I have been lucky enough to visit Bermuda twice and consider it one of my favourite island destinations. It's not your typical tropical island paradise in that it's not really tropical weather like you get in the Caribbean. There is a great laid back / safe vibe about the place (unlike many Caribbean islands.) It's hot (85F) but not sizzling in summer and mostly mild / cool in Winter except hurricane season (Oct-Nov). It's only a 2 hour flight from New York but can cost you a small fortune to visit in peak season (April-September). Flights can cost u$d500+ with beach front hotels costing up to u$d1,000 per night.
If you want to experience an amazing island with beautiful pink sand beaches you can do it for a fraction of the price in low season (November-March). I scored weekend flights for u$d150 in March and stayed at a waterfront B&B for u$d150 a night. There wasn't a great deal of WiFi when I was there so I'd recommend phone cards for calling home. Taxis are also very expensive but difficult to avoid on arrival at the airport. There are no car rentals allowed but there is a great and cheap bus service (not at airport) and you can rent a scooter/moped reasonably near the beaches.
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