WestJet usually has two good sales in July and January and usually those months have proven the best time to book for future trips. I have secured flights from Ottawa on WestJet for $300-500 return in the past, but this year $600-700 was the best sale price to SXM. Other places in the Caribbean were much lower for their sale. I've also noticed other airlines are not offering great sale prices to SXM either as they never have a problem filling all the seats. It is nice to leave directly from your home airport so it is often worth it to pay the higher price for the extra convenience.