Sheppy's Den - Review Page 1

Reviewed by Steve & Jill Wooler in 2010; updated February 2016

Regular visitors to Tobago will be familiar with the name Colin Shepherd. Best-known for his highly-regarded auto rental service, ‘Sheppy’ has expanded his business activities in recent years and now has a portfolio that includes one of the best small hotels and restaurants on the island and two, very different, holiday rental villas.

Sheppy's Den, TobagoSheppy’s first foray into the hospitality industry was the sujbect of this review - a charming 5-bedroom vacation rental villa, Sheppy’s Den. This colourful property was very much more than a business project to Sheppy. He may have justified the build on commercial grounds, but the bottom line was that he built the house because he could and wanted to. It also became his private retreat from the pressures of business. The name, Sheppy’s Den, says it all.

There are over 200 holiday rental villas on Tobago and the vast majority offer high levels of accommodation. However, most of these properties have no real sense of identity or any distinguishable association with Tobago. You could be anywhere in the world. Villas with true character are much harder to find. Every aspect of Sheppy’s Den screams Tobago. There is nothing subtle about this house. From the location to the violent colour scheme and décor, you are guaranteed a fairly unique Tobagonian experience.


The colourful groundsSheppy’s Den is located in Bacolet Park, a relatively new development next to the Dwight York Stadium, at the eastern end of the Claude Noel Highway that bypasses Scarborough.

Bacolet Park overlooks Minster Bay. Intervening scrubland inhibits sea views from the house. Beautiful Bacolet Bay beach is a three-minute drive from the villa. Upper Scarborough is a minute or two more and you can be in downtown Scarborough within ten minutes of leaving the house.

Bacolet Park is very popular with Tobagonian business and professional families. It is not a vacation rental villa development, where most of the properties remain vacant for all but a few weeks of the year. Bacolet Park currently boasts about 50 completed houses. A similar number of plots are available for future development. In truth, not much seemed to have changed since our last visit in 2010. Development is very low key. Even though the main Atlantic coast road passes just 75m behind the house, it is one of the quietest locations we have stayed in. No early-morning roosters, Chachalacas or boom boxes. Nada!

Sheppy's Den, TobagoOne thing that we particularly like about Bacolet Park is the fact that it is very much a ‘local’ neighbourhood. Most of the houses are owned by local professionals and business people. We were particularly taken with the friendliness of the neighbours and genuinely felt that they would ‘watch out’ for visitors.

It has to be said that there are no shops, bars, restaurants or other facilities within walking distance of Bacolet Park. Having your own transport is essential. In fairness, given Sheppy's primary business activities, this is hardly likely to be an issue. In fact, Sheppy offers particularly good deals when renting both the house and a car or jeep.

From this location, the island is your oyster. The journey from the airport takes little more than 20 minutes. You can drive to any of popular Crown Point/Lower Caribbean beaches in much the same time. In fact, every point of the most populated Crown Point-Plymouth-Scarborough triangle is within a 20-minute drive.

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