Simon Calder's Holiday Helpdesk: What route should we take for a driving holiday in Florida? Q At the end of November we plan to fly to New York, then hire a car and drive to Naples in Florida. What route should we take, and what should we see en route? Jane Spence, Balham A he first rule of car rental in the US: never hire a car in New York City. You'll pay more than in any other location. Furthermore the first couple of hundred miles in the general direction of Florida are certainly better covered by train than by car, not least because you do not want to have to park a car in downtown Philadelphia or Washington DC - two great locations to see along the way. The Independence trail in Philly is worth a day; and Washington can fill several days, with the Smithsonian Mall containing some of the world's great museums (and all of them free). I have just got a quote from Avis (the UK website, which I find a reliable source) of £425 for a week, picking up in Washington DC and dropping off in Naples. Personally, I'd actually carry on by train to Savannah in Georgia - an easy 11-hour overnight journey on the Silver Meteor through Amtrak.com. But you might want to explore some of the Civil War battlegrounds in Virginia. In November, you'll have them to yourself. Savannah, the 18th-century capital of the colony of Georgia, has an easy charm that stays on the right side of twee. The history rolls back even further when you cross the Florida state line to St Augustine, the oldest continuously occupied European town in North America - founded 1565. Take the freeway to Orlando, and explore the city with our latest 48 Hours guide, bit.ly/Orlando48. And Naples is almost on the doorstep.