Studying abroad in college, my parents purchased the perfect backpacking bag for me. It was an all-black JanSport with a large main compartment and a daypack that could zip right off. Perfect for hauling all of my gear around Europe and simple enough to dump the large piece off at my hostel and take on the sites with my smaller bag, filled with my daily needs; passport, calling cards, cash, camera and a notebook. 

I was excited to make use of my backbacking gear once again when I toured Peru. However, passing through the Mexico City Airport, my bag was mishandled and the zipper function destroyed. Meaning my bags had to be worn separately, completely defeating the purpose. Still, I made it through the trip, but finally had to let the thing go. 

And now, less than a month shy from a Cuba excursion, I need a new bag! Friends and I will be visiting three different areas of Cuba, which will require us to pack up all our stuff every couple of days. While we'll more than likely take a car to each of these destinations, I think being able to carry my stuff off the ground may be beneficial in areas where the roads could be less sympathetic to wheeled luggage.

Still, I'm torn on exactly what I should get. I've looked for my same JanSport bag, but everything on the market right now is way sportier than what I had. I'm not taking this thing hiking through the Rockies. Though, it may be nice to have that option later on. 

I've come across bags that have both wheels and straps. Meaning you could wheel them when appropriate and haul them when the terrain gets jagged. Only issue here is that, so far, the ones I've found have been rather clunky-looking and not at all cute. Is it wrong to care somewhat about the style? These bags are also more appropriate in size for a weekender trip, so I don't think they'll cut it for Cuba. 

Here are the top contenders per my research.

The Patagonia Headway is the most expensive of the three. It doesn't come in a color combo I particularly like and the square shape looks bulky when worn as a backpack. However, it's the lightest of the three and can be worn as a backpack or a cross body. I've nixed this one because it does not have the zip away daypack and is recommended for 3-5 days of traveling. I'll be gone a week and bringing a lot more girl stuff than the average hiker.

The Deuter Transit 50L (liter) is the smaller of this series. It also comes in a 65L. Both the 50L at $180 and the 65L at $190 come with a zip off daypack. However, I read comments that that daypack is small and can be hard to access when the main pack is full. I actually like the gray color with the lime green trim, but find the alignment of large and small pack awkward, with the little pack sitting so high on top of the main piece. This bag came with rave reviews, so I'm tempted, but not completely sold. 

I think I'm leaning towards the Osprey Farpoint 70L. With the sleekest design of the three, the most storage, a detachable day pack, and in a pretty Caribbean blue, this bag feels like a steal for the $160 price tag.

Please comment with your thoughts or if you have a bag you recommend!