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Itinerary and guide advice for Sri Lanka

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Hello fellow fodorites,

Looking for some words of wisdom about itinerary order and driver/guide suggestions.
As well as any guesthouse and must dos along the way. You've all given great advice and I'm hoping for some on this trip to get things just right.

We'll be arriving after spending 9 days in Thailand.
Here's our itinerary for 13 nights in Sri Lanka:

June 20- pm arrival, overnight in Columbo
June 21- go to Ella in AM (please suggest train or driver)
June 21-22- 2 nights in Ella, tea factories
June 23- train from Ella to Kandy
June 23-24- 2 nights Kandy, Temple of the Tooth, Dance performance and Shopping.
Stay at Helga's Folly
June 25-27- 3 nights cultural triangle; Dambulla, Sigiriya, Minneriya Park (need suggestion for $100 night or less accommodation)
June 28-30- 3 nights, travel to Trincomalee; whale watching, Pigeon Island snorkeling
July 1-3- 2 nights in Columbo; shop, eat and fly out the morning of the 3rd

Here's my questions:
ELLA: Can I take a train from Columbo to Ella or should I get a driver? Is this the right place to start our trip? Does anyone have a hotel/guesthouse reco for $100 a night or less that's near town.

DAMBULLA/SIGIRIYA: I like a little bit of town life, eat at local restaurants and shop. Which town would be better to stay in. Any recos for hotel/guesthouse $100 a night or less.

TRINCO: Any suggestion for best whale watching outfit?

IN GENERAL: I'd like a driver/guide for Kandy, Cultural Triangle and drive to Trincomalee. But not sensing I'll need one once I'm in Trincomalee,Columbo or Ella. Opinions please. And of course I'm hoping for driver recos and how to book this.

Any suggestions for Ayuveda massage, must eat restaurants , yoga studios, and high quality shopping is much appreciated. You guys haven't steered me wrong in the past.

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