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5 Lesser-Known (But Awesome) Destinations For A Stopover

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By Jean Ciolli. This list of stopover destinations includes affiliate links to trusted partners!

It’s a well-known trick among experienced travelers: stopping over en route to your final destination can save you cash, while also offering the chance to get a quick look at a place that might not have been on your radar. A stopover can also help ease your jetlag — it gives your body extra time to adjust before hopping on to the next time zone.

Stopovers aren’t to be confused with their shorter more obnoxious cousins, layovers. A long layover or worse, one that’s too short and results in sprinting through to the terminal to find out you’ve missed your connection, is something all travelers dread.

Amsterdam, Tokyo, San Francisco, Doha (Qatar) and Bogota all figure among popular stopover destinations; and with good reason. These are places worth pressing pause for, even if you’ve only got an afternoon and an overnight stay before you’re back at the airport, bright and early.

But what are some lesser-known (but amazing) stopover options? Here are five you should consider on your next trip.

P.S. If you’re traveling on a budget, make sure to check out these awesome tips for finding cheap flights.

1. Lisbon (with TAP)

people walking the streets of Lisbon, Portugal in front of historic buildings
Lisbon. Photo: Lisa Fotios / Pexels.

Traveling to Portugal is a dream trip, and Lisbon is a top destination choice in the country.

Lisbon is all about the neighborhoods. Since on a stopover you’ll only have a few days, do a little research so you can choose from Alfama, Principe Real, Graça, or Bairro Alto.

Instead of rushing around trying to see the monuments stroll the streets and watch the world go by while you sip coffee on a terrace.

There are so many things to do in Lisbon, and it’s also a great destination for those enjoying solo travel in Portugal. In fact, taking a solo trip to Lisbon is highly recommended as you’ll be able to enjoy the many things to do without needing to compromise.

If you want to go out, expect to stay up late. Try Bairro Alto after 10:30pm for bars and after midnight for clubs. If you’d rather take in some Fado, skip the cheesy dinner and a show experience in favor of a short session at the Fado Museum.

When your feet get tired ride the vintage trams around town — just be sure to avoid them during rush hour between 6 and 8pm.

Also note that there are some great Lisbon day trips to check out, like Cascais and Praia do Guincho.

2. Toronto (with Air Canada)

Toronto cityscape as seen from above
Toronto. Photo: Luis Ruiz / Pexels.

Toronto makes an amazing destination for a stopover. Why? Two words: transit and variety.

The Canadian city has one of the most heavily used public transit systems in North America, and there’s even an easy-to-use air rail to get to and from the airport in short order, too.

Once you’ve landed in your neighborhood of choice just start walking. You can sunbathe on the shores of Lake Ontario or wander the streets of Little Italy or Koreatown in search of inexpensive grub.

Oh, and did I mention the street art? With the exception of the business district, it’s everywhere and will have you whipping out your camera to snap a shot around every corner.

Love quirky museums? Check out Toronto’s tribute to footwear, the Bata Shoe Museum.

Prefer the outdoors? Explore some of the best places to hike near Toronto!

And if you have some more time to explore Canada, consider visiting Victoria BC, too, which is full of fun things to do.

3. Kuala Lumpur (with Malaysia Airlines)

Kuala Lumpur skyline at sunset
Kuala Lumpur. Photo: Zukiman Mohamad / Pexels.

Malaysia’s capital is a city of stark contrasts and is a great destination for indie travelers. Massive mosques and temples cozy up to Southeast Asia’s tallest skyscrapers. The nightlife is world-famous.

The food highlights the best of Malay, Chinese, Indian and even British cuisine. Tip: try the Kampung Baru Hawker Stalls on Saturday night and into early Sunday morning.

A short trip from Kuala Lumpur is the Batu Caves, one of the most popular Hindu shrines outside India. Just be ready to climb a few — as in 272! — stairs to get in.

4. Santiago, Chile (with LATAM)

cityscape of Santiago, Chile
Santiago. Photo: Alisha Lubben / Pexels.

Visiting Chile? Within Santiago’s city center you’ll find a wild mixture of old and new, like skyscrapers existing beside colonial churches. 

Spend a few days in this cultural and entertainment capital before carrying on. In fact, from Santiago, you can actually ski in the Andes in the morning, and soak up the sun on a beach by evening. Besides, it’s worth stopping in for a day or two just to feast on copious amounts of succulent local steak and red wine.

Want something stronger than vino?

Try a “Terremoto” at La Piojera. It’s a cocktail you could make a meal of (albeit not a particularly healthy one): house white, fernet liqueur and pineapple ice-cream.

5. Osaka (with Japan Airlines)

cherry blossoms in Osaka, Japan
Osaka. Photo: Bagus Pangestu / Pexels.

While it’s not exactly off-the-beaten-path in Japan, Osaka gets far less love than fashion-forward Tokyo or former imperial capital Kyoto, and it’s a shame.

Why? Because it just may be your big chance to see Japan at its most down-to-earth. For the most part, locals in Japan’s third largest city are friendlier, and more open to interaction than in Tokyo and other tourist hot spots.

Like so many hard-working deeply urban places, Osaka is great for grabbing hearty traditional fare at reasonable prices. It’s far from Japan’s most beautiful city, but it has loads of personality and a fair number of architectural gems — like the 16th-century Osaka Castle — that more than make up for it.

Some Final Notes on Stopping Over

Some airlines, like Iceland Air and Singapore Airlines, encourage stopovers, offering them for free and bookable online. Others like Emirates and Turkish Airlines even offer package deals that include necessary visas, accommodations, and a guided tour to encourage travelers to leave the airport and explore their hub cities.

While a stopover isn’t always going to show up in your ticket results online, there’s an easy fix: call the airline or a travel agent and talk to them about your travel plans: fairly often, you can switch from a layover to a stopover and see somewhere new for little-to-no-cost, or occasionally, for less.

What’s your favorite stopover destination?

About The Author

Jean creates and manages content for BootsnAll from the road and her home base in Barcelona.

About Jessie Festa

Jessie Festa is a New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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  1. Ray on at 12:43 am

    Interesting cities you suggested here, especially my hometown of Toronto. I have noticed that flights from Toronto to Central America some times have layovers in Houston or Miami. Personally, I would pick Houston as the general consensus is that “there isn’t much to do there.” Perfect! I like visiting off-the-beaten path.

    Otherwise, I am very tempted to fly with Icelandic Air in the future for a European trip as that airline allows you to have up to a 7 day stopover in Iceland. That’s a good amount of time to visit one of the World’s most expensive countries!

    • Jessie Festa on at 9:47 am

      @Ray: Also check out Wow Air! I just flew round-trip NYC-Reykjavik for ~$320! That was in February, but very good prices.

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