The Trans-Siberian Railway on the cheap

A long-time reader sent me an interesting essay from a travel agency I'd never heard of, which sent their intrepid reporter on a Trans-Siberian cruise from Moscow to Irkutsk.

I had a good laugh at this essay because unlike, say, transatlantic steamer traffic, the Trans-Siberian Railway is a working passenger railroad, with multiple departures each day, and with publicly available prices. That inspired me to put together for my dear readers my suggestions for a Trans-Siberian Railway adventure.

The European Part

Depending on your timeframe and the season, you might want to fly into Saint Petersburg and visit Tsarskoe Selo and Peterhof, and spend as much time as you can in Petersburg itself, a wonderful and vibrant city.

Otherwise, you'll want to arrive in Moscow. There's no reason to take the Trans-Siberian Railway to Vladimir or Suzdal, since those are short day trips from Moscow proper on commuter rail trains that cost just a few bucks each.

Once you've gotten your day trips out of the way, it's time to get on a real train.

Stop in Nizhny Novgorod if you have to, otherwise head straight to Yekaterinburg

Nizhny Novgorod (formerly Gorky) is an important city in the history of Russia but there's no obvious reason for a tourist to stop there if they're not traveling by river. I'd head straight to Yekaterinburg, the gateway to Asian Russia.

Sample Moscow-Yekaterinburg itinerary: depart 12:35 am, arrive 9:18 am the next day, $45.

Yekaterinburg to Novosibirsk

The next leg is 19-24 hours, so you'll need to decide whether you want to leave in the morning and arrive in the morning or leave in the evening and arrive in the evening the next day.

Novosibirsk was a "closed city" during the Soviet period, but has an opera house and a prestigious university located in nearby Akademgorodok.

Sample Yekaterinburg-Novosibirsk itinerary: Depart 7:49 pm, arrive 20:09 pm the next day, $40.

Novosibirsk to Irkutsk

Often described as the "capital" of Siberia, Irkutsk is located on Lake Baikal and in the winter features all sorts of antics on the frozen surface of the lake, while in the summer you can stay at lakefront resorts. Most "Trans-Siberian" journeys end here.

Sample Novosibirsk-Irkutsk itinerary: Depart 11:56 pm, arrive 7:04 am the next day, $45.

Irkutsk to Vladivostok

Now we've come to the "Trans-Siberian" part of the "Trans-Siberian Railway." Siberia is big — really big. Khabarovsk, like Nizhny Novgorod, is an important city in Soviet history but there's no obvious reason to stop there or anywhere else between Irkutsk and Vladivostok. But, you're more than free to, and you're very likely to find a local willing to take you in and care for you if you're so inclined.

Sample Irkutsk-Vladivostok itinerary: Depart 4:17 pm, arrive 11:34 pm 3 days later, $93.


I've always planned to ride the whole Trans-Siberian Railway someday, but when I lived in Russia I was too busy and too poor to take the time off to do it. But you can do it any time you like! The itinerary above comes out to $223. If you roughly quadruple that (Russian train compartments have four beds each), and have a little flexibility in dates, you could ride in a private compartment all the way from Moscow to Vladivostok, on your own schedule, taking as much time as you like in each city along the way.

If you call that $1,000 in rail fares, that means you've got a whole lot of money left over compared to a bespoke tour package.

Plus, your humble blogger is always available to serve as interpreter.

The right ways to get to Evian-les-Bains

I recently wrote about my trip to Europe which involved a very expensive cab ride about 50% of the way around Lake Geneva, from Lausanne, Switzerland, to Evian-les-Bains, France.

The basic mechanics of the problem were simple, and I knew them in advance: we were flying into Munich because we booked very cheap tickets pretty far in advance, long before we had any plans on how to spend the vacation. From Munich, the best train connection to Lausanne arrived at 7:40, giving us 20 minutes to catch the final 8:00 pm ferry to Evian-les-Bains.

The train arrived late, we missed the ferry, and that was that.

But Evian-les-Bains was a delightful little destination and we have talked about going back in the summer when it might be a little more lively. That begs the question: after doing it wrong the first time, what's the right way to get there?

Don't fly into Munich

It may seem to go without saying, but obviously don't fly into Bavaria, Germany if you want to go to Haute-Savoie, France.

Flying into Zurich

From Zurich Airport you can get a direct train to Lausanne on one of the commuter trains that leave roughly every half hour. The train takes up to 2 hours and 40 minutes, and if it's your first time finding the ferry terminal in Lausanne I would suggest arriving at Lausanne-gare no later than 40 minutes before the last ferry of the night.

You can search an entire itinerary between Zurich Airport and Evian using the website of the Swiss state railway company, SBB CFF FFS.

Flying into Geneva

Another option is to fly into Geneva and take the intercity train from the Geneva airport to the Geneva train station, and connect to the regional TER train system. Although it takes about 3 hours to get from Geneva's airport to Evian-les-Bains, this method has the great advantage of allowing you to arrive somewhat later at night. The last train that would let you connect to Evian-les-Bains leaves Geneva airport at 8:32 pm, which would get you into Evian's train station around 11:38 pm.

The best tool I found to plan this itinerary is the website of SNCF, France's national state-owned railway company.

Note that the train station in Evian-les-Bains is not in the town centre so you should arrange a taxi or hotel shuttle in advance. It's not a long walk, but again, if it's your first time you'll have no idea what you're doing once you arrive.

Wait, why do you want to go to Evian-les-Bains?

For the waters! Evian is a funny little town built around the theme of a mineral water source "discovered" there by a bankrupt nobleman with liver and kidney problems. Best of all, once you're there you get all the mineral water you can drink for free.

But seriously, I found it interesting as a once-glorious tourist destination that has managed to hang on due to its magnificent views and the skiing, hiking, and water-sports infrastructure it has accumulated over the years.

It also has a Hilton property which features strikingly low award redemption rates throughout the year, an excellent breakfast buffet, and a generous evening cocktail, hors d'oeuvres, and dessert spread in the executive lounge, which also exits onto a rooftop terrace. I imagine that during the high season that rooftop turns into a pretty solid party every night.

Sleeping the rails

As some readers may know, in a former life I worked as an English language teacher in Russia. At that time, it was typical for expats to arrive on a business visa, which as a rule only allowed you to be present in the country for 91 out of every 180 days. The idea was, you'd arrive on a business visa, get a job, and then switch over to the appropriate visa at some later date (I think of this whenever I hear about unauthorized immigrants who "overstay" their visas to the United States — that was me and most of my friends, and it was simply the way things were done).

In the winter of 2007-2008, rumors started to spread that the Russian Foreign Ministry had issued a new decree that visas could only be issued in the home country of foreign passport holders. While previously people had hopped over the border to the Baltic states, those Russian embassies were refusing to issue visas to third-country passport holders. However, we were hearing reports that the Russian Embassy in Kiev, Ukraine, was still issuing visas to third-country passport holders — for now.

With that in mind, my company bundled me off to Kiev to spend the Christmas vacation waiting for a visa. The embassy was no longer issuing one-day visas, so I would have to spend 10 days in the country while my visa was prepared. In Kiev, the hostel I ended up in was owned and operated by a fanatically racist Englishman (this is a common problem in expat communities), and after a day or two I decided I couldn't stay there any longer. But where to stay? Having just gotten off an overnight train ride, I quickly arrived at a solution. Here's a map of Ukraine:

Glancing at this map, you can immediately see there are four cities located roughly equidistant from one another: Kiev, Lviv, Odessa, and Dnipro (still called Dnepropetrovsk while I was there). Not only are they roughly equidistant, but they're also all about 7-9 hours apart by train. The solution to my housing problem was obvious: I'd board a train about midnight each night, sleep on the train, and arrive in a new city around 8 am. I could spend the day exploring the city and get back on the train that evening.

I eventually got back to Kiev, got my visa, and headed back to Russia. But that adventure has always left me wondering: could it work here?

Using Amtrak for both housing and transportation

Trying the same thing in the United States poses several difficulties:

  • our trains are far less frequent than trains in Eastern Europe, often passing through a given community as rarely as once a day;
  • our trains are more expensive than trains in Eastern Europe (although often less expensive than you think, and very often less expensive than flying);
  • and our network of train stations is more limited, with routes that typically either feature very frequent stops or very infrequent stops.

So, I decided to investigate if it's possible to replicate something like what I did in Ukraine, and if so, at what cost?

Back and forth

Due to less frequent US train schedules, the easiest way to do what I'm describing is simply to go back and forth on the same route. Head north, south, east, or west one night, and head back the next night.

For example:

  • Northeast Regional 65/67 southbound from Boston to Richmond, leaving 9:30 pm and arriving 9:29 am, and Northeast Regional 66 northbound from Richmond to Boston, leaving 7:00 pm and arriving 7:58 am, roundtrip (2 nights) from $166;
  • or City of New Orleans 59 southbound from Chicago to Jackson, MS, returning on City of New Orleans 58, roundtrip from $196.

This is, obviously, a pretty boring way to travel since you'd be bouncing back and forth between the same cities. It is cheaper than a typical downtown hotel, though, at less than $100 per night.

Hub and spokes

A more interesting way to sleep the rails would be starting at an Amtrak hub and taking individual routes out and back each day. This would give you the benefit of a little variety in your site-seeing. Amtrak, unfortunately, is a little short on hubs, with the only ones I can think of worth mentioning being Chicago (11 routes), Los Angeles (5 routes), and New York (14 routes). New Orleans is another possible option with 3 routes.

I think all three hubs are fairly promising, depending on the part of the country you want to see. For example, from Chicago you can overnight to Denver on the California Zephyr ($97), Pittsburgh on the Capitol Limited ($57), West Virginia on the Cardinal ($62), Memphis or Jackson on the City of New Orleans ($86), North Dakota on the Empire Builder ($102), Buffalo or Rochester on the Lake Shore Limited ($59), Colorado on the Southwest Chief ($102), or Texas on the Texas Eagle ($98).

Circle the country

To circle back to my original anecdote: is it possible to spend time around the country while spending every night on a train, instead of in a hotel?

The short answer is no: long-haul train schedules are too infrequent in the United States to give people the opportunity to arrive in the morning and leave the same night on most routes. Here's one option I found that illustrates the network's limitations:

  • Empire Builder westbound from Chicago, leaving 2:15 pm and arriving in Portland 10:10 am 2 days later;
  • Coast Starlight southbound from Portland, leaving 1:50 pm and arriving Los Angeles 9:00 pm one day later;
  • Sunset Limited eastbound from Los Angeles, leaving 10:00 pm and arriving in New Orleans at 9:40 pm two days later;
  • Overnight in New Orleans;
  • City of New Orleans northbound from New Orleans, leaving 1:45 pm and arriving in Chicago at 9:00 am the next day.

The route described above would cost, if booked sufficiently far in advance, about $483, and would take 7 nights to complete, from beginning to end, although you'd be on the hook for one night in New Orleans. That would give you a cost per night spent in the coach car of a train of $80.50. Not a bad deal, and a much better set of views than a roach motel in Chicago (I've seen my fair share).

Don't forget Amtrak unreliability

Of course, the stylized route above assumes that four different Amtrak trains all run on schedule. This will not happen, because Amtrak trains don't run on schedule. On most versions of this run you would end up spending many more nights on trains than I indicated, which would drive down your per-night cost of sleeping on Amtrak trains.


Unfortunately, American cities and Amtrak routes aren't very accommodating to the kind of tour I was able to take of Ukraine. Only rarely are cities served by the kind of morning and evening trains that are typical in Eastern Europe. But if you have to spend 10 days in the United States waiting for a consular official to stamp a visa in your passport, remember that we do have trains, and you can see a lot of the country in 10 days without spending very much money.

Trip delays and trip delay insurance

If you follow me on Twitter you may have noticed that I had a bumpy couple days coming back from my family's camping trip back in my ancestral homeland. As always, a disastrous itinerary for me means a blog post for you!

What is a trip delay?

When you buy an airline ticket, you receive a promise that you'll be delivered from your origin to your final destination — and not much more. If you're involuntarily denied boarding or you're delayed on the tarmac for over 3 or 4 hours you may be entitled to some cash compensation (depending on the size of the aircraft and other factors).

Of course airlines do, under some circumstances, some of the time, do more to accommodate passengers: if a flight is delayed or cancelled, they may be willing to reroute passengers on other airlines or to different airports. If a delay or cancellation requires an overnight stay, they may be willing to pay for overnight hotel accommodations and meals.

Note that "may" is the operative word here.

What does a trip delay cost?

Before I get to trip delay insurance, I want to be clear about our terms. A trip delay has a lot of costs, only some of which can or should be formalized into dollar terms.

During a long delay, you may have to pay for:

  • meals;
  • hotel stays;
  • clothes;
  • toiletries;
  • transportation.

These are your "out-of-pocket" costs during a trip delay.

But it's essential to understand that those costs do not come close to encompassing the costs of a trip delay.

If you miss a job interview because of a trip delay, you're out of a job. If you don't make it to Thanksgiving, Christmas, Pesach, or Eid-al-Fitr because of a trip delay, you lose out on precious time with your family (not to mention the food). If you arrive late to a deathbed because of a trip delay, you may not make it there at all.

These are the real costs of a trip delay, even they don't cost you a penny out of pocket.

Trip delay insurance doesn't promise to make it right

It's possible to imagine a product that immediately goes to work for you in case of a trip delay to ensure that your trip is minimally impacted. As soon as a delay is announced, such a trip insurer (or ensurer) would swing into action, proactively booking you tickets on substitute flights — no matter the cost — that get you to your destination as close as possible to your original arrival time.

That product doesn't exist. You can't buy it alongside your airline ticket when making a reservation, you can't buy it from Berkshire Hathaway Trip Protection, and you don't get it when booking a reservation with your Chase Sapphire Preferred card.

Trip delay insurance just promises to pay for your out-of-pocket expenses

That doesn't make trip delay insurance worthless. Since there are out-of-pocket expenses incurred when a trip is unexpectedly delayed, trip delay insurance is a way to recover those costs so that trip delays don't add expensive insult to inconvenient injury.

Being able to pick your hotel of choice during an overnight delay, and be reimbursed later, has real value (especially to a travel hacker). Being able to eat at your restaurant of choice, rather than wherever agrees to take your airline's funny money, has real value. Being able to buy a real toothbrush and your preferred toothpaste instead of the garbage airlines hand out to delayed passengers has real value. Hell, you can even get a couple free pairs of socks out of it if you play your cards right.

But trip delay insurance won't get you to your job interview on time and it won't get you any more time with your family. It covers your out-of-pocket expenses, but there's no trip delay insurance product out there that even tries to make you whole.


As I mentioned on Twitter, my delayed trip was paid for with a Chase Sapphire Preferred card, and I've already submitted my trip delay insurance claim.

In 5-60 days (it's insurance, after all), I'll have a post dedicated to that process.

In the meantime, just remember: your trip delay insurance covers the costs, not the consequences, of your delayed flights.

Microhacking: ATM fee refund edition

Even before most travel hackers' American Express prepaid cards were shut down last year, American Express had restricted Bluebird and Serve cash withdrawals to ATM's in the United States. That was a shame since they had previously worked as fee-free ATM cards around the world, and with reasonable exchange rates.

Fortunately, I have a Consumers Credit Union Free Rewards Checking account, which offers as one of its rewards "No ATM fees - CCU will reimburse all ATM and surcharge fees." I'd never actually made an ATM withdrawal with the card (I bank with a local credit union), so I was eager to see how this benefit works.

My experience withdrawing money in Europe

It works really well!

I made three ATM withdrawals during the two weeks we were in Europe, and incurred ATM fees on each withdrawal:

  • 30,000 Hungarian forint ($109.40), $0.87 ATM fee;
  • 200 Euro ($226.85), $1.81 ATM fee;
  • 200 Euro ($225.96), $2.26 ATM fee.

On the first of July, I received an ATM fee credit of $11.19. Since only $4.94 had been charged to my account in separate ATM fees, that leaves $6.25 in ATM fee refunds unaccounted for.

That $6.25 happens to be the sum of the difference between the first two ATM withdrawals in dollars and the next lowest multiple of $5 ($109.40 minus $105, plus $226.85 minus $225).

Now, maybe that's a coincidence ($6.25 is the sum of a lot of numbers, real and imaginary). But it's my current best hypothesis, although it doesn't explain why the odd $0.96 on my final ATM withdrawal wasn't refunded.

Microhacking ATM fee refunds?

If my hypothesis is correct, that means a simple hack is possible: intentionally make ATM withdrawals that are at least $1 more than a multiple of $5, getting the additional amount refunded the following month.

The only ATM's I've ever seen that allow such odd withdrawals are TD Bank ATM's, which allow you to specify the exact composition of a withdrawal, including $1 and $5 bills.

According to this CNN article, Chase and PNC were rolling out ATM's with this function back in 2013, but some light Googling didn't turn up any more recent information than that.

Have you tried this? Does it work? And do you have a better explanation for my mysterious $6.25 ATM fee refund?

Quick hit: things I've learned about German trains

On our trip to Italy in 2015, I reserved all our train tickets in advance, thinking by analogy to airline tickets and hotel rooms that I was locking in the best prices ahead of time. That turned out to be totally unnecessary, as Italian train tickets seemed to cost the same whether you book 6 months in advance or just walk up to the ticket counter on the day of travel.

Having learned from that experience, on last month's trip to Europe I didn't book any of our train tickets in advance, planning to maintain flexibility in case we wanted to spend more or less time in a particular city. That worked great until we got to Germany.

Buy at least a day in advance

Unlike the Hungarian and Slovak trains we took, the German national railway service Deutsche Bahn offers multiple fare types on many of their trains. The price differences aren't always very large, but if you don't know about them you might find yourself overpaying. Here are the fare options for a non-stop train from Vienna to Berlin:

Here's the train we actually took from Vienna to Regensburg to visit my partner's relatives in Bavaria:

And here's the train we took from Schwandorf to Berlin:

While the fares are reasonably close, the fixed-date and fixed-routing tickets purchased in advance would save 36.50 Euro per ticket on our routing, or 28.50 Euro per ticket on the nonstop routing.

So if it's at all possible, buy German Deutsche Bahn train tickets in advance!

Reserved seats

Like coach class tickets on Amtrak, second class tickets on Deutsche Bahn do not come with assigned seats. However, for an extremely modest charge (4.50 Euro on a sample trip), you can request a reserved seat.

You can decide whether or not this is confusing (we were extremely confused), but reserved seats on Deutsche Bahn trains are indicated by a pair of cities listed above each pair of seats. For example, seat 65 on this train is reserved by someone boarding in Leipzig and leaving the train in Hamburg:

In other words, if you are departing the train before Leipzig, or boarding after Hamburg, you're free to sit there. If you are sitting there between Leipzig and Hamburg, you'll have an irate German standing by your seat angrily gesturing at his ticket and at the digital panel above your seat.

Going by train

I've now travelled on a substantial minority of long-haul Amtrak routes, depending on your definition:

  • Empire Builder (entire route, both directions)
  • Coast Starlight (entire route, both directions)
  • Southwest Chief (Chicago to Los Angeles)
  • City of New Orleans (Chicago to New Orleans)
  • California Zephyr (Chicago to Emeryville)
  • Acela Express (Providence to New York City)
  • Northeast Regional (all over the place)

This doesn't make me anything close to an expert in Amtrak train travel, but it's given me a lot of experience. Here's what I've learned.

If you can't get to an Amtrak station, Amtrak will probably take you

I've written about this before in the context of Amtrak thruway bus cabotage, but the overall point is that Amtrak contracts with a wide range of local bus carriers in order to ferry people from cities and towns that aren't served by Amtrak to cities and towns that are serviced by Amtrak.

The one thing you need to know about Amtrak sleeping accommodations

There are three (primary) types of Amtrak sleeping accommodations: roomettes, bedrooms, and family bedrooms.

These are basically ordered by size, with roomettes being the smallest (a tiny room with two fold-down beds), bedrooms having some room to stretch, and family bedrooms being the largest, capable of accommodating up to 2 adults and 2 children.

That's all academic: the key thing to know is that only bedrooms (the middle category) have en suite toilets and showers.

Now, maybe that's a big deal for you or maybe it isn't. But either way, it's the primary difference between the room types (besides square footage).

If you choose a room type without en suite toilets and showers, you can use the toilets and showers downstairs in each sleeping car.

The food is pretty good, with limitations

As a sleeper car passenger on an Amtrak train, everyone in your compartment is entitled to breakfast, lunch, and dinner in the dining car.

These meals are pretty epic. You can order anything off each menu, and each menu has very elaborate offerings: omelettes, french toast, or pancakes for breakfast, burgers and sandwiches for lunch, and steaks, pasta, or specialty items for supper.

Of course, since you're confined to a train for anywhere from 24 to 70 hours, you should definitely not be eating that much food.

Did I mention dessert is served with both lunch and dinner?

Basically, your best move is to pick a few entrees you'd like to try over the course of a long-haul trip, and order one per day. Other than that, eat salad.

The views are completely unique

This is where you accuse me of burying the lede. Traveling by train gives you a view of the terrain of the United States that you literally can't get anywhere else.

These train routes are carved through landscapes that don't have any roads, sidewalks, or even hiking paths.

You will never see this view of the Colorado River anywhere except on an Amtrak train:

That's because there's a mountain on one side and train tracks on the other. If you're not on the train, you're out of luck.

Conclusion: go by train, while you can

Long-haul train routes in the United States are an endangered species. Some of them are subsidized by local governments seeking tourism revenue, some are subsidized by Congress, and others are subsidized by redirecting revenue from the few profitable routes, primarily on the coasts.

But that's a far cry from suggesting that such long-haul passenger train routes are "a waste." They're remarkable and unique ways to view parts of this remarkable country which are inaccessible by any other means of transportation.

You should always book one-way tickets, except when you shouldn't

Not just among travel hackers, but also in the civilian population, the conventional wisdom for a long time has been that it's usually better to make roundtrip airline reservations than book one-way tickets. There are a few reasons usually cited for this:

  • In the case of a trip interruption or cancellation, you'll only pay change fees once on a roundtrip ticket booked on a single reservation, while you'd have to pay the corresponding fee in each direction if the tickets are booked separately.
  • Since "only business travelers book one-way tickets," airlines take advantage of the opportunity for price discrimination to charge more for one-way tickets than roundtrip reservations. They may charge less for tickets with a Saturday night stay, a discount you can only secure if you book a roundtrip ticket.

I book virtually all of my airline reservations as one-way tickets these days, and thought it would be worth explaining why.

Some airlines compose all reservations from one-way segments

Alaska Airlines and Southwest Airlines treat all reservations as the combination of two or more one-way tickets. So you'll never save any money booking a roundtrip ticket on those airlines, rather than two one-ways.

In an extreme case, if you're tracking the price of your Southwest Airlines reservation in order to rebook at a lower fare, you might miss the opportunity if your outbound segment goes down in price and your return segment goes up in price by the same amount or more.

Keeping your reservations separate will make sure you capture any downward price difference in either direction.

Some airlines don't let you change your frequent flyer information after travel has commenced

If you want to credit one segment of a Delta-operated itinerary to SkyMiles and another to Alaska Mileage Plan, you're out of luck: once travel has commenced, you can't change the frequent flyer account linked to a Delta-operated reservation.

If you make two reservations instead, you can easily credit one of them to one airline's frequent flyer program and another to a second program.

Booking one-way tickets allows you to capture low-level redemptions, where available

Consider a $600 ticket, the individual components of which price at $350 each. While the roundtrip ticket is $100 cheaper than two paid tickets, if low-level award space is available on one segment, but not the other, you can buy one $350 paid ticket and redeem 12,500 miles, getting 2 cents per redeemed mile.

And of course, you can redeem 20,000 US Bank Flexpoints for the $350 ticket, which brings me to...

Price compression means more expensive tickets don't necessarily cost you any more

In the case above, the $600 roundtrip ticket (well, assuming it's actually $600.01) will cost 40,000 US Bank Flexpoints. But two $350 one-way tickets will also cost 40,000 Flexpoints! Furthermore, booking the tickets separately may reveal that a first class ticket in one or both directions costs only marginally more, allowing you to book yourself in greater comfort (and in a higher-earning fare class) without redeeming any additional miles or points. That's the phenomenon I refer to as "price compression."

When you should definitely consider booking roundtrip reservations

There are a few key exceptions to my rule of thumb that most trips should be booked as a series of one-way reservations:

  • Complicated reservations. If you're booking multi-stop itineraries in one or both directions, you want to be accommodated if you miss a connection or a flight is cancelled. If your airline can't see your onward connections in their system, they probably won't accommodate you.
  • If you're booking a revenue ticket in either direction of an international itinerary. With all of its marvelous pricing technology, the airline industry often charges less (sometimes much less!) for roundtrip tickets to and from Europe than for one-way reservations. So make sure you're actually saving money before booking one direction with cash and the other direction with miles and points.
  • If you are buying travel insurance (and actually might use it). If you buy two one-way tickets, and your outbound trip suffers an event covered by your trip insurance, your return flight may not be covered. In any case, it means paying two trip insurance premiums for a single trip and a single covered event.


There are obviously a lot of moving pieces here, but the key take-away is to check the award and revenue pricing for all flight reservations as both one-ways and roundtrips. You may end up saving a lot of whichever currency you end up deciding to use.

Easy wins: Saint Kitts edition

I was initially going to roll this into last Friday's post on the Park Inn Danube closing out from under me, since it's a related topic: looking for easy wins whenever possible. There's nothing wrong with Rube Goldberg gift card reselling machines — I occasionally indulge — but you want to go after those after you've cashed in your easy wins.

Every hotel loyalty program has regular property turnover

Someone once explained to me that hotels actually get some kind of tax benefit from leaving one loyalty program and entering a new one, but regardless of the back office details, it's a fact that properties periodically move from one chain's loyalty program to another's.

For example, the Radisson Aruba Resort, Casino & Spa was recently rebranded as the Hilton Aruba Caribbean Resort & Casino.

When that happened, guests who had redeemed Club Carlson Gold Points using their last-night-free benefit were suddenly booked at a newly refurbished Hilton rather than an aging Radisson!

That was an easy win.

The Park Hyatt St. Kitts is scheduled to open in December, 2016

When the Park Hyatt St. Kitts opens, it is going to be spectacular. It's scheduled to open in December, 2016, and they plan to start accepting reservations a few months before that.

And they might, in fact, open in December! They might, in fact, honor every reservation that's made through Hyatt as soon as reservations become available.

They also might not. And if they don't, you better believe that they're going to be offering points, nights, upgrades, and amenities to anyone who can't complete a stay they booked months in advance.

That's an easy win.

Conclusion: keep an eye out for new and renovated properties missing their deadlines

Hotels, especially new hotels, really want to put heads in beds. So they tend to err on the side of opening their reservation windows earlier, rather than later, to make sure they get the kind of occupancy rates they need to satisfy their anxious investors. That makes it worth scoping out upcoming properties and putting a reminder on your calendar to book rooms as soon as they become available.

Then put another reminder on your calendar to cancel the room within the cancellation window if the property ends up opening on schedule!

Use Hipmunk to find positioning flights

There are a lot of websites you can use to search for paid flights. Kayak is one of the most popular, but Orbitz, Expedia and Priceline will all find you tickets as well. If you're booking paid flights with Ultimate Rewards points you'll need to use their internal search engine, and the same is true of US Bank Flexpoints.

All those sites work, and they all have roughly similar search features: you can search for specific dates or flexible dates, you can specify your cabin of service, and you can filter by airline and time of day.

What none of them let you do is filter by different times of day depending on the day of the flight. Let me explain.

Award availability often requires positioning flights before or after the award segments

Award availability is the aspect of travel hacking that we have the least control over. Whether or not an airline makes seats available on the dates we need them is entirely at the discretion of the airline. While much digital ink has been spilled over the best ways to find award seats, ultimately it's not something we can predict in a reliable way.

Further, when award availability does become available, it may not exactly suit our needs. There may be award seats from an alliance hub city, but not on flights from your home airport to the hub. If you're committed to booking the award seats, that means you'll need a positioning flight: either a paid flight or an award on a different carrier that gets you to the airport in time to take your award flight.

Of course, positioning flights can be necessary at the beginning or end of a trip.

Use Hipmunk to find positioning flights

When you search for flights with every other search engine I know of, you can filter by time of departure, but that filter applies to every day searched. For example, on ITA Matrix filtering by "early morning" departures returns early morning departures for every day within the search range:

HIpmunk is the only flight search engine I know of that lets you filter by departure times across day boundaries. For example, I have an upcoming award flight booked on Air Berlin between Berlin and New York City. But I don't live in New York City, and there's no oneworld award space between New York City and my hometown, which means I need a positioning flight.

Since we don't want to go into the city (we'll be getting back from 17 days in Europe), I'd like to search for the cheapest flight that leaves either the evening we arrive in New York or the next morning. In other words, I'm fine staying overnight at the airport if it saves us some money, but I'm not willing to wait to fly out until the next evening.

Lo and behold, Hipmunk found me the perfect flight:

We'll stay overnight at JFK, leave early the next morning, and be back home early that afternoon.