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Flight and embarking on same day

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We are planning a New England & Canada cruise in Oct and was wondering if anyone has experience with same day flight and embarking. We have two choices: New York (Princess) or Boston (Royal Caribbean). At LaGuardia,our flight would arrive around 11:00 am. The distance to the port is 12 miles. At Boston, the flight would arrive around 10:50 am. I do not have information as to how far it is from Logan Intnl to the port. These arrivals are assuming the flights are on time. I believe both ships leave the port around 5pm. We will be flying from Milwaukee on a nonstop flight. Has anyone had experience with arriving on the same day as the ship leaves. Is this a big gamble?? Would appreciate any advise you could give.

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