In comparison to many of its other Caribbean counterparts, the island of Tobago can be considered a relative newcomer to tourism. In fact, using Butler’s Tourism Area Life Cycle (TALC) (Butler, 1980), Tobago can perhaps be positioned at the early to mid-stages of the development phase, given the growing levels of local and foreign investment in the tourism plant and services, an aggressive marketing campaign that seeks to distinguish Tobago as a premier leisure and ecotourism destination and a noticeable increase and acknowledgement by tourists and residents of negative social and environmental impacts, perceivably because of tourism development (Tobago News, 31 October 2008, 5 December 2008, 9 January 2009; Twining-Ward, 2008). Over the last few years, Tobago has also seen a modest increase in both its cruise and international arrivals. International arrivals grew from 23 111 in 1992 to 56 917 in 2008; and cruise passengers from 16 373 in 1996 to 22 253 in 2008 (Division of Tourism, 2009). Increased airlift from source markets, familiarization trips by travel agents, media and tour operators, representation at travel markets, personal selling, greater attention paid to the marketing mix of price, product, promotion and the introduction of its official website in 2001 have contributed to the growth in numbers. The primacy of the Internet in destination marketing and communications is well established, and destination marketing organizations (DMOs) have had to respond to competition from other destinations and the exponential use of the Internet by consumers in planning their vacations. In 2005, 200 million Americans were Internet users, and of these 84% are travellers. Consumers are now researching, planning and even booking their trips online, and travel blogs are increasingly being used as a source of travel information. This chapter examines and evaluates the official website of the Tourism Division of the Tobago House of Assembly (THA; www.visittobago.gov.tt), the public sector destination management organization charged, inter alia, with the marketing of Tobago. The chapter assesses the strengths and weaknesses of the site and provides recommendations for an improved online marketing strategy.