the Bay of Poets from Portovenere to Lerici to commemorate Lord Byron’s legendary underwater feats when he visited his friend Percy Shelley in the 19th century. It happens on a Sunday in late July or early August (2026 not yet announced) when the water is warm and the views are truly spectacular. Anyone can do it for an entrance fee of around €20 (depending on when you register) which includes a swimming cap, drinking water, advice and a certificate. It takes 2-3 hours to traverse the 8 km and there are boats that accompany swimmers for support. All participants are welcomed by cheering supporters upon arrival in Lerici where a sumptuous lunch is served at Ristorante delle Palme.
fig

Trekking Kilimanjaro the right way

The Lemosho route up Kilimanjaro takes trekkers through rainforest, moors and alpine desert, with many opportunities to spot wildlife including monkeys, antelopes and beautiful birds. The effects of altitude can affect anyone, but taking longer routes makes them difficult for most healthy, trained walkers to achieve. The summit day is long, but it gets the adrenaline pumping and requires no technical climbing anywhere on the route. However, please be aware that there are many unscrupulous operators who offer quick trips to Kilimanjaro, i.e. treks that do not provide sufficient acclimatization time and use poorly treated staff. I paid a premium to climb with Ian Taylor Trekking and I’m so glad I did. Conditions were good for trekkers and we were reassured that the staff supporting us were well paid, well equipped and had good training to support their career development. There are other good companies out there too. Do your research!
Pamela

Scenic route from the Dolomites to Venice on two wheels

We recently cycled 200 miles from Bolzano to Venice. It’s a beautiful road. Starting with the dramatic scenery of the Dolomites, we pedaled through alleyways surrounded by vineyards. We sampled Soave and Valpolicella wines during a leisurely lunch. Heading south, we took a ferry along the beautiful Lake Garda to Verona, the city of Romeo and Juliet. We loved exploring the architectural genius of Palladio in Vicenza before continuing on to Padua, the cradle of the arts. After a wonderful week with cycling expert Girolibero taking care of all our luggage and hotel, we reached the Venetian lagoon and the timeless beauty of Venice.
David Innes-Wilkin

Descend from London’s highest heliport

As I entered my 70s, I wanted to try my hand at charity. Having often seen the London Air Ambulance at Hyde Park, I knew it was a staging area for emergencies. I spoke to a pilot who told me about his charity descent from 90 meters at one of the highest heliports in Europe. What an incredible challenge, an incredible prospect, and an incredible charity. Something really different.
Angela

Winning Tip: Fancy Dress Marathon Through Bordeaux Vineyards

“marathon?!” I scoffed. It’s not a feasible plan for a noticeably average runner like me. But the marathon in question was the iconic Marathon du Médoc. This festival-like event takes place north of Bordeaux, with more than 20 stops where runners can sample the world-famous red wines and cuisine of the Gironde region. Dealer? Each stop provides access to the grounds of one of the most beautiful castles in the region. The castle boasts a timeless elegance that is dressed up again every September with the arrival of 8,500 boisterous attendees in fancy dress. The estuary town of Pauillac is the main base for the race, and of course the surrounding countryside is best enjoyed with a bottle of Bordeaux red enthusiastically gifted at the finish line of this brilliant festival. This year it will be held on September 5th.
Adam McCormack