
The North Face
Wawona 6
Spacious vestibule, strong in storms, but rainfly tricky solo.

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Those look great, but I’m trying to keep it under/around $300 if possible. I will have to look into these if/when my son gets a little older.
Thanks for the comments everyone! I checked out all of your suggestions and it helped me narrow down what I wanted. I decided on a Kelty Tall Boy 6. I liked the standard dome tent design, but I wanted to be able to stand up and put cots along the sides so the tall style was my choice. We’ve never had a tent with vestibules and I didn’t think they were really necessary or worth the extra set up time, especially since we already have a canopy. The Tall Boy also has less ventilation, which works well with the timing of our camp outs because it holds heat better and we don’t camp in the dead of summer. Finally, I trust Kelty tents because I grew up with them and never had issues, which is why I went went Kelty over some of the other brands such as Coleman, which I’ve had leak in the past. Thank you all again for your input.
See my comment below. I went with a simple dome tent from Kelty.
My son is young and I’m trying to keep him interested in camping and scouting. The tent will also double as a family tent and my wife and daughter aren’t big campers, so a little extra comfort isn’t a bad thing. With that said, we went with a simple 6 man dome tent from Kelty. I’m also an Eagle Scout, spent 10 days backpacking in the mountains of Colorado, and have multiple nights outdoors in literal sub-zero temperatures. I earned my stripes as a young man and want something with a few more creature comforts as an adult. It’s just a simple Cub Scout camp out in a field 20 feet from a car so the kids can experience running around in the outdoors, learn to tie some knots, and have a fun campfire.
I know you’re partial to Coleman, but the kelty tall boy is a simple dome tent with a 6’ center. It doesn’t have a covered exterior area if that’s important to you, but the quality is significantly better than my old Coleman.
I can set up my Kelty Tall Boy 6 on my own, and I'm only 5' tall. So totally doable! I like having a larger tent so I can set up one side with a chair & table, plus easier to change your clothes in.
You really have 2 requests: Comfortable for 2 weeks, I have one set of suggestions. But you need to fly with it. So that changes my recommendation. We have a Eureka 4 person tent in a tall configuration that we have flown with. There is a similar tent in production called the Kelty Tallboy 4. It is 5'10" in the center which makes it a little more comfortable. Also, while I know a Scout is Thrifty, considering some of your gear to be disposable might be to your advantage: pick up a ground tarp and a camp chair at a Walmart. Gift it to someone who is driving or donate it to a Goodwill on your way back to the airport.
it fits my kelty 6 comfortably with space on the size. it was very tight with my kelty 4
I have two tents (both kelty brand) a two person for solo backpacking/short trips where bad weather isn’t forecast and a 4 person for trips where I have another person in the tent with me or I plan on having to spend more time in the tent. Totally a reasonable move and the bigger tents really aren’t usually much harder to set up unless you have some huge 10 person multi room situation
Car camping means your car is right there with you. As opposed to backpacking where everything you have is on your back. It does not mean sleeping in your car. No tent will be warm. They’re for keeping you protected from the elements, not warmth. You need a better sleep system for that. Make sure your sleeping pad is good enough to keep the cold from the ground away from you. And make sure your sleeping bag is rated low enough. The temp rating is generally going to be a “you won’t die but you won’t be comfortable” number. You’ll want something below your lowest expected temps. You can also use a liner to add warmth. I’d recommend looking at at least 3 person, if not 4 person, tents. It’ll be more comfortable for this long of a trip. I would also look for one that has a rainfly that goes all the way to the ground. Better protection from things like rain or snow or wind. My husband and I got a 4 person Kelty at D1ck’s Sporting Goods (apparently that word is not allowed…lol) and it’s been good. We originally got it because I needed to spend money on anything, but now glad because a 2 person with two 65lb dogs is…technically doable but not as comfortable!

The North Face
Wawona 6
Spacious vestibule, strong in storms, but rainfly tricky solo.

Gazelle Tents
T4 Hub Tent Series
Fastest setup, durable, but bulky and awkward door.

Durston
X-Mid 2
Ultralight, spacious 2P, but not for very strong winds.

Durston
X-Mid 1
Budget ultralight 1P, spacious, but large footprint.

Naturehike
Mongar 2 Backpack Tent (Nylon)
Budget 2P, spacious for price, but not for 4 seasons.

Ranked #1
Durston - X-Mid 2

Ranked #1
Gazelle Tents - T4 Hub Tent Series

Ranked #1
Gazelle Tents - T4 Hub Tent Series

Ranked #1
Durston - X-Mid 2

Ranked #1
Durston - X-Mid 2

Ranked #1
SlingFin - Portal 2