I understand why you might be nervous about boarding Fenway, but just look for a kennel which suits you.
My family and friends have boarded loads of animals over the years, and everytime the dogs have loved it! As long as Fenway doesn't have any issues with other dogs, he will have a buddy with him almost all the time. Try to look at a few places in your area before the trip, and bring Fenway in so he can have a sniff around with you there.
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