Towing a pop-up vs. a self-contained

The pop-up is way easier to pull and back into sites. Most travel trailers need a sway bar system hooked up. It's almost a night and day difference in every aspect. Yes the hard wall trailer is more comfortable, but there is a price to pay.
Brian

We went from a popup being towed with a Highlander to a 34 foot tt pulled with a Silverado. Every aspect of towing became more challenging. Getting gas, stopping to eat, sightseeing along the way became a bit more difficult. It can still be done just not as easy. You will also notice it in gas mileage, plan on somewhere between 7 and 10mpg while towing with a tt. Plan on getting a solid truck and a solid understanding on what you need to tow the trailer You can never have to much truck. With all that being said the upgrade is worth it hands down

We had a popup for 9 years before going to a 33' TT. The difference will kinda depend on what you are towing with now. We towed with a Honda Pilot, and a 1500HD (basically a 3/4 ton truck). Pulling with the Pilot, was actually pretty similar to pulling the TT with the truck. You can really tell its back there, acceleration is slow, you really slow down on hills, you feel 18 wheelers pass etc.

If you pull the TT with a capable truck, it will not be bad. It will just take a trip or two to get used to it. Parking lots and tight areas require a little more thought.

We loved the popup, but the TT is so much easier. Packing and unpacking is so much quicker. I used to hate having to pop up to load, and unload at the house.

I do miss all of the windows and sleeping under the canvas. But we do use the the TT more in the cold and the heat as it is more comfy. We've also used the TT as a place to stay on short one night trips that with the popup we would have used a hotel.

You don't mention your tow vehicle, but the frontal area, and hitch weight of that size TT will require a TV with more power/payload than you need for towing a Pup. You will need a weight distributing hitch to transfer some of the hitch wt, and to help with sway. With the proper TV and WDH, towing the larger TT should be a good experience, that you will adjust to quickly.

Jerry

This depends on your tow vehicle. And yes, a TT is much easier to back up.

We went from a pop up to a nineteen foot TT and then from there to a 25 footer.
The biggest difference for me was the worry about pulling in and out of gas stations
We now have a 40 foot TT that is on a permanent side and we still have a 8 foot box PUP that we use to commute to the big one

Jack L

I've had two PUPs and now have a TT. PUPs are WAY easier to tow, but once you get used to towing a TT its no problem, the extra wieght and wind resistance is the biggest issue plus the much lower fuel mileage. A TT is easier to back up though.... IMHO. I LOVE the set up of the TT infinitely over the PUP.

Well, you might an extra 3 mpg. Buy all incosed everything and you'll be happier by far!