This Atlantic Ocean port, which is part of Portugal, may be the most beautiful of any in the Canary Islands or the Azores. It was once a common stopover for vessels trading between Europe and South America or Southern Africa, and passengers were so intrigued by their day ashore that many came back for longer stays. It’s now a popular resort island as well as a major cruise ship stop, especially for passengers who leave from northern Europe.
What We Love
Tea at Reid’s: Opened in 1891, Belmond Reid’s Palace hotel sits high above the port on 10 terraced acres of subtropical gardens. Reserve an outdoor table in advance and partake in a truly stylish — if expensive — multicourse English afternoon tea with an ocean view. Smart casual attire means no shorts.
Ringing in the New Year: Book a cruise that brings you into port on New Year’s Eve to witness one of the largest annual gatherings of cruise ships. There’s a huge display of fireworks and blasts from all the ship whistles.
Best Known For
The Views: After a steep climb, find a bench and enjoy a classic panorama — the view down to the port town and the harbor where your ship will dock. Go even higher via a gondola cable car to the suburb of Monte, and then onto the botanical gardens, which has its own views.
Mercado dos Lavradores: This centrally located market is frequented by locals for fish and fresh island produce and has sections for flowers and crafts such as wickerwork, embroidery, and, of course, Madeira wine.
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Who It's Best For
Anybody and Everybody: You can hike, take aerial gondola rides, visit a lovely city with shops selling appealing wares, peek inside colonial churches, wander an art or natural history museum, and enjoy luxe living up at Reid’s Palace.
Don't Say We Didn't Warn You
Buyer Beware: Be careful what you pay at the market as there is often a price for locals and a “special” price for you, the visitor.
Theodore W. Scull is a New York-based contributor to ShermansCruise who has written several books on crossings.