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The best time to visit Bermuda can be anytime. The deciding factor would just be the budget. Caribbean islands are like paradise but a vacation in one, not excluding Bermuda, can eat up quite a lot of money. Thus, if there is plenty to splurge, peak of summer (April-October) can be the best of the best. The beaches and hotels are ripe with people at this time. There are more chances to meet to new people and do lots f fun activities along the beach. On the other hand, if there is a limited supply of cash, better try the winter season. It may be too cold for the beaches but it would just be perfect for sightseeing, golfing, volleyball and other outdoor activities.