Sheppy's Den
Mini-review by Steve & Jill Wooler, March 2008
The number of invitations and requests that we receive to review properties far outstrips our ability to undertake them. In an ideal world, we would visit every accommodation property on Tobago. As a non-commercial site, we simply lack the time and resources to accomplish this.
So, the best we can do is to spend two months each year producing detailed reports on as wide a range of accommodation as possible. While conducting the main reviews, we also undertake detailed inspections of properties that we intend to stay at, and fully review, the following year.
This mini-review of Sheppy’s Den follows one such inspection. It will be replaced by a full report after our 2009 visit to Tobago. In the meantime, we believe that the property deserves inclusion in our list of “Reviewed & Recommended” properties.
Mini-Review
The name Sheppy will be familiar all regular visitors to the island. Colin Shepherd owns and operates one of the largest and most highly regarded car and motorcycle rental agencies on the island. We could hardly envisage going to Tobago and not being met by Sheppy’s huge welcoming grin and bear-hug as we step out of the Arrivals Hall and into one of his vehicles.
Although built as a commercial rental property, Sheppy’s Den clearly represents much than that to Sheppy. He built it, not just because he saw commercial possibilities and could afford to, but because he wanted to. The name, Sheppy’s Den, frankly says it all. This was a private and personal project that meant more to him than the prospect of financial return. Knowing this – and the high levels of service on which Sheppy’s success has been built – convinces me that any visitor staying at Sheppy’s Den is guaranteed the very highest levels of hospitality, as well as comfort.
The Location
Sheppy’s Den is located in Bacolet Park. This is a new development close to the Dwight York Stadium at the eastern end of the Claude Noel Highway that bypasses the capital, Scarborough. The development overlooks Minister Bay – although intervening scrubland inhibits sea views. Beautiful Bacolet Bay is just a two-minute drive away and the facilities of downtown Scarborough little more.
Bacolet Park is a new development favoured by the more affluent Tobagonian middle and business classes. At the time of our last visit, around two dozen properties were complete. On completion, the project is likely to consist of three or four times that number. However, things progress slowly on Tobago and completion will take some years. Although a new project, construction is very low key and I certainly didn’t get the feeling of being on a building site.
It has to be said that there are no shops, bars, restaurants or other facilities within walking distance 
of BacoletPark. When staying here, it is essential to have you own transport. However,given Sheppy's primary occupation, it hardly surprising to find that his best rental package for the house includes a self-drive vehicle. Bit of a no-brainer!
With your own transport, the island is your oyster. The journey from the airport will take no more than 20 minutes. You can drive to any of popular Crown Point/Lower Caribbean beaches within much the same time. In fact, every point of the most populated Crown Point-Plymouth-Scarborough triangle is within a 20-minute drive.
The Accommodation
Viewers of the BBC Doctor Who series will know what I mean when I describe Sheppy’s Den as the TARDIS. From the road, it looks like a fairly compact two/three bedroom cottage. Knowing that it had four bedrooms, plus a small annexed self-contained studio apartment, I thought the rooms must be tiny. On entry, I was amazed to find just how spacious the property is.
The first thing that strikes you, however, is the vibrant exterior of purple and green. There is no mistaking that you are in the Caribbean. If this house was the TARDIS and you had been zapped through unknown time and distance, you would have no doubt about where you had landed. Those wanting minimalist under-statement should look elsewhere. This property doesn’t believe in subtlety – it socks you between the eyes and wraps you in a thick cosy duvet of opulence and comfort. This is the lifestyle to which most Tobagonians aspire and, like their music, cars, worship and partying, it is loud and distinctive.
I visit a destination to enjoy and learn about the culture and lifestyle of the endemic population; not to stay in an antiseptic ‘international’ standard hotel room or villa which could be anywhere in the world. In that respect, this house couldn’t be better suited. It has local character in abundance. I suspect that those who stay there will only ever reflect on the visit with a huge smile on their face.
The house is furnished and equipped to standards that can only be described as unrivalled. Sheppy could not have equipped it better if he had built it for himself and his family. He is certainly not a man who believes in cutting corners.
The house is fully air-conditioned and will comfortably sleep eight – not counting an extra two in the annexed studio apartment (which is never rented out at the same time as the main house). Two of the four double bedrooms have en suite bathrooms, while the remaining two share a bathroom sited between them. The kitchen has everything you could possibly ask for, including a dishwasher. An adjacent utility room is equipped with a washer and dryer. The lounge is dominated by a huge widescreen TV and music system.
The front of the house features a large swimming pool and collection of sun loungers. Not to be outdone by the opulence of the interior furnishings, the front veranda is equipped with a large stainless steel gas barbeque that looks as if it would be more at home in the kitchen of a professional chef. To be frank, a mini-review such as this cannot start to do justice to a place with as many features as this.
Conclusion
All things considered, Sheppy’s Den is a rather unique property. It screams character and undoubtedly offers the very highest levels of accommodation comfort – all in a local environment far removed from the rather sterile and often deserted holiday home developments which are sadly a feature of much of Tobago’s rental home stock. Best of all, as a guest of Sheppy’s Den, you will also be a guest of someone whose entire success has been based upon the highest levels of personal, friendly service and goodwill.
We truly look forward to our next visit to Tobago when we will hopefully have the opportunity to spend more than a few hours at Sheppy’s Den, enabling us to report in far more detail.
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