Whirlwind Trips: How to Visit Multiple Locations on a Tight Timeline

Not everyone can clear room in their schedules for a sprawling, multi-week travel event. Some people – like a few of us here at Unbound Merino – remain tethered for the most part by work, family and social obligations. So we pick our spots when we can find them.

If that means you have to fit a whirlwind trip inside a single week, so be it. And while it’s probably most sensible to limit these short trips to a single location, sometimes the travel bug doesn’t allow for that kind of stillness and rootedness. You need to squeeze every last drop of experience and novelty from your trip. After all, you’ve ponied up the funds for a long plane ride; you might as well make the most of it.

That’s the scenario we tackle today. How do you fit multiple locations inside of a tight timeline? Below, we demonstrate that you can have your proverbial cake and eat it too, with a bit of planning, light packing and booking. Hurry – every second counts!

The Art of the Jam-Packed Trip: Developing a Route That Makes Sense

To start our guide on the right foot, let’s define parameters. When we say “whirlwind trip,” we mean a relatively short vacation centred on three or more destinations – typically in different countries or, at the very least, different regions of the same country. We aren’t necessarily talking about short layovers (though we have an article for that, too!).

The first step in the process mirrors the first step in any travel plans: choosing your destination. Some parts of the world lend themselves better to a multi-location trip than others. We’re looking for densely concentrated areas where you can explore different cultures, with each destination being a must-see stop in its own right.

Therefore, to begin thinking about multi-stop whirlwind trips, let’s throw out a few candidates. Here are some sample itineraries, ripped from trips we’ve taken and loved:

• Southeast Asia: You might land in Bangkok on Day 1; charter an AirAsia flight to Hanoi on Day 3; bus down to Ha Long Bay on Day 4; bus over to Angkor Wat in Cambodia on Day 6; and fly back for your return flight in Bangkok on Day 8.
• The Balkans: You can fly into Zagreb on Day 1; train to Ljubljana in Slovenia on Day 2; snake down the Istrian coast for Days 3-4, stopping somewhere like Split or Dubrovnik; spend one wild night in Sarajevo on Day 5; and train back to Zagreb for days 6 and 7.
• The London-Benelux Triangle: Fly into London on Day 1; take the channel tunnel to Amsterdam on Day 3; board a short train to Brussels on Day 5; take the channel tunnel back from Brussels to London on Day 7.
• The Northeastern US: This is an example of a vacation with different arrival and departure points. You can start by flying into Boston on Day 1; head to New York City on Day 3; train to Philly for Day 5; and cap your trip off in D.C. for the remaining days, flying out of Reagan Airport.

As you can see, a jam-packed trip is like a well-orchestrated piece of music. It involves multiple dovetailing parts moving along in harmony. We recommend devising a route – as we have above – that’s either circular, triangular or (in the case of different arrival/departure points) a straight line.

Yes, it’s a tall order. It requires planning, purpose and a streamlined travel bag. In the sections below, we offer concrete tips for pulling it off.

Credit: vgstockstudio Via Freepik

Planes, Trains and/or Automobiles: Locking Down Transportation

Once you’ve booked your primary flight, you need to start locking down “inter-destinational” trips (that’s not a real word, but you know what we mean). Here, you have options.

If you’re in a part of the world blessed with low-cost carriers, consider them a viable option. While they often levy strict baggage requirements, they can get you to a destination faster than ground travel. Example airlines include Europe’s Ryan Air and EasyJet, Asia’s AirAsia, and North America’s JetBlue and Southwest.

However, there are times when using these airlines doesn’t make sense – especially between near-at-hand locations serviced by good rail or bus lines. For instance, if you’re headed from London to Amsterdam, it’s quicker to show up for a train at the last minute than wait around an airport for two hours to board a quick flight.  

Do your research, and choose your ideal transportation type(s) based on availability, proximity and price.

Planning Your Next Move: When to Travel for Maximum Enjoyment

Having determined how you’ll travel, you have to figure out when to travel. Here, you have a challenging decision on your hands.

With a short, tightly-packed trip, every minute counts. And every minute you spend in transit is one you won’t spend enjoying your destinations. Nonetheless, sacrifices must be made. You have to decide whether you’re willing to sacrifice your evenings, mornings or a mixture of the two.

The first option is nighttime travel. With overnight trips, you kill two birds with one stone by essentially booking accommodation and travel simultaneously (and saving money on the former). However, you sacrifice nightlife – and potentially a good night’s rest – in the process.  

The second option is morning or afternoon travel. With daylight transit, you miss a pivotal sightseeing part of the day but get better sleeping arrangements. Plus, you free up your evenings for wining, dining and fun.

The last option – the one most travelers organically gravitate towards – is a mix of the two. It’s the Goldilocks option. You miss a night here, a morning there. But all in all, you enjoy a balanced mix of evenings and days in your various destinations.

Packing Light: Lightening the Load for Easier Movement

You've squared away all of the nitty-gritty itinerary-related arrangements. Now, you have to prepare yourself to actually execute the plan. This process involves cutting down on excess items, lightening the load, and assembling an effective, streamlined piece of travel luggage. With a light, optimized bag, you can move around freely, pick up and go at a moment’s notice, and – crucially – skirt those baggage restrictions on cheap flights and ground transit.

The best way to streamline your travel luggage is with Unbound Merino clothing, made to withstand the rigors of travel. Yes, perhaps we’re biased. But then again, ask the countless minimalist packers and travel enthusiasts who rely on Unbound Merino – they aren’t biased.

Our travel-optimized clothing is the complete package. It’s insulating in cold weather. It’s breathable and sweat-wicking in warm weather. It’s wrinkle-resistant, meaning you can stuff it at the bottom of a bag. It’s also stylish, meaning you can pull it out from the bottom of that bag for a night on the town. And best of all, it's antibacterial and odor-resistant, meaning you can feel fresh in that same men’s shirt or women's merino travel dress all week long – only one garment required.

Seriously, you don’t need many Unbound Merino articles for a quick but jam-packed trip. Check out our button-up shirts and lightweight travel pants for a more formal look. Or, for a more casual look, shop our packable hoodies for men and leggings for women. Complete the wardrobe with some fresh-keeping underwear and socks, and you’re off to the races.

Beyond our versatile travel clothes, opt for a streamlined set of essentials. Buy travel-sized toiletries or decant your preferred toiletries into travel-sized bottles. Keep digital documents of anything you don’t need a physical copy of. Leave your jewelry and flashy valuables behind. And as hard as it sounds, consider – just consider – bringing only one pair of shoes. A typical one-bag pack for a summer trip (men’s) might look something like this:

• Two pairs of Merino wool underwear
• Two pairs of Merino ankle socks
• One Merino wool t-shirt
• One Merino wool button-down shirt
• One pair of shorts
• A phone plus charger
• A svelte toiletry kit consisting of a toothbrush, travel-sized toothpaste, travel-sized deodorant, (optional) travel-sized hair product and pertinent medications (you can find sunscreens, shampoos, etc. at your destination – don’t worry about them here).
• The pair of shoes you’re wearing on the plane plus an optional pair of flip-flops
• Your passport and relevant documents

That’s the whole shebang. With your clothes nestled tightly in an army roll, you should be wearing a compact, easily maneuverable personal item.

Credit: Freepik Via Freepik

The Admin End of a Multi-Location Trip: Visas and Currency Exchange

If you plan on crossing national lines, the last thing you want is to stall at the border while some unhurried bureaucrat slowly processes your paperwork. That kind of administrative tedium can seriously eat into your enjoyment time.

Instead, research visas in advance. Some multi-spot areas, like the EU and Central America, allow a breezy in- and outflow of traffic for most passports, and you won’t need to worry. Other areas like Southeast Asia, the Middle East or West Africa require a patchwork of “visas on arrival,” “eVisas” and pre-arranged visas. Do some digging and get your ducks in a row before you fly out.

Next, consider currencies. In an age of universal credit cards and Apple Pay, physical currency isn’t (usually) necessary. Still, it’s a good thing to have for those smaller vendors like street food purveyors and local shops. You can either order foreign currencies in advance at your local bank (although it’s slightly risky to carry wads of cash in transit) or take it from an ATM at each destination (which costs a nominal fee and might not recognize your card). The choice is yours!

Getting Over Jet Lag Fast

Again, your time on a short trip is precious. You don't want to lose a day or two to jet lag. Elsewhere on this blog, we've reviewed strategies for avoiding – or at least mitigating – the disorienting, crummy feeling of jet lag. We recommend drinking lots of water on the flight (more than you might think is necessary) to counteract the airplane’s dehydrating atmosphere.

If you can, we also recommend getting a head start on your new time zone. A day or two before flying, try to push your sleep schedule forward or backward to mimic your destination. For instance, if you’re flying five hours ahead to London, try getting to sleep earlier each night and waking earlier each morning. With any luck, when you do reach London, you won’t be fighting an uphill battle to adjust to the new time zone.

Making the Most of Each Destination: A Healthy Mix of Pre-Planning and Spontaneity

You’ve finally made it. The goal now is to maximize your time at each destination.

We understand that no two travelers are alike. Some like to plan their every minute in a bid to cram in as much culture and excitement as humanly possible. Others take a laissez-faire approach, moving whichever way the wind takes them. Sometimes, these two archetypes meet and start a relationship and then argue incessantly about which is the better way to travel (let us know in the comments if this sounds like you).

We won't say which is best because both philosophies have their merits. Instead, we’ll be diplomatic and advocate for a balance between the two: a healthy mix of planning and spontaneity. Pre-planning ensures you tick all those must-see boxes off your list (the Buckingham Palaces and Angkor Wats of the world). Meanwhile, the spontaneous side allows you to remain open to life – all those experiences you can't possibly plan for but, in the moment, you can’t possibly imagine doing without.

If you want a way to methodize this approach, consider the rule of threes. Pick three things each day that you absolutely must do; these might be museums, art galleries, monuments or walks. Pick three food items at each destination you must eat – a pho in Hanoi or a ceviche in Ecuador, e.g. And pick three longer excursions for the entire trip: a day trip to a Japanese onsen, an evening river cruise down Porto’s Douro River, etc.

Everything else, you can leave up to chance. Sparking a quick friendship with a local, which somehow turns into a fourth drink at 1 AM as you plan weekend trips together. An unlikely detour through a charming part of town you’d never read about. A smell so irresistible wafting from a street food cart that you have to abandon your dinner plans. The stuff that makes travel so life-altering.

How do you prepare for a whirlwind trip? Let us know in the comments below. And before you fly, consider checking out our always-growing line of versatile travel clothing.