My brother, his wife, and my folks went back to Bermuda late last year for my brother's 50th birthday (he was born there); they had a GREAT time. Of course, much had changed since we lived there 1959-1962, but they did manage to find one of the houses we had lived in. Hope you and Kara have the same enjoyable experience!
Kara and I have been back on three trips via cruise ships including the one last June. Change is visible everywhere. Some hotels, and stores we knew as long standing landmarks such as The Belmont, The Bermudiana and Trimingham's no longer exist but the island remains to be as charming as it ever was. I know we're going to have a great time.