More than 36 years since being granted Test status, this is just Sri Lanka's fourth Test tour of the Caribbean and the first involving more than two matches.
On their last campaign to the region ten years earlier, the team led by Mahela Jayawardene claimed their first Test victory in the West Indies in a shared rubber.
Sri Lanka will be keen to extend the form of their last seven matches in which they were beaten just once, away to top-ranked India, and enjoyed an historic 2-0 triumph over Pakistan in the UAE while also prevailing at home over an improving Bangladesh side by the same margin in their last Test action in February.
However, their preparations for this series have been hampered by unexpected setbacks involving key players.
Concerns also linger over a number of seniors in the squad who are being managed very carefully with a view to ensuring their readiness for the World Cup in England in 11 months' time.
Opener Dimuth Karunaratne misses the tour because of injury, as do fast bowlers Dushmantha Chameera and Nuwan Pradeep.
Emerging batting star Dhananjaya de Silva was due in Trinidad on Monday having stayed at home when the touring party departed Colombo because of the shooting death of his father, a local councillor in the Sri Lankan capital, the evening before they were due to start the journey to the West Indies on May 25.
It is unlikely that he will be considered for the first Test although he is expected to be back in the key number three position come the second Test in St Lucia and the final match in Barbados, the first-ever day/night Test to be played in the West Indies.
Of the trio of senior statesmen in their side — left-arm spinner Rangana Herath, former captain Angelo Mathews and fast-medium bowler Suranga Lakmal — only Mathews featured in the lone warm-up match ahead of the Tests, a drawn three-day fixture against a Cricket West Indies President's XI highlighted by captain Dinesh Chandimal's assured hundred.
All three are expected to play key roles in the quest for a first Test series triumph in the West Indies although Sri Lanka's selectors have already indicated that concerns over their long-term fitness are likely to result in their being rested for at least one of the three matches.
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