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For as long as booking travel online has been a thing, so too have last-minute (and, more recently, last-second) trips. Whether your sister goes into labor unexpectedly or you need to de-stress when the pressure suddenly mounts at work, it’s difficult to understate the benefit of this feature.

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On the other hand, some trips—including epic ones that are probably on your bucket list—need to be booked well in advance, often a year or more. Here are five trips you need to book well in advance of when you actually want to travel—and a couple instances in which you might want to hold off and be just a bit more spontaneous.

Machu Picchu, a Peruvian Historical Sanctuary in 1981 and a UNESCO World Heritage Site in 1983. One of the New Seven Wonders of the World

Machu Picchu, UNESCO World Heritage Site and one of the New Seven Wonders of the World.

Hiking Machu Picchu’s Inca Trail

Experiencing the wonder of Machu Picchu is going to take some planning. But the good news is that Peruvian tourism authorities post availability for the Inca Trail permits online, so you can browse available dates for this popular four-day trek right at the time you start planning your trip, ensuring you avoid disappointment. The bad news? They’re often sold out a month or a year in advance, so the more flexible you can be regarding your dates, the better.

If you aren’t set on doing the Inca Trail, you can still visit the historical site, either by doing the less popular (and easier!) “Jungle Trek,” or simply riding a train from Cusco to Aguascalientes and taking the two-hour hike from the town center. Keep in mind that if you want to visit Huayna Picchu mountain, which sits inside the ticketed area and perhaps offers the best view of the complex, you’ll need to make sure you are one of the first 400 people to enter Macchu Picchu that day.

Italy is just one of your European options this summer.

Iconic gondolas in Venice, Italy

Living “la dolce vita” in Italy

Italy is one of the most popular tourist destinations in Europe, the consequences of which have been both positive and negative. Economic benefits notwithstanding, residents from the “floating city” of Venice to the seaside villages of Cinque Terre have complained about the effect of mass tourism on their daily lives, leading to previously free areas now requiring expensive tickets, and some being made off-limits to visitors entirely. Also, in the case of Cinque Terre, accommodations in some of the smaller cities can be limited and expensive, so the sooner you book, the better choice you’ll have.

The Italian government has also announced restrictions on the country’s increasingly popular Dolomite mountain range, which will make it much harder for unprepared tourists to explore this scenic region. Only 350 cars per day (200 in the morning and 150 in the afternoon) will be able to enter the Passo Sella highway, and while the “tickets” you need to do so will be free, they are valid for just one hour.

ALSO: No matter when you book, you’ll earn instant travel rewards with Orbitz Rewards

European Road Trips-Flickr

Iceland’s Ring road | Flickr photo by Moyan Brenn

Driving Iceland’s Ring Road in summer

You don’t have to search the web very deeply to read about Iceland‘s tourism woes, which have ballooned during the summer season, when low-cost carriers like Icelandair and WOW Air offer dozens of daily flights to both Europe and North America. The number of travelers notwithstanding, locals have complained about tourists littering in their pristine national parks, crowding narrow roads and generally disturbing the quiet life that exists outside the national capital of Reykjavik.

While the Icelandic government has yet to institute policies as strict or specific as those in Peru or Italy, it’s worth considering whether you should actually visit Iceland during peak summer season. Winter, for example, is the best time to see the Northern Lights in spite of limited daylight and cold temperatures; the “shoulder” seasons of winter and spring are often rainy, but much less crowded than summer as well.

Blue-footed boobies of the Galapagos Islands

Tracing Darwin’s trail in the Galapagos

A popular misconception about Ecuador’s Galapagos Islands is that you can’t see them unless you book an organized tour. This is mostly false—local boats travel between the islands and anyone can buy a ticket to the national park; however, if you want to book a Galapagos cruise, the farther in advance you can decide, the better.

As far as when to start searching, a year is a good rule of thumb, though this will depend upon what time of year you want to visit. If you plan to go during the Christmas holiday, which is probably the busiest time, you might even want to book even further in advance. On the other hand, the months of April, May, September and October are generally regarded as the low season, and are a better choice for travelers who want to be less locked in.

Santorini, Greece

Santorini, Greece

Getting the perfect sunset selfie at Santorini

Oia is a mountainside village on Greece’s Santorini island that’s become emblematic of the country as a whole for many travelers. While savvy selfie-takers can get the perfect sunset shot without hundreds of photobombers in the background, difficulties for would-be visitors to Santorini can be much more fundamental than this. Namely, during the “high” season between the beginning of June and the end of August, the more reasonably-priced hotels on the island and the ferries to it can fill up weeks or months in advance. Even flights from Athens to the island, which are frequent but limited in number, can be fully booked before you know it. If you plan to visit Santorini next year, now might be the time to start planning your trip.

Himeji City, Japan

Himeji City, Japan

Seeing cherry blossoms in Japan

“The sooner you book, the better” says the old travel refrain. But there are a few places where that isn’t necessarily true. It might seem counterintuitive to wait until the last minute to book a trip to see Japan’s cherry blossoms, but waiting affords you be the best chance of actually seeing them. While this annual spectacle is what makes April the busiest and most expensive month to visit Japan, these pink-and-white trees are extremely temperamental, and weather patterns in February and even March can push the mankai (full bloom) forward or backward by as much as two weeks. On top of that, the peak flowering period can be as little as a few days, so timing is really of the essence.

Visiting Antarctica

Unlike the Galapagos, which you can either see independently or with an organized cruise, Antarctica is only accessible via registered cruise. While many people book these cruises far in advance, since the cost of flights to Ushuaia, Argentina (the most popular point of embarkation) increases the closer to departure you get, the best prices on cruises themselves can actually be found at the last minute. Tour companies would rather slash prices on unsold cabins, rather than let boats sail even partially empty, as Jezebel’s Rachel Anderson describes in greater detail here.

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Tagged: Europe, Greece, Iceland, Italy, Latin America, Peru

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Robert Schrader
Robert is a writer and photographer who's spent the better part of the past decade roaming the globe. Read hundreds of inspiring, informative travel articles on his blog Leave Your Daily Hell, or see the world through his eyes on Instagram, where he's @leaveyourdailyhell.

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