One of the reason I go into photography a year ago was because the wife and I are going on a month vacation to the Azores and mainland Portugal. I wanted to learn how to take good pics. Of course everything exploded from there and I am now burdened with very expensive equipment. Here is my quandary and my questions: 1. The gear. I have expensive camera and glass is there insurance you can get for your gear when on vacation? 2. I can fit all my gear in a camera backpack. In the Azores I have no problem always carrying it with me. But on the mainland there are going to be some nights or even time during the day, especially in the cities where I only want to take the camera and one lens. What the hell do I do with the rest of my gear? I don't want to just leave it in the room I am staying in. What do you guys do? Just take your gear everywhere? I do have lesser expensive camera and cheaper lenses but I really would like to bring the best for this trip. Especially not having my 300mm for wildlife will make me want to cry. 3. Maybe I am trying to bring everything and the kitchen sink and just having a hard time to leave something behind. Here is what I would like to bring (not what I should): Option 1: Small backpack. EM1 MkII 12-100mm f4 IS Pro 40-150 f2.8 Pro 300mm f4 IS Pro 60mm f2.8 macro 17mm f1.8, MC-14 FL600R Small foldable diffuser Tripod "13 laptop **EM5 MkII - for my wife to use and carry also as a backup camera Option 2: If I leave the good stuff behind I can go with a messenger bag. EM5 MkII 14-150mm f4-5.6 II 75-300mm f4.8-6.7 II 60mm f2.8 macro 17mm f1.8 FL600R Small foldable diffuser "13 laptop My big worry, as stated earlier, is for those times I want to go out and about with just one camera and lens, going out to a nice dinner or a romantic walk at night where I don't want to drag all my equipment around. Going with option #2 will alleviate much of that since I can take a light messenger bag. I am sure I am not the only one who has dealt with these question before going on vacation. What did you do? Also if anybody has any recommendation for places to visit in Portugal, anywhere between Porto and Lisbon, please let me know.