Points, Miles & Life

Travel adventures on this earthly pilgrimage

Category: Trip Planning (page 1 of 2)

Hope for the best, plan for the worst

One of the most frustrating things about traveling is watching all your well-laid plans go completely out the window. Hours of planning and preparing, all for nothing. This is why you should actually *keep* preparing for reasonably foreseeable problems that may arise.

I am constantly reminded how unpredictable travel can be. My wife and I have had our share of incidents, from minor delays, to unpredictable driving conditions (read: landslides), to completely canceled flights. Two of the worst incidents include our recent detour around the 101 slide (SEE: So close, yet so far), and being completely hosed by United on our trip to Quebec (SEE: Our First United Horror Story).

Planning for FT4RL

When I booked my recent flight to Orlando for the Family Travel 4 Real Life conference (SEE: Invaluable Disney travel hacks and other things I learned at FT4RL), I was poignantly aware that I had chosen an itinerary with only a 35 minute connection in San Francisco. The ticket was the best I could find to fit my $500 budget with my Merrill Lynch points that only had one connection. It also had good departure and arrival times.

Normally, this would be everything I’d want in a flight. Except I understand all too well United’s track record flying between Arcata and San Francisco. That route may have the worst on time performance of any in the whole U.S. I’m serious. Delays are pretty much inevitable on the route.

My “worst case” plan

Because the late morning flight from Arcata has such an abysmal on time performance (it’s one of the lovely options in Google Flights that gets the “often delayed by 30+ minutes” designation), I made sure I researched some alternate flights. Rather than simply let an agent rebook me into whatever makes sense to them, I like to understand all my options. Being prepared in the event of a delay could save me substantial time and headache.

For example, I knew I would prefer flying part of the way on a connecting flight rather than take the next nonstop flight to Orlando. If I had missed the 12:55 p.m. departure out of SFO, I would have been stuck waiting until a 10:40 p.m. departure! This would be an awful red-eye,  arriving at a little after 7:00 a.m. eastern time. There is no way I wanted that flight, even if it is a nonstop.

Instead, I would prefer to fly to one of United’s hubs. I specifically identified Houston as the best one, mainly because hotels are cheap (in case United wouldn’t comp me), and because there are a LOT of flight options, both from SFO to IAH and from IAH to MCO. More options = less chance of significant delays.

Chicago was a secondary option to Houston. There are just as many flights to Orlando each day. But it would be a slightly longer trip. Either way, I’d given myself enough travel time that an overnight delay wouldn’t kill the trip.

I jotted down some preferred flight numbers for both options, in case I missed the flight to Orlando. I wanted to be able to feed the agent the exact flights on which I desired to be rebooked.

The final precaution

The last thing I ended up doing was changing my reservation in Orlando at the Country Inn & Suites. If I missed my flight and couldn’t make it, I would be out the points. Instead, I planned on either booking an IHG hotel on points at the last minute, or using cash if rates were decent. Orlando was actually one of the best options for earning at least a small number of bonus points from my Q2 IHG accelerate offer, so I opted for cash.

Ultimately, everything turned out fine. The flight out of Arcata left a mere 5 minutes late, which is unheard of. We landed a few minutes late at SFO, and I literally walked off one flight, down the terminal, and onto the other. It was the closest connection I’ve ever had that I’ve actually made.

In this case, planning for “the worst” wasn’t necessary. But I know that things won’t always go that smoothly!

Leveraging the Flexibility of Hotel Award Bookings

Travel plans can be fickle things. Sometimes you can have a plan in place for weeks, or even months, and have it go sideways on the last day. And it makes me grateful hotel award bookings are nearly always flexible.

My wife and I have had our share of crazy travel incidents. We actually joke that we can’t go on a trip without *something* happening that throws a wrench in our plans. Our winter trip to Canada in early 2016 was botched by a canceled United flight, and our summer trip to Europe was almost completely ruined by the fact I needed a new passport!

We can’t seem to catch a break

This trip really wasn’t much different. Maybe just a couple notches lower.

A couple days before we were to head to the Bay to fly out to Alberta, there was a major slide on Highway 101. As is typical, it was at the choke point near Leggett, California where there is literally no easy detour.

So, my wife and I decided to bite the bullet and drive narrow, winding Highway 36 over to Interstate 5 and then down to the Bay. It would add at least 2 hours to our trip.

Since I was trying hard to balance work, vacation, and PTO usage, I decided to change our Bay Area plans (yet again). I had already changed them once when I realized I was beginning to hoard my points.

Instead of arriving late in the evening the night before our flight, I decided we would head down a day earlier than planned. This meant we would spend 2 nights in the Bay. I would work an uber long day out of our San Francisco office, and we would fly out early to Calgary on Thursday.

Doing the award travel shuffle

This trip was another case study on why I am glad hotel award bookings are so flexible. Unlike airline award bookings (Southwest being an exception), hotel award bookings aren’t locked in until usually 24 hours before check-in. I was able to leverage this fact to rebook our hotel plans at less than 48 hours from our check-in time.

Our initial reservation was at the Hampton Inn SFO on Hilton points. I also had booked parking at the same hotel. I cancelled all this (glad I paid the $2.99 trip protection fee for the parking), and booked the Staybridge Suites with our 2 free IHG night certificates that had just posted.

While not the best use of the certificates you could dream up, it would put us in a comfortable suite with a full kitchen for my wife. Well worth it, in my opinion. Dan Miller, who runs Points with a Crew, “wasted” his for a similar hotel in London a couple years ago.

The new parking plan was at the BART station in San Bruno. It turned out to be $25 cheaper than the other off-airport parking (before the cost of any BART tickets). If you’ve never used BART, check out why it is a great option in the Bay Area.


All in all everything worked out just fine. We didn’t lose any money on any pre-paid bookings. I do book pre-paid now and then (such as our upcoming night at the Aloft Calgary), but I don’t recommend doing this in general. It can make sense if you are getting a great rate, but sometimes you don’t know what will come up and it is better to have the flexibility. And award bookings give you flexibility.

The actual travel turned out to be better than I hoped as well. Yeah, it was a 7-hour trek, but we made it. My wife had an easygoing day in San Bruno while I worked my tail off in downtown SF. Now we are signing off for the weekend to enjoy all that beautiful Banff has to offer.


Resisting the tendency to hoard points

There are two distinct sides to travel hacking:

  1. Earn points and miles
  2. Burn points and miles

The earning is the easy part. My wife and I have been able to accumulate serious miles over the past couple years by many credit card sign up bonuses. And lately I’ve been pulling in some more from gift card reselling (SEE: My First Three Months of Reselling Gift Cards). 

Burning miles is, oddly enough, where I often run into trouble. I often end up hoarding my points and miles.

It is not that I don’t want to use my miles. I earned them with the obvious intention of using them. But too often I fall into the trap of the travel hackers “analysis paralysis”. Instead of using the miles or points for a *good* flight or hotel stay, I find myself trying to use them only on the *best* flight or hotel stay. I mean….why use them now if I’m not getting the BEST value!

Running off the “Analysis Paralysis” cliff

I recently ran straight off the cliff of travel hacking analysis paralysis this week. While trying to finalize hotel plans for our upcoming trip to Alberta (SEE: We’re going to Banff!), I couldn’t find a great use of my hotel points. We are already planning on one splurge: a cash night at the Fairmont Banff Springs. This will be covered by a checking account bonus offer from Bank of America, so it’s really not that bad.

But for the rest of the hotel nights we need, I couldn’t find a good redemption option. “Good” meaning I couldn’t get the value I expect from my points.

So I booked us at the Aloft Calgary University for 2 nights for $279 CAD. I came to the same decision on San Francisco Airport hotels. There were no “good” (read *best*) options, so I booked a night at a cheap (for SF) airport hotel through Expedia for just over $100 including taxes.

Making the conscious decision to use my miles and points

When I woke up this morning, I had a reality check. Why was I about to spend $300 on hotels when we could spend $0? Isn’t that the whole point of this hobby?

So I canceled both my bookings. I’m not thinking straight or hard enough, obviously, if I can’t find at least one option where we can use points.

I finally settled on using Hilton points for a night at the Hampton Inn SFO. Yeah, it is 37k Hilton points, but it is free. And the “value” of the stay is about $185 (which is still painful to me when are going to be there only long enough to sleep).

It also made sense because we could pay for parking at the Hampton Inn and simply leave our van there while away. Easy.

The Delta hotel at YYC is nice. And free with a certificate.

For Calgary, I settled on using a Marriott Annual night certificate for one of the nights. Yeah, it means we split our nights in Calgary, but one will be free. Plus, it’ll be an airport hotel connected to the terminal, which will make flying out super convenient.

We are still paying cash for the other. I still couldn’t bring myself to redeem either IHG or SPG points for horribly low value. But we are going to be able to now cover *both* the rental car and the single night at the Aloft with the remainder of our Chase Sapphire Reserve credit.

Analysis paralysis crisis averted

So now we will be out only the cost of gas for the drive to/from SFO and parking. The lodging is covered by free nights, points, and travel credits. The car is covered by the CSR credit. The flights were predominantly covered by Delta gift cards and United vouchers and a small amount of cash (like $60). Overall, it is going to be another cheap trip. I feel so much better about our plans, having made these adjustments.

This is yet another incident that is helping me learn to be okay spending miles and points for travel now rather than hoping to use them for the *best* possible trip later. Remember to “earn and burn” in this game. There is some wisdom in keeping a small stash of points in case something unexpected comes up, but don’t hoard. The value will only ever go down.

Header image courtesy of Lawrence OP under CC 2.0 license

The Grand Italy Plan


Summer is calling. If you recall my 2016 travel wishlist, I had two main international destinations in mind for an expended trip this year: Italy and Japan. After waffling back and forth for several weeks on the pros and cons associated with arranging a trip to either one of those countries, a real plan started to form around visiting Italy, and I decided to roll with it.

Before actually making any semi-concrete plans, I had to make a good guess regarding the timing of our adoption trip. My wife and I submitted our dossier to Costa Rica at the beginning of January, expecting to hear back from the Patronato Nacional de la Infancia (PANI) by the end of February. That date came and went, and when communication from PANI finally arrived around the end of March, it wasn’t quite the approval we had hoped for. You can read about it on our adoption blog. We are still very hopeful, and my wife and I pray daily that we will be united with our children this year. But it is not looking like it will be in very near future. We have just finally submitted our responses to PANI’s inquiries, and we hope to have an approval by mid-June. Even if we were matched with out children immediately, we wouldn’t have to travel until mid-August.

Thus, a summer adoption trip is looking almost certainly implausible at this point, and this left the door wide open for another option. Over a few weeks in March and April, the “Italy Plan” began to coalesce. Some very good award options were available in northern Italy and along the French Riviera, and the plan we were putting together made far more sense than what I was piecing together for Japan. But booking award travel is never really easy. There are too many variables in play. As I began to nail down an itinerary, I found that I had two main struggles:

  1. It is often hard to settle on a plan when you have too many options. This problem plagues me. I like to maximize the value of our miles and points, but there are so many competing interests. Is this the place we really want to see most? Should I spend the points for one very nice hotel night or three nights at a standard place? Which points currency provides optimum value? Will we have easy transportation options to and from the hotel? Will we encounter any problems finding food for my wife? And on and on. This makes settling on any plan hard. I basically had to force myself to decide on one general idea, book the award flights, and then begin to build the itinerary from that starting point. Which brought me to point #2…
  2. Summer award flight availability is abysmal. I should have been prepared for this. Last summer when trying to book a flight to Guatemala to join our church’s mission team, I had extremely limited options. My only option came down to a business class ticket (not a lie-flat seat) on a 1 a.m. flight out of SFO. Definitely less than desirable. As I researched options for our trip this summer, I literally watched both Delta and United award seats get snapped up day after day. American’s award space to Europe was nonexistent to begin with, and unless we wanted to pay exorbitant fuel surcharges on a British Airways partner redemption, my AA miles were pretty useless. I pulled the trigger on the award flights near the end of March, afraid that we might lose out entirely.
www.public-domain-image.com (public domain image)

We tacked the Emerald Isle on to our trip due to limited award options headed home!

But that gave us the starting point, and now our current itinerary is pretty well settled. All the hotel bookings are locked in, the flights home are booked, and we even tacked a stint in Ireland to the tail end of the trip. My wife is beyond excited. If she had things her way, we would have left yesterday. Two or three times a week she asks if we are heading to Italy yet. But I really can’t blame her. Our itinerary includes Milan, Florence, San Marino, Rome, the French Riviera, and Ireland! It’s yet another dream trip, made entirely possible by miles and points. Now for the numbers…

All said and done, we are using a total of 120,000 airline miles, 367,000 hotel points, and 6 “free” night certificates for the trip. A meager 4 nights will be paid for by cash, mainly because there were no hotels in any of the chains we utilize at those locations (i.e. San Marino). Even after all the bookings, we are still sitting on 260,000+ hotel points and various airline miles. I am also pleased that there is only one booking where we are not really getting optimum usage out of our points. Sometimes saving cash is more important. Value is subjective anyway. When we can save $600 on a 5-night stay at a nice hotel in a place we really want to see, I have to remind myself that it is a good redemption. The travel hacker in me still screams, though.

Now all we have left is to put together a travel manual (more on this in a future post). This is something I like to do for every big trip we take. Our winter trip to Canada was the first trip for which I failed to do this, and I definitely regretted it. We missed out on some attractions and wasted time traveling across Montreal on multiple occasions because I hadn’t done my legwork. There is no way I want to let that happen this summer!! It is another trip of a lifetime.

Piecing Together A Cheap Around The World Itinerary…..For Kicks

Route_plane_on_earth_GFDLWhat started as a Sunday afternoon browsing of dirt cheap intra-Europe fares on RyanAir turned into a self-instigated challenge to find a “cheap” round-the-world itinerary on cash, hopefully ringing in less than $1,000, with at least 7 stops along the way.

The problem is almost too big, and there are innumerable ways to solve it. I promptly decided that the route should start in the Bay Area, the home of the closest major airports to where I live. This made the first flight of the route pretty much a no-brainer, and I went from there:

  1. Oakland to Stockholm – Norwegian – $179 – Sometimes this flight comes down to about $150, but $179 was the current low price I could find this Spring. You can sometimes find a return for $130. This is honestly insane.
  2. Stockholm to Berlin – Norwegian – $35
  3. Berlin to Rome – Ryanair – $22 – There will be a bag charge as well for a carry-on, so I will take that into account.
  4. Rome to Istanbul – Alitalia – $69
  5. Istanbul to Cairo – Aegean – $90 – Aegean is a StarAlliance partner that I really hadn’t looked at until now.
  6. Cairo to New Delhi – Oman Air – $239 – I tried and tried options with a stop in the Middle East to get the cost below $300. The Cairo stopover was the best I could find at the time.
  7. New Delhi to Kuala Lumpur – AirAsia – $109 – Pretty good price for a 5+ hour flight. It’s nearly the same as flying SFO to JFK.
  8. Kuala Lumpur to Hong Kong – AirAsia – $43 -AirAsia seems to be RyanAir’s oriental counterpart.
  9. Hong Kong to San Francisco – Air China – $484 – I couldn’t find a transpacific flight for less than this. You can snag a round-trip for under $600 at times to Hong Kong (see my thoughts on United’s goofy ticket pricing), and I was mildly surprised you couldn’t find a one-way for much less than $500.

This comes to a total of ~$1,300. It is unfortunate that the trans-Pacific flight simply breaks the budget. Still, it isn’t bad at all for a set of flights that stop in 8 different places for at least a few days in each. If you consider tacking on the trans-Pacific leg as an award flight, you can probably get the cash portion down to $850.

Flying economy around the world may not sound that appealing either, but if each flight is limited to 3-5 hours at a time (not that all these are), it wouldn’t be all that bad. The three longest legs are Oakland to Stockholm, Cairo to New Delhi (via Muscat), and Hong Kong to San Francisco (via Beijing). The transatlantic and transpacific legs would probably be the most brutal.

Also note that most of the flights were searched roughly 3-6 weeks out in non-peak season (i.e. not summer). Personally, I am not crazy about summer warmth, so I really don’t mind traveling places in so-called “shoulder” seasons, as long as there is not typically severe weather in the region, or anything that would make exploring a location sub-optimal.

In any case, with plenty of time to spend in each destination, I think this itinerary would make a great trip. I am currently in the process of planning a summer adventure in Italy, but seeing how (relatively) cheaply an around-the-world ticket can be put together makes it a tempting future option. With a little more time and research, I bet I could ring in under the $1,000 threshold.

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