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If you go in a fishing boat they only take a maximum of 4 persons as when you spot a whale you have to give chase quickly to catch them. Trincomalee is one of the deepest natural harbours in the world and thus the reason the blue whale & sperm whales choose to come here to mate.
I saw about 4 whales but my husband saw about 20 on a separate trip. Don't eat before you go & it is advisable to take sea sick tablets even if you don't think you get seasick. Make sure you protect your camera from any water splashes and go in a boat with a sunshade. Expect to pay on average 10,000 for the boat or a cost p/h for 4 persons may be slightly higher cause of greater kerosene costs.
North of Trinco town, on the road to Nilaveli, is the British war cemetery. It's well worth stopping off for a quick look if you're heading that way. If you're particularly interested in WW2 cemeteries and history then there's enough to keep you occupied here for a while. I think it's the biggest British cemetery in Sri Lanka, partly due to the Japanese air raid on Trinco in 1942. Talk to the man in charge - he can show you lots of documents and historical artefacts from the time. Many British people come here to visit the graves of relatives - many don't actually know where they were buried. If so this is a good place to find out as there are extensive records. The cemetery has been caught in crossfire and bombed countless times during recent decades but it's still well kept and in good condition. The bay (or rather bays) are what Trinco is most famous for. There are three main bays - Back Bay to the north of Fort Frederick, Dutch Bay to the east of the town, and the Inner Harbour to the west. Trinco is on a peninsula so the town is surrounded by water. The Inner Harbour is the main deep-water port, but all three are used for fishing and sailing. There isn't really anything to see, apart from the fishing boats coming in at the end of the day, but there are always lots of people about and a lively atmosphere. Take a walk around Dutch Bay at sunset and there are fishermen bringing in their catch, kids playing football, women sat around chatting and cooking and so on.
The beaches of Back Bay and Dutch Bay don't quite compare to Nilaveli and those up the coast, but nonetheless they're surprisingly attractive and welcoming and the water looks (don't know whether it actually is) clean and inviting.