So. Many. Options!

[ninjasurfer99]

Really, I just need a space to get all this stuff out of my head and this seemed like a good place to do that and get some good feedback at the same time.

The major thing on my mind right now is maximizing our travels for the next year, potentially by utilizing some of the more complicated tricks Drew has been posting about. What I'm struggling with is that my wife and I are finally in a position where we can create our own schedule - this new found freedom is amazing, don't get me wrong, but man it's made thinking about travel VERY different. It's opened up, as the title says, So Many Options! Oh, and Thanks @Matt for that one post forever ago; the one about taking the time put into this hobby and investing it in a side hustle instead!!

Before, if we wanted to go to Hawaii, we'd find the 7-10 days we had available and book the trip- it was simple. I was always envious of people that could maximize routings with stopovers, open-jaws, etc. Now that I have the potential to book those types of trips I feel overwhelmed with all the options out there.

We have two big trips in mind that I'm working through -
Big Trip 1) My Wife and I are trying to visit friends in Hawaii in May/April before they move back stateside this summer. I thought the smartest thing would be to use Korean Miles to book from the East coast for 25k r/t each, BUT Drew had to throw a wrench in the works and showed us some awesome potential using United miles and he just complicated that further with his latest post on Alaska miles.

So I'm trying to figure out if it's better to do a straight redemption using Korean or if we maximize the amount of travel utilizing the other programs since we don't have any restrictions with time. We could one way to HI and use the programs from there to get a free one way back at a later date, etc, etc...

Big Trip 2) Our Five Year anniversary is next September and we'd like to do something special for that. We've been wanting to go to Greece and we can get there from BWI for $480. Realistically, we'll probably do Rome for $430 and skip over to Greece from there. Anyway, same challenge as above - trying to decide if its worth paying for this flight while it's so low, or utilizing miles and putting together a crazy trip.

***Really, I've been lax the last year or two keeping up with everything and I'm overwhelmed trying to catch up. The one thing I'm stoked about, is that not much has changed other than churning rules - there's still crazy deals and redemptions to be had.

I don't know, maybe utilizing an award service makes sense. I'd welcome any thoughts, suggestions, snide comments, etc. Sorry for word vomit, you can blame @Travelisfree for making this so hard (read: awesome).

 

[italdesign]

A few considerations might be:
-do you enjoy putting together complicated itins? Is the reward worth the effort?
-do you enjoy taking long trips in multiple continents? Or do you prefer to stick to one region per trip?
-do you have more miles than you can use even for premium cabin? If so, then maybe redeem for that even if Y flights are cheap.

 

[ninjasurfer99]

A few considerations might be:
-do you enjoy putting together complicated itins? Is the reward worth the effort?
-do you enjoy taking long trips in multiple continents? Or do you prefer to stick to one region per trip?
-do you have more miles than you can use even for premium cabin? If so, then maybe redeem for that even if Y flights are cheap.

Great questions!
- I do enjoy putting together complicated itineraries, it helps me learn more and I love the challenge
- Multiple continents - how much can I fit in on one "trip."
- I do not have more miles than I can use, but I don't fully subscribe to earn and burn either. I'd rather see two places economy than one in business/first. Of course, for the anniversary trip, I would certainly consider burning a few extra miles off for that level of service.

 

[MickiSue]

Putting together complicated itineraries is not the same as traveling them. The complications are only worth it if you will love the vacation that results. Even when self-employed, you still have limits (unless you're Drew) with how long you have for traveling.

For me, at this stage of my self-employment, that's about three weeks. And I really do prefer to find a base of operations, and then take side trips from there. For the anniversary trip, for example, I could see a week and a half each in Rome and Athens, utilizing trains for a day (or two) trip to Naples and Pompeii. I've been to Pompeii twice, once with Husband and once with Daughter, and would gladly return to see the parts I've still not seen.

Making Athens a base gives you a LOT of history to see in Greece, along with the option for a night or two on one of the islands to experience where Greeks go on vacation.

 

[Maverick17]

Here's an example:

BWI-SEA-HNL: One way ticket with AS. You can have a stopover for as long as you want in Seattle and explore the Pacific Northwest, then continue on to Hawaii. You could have the stopover in LA, PDX, DFW or anywhere you can get routing. Then you have the Hawaii trip you have planned.

HNL-HOME-ATH: One way ticket with AS. After you have finished up in Hawaii, you route to Europe on a one-way with AS, and have your stopover for 4 months at home, or as close to home as you can get the routing. Or you could add another US location if you're truly able to stay as long as you want in other places. Has to be an AS destination because you can only have one other airline and need that for getting to ATH. Then for the anniversary continue to ATH on AF, KLM etc.

ATH-USA-Cabo: One way ticket with AS. So you go home, or again close to home, and then have the leftover to route to anywhere in MEX you can get to, say Cabo. This would have to be an AS destination, again, since you can only fly with the one partner.

Cabo-LAX-BWI: Same deal as above.

So for 4 one ways, you get SEA trip, HNL trip, ATH trip, Cabo trip, LA trip. Or if you're truly mobile, skip the "home" portion and add something else on the way from HNL to Europe, such as another US location, or even DXB. Then of course if you like the "layover" vacations, you could add some crazy routings to see a few more places.

The key is just planning ahead one step. If you're able to work out routings where you can use "home" as a stopover, you can do this endlessly.

But are you really saving much? Let's look.

BWI-SEA-HNL-HOME: AS RT with stopover.
BWI-ATH-HOME-Cabo: AS RT with stopover
CABO-LA-HOME: AS one way with stopover.

So for me, I think that the stopover trick likes to make things look great, but really you're only saving 1 one-way ticket. But you have to deal with working a great routing to get home. So if you live in a hub, it can be great. But if not, it's pretty meh.

The better use for me is just adding that one destination. Like instead of Italy, you could easily do CDG, AMS, or DXB on the way to ATH, and have it included.

I'm forgetting much of the new United stuff though. And frequently Hawaii has been key to some good values. So I'd look at that more closely.