Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger

Sri Lanka doesn’t really have a good infrastructure for budget travelers at this point. There are loads of nice hotels if you are willing to pay US$40 or more per night, but almost nothing below that except for a few hostels. I haven’t been to Palawan but I have been to Boracay and Palawan can’t be too much cheaper. Boracay doesn’t have many budget options either, so my guess is that Thailand or Cambodia is your best bet.
Trekking in Nepal during peak season might not sound like the most sensible choice for penny-pinching backpackers. But you can still enjoy the ideal weather without spending a fortune on in-demand hotels and expensive permits if you're happy to swap big-name trails, like Everest Base Camp and the Annapurna Circuit, for quieter treks to Kanchenjunga Base Camp and around the Langtang Valley. Idyllic conditions (dry but not witheringly hot) are also on offer in Rajasthan, one of India’s most vibrant and varied states. Chug between notable, attraction-rich cities like Jaipur, Jodhpur and Udaipur on an atmospheric and wallet-friendly Indian train, snacking on spicy pakoras and sipping sugary chai en route.
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