December-March: This peak tourist season in the U.S Virgin Islands coincides with that of many other Caribbean islands, and hotel and resort rates can rise by an additional $150 or more per night
Weather. With the highest average monthly rainfall (4.5 inches/115 ml), least daily hours of sunshine, and some of the coolest temperatures of the year, January in Santorini is not the best month weather-wise. But despite this, temperatures remain mild or even high by European standards at this time of year, with 48-57°F (9-14°C) the averageYou can get very sunny days, but you may also get rain and wind. You may be able to go for a swim, but some people will find it too cold. Additionally, most people will need a jacket in the evening. The average temperature in November in Santorini is around 17˚C, with highs of 19˚C and lows of 14˚C.
Low Season (December through February, with the exception of Carnival): Winter is the low season in Tuscany. Cold weather brings the best chance for lower airfares and discounted accommodations, and few worries about crowds or long lines. While it may be chilly, snow is unlikely, just plan to bundle up and plan your itineraries around shorter days.