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The largest and most storied of the Sydney Harbour islands, Cockatoo was once an Aboriginal fishing ground, a naval shipyard, a girls’ reform school, and a gruesome prison. Today, it offers fascinating walking tours, a casual café, and a number of events such as the Biennale of Sydney. When most visitors line up in the evening to catch the ferry home, those staying on the island are just setting off on a leisurely sunset stroll. They can watch the city light up from what feels like another world and then retreat to their campsite, canvas “glamping” tent, heritage home, or modern apartment until they wake up to birds and boats the next morning.

Last week we spent 5 days in Copenhagen, Denmark. October is, for me, the best time to visit. It’s colder and there are more chances for rain but the number of tourists is drastically lower. I did not feel suffocated by them at all. Nyhavn harbor was almost empty every day. I love traveling in the shoulder season.

The brick-and-iron warehouses of the old Eveleigh Railway Workshops host a diverse lineup of experimental music, theater, film, and fine art. Located on the border of Redfern and Waterloo, Carriageworks was restored to keep the historical roots intact while providing a space for cutting-edge culture. Every Saturday, more than 70 stalls fill the former railyard outside with organic produce, artisan breads, specialty coffee, and exotic flowers as well as street food from the likes of chef Kylie Kwong during the farmers’ market. Fuel up at the market and then get inspired by whatever is on display inside this artist-run venue. Big annual events for Sydney Contemporary, Pacific Runway, Sydney Gay and Lesbian Mardi Gras, and the Sydney Festival are also held here throughout the year.

The meat pie is synonymous with Australia, and no place is more iconic in Sydney than Woolloomooloo’s Harry’s Cafe de Wheels. What started out as a simple stand turned into one of the first food trucks when local ordinances dictated that mobile food carts had to move at least 12 inches every day. There are now dozens of Harry’s around Sydney, each serving up their famous pies. “The Tiger” is the most well known: a pie topped with mashed potatoes, gravy, and mushy peas. There are no tables to speak of, but rather a counter attached to the truck. Thousands of celebrities, politicians, and locals have flocked to Harry’s for their pie fix. And the place is open until 2 a.m., making it a great late-night spot.

Opened in time for the 2000 Sydney Olympics, the Establishment is a pioneering 31-room boutique hotel housed in an 1890s steel plant near the modern-day stock exchange building downtown. Managed by the hospitality group Merivale—which started as a fashion house specializing in fascinator hats and mini skirts—the hotel is popular among brand executives who book the 328-square-foot Loft Penthouse for product launches and photo shoots. Rooms feature wood furnishings, swinging metal doors, animal hides, and suedelike daybeds as well as such amenities as Apple TV, Bose surround sound, and Lululemon yoga mats. Bathrooms are particularly luxurious here, with marble floors, freestanding tubs, Bulgari products, and tall windows that open up to Sydney’s bustling business district. The best part about the Establishment, though, is the internal access it offers to some of the city’s hottest bars and restaurants, which are housed within the same complex as the hotel. And after enjoying live music and a few stiff cocktails at the speakeasy Palmer & Co, guests are welcomed to bed with Sleep Tight tea and a homemade chocolate chip cookie.

Reykjavík’s old harbor, built between 1913 and 1917, has seen quite the transformation in recent years, morphing from a mainly functional area dominated by ships and their fishermen to a lively, modern tourism area that’s almost a new city district of its own. The sparkling, award-winning Harpa concert hall and conference center has dominated the area since it opened in 2011, and several restaurants and cafés, along with offices, now line the harbor promenade, interspersed with the occasional cultural spot such as the fascinating Reykjavík Maritime Museum. The boats, trawlers, and whaling ships are still there, of course, and remain a big part of the atmosphere, but they’re today joined by a number of tourist boats offering whale-watching and puffin tours.

The most stunning dining room in celebrity chef Neil Perry’s restaurant empire has got to be Rockpool Bar & Grill in Sydney. Seated amid soaring green marble columns and Art Deco windows in a space designed by Emil Sodersten, diners can choose between the finest steaks, seafood, cocktails, and wines—more than 3,000 of them—that Australia has to offer. Dry-aged beef and sustainable fish are simple yet succulent, cooked over an open flame or in the wood-fired rotisserie. Start with the signature Four Raw Tastes of the Sea before savoring the Wagyu or Cape Grim steak, or opt for classy appetizers and cocktails in the candlelit bar, adorned with 2,682 hanging Riedel riesling glasses.

Set on the western side of Circular Quay, the Museum of Contemporary Art Australia (MCA) is the country’s leading institution for modern art. While access to touring international exhibitions from the likes of Tatsuo Miyajima and Annie Leibovitz incurs an entrance fee, the permanent collection of more than 4,000 contemporary works by Australian and Torres Strait Islanders, from Gary Carsley to Lena Yarinkura—plus a rare collection of artist notebooks, music, letters, and sketches—is always free. Come on Wednesday night when the gallery is open until 9 p.m., or for the adults-only Art Bar on the last Friday of the month. The rooftop café offers occasional live music and DJs plus glittering views of the Sydney Opera House and Harbour Bridge after dark.

What started in 2002 as a little café tucked into a Newtown laneway, Campos has become one of the biggest household names in Australian specialty coffee. The company’s success stems from its simple but ambitious mission: to buy, roast and serve the finest quality coffee. Today, the Campos menu rotates more than 10 direct-trade coffee varieties grown in nine regions around the world. The café continues to experiment with beans, machines, and barista techniques to maintain its order pace of hundreds of coffees per hour. Now operating in Queensland and Melbourne as well as Sydney, Campos has recently introduced cupping classes Thursday through Saturday held in a dark upstairs lounge above the Newtown location. Customers pay $30 to compare five coffee varieties from different regions and learn the different processing and preparation styles. Sydney’s newest Campos café in the Alexandria neighborhood features a siphon bar that only serves select single origin coffees.

The flavors and textures of a banh mi—crispy, chewy, spicy, sweet, tangy with ingredients of mayonnaise, pâté, pork (or sometimes chicken or tofu), pickled vegetables, cilantro, and chili, all piled into a crusty baguette—help to explain the allure of this iconic Vietnamese sandwich, and why it’s been successfully replicated at restaurants around the world, from New York to Sydney. Hoi An has many fine banh mi sellers, but among the top two are undoubtedly the holes-in-the-wall Madam Khanh (or Madam Queen) on Tran Cao Van Street and the always-busy Banh Mi Phuong on Phan Chu Trinh, popularized by Anthony Bourdain in his program No Reservations.

On a promontory within Bouddi National Park, overlooking a secluded bay and a short walk to an empty rust-red beach, Pretty Beach House lives up to its (classically understated Aussie) name. It’s hard to believe this intimate retreat is only a 90-minute drive from Sydney city center. Its location is spectacular and historic—spot the 2,000-year-old Aboriginal rock drawings on a nature walk nearby.

There are four guest pavilions, each outfitted with wood-burning fireplaces, deep-soaking clawfoot tubs, and sun-drenched decks overlooking Broken Bay and Angophora treetops (three have their own private plunge pools). Dining is included in the stay, and it’s exceptional: Celebrated chef Dean Jones takes freshly caught seafood and local produce and crafts them into modern Australian dishes, which you can enjoy anytime you like in the Beach House’s safari-chic dining room or poolside beneath the shady gums.

Australia is world-renowned for scuba diving, but you don’t have to go all the way to the Great Barrier Reef or Ningaloo. Most people don’t know there is plenty of good diving in and around Sydney, too. One of the best sites is Magic Point off the tip of Malabar Headland National Park south of Maroubra. There’s an extensive reef system and large caves that are home to weedy sea dragons, stingrays, and a recovering colony of grey nurse sharks (which by most accounts are harmless to humans). Local outfitters such as Frog Dive Scuba Centres can lead you there.

Caesarea, the city and harbor that Herod built, is now preserved as a national park. A walk along its pathways allows visitors to experience the city’s role as part of ancient Rome and its days during the Crusades in the Byzantine era. Check out a concert at the partially restored amphitheater, or dive in Caesarea’s sunken harbor and underwater archaelogical park. Ancient ruins, including the remains of Herod’s palace, sit along the coastline. A state-of-the-art visitor center offers a historical perspective, complete with famous figures presented as hologram tour guides: King Herod, Rabbi Akiva, the Apostle Paul, and Hannah Senesh. Right outside the park’s boundaries, find a modern city with restaurants, cafés, and some eclectic galleries selling wine, cheese, olive oil, and jewelry—plus a lovely stretch of Mediterranean beach.

Every December 7 at Pearl Harbor, there is a memorial to those who died in the awful attacks that day in 1941. Survivors gather here, though fewer every year remain alive. Oil still rises from where the USS Arizona lies in the harbor. The horrific events of December 7 are still a raw part of the history here. Several months ago, the civil defense sirens went off all over Oahu. It was a glitch in the system, but I remember an elderly woman in downtown Honolulu who said she looked at the sky because she remembers when there really was an air raid, and the sirens bring her back to that time of eminent danger when what seemed impossible unfolded in front of her young eyes. For history buffs, students, and all sorts of tourists, this is a “must visit” National Park on Oahu. Tickets to take the boat to the memorial are cheap (but do require an advanced booking of a couple days), and there are several other activities and museums at Pearl Harbor to explore including a walk through the USS Bowfin.

The hike from Coogee Beach to Bondi Beach in Sydney, Australia, is one of the best urban paths I have experienced. Although you’re never far from the city, the walk feels quite scenic at times, and the many beaches you come across along the way are all beautiful. Of course, you can always walk from Bondi to Coogee if you find yourself heading in the other direction. Either way, you’ll find yourself at one of Sydney’s top beach destinations. The hike is an easy walk that will include towering cliffs, sandy beaches, public pools, rock formations, parks, and epic vistas along the 6-kilometer trail. You could do the hike in a few hours, but it would be best to allocate at least three hours to fit in a stop at Bronte Beach for lunch or drinks. And if it is a hot day, you’ll want some time for a swim!