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Bermuda cruises sail from April through mid-November, mostly during Bermuda's high or "beach" season. Most people travel during the summer months (June through August), making those voyages pricier, but you'll find deals on spring and fall departures (April through early June and September through November).
Bermuda has temperate weather year-round and is less affected by hurricanes than its Caribbean neighbors. If it's too chilly for the beach in the shoulder season, you can always try out the island's many golf courses and spas. October tends to be the rainiest month. Bermuda's big weather caveat: Hurricane season traditionally affects the island at least once a year between late August and October. May is your best bet for shoulder season travel.
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