My Best Trip Ever: Richard Branson on an Italian Cycling Odyssey


Last month, when we chatted with Richard Branson about his trailblazing scuba diving park in the British Virgin Islands, we also got to ask him one of our favourite questions — what’s the best trip you’ve ever taken?

His answer might mark the most ambitious trip ever to cross this travel editor’s desk.

“My best vacations have been my annual challenges with my grown-up kids,” Branson began. “Last year we did a 2,500km bike ride, [after a] 10-day hike, from the south of Switzerland to the toe of Italy. Then we swam to Sicily and marathoned up to the top of Mount Etna.”

You probably have to take a deep breath after just reading that.

This is not everyone’s idea of a restful break, and Branson knows that. “As a family, we are gluttons for punishment,” he said.

They’re also inclined toward purpose- based travel, so it’s no surprise that the triathlon-style, monthlong vacation was part of a Virgin-run programme called Strive Challenge, which takes physically fit travellers out of their comfort zones to foster personal growth, all while fundraising for a UK-based youth empowerment organisation called Big Change.

Strive runs events only once a year — at most — and a challenge for 2017 hasn’t been announced. But with a little help, you can recreate the Branson family’s cross-country, multisport marathon, starting in the Swiss alps. Here’s where to begin:

From Switzerland to Italy — on Foot

“Don’t underestimate the difficulty of this trip — beginning with the hiking in Switzerland,” said Monika Leuenberger, a Swiss native who has worked as an adventure travel specialist with Avenues of the World for nearly 30 years. “Swiss hikes have a tendency to go straight up in a way that Americans aren’t accustomed to — and then, once they’re done, going straight up, they just go up. On many trails, there’s no such thing as an easy uphill, really.”

At the summit of the Matterhorn, where the strive Challenge 2015 culminated

Lace up your shoes in Zermatt, where Leuenberger recommends skipping the most high-end hotel in town, Grand Hotel Zermatterhof, to stay at a smaller independent property such as Chesa Valese, where it’s easy to get a balcony facing the Matterhorn. “The Matterhorn is such a feature in Zermatt and you need to make sure that when you open the curtains in the morning, you’re looking right at it,” she explained.

Bolster your confidence with fondue and rosti (a Swiss dish that uses skillet hash browns as a base for such toppings as cheese, eggs and bacon) at the al-fresco Findlerhof, a rustic spot with authentic, carefully prepared recipes and a smart wine list. Then it’s up and down through the alpine passes that lead to Zermatt’s twin city of Cervinia, just across the border. Next up: Cycling in Italy.

Biking on the Riviera

Branson and his family never cheated on their itinerary: They did Italy from tip to toe, all by human-powered transport. But here, Leuen- berger suggests taking a shortcut, particularly if you don’t have 30 days to spare. Take the train or drive to Genoa, she says, which you can use as a starting point for a bike ride spanning the country’s entire western coast.

“Genoa is still very much a port city: It doesn’t have the charm that other places have in Italy. So get in and get out,” she recommends. Rent your bikes and begin cycling straight for Portofino, which is fewer than 25 miles away — and where you should check into the seaside Belmond Hotel Splendido. For such a plush property, Splendido offers plenty of adventurous excursions. They include kayaking to nearby lighthouses or outlying islands, fishing, or hiking around olive groves.

Then it’s off to Cinque Terre. The slightly hilly ride there hugs the Ligurian shore for a majority of its 40-mile (64.4km) route. Once among the famous five cliffside villages, you’ll need to switch to your feet. “You could easily spend two days hiking the villages here,” said Leuenberger, though it’s possible to cover plenty of ground in a single day.

Up next: A choose-your-own-adventure moment. As you continue south along the coast, you could cut inland to Lucca, one of Tuscany’s most charming small towns, with easy access to some of the region’s best vineyards. Or you could head straight down to the Tuscan beach resort of Livorno, to lounge around under a sea of sunshades with chic Italians and Europeans. By now you’d need the break, but make it a short one: There are still 650-odd miles to get to the tip of the boot.

The Shortcuts Worth Taking

At any point along the journey, Leuenberger says, you can cut yourself some slack. “You can always cycle or hike for half the day, then head to the spa and get driven to your next point,” she said.

Next up on Branson’s itinerary was Lazio, the region that encompasses Rome. If there was a time for a shortcut, this might be it: Drive the distance or take the train — either to Rome itself, where a carbo-load at the devilishly good pizzeria Roscioli is the only correct answer, or to Ladispoli, a lovely coastal town with access to excellent wineries. There you’ll find a charming villa-turned-hotel called La Posta Vecchia that’s always a home run. (It looks like the Italian interpretation of a Wes Anderson film, with traditional trappings reworked in vivid colours — and service is excellent.)

Eventually you’ll make it to Naples — by bike, train, or some combination. That’s where you can make up the distance that you’ve saved by taking the train. Cycle over to Sorrento “for the best scenery”, says Leuenberger, and take sailing or hiking trips out to Capri or Ischia.

Then eat up all the calories you’ve burned: The Amalfi coast is seafood heaven and in the hands of the chefs at the area’s two Michelin starred restaurants — Don Alfonso 1890 and Il Buco — you can get some of the country’s best linguine alla vongole, with plump and juicy clams, and meaty Neapolitan ragouts. Sleep it all off at the iconic Grand Hotel Excelsior Vittoria in Sorrento, or at the intimate cliffside monastery that’s now Monastero Santa Rosa.

The Final (Bike) Stretch

The last leg of your bike tour will test your endurance. It’s roughly 250 miles of unobstructed countryside, largely through olive groves and protected national parks. Insiders consider Calabria — the region at toe of Italy’s boot — to be the “secret” coast, with wilder terrain and very few crowds. Between the distance and the sheer beauty of the place, it makes sense to break up this leg into multiple days of cycling, as Branson’s team did.

Praia Art Resort is a particularly special place to stop. It has only-in-Italy trappings such as whitewashed beamed ceilings and terrazzo floors, with hammocks that are barely suspended above the Ionian sea and a spa that specialises in lymphatic drainage. For sore muscles, no treatment is better.

One Last Stop

To get to Sicily, most people take the ferry. Branson swam across the Straits of Messina. That two-mile-long body of water might not be daunting in distance, but it represents extremely choppy waters — not to mention that the straits are packed with boat traffic, as one of Italy’s busiest shipping lanes.

Residential buildings stand above the shore
in Alcamo Marina, sicily. to get to sicily, most people take the ferry

Most Strive Challenge participants had to take a ferry and swim a comparable distance on the northern shore of Sicily, but if you’re dead set on swimming the straits, you’ll need to get one of 21 daily permits and have an entourage of flagged boats to protect you from incoming traffic.

Don’t worry. Even if you take a speedboat, you’ll get one last chance to prove your athletic prowess with a marathon (or a very intense hike) up volcanic Mount Etna. The northeastern rift is the most impressive route, says Leuenberger, as it’s the most visible convergence of woods, craters and lava-flow fields.

Your reward? One last place to indulge: Villa Ducale, a small, four-star hotel that punches above its weight with rooms that look plucked out of an Italian movie set. Sleep in as late as your body desires, then order room service to your private terrace overlooking the bay — and take pride in the fact that, at least in one regard, you’ve achieved as much as one of the world’s richest men. — Bloomberg