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My girls are 2 1/2 years apart (almost to the day) and I bought a used double stroller after my DD2 was born. I didn't worry about it with my first and just used a single one then. She walks for the most part but if we are going to the zoo or on a long walk it's nice to have a place for her to sit down. I have 3 strollers now: double, the single travel system, and a umbrella. I could go without the single travel system (it's bulky and I hate it but it works.)

I think you should look very carefully at your lifestyle---do you mostly drive and go to stores where you use a shopping cart? Will you be lifting a heavy stroller in and out of your car trunk alone? How often do you go for walks and how far do you go?

I've found that my suburban/country friends don't use strollers much at all after the infant stage. As soon as their kids can sit in a shopping cart, they use those at places like the grocery store, target, BB&B, etc. And if they go to parks, they drive to them and don't use strollers then either. Strollers are only used at the Mall or maybe for an outside walk, but the older kid is more likely to just walk since they don't go far.

On the other hand, I live in an urban place and my stroller is like my car. I walk to the grocery store and do all my shopping by loading my bags on my stroller, I walk to doctors appointments, to playdates, to restaurants--I never put my big stroller in the car. So I wanted a heavy duty stroller and went for the Britax B-ready which turns into a double with an added seat, and has lots of configurations. And we have an umbrella stroller for air travel and trips.

I think there's no need for a super pricey stroller when you live in the suburbs unless you are outside walking from your house a LOT.

We have the City Mini GT and LOVE it. We do a lot of walking around the neighborhood now. When DS is old enough we'll use it to walk to the park, some errands, etc.

Even though we want a 2nd child, we decided not to choose a stroller based on that. The City Mini GT was our favorite, and so that's what we got. It's super easy to sell nice strollers, so if we need a double stroller anytime in the near future we'll just sell the GT and use the money towards a double.

I had the City Mini GT for my first and we still love it. She's almost 2.5. Lightweight, easy to maneuver and Fold. It also works well in places like parks. It has been our only stroller. We used the infant seat adapter when she was in the infant seat great, but you can't use the huge sun shade when the adapter is on.

I'm due with my second in 6 weeks and they will be 2.5 years apart. We bought a used City Select to use with both for things like, zoo, parks, the mall. We also walk around our neighborhood a lot for exercise and number one is still stops to look at everything or tries to run. We also walk to the pool, ice cream shop and a few eating places even though were are in the burbs. It will live in our car trunk since we don't have a garage and no place to store a stoller in our foyer. The Select is a lot heavier than the GT City Mini. When number one is completely done with the stroller we will likely sell the select and go back to the City Mini GT.

I would get the GT and worry about #2 later. We just went through selling a City Select because it was way too heavy for me to deal with all the time (I live in the city and had to fold and lift it often). I had bought it because it could convert to a double but I really couldn't deal with the weight. We just got the GT and I am thrilled with it so far. We had a normal city mini prior to the City Select and that was a good stroller too (I just wanted the upgraded wheels on the GT since we get snow often and the normal city mini gets stuck in snow).

I have a 21m old LO
We originally registered for the big jogger and hated it and returned it about 6months after LO was born
http://www.toysrus.com/product/index.jsp?productId=18046766&cp=2255957.2273447.35475976.11614155&parentPage=family

our line up is Snap n Go for the bucket seat (used this exclusively for the first 8 months) http://www.toysrus.com/product/index.jsp?productId=12881350&cp=2255957.2273447.35475976.11614155&parentPage=family

We returned the jogger for this Graco one and the dimensions suited us much better, It still had the ability to pop the car seat in, and fit our needs. http://www.toysrus.com/product/index.jsp?productId=58698686&cp=2255957.2273447.35475976.11614155&parentPage=family

and we have a cheap $30 umbrella stroller that comes in handy and is easy to stash in my trunk - malls dont have easily accessible shopping carts

My SIL picked up a combi double umbrella stroller to keep at the beach house (we do a lot of walking and its great to stick both kids in there almost 2 and almost 3) and we love it.... I'm pretty sure she picked it up used at a consignment sale http://www.walmart.com/ip/Combi-Twin-Savvy-E-Compact-Portable-Side-By-Side-Stroller-Red-Chevron/37300169

My kids are 20 months apart.

How did you plan your stroller situation?
I was uneducated about strollers and went with a cute purple chicco travel system. I HATE THAT THING! I would never go with that again. I should have thought more about it. I knew my kids were going to be close in age. I probably should have researched it more and gone with something that could convert to a double.

Did you have to buy a double stroller after you had your second?
Yes - we got a city mini gt.

At what age do kids stop needing/wanting to be in a stroller? By about 2.5, DS1 stopped wanting to be in the stroller. He is good and not a runner, so I usually take him out and he stays close by. I am that mom pushing a double stroller with no kids in it. We really used the double stroller with both kids in it all the time for maybe 8 months? I definitely needed something for 2 because early on DS1 still needed to ride in it, but him wanting to be in it didn't last long.

I live in the country/suburbs so we use the double stroller mainly for shopping trips to the mall or the zoo.

Think it through! I really wish I had done my stroller situation differently. But then again, you never know. I see big kids (like age 3 or 4) sitting comfortably in a stroller and not begging to get out. Totally depends on your kid.

I knew I would almost only use my stroller for running, the park or going to the field so I only have one- the BOB Revolution SE. I'm so happy with my decision. I can drive my stroller over anything and it serves its purpose.

DD has never been big on strolling. Shes been walking since 10 mo and prefers to push the stroller to sitting in it. Now, she'll let me put her in to go to the park but that's about it.

We're expecting our second in September (19mo apart) and I'm thinking of investing in a BOB duallie for next summer. Until then I know I can get away with one in the stroller and the other one being worn/walking depending on the kid in need.

We have a City Mini! I liked it the handful of times I used it with my first (I could probably count on two hand how often I used it and it was only used in the NB stage). I baby wore 99.9% of the time. My second has never been in a stroller. She's 18 mo and my LO's are 31 mo apart. We are expect a 3rd and I will just wear or tandem wear.
I personally, knowing what I know now, would skip the stroller and invest in a good carrier (personal preference is a stretch wrap during the NB phase and a Tula (so much more comfortable than my Ergo) when baby is older/bigger.

Even though we talk about having more than one child, we try to take it one child at a time and we got the GT. We love it for walks in the neighborhood and on paved trails. Sometimes we take it into a store, sometimes we put LO in a cart.
I thought we would have bought a more lightweight stroller by now but we have not needed it yet. LO is 9 months. We are planning to TTC soon and depending on if/when we have another LO we'll decide if to get a double stroller or not.
Being able to get the stroller in the trunk of the car and still have room was a big factor for us. We also like the large shade on the GT, it's easy to open, easy to set the break, and we also really like the tires and handle bar.