Raven and I made a deal.
We were packing for a seven day cruise to the Caribbean with three additional days to be spent in Puerto Rico. From formal wear to beach, we agreed we could only take what would fit in our Osprey Waypoint 65 backpacks.
For once, Raven barely had an advantage over me. The Men’s Medium Waypoint 65 measured 1.5 cubic inches larger than my Woman’s Medium: 26x14x14 cubic inches versus 27.5x15x15. Each held just over 3,000 cubic inches in the main pack with an additional 900 cubic inches available in the detachable day pack, which measured 19×11.5×7 inches. Both weighed in at 5 pounds and 8 ounces. It was up to us to figure out how to pack them.
We’d decided on the Waypoint 65s after much serious searching. Our traveling had changed from the days of suitcases or small wheeled bags. We wanted something lightweight and easy to carry not only at the airport, but while hoofing it to hotels, ferries, or while crammed into a bus. Internal organization was a plus, durability a necessity, and transportability the guiding principle. We found it all in the Waypoints.

Storage and pouches! Easy to keep organized and to find things when needed (if you remembered to bring them!)
Side pouches, one accessible from the exterior of the pack, as well as mesh pouches on the flap provide internal organization. Each pouch, side and flap, are different sizes so that you aren’t half filling one while wishing for more room in the other. The main compartment opens like a traditional suitcase with a wide zipper. This means no stuffing essentials into one cavernous opening or hunting for something on the bottom like a squirrel desperate for buried acorns. You can actually open up the suitcase and find things! Even better, clothing and other articles can be packed, secured with the cross straps like traditional luggage, and then will stay in place. Amazing idea!
The detachable daypack was an attractive bonus that I hadn’t considered while searching for travel packs. It zips and clips securely to the larger main pack. No running for the train only to have it fly into the bushes while spewing contents with this item. With pouches designed to carry valuable electronics in cushioned safety as well as other essentials to keep yourself distracted or working while in transit and the main pack was tucked elsewhere, I thought the daypack a superb touch.
And the glory of the whole design is the hideaway straps. Hidden safely behind a zippered fabric flap are real and padded backpack straps with a waist harness. Adjustable for torso as well as arm comfort, when needed the straps allow you to carry the backpack for a full day. When not needed – and potentially a detriment like dropping off a pack as checked luggage, the straps can be securely tucked out of the way. This is a pack with well thought out features.
The only debate was the size. Did we get the Waypoint 65 or 85? The 85 was larger and could carry more. However, there was a chance the 65 would not have to be checked at airports. For Raven, the choice was easy. Less room meant less crap which equals less weight. I always want to add that one more item. But he is right. Less stuff means less weight. We went for the 65s.
The trial run was the cruise and Puerto Rico.
The first – and ONLY – disappointment came at the airport. There was no way in our current modern era that the 65 was anything CLOSE to fitting as carry-on luggage. Maybe years ago or maybe in a non-US airline would we be allowed to walk on a plane carrying the Waypoints, but not from Boston to Puerto Rico. We had packed for that potential. So while waiting to check in at the airline, we unzipped the daypacks for the flights and made sure any fluids were in quart bags. Then we stowed the carry straps and wished our bags a bon voyage.
It was wonderful zipping daypack to backpack, un-stowing the straps, hoisting the backpack, and walking out of the airport in San Juan with hands free. While on the cruise, I found I had plenty of clothes. Yes, we did do laundry in the sink in true hard-core traveler fashion, but we also didn’t have to wear the same clothes or shoes every day. On island, Raven and I alternated carrying a daypack and the new-hyrdopack I’d gotten for Yule (I should have guessed it was blue for a reason!). We always had more than enough room for day supplies between the two.
Truly, I cannot think of many negative comments about the Waypoint 65. It isn’t the most comfortable, long term backpack I have ever put on. I don’t think I’d hike the AT with it as a first choice, but I also think it would work if needed (there aren’t that many places to strap outside gear onto if you needed to carry a bedroll or tent, so you’d have to get inventive). But it does work! For a functional travel backpack, transitioning from luggage to backpack, it is lovely. I think my biggest complaint is that once the daypack is attached, there is no way to access its main compartment but by un-attaching it. Slightly frustrating if you realize you left your passport in its depths, but also a good feature to know the person behind you in line isn’t trying to riffle through your stuff!
To me, the coup d’etat for owning the Waypoint came as the cruise ended. As we waited to disembark, an announcement came over the loudspeaker: Any passenger with all luggage could leave now, otherwise you had to wait your turn. Our turn was over an hour away.
Raven and I looked at each other, gave my mom a hug while promising to meet on dock, shouldered our backpacks, and walked off the ship. This is a really good travel backpack.
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