Cover Star: Phil Hindle

I thought it would be a good idea to go on the trip – and my wife is always fed up with me wearing black jeans and not having had my hair styled for the past 20 years. They trimmed my beard before the photoshoot – and I've kept it short since – but there wasn't much they could do with my hair. It was nice to be the centre of attention, get a new outfit and enjoy all the razzmatazz.

The shopkeepers at the mall were all so generous. Lots of them gave us gifts and goody bags. I got a Le Creuset mug and lots of other odd bits. We were all given a $100 voucher for a jewellery store, so I got my wife a nice necklace. She wanted to get me out of the habit of wearing black jeans all the time – but I ended up buying two pairs of black Levi's. So now I am back to wearing them every day.

I went to Boston about 20 years ago and it's changed so much since then; a lot of the traffic has gone underground. We went on a walking tour, which included the Skywalk Observatory, and used the Metro. Public transport in Boston is dead easy to use – you don't need a car. I went off on my own and just hopped on the Metro to go to Quincy Market, next to the original town hall. There were lots of food stalls and places to eat such as the Hard Rock Cafe, as well as a big visitor centre.

Everything was so easy that I had no problems exploring on my own. We also went on a drama walk with two actors who showed us locations such the bar used in the TV series Cheers and the bench from the film Good Will Hunting starring Robin Williams, which has become a tribute to him since his death. It's a lovely city to wander round and so friendly; I was pleasantly surprised.

I didn't have a clue what to expect. I was expecting seaside because it's where the Americans go on holiday, but it was much more picturesque than I thought it would be. There were lots of little towns with independent shops, unspoilt beaches and wildlife. The 4×4 trip over the sand dunes was a real highlight. There were houses on the dunes built on stilts – some were like garden sheds and some are really funky.

It gave me extra confidence to sell the area. I have already sold a couple of trips to the region, but it's something I hope to sell more of now.

Phil's ‘James Bond' styling was tailored by Bloomingdale's The Outlet Store at Wrentham Village Premium Outlets. With more than 100 years of history, Bloomingdale's is synonymous with designer shopping in the US.

Phil's shoes were provided by Wrentham Village's Rockport store. Wrentham Village Premium Outlets offers discounts of 25%-65% in 170 designer and brand-name stores.

Boston Common Coach provides commissionable packages from all of Boston's major hotels.

• If clients are interested in history, this is the area to recommend, as it is where the first settlers arrived on US shores.
• Boston is a great alternative to New York and much more manageable in scale.
• It's an easy holiday to tailor-make but there are also plenty of operators offering packages.

personal travel agent, The Midcounties Co-op Travel, Taunton assistant manager, Cathedral City Travel, Wells owner, Thyme Travel, Taunton

Travel Weekly Cover Stars 2015 is running in association with headline sponsors Massachusetts Office of Travel and Tourism and Brand USA, travel partner Virgin Holidays and makeover partner Simon Shopping Destinations.

Standing on the beaches where the first US settlers arrived in the US certainly gives Cape Cod a unique selling point, according to Phil Hindle.

"These are the beaches where the Pilgrim Fathers arrived. They moved to Plymouth, where it was more sheltered, but this is where the European settlers started,” he enthuses.

For those interested in history and the educational aspect of a holiday, Cape Cod has plenty to offer.

"At the Plimoth Plantation, there is a depiction of life as it was when the settlers arrived, with re-enactments. It was very educational. There is also a Native American encampment, where we were told about what it was like before the Europeans arrived.”

Other highlights included a copy of the original 17th-century Mayflower ship – the Mayflower II, which was constructed in the 1950s – and the history of the Kennedy dynasty in local museums.