Connecting more than one Bluetooth speaker or headphone depends largely on the device you have and the native Bluetooth version supported on your phone. For example, Bluetooth v4.2 supports only one-on-one device connections up to 30 meters. Bluetooth v5, on the other hand, extends the connection up to 120 meters and lets you connect two devices at once. Some speakers from Bose have their own audio apps that provide the functionality to pair two speakers together. However, not all companies provide this facility.
How to connect two Bluetooth headphones and speakers to one phone
Most phones today feature dual audio (on Android) and audio sharing (on iPhone), meaning the ability to play audio from two devices at the same time. iPhone 8 Models and above support audio sharing, so unless you have a very old handset, chances are your phone natively offers it for you. Then the first step would be to try connecting them one by one when you first connect your headphones and speaker to your bluetooth.
Similarly, if you have Samsung Galaxy S8 series or later, the company basically offers a dual audio option that allows the user to pair multiple speakers and headphones. This can be found in the bluetooth settings. Other users can try this method, provided they have the proper devices:
Android users will have to go to the Bluetooth settings and pair the Bluetooth headphones or speakers one by one.
Once connected, tap on the three-dot icon on the right and click on Advanced Settings. Toggle on the ‘dual audio’ option if it is not already turned on. It enables the user to connect to two devices simultaneously.
For users running Android 10 and above, they can access their connected Bluetooth devices by clicking on Media in the Quick Panel and selecting both paired devices for audio output.
iPhone users will have to go to the Control Center. Tap the Airplay icon and select Paired Wireless Headphones or Speakers to output audio simultaneously. Deselecting either of the headphones or speakers will stop audio sharing on that particular device.