Mount Hakodate rises 334 meters above the city and is famous for offering one of the three best night views in Japan. By day, a ropeway or scenic drive carries you to the summit observation deck for sweeping views of Hakodate's distinctive hourglass-shaped isthmus framed by sea on both sides; after dark, the twinkling city lights create an unforgettable panorama.

Goryokaku is a striking star-shaped Western-style fortress built in the final years of the shogunate and the site of the last battle of the Boshin War in 1869. Today the moats and earthworks form a beautiful park that is one of Hokkaido's most famous cherry blossom spots in spring. The adjacent Goryokaku Tower offers a bird's-eye view that reveals the fort's remarkable five-pointed design.

The Motomachi district climbs the slopes of Mount Hakodate and is the city's most atmospheric neighborhood, shaped by Hakodate's early opening to foreign trade. Its sloping cobbled streets are lined with beautifully preserved Western-style buildings, churches and former consulates, including the Old Public Hall and Orthodox and Catholic churches, all enjoying lovely views down to the harbor.

The Kanemori Red Brick Warehouses are a row of handsome late-19th-century brick buildings along the Hakodate bayfront, once used as trading warehouses and now restored into a stylish complex of boutiques, cafes, restaurants and a beer hall. It's a wonderful place to shop for local crafts and sweets, enjoy harbor views, and soak up the romantic atmosphere—especially beautiful when lit up in the evening.

The Hakodate Morning Market is a lively warren of some 250 stalls and shops just beside Hakodate Station, brimming with the fresh seafood Hokkaido is famous for. Browse tanks of king crab, scallops, sea urchin and salmon roe, watch vendors at work, and tuck into a kaisen-don rice bowl piled with sashimi. Adventurous visitors can even try catching their own squid in a tank—an iconic Hakodate experience.

The Old British Consulate of Hakodate served as Britain's diplomatic office from 1859 until 1934, in the years after the port opened to international trade. The beautifully restored colonial building now houses a museum on the city's opening to the world, an English tea room serving scones and Victorian-style afternoon tea, and a charming rose garden—a delightful glimpse of Hakodate's cosmopolitan past.

Hachiman-zaka is the most photographed of Hakodate's many sloping streets, a perfectly straight cobblestone hill in the Motomachi district lined with trees and gas lamps. From the top, the view sweeps down between the buildings to the harbor and a moored historic ship, framing a postcard-perfect scene that has featured in countless films and commercials—especially magical when illuminated at night.

The Trappistine Convent, founded in 1898, was the first women's monastery in Japan and remains a working community of cloistered nuns on the outskirts of Hakodate. While the inner buildings are closed to visitors, the peaceful gardens, brick chapel and tree-lined approach are open to all, and the on-site shop is famous for the nuns' handmade butter cookies and madeleines—a serene and sweet end to your tour.