I recently traveled roundtrip clear across the country (New Hampshire to Florida to California, and then back to New Hampshire). I was in a camper, so I slept wherever I stopped for the night and didn’t have to think about (or pay for) lodging. But I did get a good sense of multiweek, long-distance travel. Personally, I really like the large truck stops, both to sleep at and to take breaks at. They usually have a section for passenger vehicle travelers, are open 24/7, have restroom and shower facilities, and are well-lit and quite busy (so fairly safe). They always have food options, too, although not always the healthiest or freshest options. And they don’t mind if you sleep in your vehicle, in general, as long as you are gone in the morning, but they tend to be so busy that they don’t even care if you stay longer. Some of the places I’m thinking about are “Flying J,” “Pilot,” and “Love’s.”
I saw people with pets at these places all the time, all over the country, and they just took their pets to the edge of the parking lot, where there is grass. I don’t recall if these were designated pet areas, but there seemed to be some sort of designated (or at least tolerated/accepted) pet area in most of the truck stops I am recalling.
Note that the big interstate truck stops I am talking about are not the same as normal gas stations at the big intersections. I am talking about the sorts of stops where truckers go specifically to refuel and rest. Normal gas stations can be dark and sketchy, so the distinction is important. I have frankly found this to be true of official rest stops, too. I never had a sketchy feeling at a trucker’s stop – probably because they are well-lit, busy, and full of truckers.
Other gems to stop at are casinos and Wal-Marts. They generally let you park overnight – sometimes as long as you want – and they don’t bother you because they assume they will benefit from you stopping at their establishment for food, gambling, or shopping. They are usually right! I never stopped at a casino without going inside and looking around and eating something (I don’t gamble, though). And if I stop at a Wal-Mart, there’s usually something I need inside. Camping World is a good option, too. Note that you need permission in advance to stay at a Wal-Mart or a Casino overnight. Usually they will tell you outright if you just call in advance, and the only impediment is local rules (some towns/cities do not allow overnight parking in public places).
State parks, BLM land, and local parks are good gems for a break, though they sometimes have no amenities to offer.
I avoided driving through cities like the plague, and I never stopped in a city. In fact, if I had to drive through one, I made sure that both me and my gas tank were full so that I wouldn’t have to stop until I got to another truck stop, casino, or Wal-Mart.
Frankly, if you’ve got the space in your vehicle and the weather cooperates – and you want to save serious money – you could sleep in your car at all the places I mentioned, get a shower in the morning (at a truck stop), and not pay for lodging, at all. That is easier in a camper, but plenty of people do it in a car. Make sure you have blackout or reflective panels for your windows for both light-control and privacy. Truck stops can be loud at night, but with ear plugs and a sleep mask, it’s not a problem for me. I felt safe sleeping at a truck stop, but I probably wouldn’t dare sleep in my car in a Wal-Mart parking lot or one of the state rest areas that is open 24/7 (I found them to be poorly-lit and poorly-guarded, in general).
Personally, I would not tent camp alone anywhere where they would let you tent camp alone. I would want at least my camper walls between me and predators (of the 2- or 4-legged variety) or the elements. Having a dog would help, but I prefer busy and well-lit areas, despite the noise and light pollution.
To what extent do you plan to “caravan” together with these other folks? If you are not even sleeping in the same place, what’s the point? You will depart from different locations and arrive at different locations each day, no?
But, if you are somehow actually caravanning together, and if you and your friends have never caravanned before, I strongly recommend you and your caravan members establish a pattern and a timeline for the trip. If you both agree to haul it to your destination, then just haul it. Otherwise, one tried-and-true method (this is assuming your goal is to take your time and avoid stress on the road) is the 2/2/2 or 3/3/3 rule:
1. Plan to arrive at your destination for the day at 2PM (or 3PM). This gives you time to get lost, have daylight to navigate, and set up and rest before dinner. It also gives you time to socialize with your caravan members.
2. Drive no more than 200 miles (or 300 miles) in a single day. This ensures you do not become overtired of driving over a period of a week or more.
3. Take a break at least every 2 (or 3) hours. Stop, stretch, and have something to drink or snack on.
This means everyone in the caravan resolves to be ready to roll the next morning at 10AM or so. If you are in different sleeping locations, you can just agree to arrive at the next destination by 3PM the next day.
Good luck on your trip, whatever you decide!
One other thing: keep in mind that a trip like this asks a lot of your car. Please make sure it is in tip-top condition and ready for the trip. Nothing will ruin your trip (or your caravan member’s trip) more than a serious mechanical failure on the open highway at 6PM with a snowstorm coming in. In fact, that sort of problem could add a week or two to the trip, as well as all the associated headaches and expenses.
