Imagine being unfettered and being able to do what you want to do, when you want to do it. Retirement provides the opportunity for travel. Don't be intimidated by traveling alone. Lots of people just like you do it all the time. In fact, seniors traveling alone will often find a community of other travelers doing exactly the same thing they are doing.
Here are some tips on traveling alone for retirees:
Plan: There are lots of questions to anwser. How long is the trip? Where do you want to go? Budget, luxury, or in-between? When to travel is another question - peak, off-season, or shoulder season? The Professor suggests on planning an itinerary using a major city (or cities) as a base and taking day trips, if possible from there. For instance, Madrid is an excellent base for taking day trips to Toledo and Segovia. Padua is an excellent base for day trips to Venice, Verona, and Vicenza. A good way to research and preview destinations is to watch YouTube videos on traveling to a particular destination.
Lodging: If you ask The Professor, his days of staying in hostels are over. AirBnB sounds good, but how would you meet other travelers or ask anyone about restaurants, shops, or transportation? There are no desk clerks at an AirBnB. That's why a hotel is recommended. Stay in the center of the city in a hotel with the amenities you want.
Pack Light: The sign of a good traveler is one who is flexible with plans and makes it easy on themselves to get around. Big and bulky luggage does not promote that kind of travel where air, rail, ferries or vans are involved. See The Professor's packing tips.
Don't Eat Alone: As much as The Professor loved traveling solo, he preferred to eat with other travelers. Some restaurants, especially in places like Germany, have community tables. Food halls like those in Lisbon, Reykjavik, Florence, and Oslo enable socialization. Fairs and events give the opportunity to meet, eat and mingle with others. River cruises with buffet meals or food tours offer good opportunies. We particularly love the food tours in Spain. Think about attending church services while traveling - some have receptions afterwards where connections can be made and meals or meetups can be planned. Also, group meals are preferred rather than dining with indivdual connections, for safety and other reasons.
Safety: Most European cities are safe during the day. Use common sense. Stay where crowds are and don't go to isolated areas. Tell someone at home what your itinerary will be. Carry a good travel insurance policy.
Pick a Group Tour: Going on a group tour isn't exactly traveling solo, but group tours provides instant traveling companions. However, in general, never travel with a group with a size of more than 20 people. Probably 8-12 people is optimal. The exception would be if taking a cruise, which is a great way to travel alone, but surrounded by lots of people.
Do the "Free" Walking Tour: Just about every city has some sort of "free" walking tour. In Madrid, Copenhagen, Florence, and many other cities they all meet in the town square. Just pick and choose the one that is most appealing. It's the best way to get to know a destination and to connect with senior travelers just like you. Other cities like London, have great small group walking tours for a small fee. See walks.com for instance.