Holidays that put you in the driving seat

If you really want to explore a country, one of the best ways to do this is to ‘hit the road’. A self-driving holiday gives you the complete flexibility to go wherever you want and to veer away from the well-trodden tourist trails.

The sense of freedom that comes with a self-driving holiday appeals to lots of people from all walks of life and the choice is endless.

All Things Business spoke to Rob Gower of Dragonfly Traveller and got his recommendations for best road trip holidays.

Route 66

Route 66, from Chicago to the Santa Monica Pier, is a once in a lifetime drive. Your journey will take you over 2,400 miles through the contrasting landscapes of the USA. Take in the stunning blue rivers of Chicago, sample some of America’s famous diners or stop at one of the many roadside viewpoints at the Grand Canyon - one of the seven natural wonders of the world. Many car enthusiasts choose to hire a classic Mustang, Ford or Chevy to cruise along this iconic route and experience a true slice of America.

New Zealand

New Zealand is ideal for self-drive holidays. At many points along the coastal roads of the South Island, you’ll find yourself driving by the Southern Ocean or the Tasman Sea to one side and the Southern Alps on the other. Journeying down the east coast from Nelson, you will come to Kaikoura which is famous for the whales that visit the shores all year round. Sperm whales and other species can be seen at any time of year and if you’re visiting in winter, you might also see migrating species such as humpback whales.


Italy has some of the best road trips in Europe. One of the most fascinating routes is through the Tuscany hills. Start your journey at San Gimignano where you can witness the marvels of the historic town and its high stone wall. From there you can drive down to Siena where you can witness the charm of restored cathedrals and castles. After you have taken in the sights of Siena, you can head out to the famous Chianti Wine Region, enjoying fine wine tasting under the Tuscan sun. Don’t drink and drive though! Once you have seen enough of the wine region, you can drive towards the beautiful city of Florence and take in the beautiful views of river Arno along the way. When you are on a road trip in Europe, you will need an International Driving Permit (IDP), which in some countries is mandatory by law and you could be fined if you get pulled over without one. You will also need a valid driving licence. It also doesn’t hurt to carry photo identity along with proof of ownership/rental of the car you are in too.


Just a two-hour drive north of San Diego is a fantastic stop for those driving the California coast. Visiting Los Angeles – known as the City of Angels - feels like visiting a few different cities in one. You can easily fill a few days here, taking in some of the city’s more notable sites such as the Hollywood sign, the Walk of Stars and Mann's Chinese Theatre, along with seeing the colourful billboards and restaurants of Sunset Strip. In comparison, Beverly Hills has a more upmarket feel about it. You can while away hours wandering around the designer boutiques of palm-lined Rodeo Drive. For the beach, Santa Monica is a clear choice. From here you can visit Venice Beach and Santa Monica pier on foot with the latter creating a beautiful silhouette as the sun sets behind it.

Rob and Lisa Gower of Dragonfly Traveller work as travel PAs, building bespoke holidays and trips for their customers. Call 01604 661100 or visit to find out more.