395 north, first night at Goose Lake SP. From there NE to LaPine and LaPine SP. Plan a few days here high desert museum, lava lands visitor center. If you dont mind a drive, from here you might make a day trip to Crater Lake, but June it could still be snowed in. From here you could go over MT Hood, or cross the south side of the mountain to Hood River and the Columbia river gorge, I5 north, be sure to visit Mt St Helens. Return via 101 down the coast. Any place you plan to stop be sure to get reservations. Oregon state parks, especially on the coast fill up early.