To Fly or to Drive.. (from Oregon).. HELP!

If we drove we could pack more (I am admittedly a MAJOR over packer :eek:) and bring a stroller (vs renting one) and not worry about how many souvenirs we end up with...

Why can't you bring your own stroller and check it in at the gate? We did on our most recent Southwest flight to Disneyland without any problems.

From Southwest's website (https://www.southwest.com/html/customer-service/baggage/carryon-bags-pol.html):

Strollers and Child Restraint Systems (CRSs) or Car Seats
  • Customers traveling with children will be allowed to check one stroller and one Child Restraint System (CRS) or car seat per child without charge. This is in addition to the regular free baggage allowance.
  • The stroller and CRS or car seat allowance applies to any type of stroller (umbrella, full size, jogging stroller, etc.) and CRS or car seat.
  • The Customer may check the stroller and CRS or car seat at the curb, ticket counter, or gate.
  • Southwest Airlines will not assume liability for damage to strollers, CRSs or car seats. (An optional Southwest-branded reusable car seat/stroller bag is available for purchase at any Southwest Airlines ticket counter for a $15 one time fee.)
 
Why can't you bring your own stroller and check it in at the gate? We did on our most recent Southwest flight to Disneyland without any problems.

From Southwest's website (https://www.southwest.com/html/customer-service/baggage/carryon-bags-pol.html):

Strollers and Child Restraint Systems (CRSs) or Car Seats
  • Customers traveling with children will be allowed to check one stroller and one Child Restraint System (CRS) or car seat per child without charge. This is in addition to the regular free baggage allowance.
  • The stroller and CRS or car seat allowance applies to any type of stroller (umbrella, full size, jogging stroller, etc.) and CRS or car seat.
  • The Customer may check the stroller and CRS or car seat at the curb, ticket counter, or gate.
  • Southwest Airlines will not assume liability for damage to strollers, CRSs or car seats. (An optional Southwest-branded reusable car seat/stroller bag is available for purchase at any Southwest Airlines ticket counter for a $15 one time fee.)
I was thinking the same thing. So, for your family of 4 on Southwest you can pack EIGHT checked bags, FOUR carry-on size bags, FOUR personal items (backpacks), AND your own stroller. Even an overpacker should be able to fit in that, I would think, lol! (Now, getting all that transported from the airport to the hotel might be interesting .... Oversized Uber anyone?)
 
I am just so ridiculously jealous and wish I hadn't booked our July flights with Jet Blue already. I love SW, but we needed to be at the Long Beach airport to pick up my daughter from a Girl Scout trip. I paid $400/two of us. Your prices are amazing and I hope it helps make your trip even more magical. Something about airplane travel and the wonder of it all (especially for kids) makes a trip seem more like a vacation from the ordinary for me!
 
we paid $600 for 5 of us for May on Alaska...also had a $300 credit from them from a previous flight to Hawaii that got lowered so our flight was only $300 and change...unfort its through LAX
 
I say fly. We're driving from Portland in the fall- done it a million times (my Dad lives in Solana Beach/SD area). Not because I WANT to, because I married Clark Griswold. He LOVES road trips, loves to see the biggest ball of twine, loves the spontaneous options of the drive- to be able to pull over at any moment when we have a "cool, look at that" moment. We stop in Sacramento for the night so as not to drain ourselves which is the only thing that makes it bearable because I hate the drive. But technology helps and we've made plenty of memories :) obviously, my vote is fly!
 
I'm late to the party as well, but I would say drive, lol. We drive from Portland to Disney every year. I love it. I love road trips. I love making memories with the kids. I think of it as part of the vacation itself!

You got a great price on the flight though!! Have fun!!
 
I'm late to the party as well, but I would say drive, lol. We drive from Portland to Disney every year. I love it. I love road trips. I love making memories with the kids. I think of it as part of the vacation itself!

You got a great price on the flight though!! Have fun!!
We are soooo different. Returned tonight from our road trip through the Redwoods and down to Disney and all I could think the entire drive home is, "Next time we fly." Hahaha! I'm glad it is a memory maker for you and others though. My family just does not love road trips!
 
Ha, mine either. I couldn't imagine driving from Portland! That's just taking away from the time we can spend in the parks!
 
If you travel light... fly. I hate hitting traffic congestion that adds to the hours to the trip.

If you travel heavy.... drive. I hate luggage weight surcharges. When in San Francisco.... I load up on fortune cookies! A June trip means lots of daylight to ease the drive.

In addition to fly vs drive.... what about Amtrak or Greyhound?

Vancouver/Seattle residents have another option... cruise ship repositionings in May, August, September.
 
I vote fly. We are a 6 hour drive away and even that drains us. When you finally get there everyone is antsy/cranky/tired/excited and it's just exhausting. We too are major over packers and with staying 6 nights we have a lot of stuff. We always fly southwest and love that we can bring a carry on plus two checked baggage items at no additional cost. They usually have great deals. We always choose The short 55 minute flight over the long drive.
 

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