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In the ever-evolving world of travel, savvy travelers are constantly seeking ways to maximize their experiences while minimizing costs and complications. You are probably familiar with one-way and round-trip plane tickets. You pick a destination, buy a ticket and off you go. That is the traditional way to travel, but what if you are more adventurous and want to see more for your money? Well, you are in luck! There is something known as “Nested Itineraries” or “Nested Tickets”. This technique can open up a world of opportunities, offering flexibility and savings that traditional ticketing methods often lack.

Ever dreamt of exploring Paris, then hopping over to Rome, and maybe even catching a sunset in Santorini – all on one incredible trip? What if I told you that not only is this dream achievable, but it can also be a game-changer for your travel budget?

Welcome to the world of nested itineraries! Forget the old “one destination, one ticket” mentality. By strategically planning your trip to include multiple stops, you can unlock significant savings on airfare and experience so much more of the world.

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What Exactly is a Nested Itinerary?

“Nested itineraries” refer to a strategy where you book multiple flights or trips in a way that they overlap or are interwoven, often to save money or maximize travel opportunities. Instead of simply booking a single round-trip, you create a more complex travel plan.

Here’s a breakdown of what nested itineraries generally involve:

• Overlapping Bookings: The core idea is that one flight booking is “nested” within another. This means the dates of one trip might fall entirely or partially within the travel dates of another, larger trip.
• Multi-City Travel: This is a common form of nesting. Instead of booking separate round-trip tickets for each city you want to visit, you book all your flight segments on a single multi-city ticket (e.g., New York to London, London to Rome, Rome back to New York). This can often be cheaper than buying three individual round-trip tickets.
• Open-Jaw Flights: This is where you fly into one city and out of a different city. For example, you might fly from Los Angeles to London, travel overland or by a separate low-cost flight to Paris, and then fly from Paris back to Los Angeles. This saves you from having to backtrack to your arrival city.
• Stopovers: A stopover is a planned layover in an intermediate city that lasts for more than 24 hours (for international flights) or 4 hours (for domestic flights). Airlines sometimes allow free or low-cost stopovers in their hub cities, giving you the chance to explore an extra destination without buying a separate ticket.
• Strategic Booking to Circumvent Fare Rules (with caution):
  • Back-to-back ticketing: This historically involved booking two round-trip tickets that overlapped to meet “Saturday night stay” requirements, which often made leisure fares cheaper. While less common now due to changes in fare structures, it’s an example of nesting to get around fare rules.
  • Hidden-city ticketing (Skiplagging): This is booking a flight with a layover in your actual desired destination, and then simply disembarking at the layover city and “throwing away” the rest of the ticket. This is done when the overall flight to a further destination is cheaper than a direct flight to the layover city. However, airlines generally prohibit this practice and can impose penalties like canceling future flights or revoking frequent flyer miles if they detect it.

My Adventures in Nested Itineraries

Over the years, I’ve had the incredible opportunity to craft some truly epic nested itineraries, proving just how much you can see and save. Here is a list of some of my favorite nested itineraries from different continents:

The Around the World Itinerary:

We kicked things off in Los Angeles, flying to Dubai for a fascinating three-day stop. From there, it was a quick hop to the Maldives for four days of pure paradise. Our adventure then took us to New Delhi for a six-day deep dive into India’s vibrant culture and visiting the majestic Taj Mahal in Agra by train and car, followed by a four-day exploration of Kathmandu, nestled in the Himalayas. Finally, we squeezed in a full day in bustling Tokyo before catching our flight directly back to Los Angeles. This trip wasn’t just a vacation; it was literally a journey traversing continents, all made possible by smart nesting!

The South America Itinerary:

Another incredible nested itinerary we enjoyed was our South American adventure. We flew from Los Angeles to Santiago, spending three days exploring Chile’s vibrant capital. Next, we took a flight to the mystical Easter Island for three unforgettable days among the Moai statues. From there, it was off to Chilean Patagonia for a four-day immersion in its breathtaking landscapes. To add to the adventure, we traveled by bus across the border to Argentinian Patagonia for three more days of exploring. Our journey culminated with a flight from El Calafate to Buenos Aires, where we spent four days soaking in the city’s lively atmosphere, before flying back home to Los Angeles. It was an amazing way to experience diverse cultures and stunning natural beauty all in one seamless trip!

The Asian Adventure Itinerary:

A few years ago, I orchestrated an incredible Southeast Asian and Sri Lankan exploration. We began by flying from Los Angeles to Phnom Penh, Cambodia. From there, I drove to Siem Reap, spending four days marveling at the ancient wonders of Angkor Wat. Our journey then took us to Colombo, Sri Lanka, for a three-day visit, followed by a flight to Kuala Lumpur, Malaysia, where we enjoyed three vibrant days. A short hop brought us to Singapore for another three days of city exploration and lounging by the world-famous Marina Bay Sands Resort swimming pool. Finally, we flew back to Phnom Penh for a quick two-day revisit before heading home to Los Angeles. It was an intricate, yet deeply rewarding, way to experience so many distinct cultures and landscapes within a single trip!

The Scandinavian & Easter Europe Itinerary:

Believe it or not, my very first foray into nested itineraries was an ambitious Nordic and Eastern European adventure. I started by flying from Los Angeles to Iceland, making the most of a 24-hour stopover to glimpse its unique landscapes. Then it was off to Bergen, Norway, for four days, followed by a two-day stay in Oslo. From there, I enjoyed scenic train rides, first to Stockholm, Sweden, for two days, and then onward to Malmö for a four-day visit, which included a day trip by train to explore Copenhagen, Denmark. My journey then took me southeast with a flight to Sofia, Bulgaria, before ultimately flying back home to Los Angeles. It was an eye-opening first experience that truly demonstrated the potential of nesting to see more of the world!

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Why people use nested itineraries:

• Cost Savings: This is the primary driver. By combining flights, leveraging hub cities, or strategically using stopovers, travelers can often find significantly cheaper overall airfare than by booking individual round-trip tickets.
• Maximizing Travel: It allows you to see more destinations within a single trip, making the most of your travel time and often the long-haul flights.
• Flexibility: While seemingly more complex, it can offer more flexibility in terms of how you structure your journey and which cities you visit.
• Leveraging Points and Miles: Frequent flyers often use nested itineraries to maximize the value of their points and miles, especially when taking advantage of alliance networks and stopover rules.

It’s important to note that while nested itineraries can be highly beneficial, they require careful planning and understanding of airline rules. Booking separate tickets, for instance, means you’re on your own if a delay on one flight causes you to miss a connection on another, unlinked ticket. Also beware, if you booked one continuous ticket for the entire itinerary, because if you miss one flight…you will most likely lose the rest of your booked tickets. That happened to us, and it was very unpleasant! Phew!

How Does This Save You Money?

The magic of nested itineraries lies in a few key areas:

1. Avoiding Redundant Round-Trips: Booking multiple round-trip flights can be incredibly expensive. By combining your travel into one fluid itinerary, you often pay less per segment.
2. Leveraging Hub Cities: Airlines often offer competitive fares to major hub cities. By routing through a hub and adding a connecting flight or stopover, you can sometimes snag cheaper overall tickets than flying direct to a less popular destination.
3. Capitalizing on Airline Alliances: If you stick to airlines within the same alliance (Star Alliance, SkyTeam, Oneworld), you can often piece together complex itineraries more seamlessly and sometimes even earn more rewards.
4. Minimizing Backtracking: Smartly planned nested itineraries reduce or eliminate the need to fly back and forth over the same ground, saving both time and money.

Beyond Savings: The Added Perks!

The financial benefits are just the beginning. Nested itineraries also offer:

• More Exploration: Obviously! You get to tick off multiple dream destinations in one go, maximizing your travel time.
• Reduced Travel Fatigue: By breaking up long journeys with exciting stopovers, you can combat jet lag and arrive at your next destination refreshed.
• Unique Experiences: Imagine a long layover in Iceland on your way to Europe, allowing you to explore its otherworldly landscapes before continuing your journey. These unexpected detours can be some of the most memorable parts of your trip!
• Increased Flexibility: While you’ll need to plan carefully, nested itineraries can offer a surprising amount of flexibility in terms of how you structure your journey.

Ready to Start Nesting Your Next Adventure?

Here are some tips to get you started:

• Be Flexible with Dates: Even a day or two difference can significantly impact airfare.
• Use Multi-City Search Tools: Most major flight search engines (Google Flights, Skyscanner, Kayak) have excellent multi-city or “add flight” options.
• Consider “Hidden City” Ticketing (with caution!): This involves booking a flight with a layover in your desired destination and then simply not taking the final leg. However, be aware this can be against airline terms and conditions and may result in penalties or loss of frequent flyer miles.
• Research Open-Jaw Possibilities: Sometimes flying into one city and out of another offers better deals than a traditional round-trip.
• Think About Different Modes of Transport: Between cities, consider trains, buses, or even budget airlines to connect your dots.

Don’t let the idea of complex planning deter you. With a little research and creativity, you can unlock a world of travel possibilities and significant savings.

Have you ever used a nested itinerary to save on airfare? Share your tips and experiences in the comments below! Let’s inspire each other to travel smarter and see more of our incredible world!