On the road: a trip around America and Canada

It’s 20 years since iconic twosome Thelma and Louise came accelerating on to the big screen and women everywhere went faint over a young guitar-welding Brad Pitt. So how would Charlotte Ward and a girl pal fare on their own epic road trip through the US and Canada?

JFK to Jamaica 15 miles 

Our adventure begins in a car rental lot at JFK where after a seven hour flight we are already battling to open the boot of our hire car.

Shoving our huge heavy suitcases in the back seat of the car, we drive to the security gate and ask for assistance. The burly security man is flummoxed too. He directs us to another car – a huge Pontiac G6. It has taken an hour to drive out the rental lot alone. Not a good start to begin our mammoth 1,500 mile trip around North America!

After a couple of scary wrong turns we find our budget hotel in Jamaica and spend another half an hour trying to manoeuvre our frankly huge hire car into the packed car park. I am pretty sure the hotel reception must be watching our blonde antics on the security camera.

How the hell are we going to make it round America and Canada? As we eventually clamber down the hotel stairs straining with our huge pink suitcases the reception staff are definitely smirking.

JFK to Southampton 106 miles

After five hours sleep I’ve woken up with a sore throat akin to swallowing razor blades. Clare just has plain old sleep deprivation thanks to the couple occupying the next door room who got pretty ‘friendly’ at 4am.

After some bad navigation (Buy a map? Now, that would be sensible!) we finally find ourselves on the Southern State Parkway that will take us all the way to The Hamptons.

A scary orange light has appeared on the car dashboard. Pulling over at a garage, the mechanic says it could mean ‘anything’ but tops up our oil which seems to have diminished rapidly.

We nervously set off again. Every time Clare breaks we can smell oil. The scary light is still on. And now our breaks are squeaking angrily everywhere we go. Great.

Arriving in Southampton we are greeted by our friend Sally who is living in The Hamptons with her husband and baby daughter.

That afternoon we’ve managed to get on the guest list for the Bridghampton Polo, frequented by The Hamptons it-crowd.

We get talking to a nice chap who reveals he collects sports cars. ‘How many Ferrari do you have?' I enquire nonchalantly. 'Oh just a few,' he replies. 'No more than a dozen.' Blimey.

Before we headed out to The Hamptons we’d been warned that everyone drives and taxis are not only costly but few and far between. Did we listen? No.

With the polo over we traipse across the fields in the faint hope of picking up a taxi. From the gate we are eyeballed in a bemused fashion by the occupants of the queuing cars waiting to drive out. This is clearly not Hamptons etiquette and we seem to be creating quite a commotion as we totter along a dusty track in our high heels.

The nice man with the collection of Ferrari’s offers us a lift. But we’re frightfully English and decline. It takes us over two hours to get home. We were supposed to be going to hip Hampton nightspot Axe at 11pm to meet the Ferrari millionaire but by 9pm both Clare and I are in a jetlag coma and have to go to bed. Pathetic.

Southampton to Montauk (and back again) 54 miles

This morning we called the car company who tell us helpfully that ‘if we want’ we can drive our car back to JFK and get it replaced. Helpful, seeing as we’re now almost 100 miles away.

We decide to journey on and enjoy a couple of hours on the idyllic Coopers Beach before heading off on a pleasant drive to Montauk, passing en-route through picturesque little towns. We also take a wander around the pretty Montauk Point State Park which leads to lovely clifftop views of the Montauk Point Light - the first lighthouse in New York state.

We spend the evening sipping G’n’Ts at The Surf Lodge in Montauk, which has live music and a killer sunset. Perfect!

Southampton to Rhode Island 115 miles

We’re on the road to err, Rhode Island and have a jolly drive through Long Island’s North Fork gazing in awe at the plethora of wineries – we count around a dozen on the RT 25 (Main Road) and of course stop to stock up for later in our trip.

Arriving at Orient Point we drive onto the Long Island Ferry to New London where I bodge up the parking, prompting a car attendant to direct me moodily as I reverse back and forth half a dozen times and the car brakes squeal with ear-piercing ferocity.

It’s a gorgeous day but while we assume the ferry ride is about 30 minutes, it is a good hour and a half before we return to our car, Clare’s shoulders now lobster pink. Oops.

The US are very well equipped for ill-prepared road trippers and en route to New Port we discover a handy visitor centre (the first of many on our journey) on the side of the freeway where the friendly guide not only gives us free maps, but detailed instructions about how to get to our hotel. God Bless America!

We spend the night at the gorgeous Vanderbilt Hall which was originally built in 1909 by Alfred Vanderbilt as a residence for his mistress! It’s a gorgeous hotel with gorgeous homely suites and impressive indoor and outdoor pools and an amazing roof terrace looking out onto Newport Harbour and Narragansett Bay.

After a lovely walk around Newport’s pretty harbour and quaint streets we dine in at The Black Pearl in the Commodore's Room - a cute dining room with pristine white tablecloths, forest green walls and a nautical theme. The menu is mainly sea food and the scallops are delicious.