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Many educational guides liken their tours to college seminars (usually with more walking than sitting, though). Using that analogy, the cruises offered by Academic Arrangements Abroad, an educational trip outfitter, are more like semester at sea programs for VIP students. All feature lectures by on-board scholars, plenty of behind-the-scenes access, and top-notch accommodations and food. Italian Masterpieces: Rome to Naples Aboard the Sea Cloud II, a voyage Academic Arrangements Abroad is running this September, is no exception. The trip includes an after-hours visit to the Sistine Chapel, a private viewing of the Doria Pamphilj Gallery, a glimpse of the private collection of Cardinal Scipione Borghese (at the Borghese Gallery) and a dinner with Principessa Stefania Raffadali—inside the royal’s very own palace. The first two nights are on-shore in Rome, at the Hotel Majestic (www.rome-hotels-majestic.com), a former stomping ground for Roman high society, while the remaining days and nights are spent cruising around Sicily (where stops include the medieval village of Eric and the ancient city of Segesta), the Aeolion Islands and the Amalfi Coast.

For the sailing part, accommodations are on the Sea Cloud II, sister ship to the Sea Cloud, the former private yacht of Post Toasties heiress Marjorie Merriweather Post. This boat is larger than the original (it holds up to 90 passengers) and though it comes equipped with a fitness area, a watersports deck and all modern-day amenities, the décor is decisively old-school, with elegant curtains, four-poster beds and mahogany-paneled walls. Throughout the journey, Mike Norris, a medieval specialist at the Met, and Karen Manchester, an antiquities scholar from the Art Insititute of Chicago lead on-board lectures and discussions. Post, herself an avid sea traveler and collector of fine art, would have approved. From $6,495; September trip still has availability.