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If you want to experience world-class surfing without having to break the bank, San Diego in the winter is your destination. Surfing there is on the great American bucket list. The city is one of the coolest surfing towns in the world. It has awesome wave pools in addition to a plethora of good surf spots. You can find hotels for under $100 per night (usually at their lowest this time of year). Flights from New York go for about $300 round trip.