People & Places
Whirlwind Trips: How to Visit Multiple Locations on a Tight Timeline
Updated: March 01, 2024
Not everyone can clear room in their schedules for a sprawling, multi-week travel event. Some people β like a few of us here at Unbound Merino β 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 itβs probably most sensible to limit these short trips to a single location, sometimes the travel bug doesnβt allow for that kind of stillness and rootedness. You need to squeeze every last drop of experience and novelty from your trip. After all, youβve ponied up the funds for a long plane ride; you might as well make the most of it.
Thatβs 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 β every second counts!
The Art of the Jam-Packed Trip: Developing a Route That Makes Sense
To start our guide on the right foot, letβs define parameters. When we say βwhirlwind trip,β we mean a relatively short vacation centred on three or more destinations β typically in different countries or, at the very least, different regions of the same country. We arenβt 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. Weβre 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, letβs throw out a few candidates. Here are some sample itineraries, ripped from trips weβve 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 β as we have above β thatβs either circular, triangular or (in the case of different arrival/departure points) a straight line.
Yes, itβs a tall order. It requires planning, purpose and a streamlined travel bag. In the sections below, we offer concrete tips for pulling it off.

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Planes, Trains and/or Automobiles: Locking Down Transportation
Once youβve booked your primary flight, you need to start locking down βinter-destinationalβ trips (thatβs not a real word, but you know what we mean). Here, you have options.
If youβre 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 Europeβs Ryan Air and EasyJet, Asiaβs AirAsia, and North Americaβs JetBlue and Southwest.
However, there are times when using these airlines doesnβt make sense β especially between near-at-hand locations serviced by good rail or bus lines. For instance, if youβre headed from London to Amsterdam, itβs quicker to show up for a train at the last minute than wait around an airport for two hours to board a quick flight. Β
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 youβll 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 wonβt spend enjoying your destinations. Nonetheless, sacrifices must be made. You have to decide whether youβre 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 β and potentially a good nightβs rest β in the process. Β
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 β the one most travelers organically gravitate towards β is a mix of the two. Itβs 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 momentβs notice, and β crucially β 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 weβre biased. But then again, ask the countless minimalist packers and travel enthusiasts who rely on Unbound Merino β they arenβt biased.
Our travel-optimized clothing is the complete package. Itβs insulating in cold weather. Itβs breathable and sweat-wicking in warm weather. Itβs wrinkle-resistant, meaning you can stuff it at the bottom of a bag. Itβs 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 menβs shirt or women's merino travel dress all week long β only one garment required.
Seriously, you donβt 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 youβre 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 donβt need a physical copy of. Leave your jewelry and flashy valuables behind. And as hard as it sounds, consider β just consider β bringing only one pair of shoes. A typical one-bag pack for a summer trip (menβs) 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 β donβt worry about them here).
- The pair of shoes youβre wearing on the plane plus an optional pair of flip-flops
- Your passport and relevant documents
Thatβs 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 wonβt need to worry. Other areas like Southeast Asia, the Middle East or West Africa require a patchwork of βvisas on arrival,β βeVisasβ 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 isnβt (usually) necessary. Still, itβs 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 itβs 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 β or at least mitigating β 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 airplaneβs 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 youβre 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 wonβt 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
Youβve 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, weβll 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 β all those experiences you can't possibly plan for but, in the moment, you canβt 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 β 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 Portoβs 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 youβd 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.