Get a soil thermometer, if the soil temp is 60F or greater go ahead. If the bags are 16" in diameter then you can grow both in it. I grow only in pots and I've often put 2 in a 16" pot. I see you are doing well with the plants, but I caution you to not overwater when you move them into the larger container. It is an easy thing to do when moving into a much larger pot. I also would put a 4 TBSP of 10-10-10 into the soil before planting. And when you plant add a 500mg tablet of calcium. CVS oystershell calcium. This helps prevent blossom end rot. Just put the tablet by the roots. Also when the bottom leaves yellow, cut them off and put in trash as they are diseased and you don't want them around. Another thing, don't grow in the same bag/pot/area year after year. You need to move them around as the blight gets in the soil. Plant something else in there instead. In July add some 5-10-5 fertilizer, couple of TBSPS. If you overfertilize a plant it will not flower as it will be happy and not want to expend the effort. This is especially true of peppers. Also if the temps get really hot, bees will stop pollinating and plants will stop flowering, this is normal. You can be the bee if there are flowers. Always water in the morning and water the ground not the plant. This helps slow down late blight.

OK, a lot depends on where you're located (whether there's still a risk of frost). One plant at a time in the garden - shake them apart in a bucket of water (gently!) if you need to separate them. Plant them deep - you can transplant them in the garden deeper than they are in the pots now, nearly up to the first leaves. I like to cut the bottom out of a plastic 1-gallon milk jug and cover the small plants with those for a week or two to let them toughen up once I put them in the garden (pull the cap off the jug). Firmly press the soil around the roots & soak the ground well. Tomatoes like heat and humidity, so if your temps are still cool, don't mulch the plants or you'll keep the ground from warming up like it needs to. Keep them reasonably watered (without knowing your soil type I can't give you the specifics, but even in heavy soils I would water at least every 3rd day). Fertilize on occasion, keep the weeds down, and enjoy!! Give them at least 30" of space between plants, and ideally put a wire cage around them to help support them.

Id say wait one more day and then you can do your transplant them. Thats almost what mine looked like when i transplanted them.

Can I still separate the multiple one without damaging their roots?

I need ur advice on my tomato seedlings as I am everything but patient I will like to know if at their stage is it safe to transplant them into their final pot/growbag outside I know some of them are multiple and that’s my intention to put them in a grow bag like that!

Any advice will be apreciated, thanks in advance.