Hong Kong International is one of the best-connected airports in Asia, with direct long-haul services from most major European, North American and Australian hubs, and short-haul links across the whole region. The Airport Express train reaches the city centre in around a quarter of an hour and runs frequently from early morning until late; airport buses are slower but cheaper and cover far more districts. Immigration is efficient, and the arrivals hall has clearly signed transport desks before you reach the exit.

High-speed rail connects Hong Kong to the mainland Chinese network from a terminus in West Kowloon, with services running north into Guangdong and onward to the long-distance network. Border formalities are handled inside the station rather than at the frontier, so allow extra time before departure and carry whatever permits your nationality requires for entering mainland China. Conventional cross-border trains and through-services also run from Hung Hom.

Buy a stored-value transport card at the airport and use it for the metro, trams, buses, ferries and most convenience stores. The metro is signed in English throughout, the ferries run to a published timetable, and taxis are metered and plentiful but colour-coded by the area they serve. Almost nothing on a normal itinerary requires a car.

Hong Kong

Ten days built around the harbour, the hill trails and the ferry piers, deliberately booked for the dry, clear window at the end of the year.

It costs almost nothing, takes under ten minutes, and remains the single best introduction to the shape of the city. Take it from Tsim Sha Tsui to Central at dusk, sit on the lower deck where the windows are open, and watch the towers switch on behind Kowloon. Then take it straight back the other way so you have seen both approaches.

Ride the Star Ferry across Victoria Harbour

A ridge trail on the eastern end of Hong Kong Island that turns a skyline city into a coastal one in about half an hour of climbing. The path is well marked, mostly shaded, and ends on a beach you can swim from. It is the clearest demonstration that this is a territory of hills and islands with a financial district attached.

Walk the Dragon’s Back to Big Wave Bay

The neighbourhood diners are where the city actually eats. Milk tea strong enough to lean on, macaroni soup, scrambled egg on a bun, all served at a shared table with no ceremony at all. Order by pointing if you need to, expect to be seated with strangers, and do not linger once your cup is empty.

Eat breakfast in a cha chaan teng

The double-decker trams have run along the same corridor for well over a century. Ride the full length upstairs at the front, from Kennedy Town out towards Shau Kei Wan, and you get a slow, street-level cross-section of the island that no photograph of the skyline will give you.

Take the tram along the north shore end to end

Temple Street and the Mong Kok markets change character entirely after dark. Stalls fold out into the road, the food stops being incidental, and the crowd shifts from shoppers to people eating. Go hungry, go late, and treat the first pass as reconnaissance rather than shopping.

Spend an evening in a street market

Lamma, Cheung Chau and Peng Chau are all short ferry rides from Central and all substantially slower than the mainland districts. No cars, seafood restaurants along the waterfront, and footpaths instead of roads. One of these is the correct answer to a day when the city feels like too much.

Cross to an outlying island for a day

Two points can sit two hundred metres apart and still be separated by a hill, an escalator system and a footbridge network. Distances here are measured in levels as much as in blocks, so read the elevation before you assume something is walkable.

Plan the day around the vertical, not the map

The most memorable parts of my itinerary are all water crossings, and they run to a schedule rather than on demand. I build each day outward from one crossing and let the rest fall around it, which stops the trip becoming a forced march between restaurants.

Let the ferry timetable set the pace

Air conditioning is set aggressively in malls, trains and restaurants, and the gap between a humid street and a cooled interior is large enough to be uncomfortable. A light long sleeve lives in my bag from the moment I land.

Carry a layer for the indoors

The consensus best window, and the one I have booked. Humidity finally drops, the haze clears enough that the hills are worth climbing, and evenings are comfortable outdoors. It is also the busiest stretch for hotels, so book earlier than feels necessary.

Genuinely cold by subtropical standards and often overcast, but quiet and cheap. Good for museums, markets and long eating days; less good for the ridge walks, which can sit inside low cloud for days at a time.

Heat and humidity are relentless and this is the typhoon window, when signals can close transport and shut the airport at a few hours’ notice. Avoid unless the dates are fixed for you, and if you do go, build slack into every connection.

The standard approach, and the one I am taking. High-speed ferries run frequently across the Pearl River Delta from terminals in Hong Kong to both the Macau peninsula and Taipa, with the crossing taking around an hour. You clear immigration on both sides, so treat it as an international departure, arrive well ahead, and keep your passport accessible rather than packed.

A long sea crossing links Hong Kong, Zhuhai and Macau by road, served by shuttle buses that run around the clock. It is generally cheaper than the ferry and less affected by rough water, though you change vehicles at the border posts. There is also a land frontier with Zhuhai on the mainland Chinese side, used heavily by day visitors.

Macau International sits on Taipa and handles mostly regional routes across East and Southeast Asia rather than long-haul traffic. Most visitors from further afield fly into Hong Kong and continue by ferry or bus, which is usually faster and better connected than trying to route directly.

Macau

Four days on the peninsula and the islands, aimed squarely at the old town, the food and the quiet streets behind the casinos.

The old town is a UNESCO-listed collection of squares, churches, fortifications and civic buildings that are best understood in sequence rather than as separate sights. Start early from Senado Square, work uphill, and let the pastel facades and calçada paving carry you between them. It takes a morning at a slow pace.

Walk the historic centre in one continuous loop

What survives is essentially a stone facade and a staircase, which sounds thin until you are in front of it. Arrive within the first hour after sunrise and you get the carving to yourself, along with a view back down over the rooftops that disappears completely once the steps fill up.

Stand at the ruins of St Paul’s before the tour groups

Macanese cooking is its own cuisine, built over generations from Portuguese technique, Cantonese ingredients and the trade routes in between. Minchi, African chicken, bacalhau treated locally. Look for the small family restaurants rather than the hotel dining rooms, and expect portions built for sharing.

Eat Macanese food, not Portuguese or Chinese food

The islands hold the version of Macau that the skyline hides. Taipa Village keeps a run of colonial-era houses and a working market street; Coloane is quieter still, with a small waterfront chapel, hiking trails and a beach. Both are a short bus ride and a different pace entirely.

Cross to Taipa and Coloane

The highest point on the peninsula, with a seventeenth-century fort, the oldest lighthouse on the China coast and a chapel with surviving frescoes. It is a genuine climb or a short cable car, and the reward is the only vantage point from which the geography of the territory makes sense.

Climb Guia Fortress and its lighthouse

Gaming is why most visitors come and ignoring it entirely would misrepresent the place. Walk through, look at the scale of it, understand that it funds much of what you saw during the day, then leave. One evening is enough to have seen it; more than that and you have not really visited Macau.

Give the casino floor exactly one evening

Sailings sell out on weekends and around public holidays, and the return leg is the one people forget. Fixing both crossings in advance costs nothing extra and removes the only genuine logistical risk in the trip.

Book the ferry both ways before you land

The casino resorts run frequent complimentary buses between the ferry terminals, the airport, the border and their own properties, and nobody checks whether you are a guest. Used sensibly, they cover a large share of the routes you actually need.

Take the free hotel shuttles seriously

The old town is paved almost entirely in calçada, the traditional Portuguese mosaic stone. It is beautiful, it is uneven, and it is genuinely slippery in the rain and after a run of humid days. This is not the destination for a smooth sole.

Wear shoes with grip, not style

The same window that works for Hong Kong, for the same reasons. Humidity drops away, the old town is walkable at midday rather than punishing, and the light on the stonework is at its best. This is when I am going.

Pleasant temperatures and fewer visitors, offset by a persistent sea fog that can sit over the territory for days and occasionally disrupts ferry crossings. Worth it if you want the squares quiet and do not mind soft grey light.

Heavy heat and the same tropical storm season as the wider delta, with the added complication that ferry services suspend before an approaching signal. If your dates land here, allow a spare day at each end of the crossing.

Almost everyone arrives by air, most commonly into Auckland, with Christchurch and Wellington also taking international traffic. From Europe it is a two-leg journey via an Asian, Middle Eastern or North American hub and comfortably over twenty-four hours door to door; from the west coast of North America and from Australia it is a single long sector. Biosecurity control on arrival is strict and thorough, so declare anything organic and expect walking boots to be inspected and cleaned.

There is no comprehensive long-distance passenger network. What exists is a small number of scenic services, most notably the coastal route north of Christchurch and the alpine crossing to the west coast, plus commuter lines around the main cities. These are worth riding as experiences in their own right, but they cannot form the backbone of an itinerary. Plan around a vehicle and treat the trains as set pieces.

Self-driving is the default and driving is on the left. Roads outside the cities are narrow, frequently single lane at bridges, and slower than the distances suggest. Long-distance coaches connect the main towns reliably, and domestic flights cover the big hops, but a vehicle is what makes the west coast and the interior possible.

New Zealand

Five weeks over both islands at the end of the southern summer, self-driving, with the route built around daylight rather than distance.

The road down the western side runs between the Tasman Sea and the Southern Alps with almost nothing in between, through rainforest, past glacier valleys and over one-lane bridges. It is the single stretch of road that most justifies the whole trip, and it demands unhurried days because there is nowhere to make up time.

Drive the South Island west coast

The named multi-day tracks are the country’s best-known walking, and the huts book out months ahead. If the full circuit is not realistic, most of them have a day section that reaches the best of the scenery and returns the same evening. Book what you can, plan a day alternative for what you cannot.

Walk at least one Great Walk section

The central North Island sits on an active volcanic zone, with mud pools, silica terraces, geysers and steaming ground in the middle of ordinary towns. It also has deep significance to local iwi, and the guided visits that explain that context are considerably more interesting than walking the boardwalks alone.

Spend real time in geothermal country

The inter-island ferry takes a few hours and spends a good part of them threading through the Marlborough Sounds. Flying is faster and cheaper on time, but the crossing is one of the better things you can do on the whole itinerary, and taking a vehicle across removes an entire rental changeover.

Cross Cook Strait on the ferry rather than flying

Parts of the country hold formal dark sky reserve status and the southern sky is genuinely unfamiliar if you have only ever looked up in the north. Clear, moonless nights well away from towns, warm clothing, and an hour with no screens is all it takes.

Go looking for dark skies

The best days I have had in countries like this were unscheduled ones in places with a single main street, a bakery and a museum run by volunteers. Build two or three of these into a five-week route deliberately, because a fully booked itinerary leaves no room for them.

Stop in small towns without a plan

The roads are slower than any map application will suggest, and the whole point of the route is the stopping. I plan around three or four hours of actual driving a day at most, and I have never once wished I had scheduled more.

Halve the distance you think you can drive

Accommodation on the popular tracks and vehicle space on the inter-island crossing are the two things that genuinely sell out. Everything else on this itinerary can be improvised; these two cannot, so they get fixed first and the route is built around them.

Book the huts and the ferry before anything else

Weather in the mountains and on the west coast turns fast and without much warning. Waterproof shell, warm mid-layer and sun protection travel together in the day bag every single day, regardless of what the morning looked like.

Pack for four seasons in a single afternoon

Late southern summer, and my chosen window. The peak-season crowds have thinned after the New Year rush, the weather is at its most settled, and there is still enough daylight for a full day of walking followed by a long drive.

Alpine flowers, waterfalls at full volume from the snowmelt, and fewer people than high summer. The trade-off is genuinely unstable weather and some higher tracks still closed or under snow well into the season.

Cold, short days and a completely different trip: ski fields open, the west coast wild, the walking limited. Excellent value and very quiet, but not the itinerary I am planning.

Rome has two airports. The larger one to the west handles most long-haul and full-service traffic and is linked to the central station by a direct non-stop express train in around half an hour, plus slower regional services to other city stations. The smaller airport to the south-east takes much of the low-cost European traffic and is connected by coach rather than rail. Both have official taxi ranks with fixed fares to the historic centre, which are worth using over any offer made to you inside the terminal.

This is the better way to arrive if you are already in Europe. High-speed services run to Rome from across northern Italy in a few hours and connect onward to France, Switzerland, Austria and Germany, with sleeper options on some longer routes. Trains arrive at the main central station, which sits on both metro lines and is walkable to some central neighbourhoods. Booking well ahead brings the fare down substantially, and the city-centre-to-city-centre time beats flying on most Italian routes.

The historic centre is compact and walking is genuinely the fastest way through it. Two metro lines cover the longer distances and the major sites, buses and trams fill the gaps, and a single integrated ticket covers all of them. Validate before boarding and do not attempt to drive in the centre, where restricted traffic zones are enforced automatically by camera.

Rome (Italy)

Twelve days built around early mornings, long lunches and the neighbourhoods across the river, with the famous sites deliberately visited at the wrong hours.

Between six and eight in the morning the historic centre belongs to delivery vans and people going to work. The same squares that are impassable at midday are empty, the light is low and warm, and you can stand in front of the Pantheon or the Trevi Fountain without negotiating a crowd. This is the single best piece of advice about Rome I have.

Walk the centre before the cafes open

Most visitors treat the ancient centre as a walk-through on the way to the Colosseum and see almost nothing. Booked with a timed entry, started early and given four unhurried hours with a decent plan of what you are looking at, it becomes the most rewarding site in the city rather than a queue.

Give the Forum and Palatine a full half day

The rule that has never failed me in Italy: the restaurants worth your time are frequently the ones with no terrace, a short handwritten menu and a room full of people who clearly work nearby. Roman cooking is specific and repetitive in the best way, and it is worth learning the four classic pasta dishes before you arrive.

Eat lunch where the tables are not outside

The neighbourhood across the river keeps its own rhythm: quiet and residential through the afternoon, then filling steadily from early evening onwards. Narrow lanes, a basilica with mosaics worth going inside for, and enough ordinary life happening around the visitors that it does not feel staged.

Cross to Trastevere and stay after dark

The regional network reaches the coast, the hill towns and the ancient port within an hour or so of the centre. It is inexpensive, runs frequently, and the contrast of spending a day somewhere small resets the trip. The ancient harbour site in particular gives you Roman streets and buildings with a fraction of the crowd.

Take a regional train out for a day

There are hundreds of them, most are free, most are open, and a startling number contain work that would be the centrepiece of a national museum elsewhere. Walking in without knowing what is inside is one of the genuine pleasures of the city. Cover your shoulders and knees and you will never be turned away.

Sit in a church you did not plan to visit

The entire plan depends on being out of the door before seven. Two hours in the early morning are worth more than a full day from ten onwards, in every measurable way: light, space, temperature and the mood of everyone around you.

Set an alarm you will resent

The major sites now run on timed slots and the good times go first. I set a reminder for the release date rather than trying to sort it out a week ahead, and I always take the earliest available slot over a convenient one.

Book timed entries the moment they release

Not a quaint local custom so much as basic economics: the same drink often costs several times more at a table with service. Standing at the counter is also faster, and it is how the queue in front of you is doing it.

Drink your coffee standing at the bar

My window, and the best of the year. Warm enough for long days outdoors, cool enough that the middle of the day is not lost, and the city is still recognisably itself before the summer volume arrives. Book accommodation early because everyone else has worked this out too.

The other correct answer. The summer heat breaks, the light gets noticeably better for photographs, and the crowds thin from the middle of September. October brings some rain but rarely enough to lose a day.

Genuinely difficult. Temperatures make the middle of the day unusable, the queues are at their worst, and many family-run restaurants close for weeks while the city empties of locals. If you must, start at dawn and stop entirely between one and five.

Madrid’s airport is one of the main European gateways to Latin America and is well served from across Europe, North America and increasingly Asia. It sits on the metro network with a direct line into the city, and there is also a dedicated express bus to the centre running through the night, plus regional rail from one of the terminals. Transfers between terminals take real time, so leave more of it than the schedule suggests on a connecting itinerary.

Spain has one of the largest high-speed networks in the world and Madrid is its hub, with fast services radiating to Andalusia, the Mediterranean coast, the north and the French border, where they connect onward into the wider European network. Two main stations serve different directions, so check which one your service uses. Fares are cheapest well in advance and there are usually competing operators on the busiest routes, which is worth checking before you book.

The metro is extensive, cheap, clean and runs late, and a rechargeable card covers the metro, buses and local trains. The centre is flatter and more walkable than most people expect. There is no reason to rent a car unless you are leaving the region entirely, and parking in the centre is its own punishment.

Madrid (Spain)

Two weeks in autumn, structured around the art museums in the morning, the neighbourhoods in the afternoon and dinner at an hour that would be closing time anywhere else.

Three major collections sit within a short walk of each other along the same boulevard, covering European painting from the medieval period through to the twentieth century. Trying to do all three in a day is a mistake. One per morning, arriving at opening, with a specific set of rooms in mind, is how you actually see anything.

Work through the art triangle properly

The covered markets have shifted from produce halls to eating halls, and while the most central are frankly tourist-facing, the neighbourhood ones are not. Small plates, a glass of something, no table, no reservation. It is the cheapest and fastest way into how the city eats.

Eat standing up in a market hall

The old royal park is the city’s living room: rowing boats on the lake, a glass pavilion that hosts exhibitions, formal gardens, and on weekends drummers, skaters and family picnics in roughly equal measure. Bring a book and stay longer than you planned.

Spend a full afternoon in the Retiro

La Latina for Sunday vermouth and the market crowd, Malasaña for record shops and small bars, Lavapiés for the most genuinely mixed streets in the city, Chueca for its own scene. Madrid rewards choosing a district and walking it end to end far more than it rewards a monument list.

Follow the neighbourhoods rather than the sights

From Madrid you can be in Seville, Córdoba, Valencia, Zaragoza or Toledo in well under three hours, often much less. The network is genuinely fast and the stations are central at both ends, which makes a proper day trip realistic rather than exhausting.

Take the high-speed train to another city for the day

Lunch runs long and late, the afternoon slows down, dinner starts around ten and the night goes on from there. Every visitor who has a bad time in Madrid is trying to eat at seven. Shift your whole day back by two or three hours and the city opens up.

Adjust to the timetable instead of fighting it

Shifting your eating times by two or three hours takes a couple of days, and doing it on the flight and the first evening rather than resisting for a week is the difference between visiting Madrid and visiting an empty version of it.

Move your body clock before you arrive

The queues at the big three are real and timed online entry removes them entirely. The combined passes only pay for themselves if you are visiting everything in a short window, which is exactly the schedule I am arguing against.

Buy the museum tickets online, skip the combined pass

In many bars a drink arrives with something small alongside it at no extra cost. Treat it as an introduction rather than as dinner, decide whether you like the kitchen, and then order deliberately. It is the most efficient way to find the places worth returning to.

Say yes to the free tapa, then order properly

My window. The summer heat finally breaks, terraces are still usable well into the evening, and the cultural calendar restarts after the August pause. Late October brings the first real chill after dark, which is what a jacket is for.

The other good stretch. Long daylight, parks at their best, and comfortable walking temperatures before the heat sets in properly around the end of June. Slightly wetter than autumn but rarely a problem.

Madrid sits on a high plateau and summer temperatures are punishing, with many residents leaving the city entirely and a noticeable number of businesses closing for the month. Everything of interest happens after dark, which is a legitimate way to visit but not a relaxing one.

Moscow is served by several large international airports at some distance from the centre, each connected by a dedicated express rail link to a different city terminal as well as by road. Which airports and which routes are available to any given traveller depends heavily on where you are flying from, and that picture has changed repeatedly in recent years, so this is the part of the plan I will be checking last and most carefully.

The city is the centre of an extensive rail network, with the fast service to St Petersburg taking around four hours and long-distance sleepers running east across the country, including the trans-continental routes. Different destinations depart from different terminals, several of which are grouped around one square in the north of the centre, so confirming your station matters as much as confirming your train.

Entry requirements, permitted routes, payment methods and travel advisories for Russia have shifted substantially and repeatedly, and anything I wrote today could be wrong by the time this trip comes around. Before committing to any part of this, check your own government’s current travel advice and the current visa position for your nationality, and check them again close to departure. That check comes before the itinerary, not after it.

Moscow (Russia)

A research entry rather than a confirmed itinerary. What I have gathered so far on the city, the seasons and the practicalities, held loosely and revisited as the date approaches.

The older central stations were built as public architecture rather than infrastructure, with marble, mosaics, chandeliers and sculpture. A deliberate route through a dozen of the earliest stations, riding between them purely to look, is one of the few sightseeing plans I have seen recommended by essentially everyone who has been.

Treat the metro as an itinerary in itself

The walled citadel contains cathedrals, palaces and the armoury collection, and each of those is a separate ticket and a separate queue. The square outside is free to walk and changes character completely between early morning, midday and after dark. This is the one part of the trip that cannot be rushed.

Give the Kremlin and Red Square a full day

The city holds enormous holdings of Russian painting and of European art, split across separate institutions on opposite sides of the river. As with any collection at that scale, choosing a few rooms and seeing them properly beats attempting the whole building.

Work through one of the major art collections

The Moskva curves through the centre and the embankments give the clearest sense of how the city is laid out, taking in the older waterfront, the redeveloped industrial stretches and the towers further out. It is a long flat walk and the best orientation exercise available.

Walk the river embankments

Gorky Park and the larger green spaces are heavily used by residents and are where an outsider gets the most ordinary, least performed view of the city. In June the light lasts until very late, and the parks stay busy for as long as it does.

Visit the parks in the long summer evenings

Several former royal estates and walled monastery complexes sit within reach of the metro or a short suburban train, with grounds, wooden architecture and far fewer visitors than anything central. They are the best single-day escape from the scale of the centre.

See the estates and monasteries on the edge

Not the language, the alphabet. A few hours of Cyrillic turns station names, street signs and menus from opaque into merely unfamiliar, and it is by some distance the highest-value preparation for the amount of effort it takes.

Learn the alphabet before anything else

How foreign cards and phones work varies and has changed more than once. I will be confirming what actually functions for a visitor close to the date rather than assuming, and carrying a fallback, because this is the practical detail most likely to catch a traveller out.

Sort payment and connectivity in advance

This is the one destination on the site I am publishing as research rather than as a plan. If the situation makes the trip unwise or impossible, I will say so here plainly and take the date off rather than quietly leaving an outdated guide up.

Hold this whole page loosely

The window I am looking at. Late spring into early summer brings comfortable temperatures, the parks at their best, and daylight stretching well into the night, which makes the long walking days realistic.

The other strong option. Crisp rather than cold, noticeably fewer visitors than midsummer, and the parks and estates at their most photogenic before the weather turns properly.

A serious winter with temperatures well below freezing for weeks at a time and only a few hours of usable light. It is a genuinely striking way to see the city if you are equipped for it, but it is a specialist trip rather than a first visit.

Where I am going, and roughly when

Hong Kong

Macau

New Zealand

Rome (Italy)

Madrid (Spain)

Moscow (Russia)

The guides change as the trips get closer

Where I am going, and roughly when

All destination guides

Hong Kong

Macau

New Zealand

Rome (Italy)

Madrid (Spain)

Moscow (Russia)

The guides change as the trips get closer