Amanda Pressner: When I decided to go solo, I was already traveling, so no one found it that weird. I was in Australia, so in fact, people were like, "Way to go! Great decision!" It was only after I returned, and realized how many other travelers there were who traveled solo (especially as women) did I realize it was far more unusual to stay in a group of three for a full year. Note the number of blogs written by three women...not many!
What is the best way to meet new people on the road?
Christine Maxfield: Staying at a hostel or bed-and-breakfast is a great way to meet other travelers, since the proprietors tend to organize group outings for guests to local hotspots or restaurants that they might not know about otherwise (or feel comfortable visiting on their own). At the very least, the property should have a community board where you can post your contact info to meet up with other guests and check out the surrounding sites together. Whenever I want to get to know a culture better and make local friends quickly, I join a work-exchange program like WWOOF.org, HelpX.net, or WorkAway.info. Work exchange is a little different than volunteering because you barter your time for food and lodging with a host rather than spending money for the opportunity. I've learned the most interesting jobs that way, from black-pearl diving to working at a sea-turtle hatchery, and it only cost me my hard work! It was a very fulfilling way to travel, and I also made lifelong friends with my hosts so I was never lonely.
Beth Whitman:Global Freeloadersand Couchsurfing are great ways to meet people who live in the destination you're visiting. You don't even have to stay with them. Many people are available for coffee or to just show a person around their town—this is such a great way to connect with the locals!
Julia Dimon: I like to stay in hostels, B&Bs, and with friends of friends. If there's a way to stay with the local people (ie. Couchsurfing, renting a room with roommates, or doing a house swap) you'll often feel more connected to the local culture than staying in a hotel chain. Being friendly, smiling, and striking up a conversation in whatever scenario you find yourself in is the best way to meet new people. Asking for locals' recommendations on where to eat and visit can also spark a new friendship. Joining a group tour or day activity (say white-water rafting, wine tasting, or bike touring) is a great way to meet other travelers. Shared experience is a great way to bond with your fellow travelers.
Amanda Pressner: You can do it the digital way—using your blog and social media connections to find others around you—or you can do it the old fashioned way...just getting out there and seeing the world. There are a few ways to make breaking the ice a little easier though. Asking someone to take your photo is a time-tested conversation starter (and healthier than bumming a cigarette in the hostel bar!). Sign up for a cool tour or a volunteer opportunity while you're traveling so you're thrown in with other locals and travelers and have something to talk about. Take public transportation (overnight trains are awesome for meeting other people, since you're often grouped together in shared cars). If you're intimidated about saying hello, just remember that this isn't high school, and you're not the only new kid—this is traveling, and everyone is the "new kid!" Be friendly...people will be friendly back!
What can solo travelers do to NOT attract the wrong kind of attention in a new place?
Christine Maxfield: When women travel alone, they automatically draw some attention to themselves, but keep in mind that you can get catcalls in your own country as well. The key is to dress modestly, never go out alone at night until you learn the rules of the area, and never get drunk or visit the beach by yourself. If you're traveling in a very conservative region like the Middle East or in a Muslim country, cover your arms and legs, wear sneakers or closed-toe shoes, and wear hair on top of your head (loose hair is considered rude!).
Beth Whitman: Women can often be seen as an easy target. It's therefore very important to be vigilant whenever we're on our own. We need to protect our personal items and also be aware of not putting ourselves in situations that could get dangerous (taking a taxi by ourselves, for example). Assuming this is more geared toward women, the best thing a solo traveler can do to not attract attention is to avoid conversations with single men and not put themselves in situations where this might happen. One thing a woman might do is join a group of people walking down a street if she thinks someone might be following her.
With most travel deals based on double occupancy, the total price is often higher than what is advertised for single patrons. Here's how to avoid the extra charge.
Check out options from tour companies like G Adventures and Intrepid Travel that allow you to pair up with a same-sex roommate during your trip as a way to get around the pesky single supplement. Grand Circle Travel offers the same service for travelers ages 50 and up while Contiki offers a similar plan for 18-35 year olds.
While you'd normally have to worry about paying double (since cruise cabins are almost always based on double occupancy), Norwegian Cruise Lineshas another, more affordable option. On the Pride of America ship (based in Hawaii), Norwegian Epic, Norwegian Breakaway, and the soon-to-be-christened Norwegian Gateway (coming in February 2014), you'll get your own room and the chance to mingle with fellow solo cruisers in the Studio Lounge, all for less than the cost of your usual solo cruise ticket. From $1,099 per cabin; check NCL.com for pricing details based on your actual cruise dates.
As seen on TV! We've followed Don Draper for seven seasons as he's crisscrossed the globe, be it via Cadillac or TWA flight. As the final episodes air, we're taking you back to the Golden Age of travel with a 'Mad Men'-inspired vacation guide for retro-style trips to cities Don visited.