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''It's just being aware of the situation, being nimble,'' he explains. ''I never fly down the day of. If you push everything to the end, if you have a lot of steps – connecting flights, flying the day of the cruise, cabs, security – if everything's really tight, I just think you're asking for trouble. Take an extra day and decompress.
''That ship is going to leave no matter what. What do I need to do to ensure I'm there to catch that boat? If that means taking an extra day off, it's worth it. Arriving day of departure can be very hazardous. What's Plan B?''
When it comes to planning and trip insurance, Brian Van Wey, of Minneapolis-based Brand g Vacations, takes a similar tack. When the price point starts to make you nervous, go ahead and buy it – though that's no guarantee of a happy ending.
''More often than not, with insurance, you would probably just not go on the trip,'' he explains. ''You're going to get your money back. You won't go, but you wouldn't have lost money. The whole purpose of trip insurance is to mitigate those risks, but it's a crap shoot.''
When it comes to getting to the port in time for departure, he's still singing Shore's song.
''If possible, we always recommend coming in a day beforehand,'' he says of Brand g clients heading to his company's cruise vacations. ''With air travel, the slightest thing can throw it off. … Whether it be a family member that passes right before your trip, maybe you and your boyfriend broke up, or you might get a job promotion, there are a lot of factors that may impact a well-planned trip.''
The bottom line is that when you make those plans to head to the sun, keep in mind that bad weather is even more likely in winter. In blizzard season, a little extra time and insurance can go a long way.