The problem:

When traveling, I often head out for the day planning not to return until late in the evening (perhaps off of a cruise ship to explore a city or an island; perhaps on a trip to a nearby town; or any number of reasons why I might not be able to return to my lodging throughout the day).

So I need a bag that is able to comfortably carry everything needed to tackle an adventurous day: cell phone, PDA, passport & wallet, camera, cosmetic bag, keys, sunglasses, glasses, water bottle, snacks, umbrella, raincoat, maps & guidebooks, laptop & charger, pencils & papers, paperback book, extra layer of clothing (over-shirt or light sweater), and still have a little room for stuff I might buy along the way - so it cannot be tiny!

And I would like this bag to be my carry-on luggage, as well as be able to go on my back when I need my hands for riding a bike or carrying something else. And then there’s all the gear you need at the beach.

Here's what I am looking for: ONE bag that can be used as my carry-on on the airplane, as my shopping bag in town, as my beach-bag, as my backpack on a bike ride, and a purse when I go to dinner. Tall order, I know, and I understand that ideally I need a Mary Poppins bag - huge enough on the inside for a lamp, but tiny on the outside - but I cannot find one anywhere – can you make that?

Why not use a traditional daypack?

Most mid-size daypacks hold all of this stuff just right, but a pack on your back, while comfortable for lots of walking, is inconvenient for reaching into to grab water, maps, sunglasses, etc., so the Perfect Bag also needs to have a long strap to go across your body and over the opposite shoulder and hang at your side so your hands can be free and you can reach into it easily to grab your wallet while shopping.

The other problem with daypacks is that they do not dine well. Nothing says "American Tourist" like a bulky daypack in a restaurant. So, the Perfect Bag needs to look nice too. Now, your Windflower carryall looks good enough to go to a restaurant, holds all of the stuff I need, carries a laptop well, has two of the three carrying systems I need (missing backpack-style) and (unlike me) it even has a great bottom for the beach!

The main thing it needs is some modifications to the straps to work as a backpack. (And we can improve the across-the-body shoulder strap). I like the way your Switchgrass bag does the backpack thing, but it doesn’t have long handles or a shoulderstrap. I would have started with that bag, but it doesn’t have a zippered top, so I chose to fix the Windflower instead. It is easier because it already has removable straps (and I refer to the halves of the clasps that connect the straps to the bag as “innie” and “outie”).

First, my backpack solution:

Since the handle straps have “outie” clasps on the ends, you need to add two more “innie” clasps to the sides of the bag, near the bottom. I had a shoemaker sew these on; you could do it in the same tasteful little pockets that the top clasps have.

Side clasps added

Now, to make a backpack, just clip the strap ends to the sides.

Second, my shoulderstrap solution:

Dispose of the fat shoulder strap – it’s a hassle to carry a separate item, and the connectors you chose are most frustrating to operate. Instead, I put 2 more “innie” clasp halves into the ends of the shoulder pad, and the straps connect from it to the bottom clasps for an across-the-body shoulder bag.

The caribiners I put through the vestigial old shoulder-strap tags are handy for holding the new shoulder straps to the bag, and I like to hook my waterbottle outside the bag for easy access.

An improved solution:

A better way to do this would be to use innie-outie clasps in pairs: each strap gets an innie end and an outie end, the bottom clasps are one innie and one outie, the top clasps are one innie and one outie on each side face (opposite each other). Now you use 5 full sets of clasps (instead of 4 outies and 8 innies). Note that the backpack can only be done one way due to the asymmetry. You want it such that the zippered pocket faces away from you and the magnet open pocket is against your back - making it harder for others to reach into the bag. So you have to pay attention to the parity of the innie/outies on the bottom with respect to the top ones. (Easier shown than explained).

For the shoulder strap you can connect the 2 straps directly together (removing the sex-change provided by the shoulder pad) and just slide it through the shoulder pad. (I did not implement this because I didn’t want to tear apart two of the top clasp pockets).

The best solution:

Of course, the best solution would be to find clasps that are unisex – they are all alike – so you have no innie/outie parity issues. I have not researched whether such a clasp system exists. Maybe those hourglass clasps would work (similar to the one pictured below, but fully symmetric)?

I am planning to take this on a 2-week trip to 7 Caribbean islands and a couple of boats. This will be my One-Bag Vacation test!

Now, I think there is just one more change I need (but I reserve the right to come up with more by time I return from the trip).

I think the bag is big enough, but I’m carrying an extra expandable baggalini in it just in case. It would be nice if it expanded the way luggage does – special zipper around it that lets out a couple of extra inches of length – just in case you shop too much. I can't do that, but you guys probably can.