The Viral Undereye Masks I Always Pack For Jamaica, Plus 9 Other Items to Bring

Sonos Roam 2 Portable Speaker ($179)

I bring a portable speaker with me on every trip. Being able to listen to music and podcasts while I'm in my hotel room or at the beach is something I cannot do without. This little Sonos speaker has traveled with me across the U.S., Asia, the Caribbean, and Europe. It's super lightweight, has fabulous sound, and fits very easily in my luggage.