Trail, picnic blanket, back porch, long loop around the lake: the soundtrack should come along, and it shouldn’t drown out the birds or the bike bell behind you.
Bose SoundLink Flex

The one to throw in the beach bag without a second thought. It’s rated IP67, which means waterproof and dustproof, so sand, splashes and a surprise drizzle aren’t a crisis. Battery life runs up to twelve hours, enough for a whole day outside.
The sound is the bigger surprise for something this packable. One listener describes deep, punchy bass, clear mids and crisp highs, and especially likes that the speaker tunes its sound to how it’s positioned: standing up, lying flat or hanging from its utility loop. Hang it from a branch at the campsite and it adjusts on its own.
Best for: beach days, backyard hangs and campsites.
JBL Clip

See that loop on top? It’s a built-in clip, so the speaker hooks onto a backpack strap, belt loop or stroller handle and rides along hands-free. It’s tiny, but it still delivers the full, rich sound JBL is known for. Pick from a bunch of colors, from the soft pink here to more trail-friendly shades.
Best for: hikes and walks where you want music at your hip, not in your ears.
Bose SoundLink Micro

Bikers, take note. The Micro has a tear-resistant strap on the back that wraps around handlebars, chair frames and backpack straps, so it stays put even when you’re moving. It’s easy to pack and gives bold sound with around six hours of play on a charge, which covers a long ride with a coffee stop in the middle.
JBL Go

The smallest speaker of the bunch and maybe the easiest to love. It fits in a jacket pocket, comes in a range of bright colors (red, blue, black and more) and is water- and dustproof, so a damp picnic blanket is no problem. Expect up to five hours of playtime per charge and stronger sound than its size suggests. A good pick for kids, or for a second speaker on the other side of the yard.
Open-Ear Sport Headphones

Sometimes you want music that only you can hear, without sealing yourself off from traffic and trail chatter. These open-ear buds rest outside the ear canal on a hook, so the world stays audible while your playlist keeps going. They are waterproof, built with sports in mind, and even come with a smart digital display.
They also pull double duty for calls. One reviewer says callers hear him perfectly and that the mic is clear enough for work calls, handy if your walking meeting really is a walking meeting.
Best for: solo runs, commutes on foot and busy park paths.
Bluetooth Beanie

For when the season turns crisp. This knit beanie has Bluetooth headphones tucked inside, so it keeps your ears warm and plays music in one go, with no earbuds to fumble with under a hat. Runners who don’t stop for cold weather will get the most out of it, but it works just as well for dog walks on frosty mornings. There are plenty of colors to choose from.
Charge everything the night before, pack a snack, and go find a good spot in the sun.