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Start with a short trip. Research cities or countries that are safe for solo travel. Check out travel touring groups for solo travelers; you might meet a new travel partner. Book tours to be with other people. Although I have no problem dining alone, sometimes I like to go on a food-tasting tour. I have found great food tours on Viator.
I have a whole post about carry-ons, but only my tips for packing a carry-on. My biggest tip is to use sample-size toiletries and roll your clothing into packing cubes.
Sign up for Global Entry. With Global Entry, you will also get a TSA pre-check. Be organized when going through the TSA line. Do not bring liquids larger than 3.4oz. Have your boarding pass ready. Take everything out of your pockets BEFORE you get to the machines. Apple Maps now has a new feature that shows gates and amenities. Another good app is GateGuru.
My favorite travel app is TripIt, which I could not live without. Here is a list of my other favorite travel apps.
I use Google Flights, Trip Advisor, and Pinterest the most when planning a trip. I enjoy research, so I use multiple sources and scour reviews. When I am looking for tours, I use Get Your Guide and Viator.
Skyscanner and Google Flights are the main places that I will look for flights. I set notifications for the flights that I am considering. If your travel dates and or location are flexible, you can use Google Flights to locate when and where to fly the cheapest.
Yes, it would be best to protect your investment. If you plan to travel long, check out Safety Wing for Global Medical Insurance. I use Travelex Insurance most often to protect my trips. Another reputable company is AXA Partners.
I have a whole post HERE for preparing for a long-haul flight.
Contact your cellphone carrier to inquire about the cost of an International plan. Often, this is an expensive option. Buy a SIM or eSIM card for the destination you are traveling to. This is often the most economical option. If you don’t want to use a SIM card, put your cellphone into airplane mode and only use it to connect to Wi-Fi. To find the best eSIM or SIM card, check out Airalo.