Car Rental : a Review of Sheppy's Car Rentals

A review of the myTobago preferred car rental agency

Sheppy Car Rental offices in Crown Point

Colin Shepherd, known to one and all as Sheppy, started his business in 1997. His reputation for amazing service spread and within 10 years he had become one of Tobago's three largest car rental agencies with a fleet of more than 50 cars, jeeps, SUVs, mini-buses, mopeds, scooters and motorcycles.

When we first met and starting using Sheppy, he was a full-time policeman operating the rental service part-time. He retired from the police in late 2004. Concentrating on the business full-time made a huge difference and allowed him to take the service to new levels.

I was aware of Sheppy’s reputation for the highest standards of service and friendly, accommodating manner, but what were his vehicles like? We decided to find out by using him for the final two weeks of our 2003 trip. We were about to be joined by family, so needed a vehicle big enough for six adults. Large vehicles are in short supply on Tobago and expensive to hire. I wanted to demonstrate a degree of restraint, so I had booked an economical Suzuki Carry 7-seater.

I won’t bore you with the details of the hand-over. Let’s just say that it could not have been more casual, although he did offer to demonstrate the vehicle controls. Sheppy's attitude is very much more informal than the larger agencies. That's not to say he is less professional, but his attitude and manner is just so typically Tobagonian. You are guaranteed to part with a grin on your face. Sheppy is the personification of that favourite Tobagonian saying - 'no problem, man'.

Anyway, the Suzuki Carry. Well I must start by saying that on delivery, Sheppy, who was unaware of my involvement with myTobago, apologised that it was such a basic vehicle and promised to upgrade me, without charge, as soon as he had a better choice available. This was highly surprising. After all, I had booked a Suzuki Carry and that was the vehicle he was providing.

I guess the Carry was about five years old. It was in excellent condition, particularly for it's age. However, at the end of the day, it was only a Carry and I soon appreciated Sheppy's slight concern. Now I know what happens to old baked bean cans.

Sheppy Car Rental offices in Crown PointA few hours later, our family's flight arrived. There was no chance of getting everything into the Carry, so a taxi followed with the luggage.

Going on holiday with other people is always risky. Well, it wouldn’t have been a problem but for that bloody vehicle. Try taking six people with a combined age of 375 years around Tobago in a Suzuki Carry. It was not fun! I was convinced that the air-conditioner was a hair-dryer, until somebody pointed out that the hairdryer was actually the engine. Mind you, it did get up the steepest hills, even if I spent more time in first gear than top.

However, that's all beside the point. Back to Sheppy. Bless his heart, he kept his promise. On the evening before our departure, he arrived at our villa in Arnos Vale with a Nissan Serena. Typical of Sheppy, he didn't phone and see if we were there, he just brought the vehicle all the way out from Crown Point anyway. I thanked him, but assured him that a changeover wasn't necessary when we would be returning the vehicle in less than 24 hours. Sheppy was adamant that having said that he was going to upgrade the vehicle, he intended to keep his promise.

My conclusions. Well, the Carry was my choice, not Sheppy's. As a specimen of the model, it seemed in excellent condition. It was considerably cheaper than similar offerings from other agencies and half the cost of the Mitsubishi Space Wagon that I would have liked. As regards Sheppy's service, well, you simply couldn't ask for more.

2004 Update

Sheppy Car Rental offices in Crown PointWhile I would happily have used any of the firms that we tested in 2003, I must confess that when it came to arranging a vehicle for our 2004 trip, I immediately turned to Sheppy.

The last year has been kind to him. He has made considerable investment in his fleet. Apart from substantial expansion, he has replaced all the older vehicles and now has several brand new vehicles. He gave me a lot of ribbing over my comments about Suzuki Jeeps and was keen to prove that his new Suzuki 4x4s are a major improvement over the old models that I constantly berate, but to be honest, saloon cars still offer better ride quality, shade and security, so I declined the offer.

I won't bore you with the details of the cars, other than to say that they were clean, well presented, in full working condition and totally reliable. I visited Sheppy's compound several times, just to say hello, and was impressed with every vehicle that I saw there. He's come a long way in the last year or two and good luck to him. Fortunately, Sheppy is still Sheppy and his service and prices continue to represent some of the best all-round value on the island. The great thing about Sheppy is that he is just so approachable. Don't expect things in a hurry, but expect to go away happy.

After careful consideration, Sheppy is now our personal preferred Tobago car hire service.

Further Information:

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GBP = $8.61 

   USD = $6.77

EUR =  $7.66 

   CAD = $5.17

  Mid-market rates per

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Page Updated: 18 Aug 17