Contemplating First Solo Trip

I can only say 'don't worry about going solo - just do it and enjoy'! I do several solo Disney World trips a year - I do a few trips with friends or family, but the combination of the fact that none of them would want to go as often as I do, and the fact that I have so much more of a relaxed and enjoyable time when I go solo where I can wake when I want, go where I want, eat when I want, ride or don't ride whatever I want, and head back when I want. It's great to go with family or friends too - but different - usually it's about them or their schedule because they all know I'm a 'regular' and go so often.

I'm a middle-aged man, so can't comment on how solo women would feel, but have a hard time imagining anyplace that would feel safer than on Disney property, staying at a Disney resort, and using Disney transportation to get around. I encounter dozens of solo travelers when I go there, both male and female, and never heard anyone mention any fears or worries.

I mix the dining based on what I feel like, but often do table service...no qualms about getting a table for 1 - if I want the food, I enjoy the atmosphere, and find it amazingly easy to start up conversations with others at nearby tables if one desires. Cast members are also very friendly with solo diners, and seem to do a better than average job keeping an eye on drink refills and such.

Disney World has so many people from all over the country and the world, and everything from solo travelers to groups of 20 - I have never felt lonely there when traveling solo - people are naturally chatty and friendly so if you want to talk with someone it's easy - and if you are enjoying the alone time and don't want to, that's easy too. There are times I'm very happy to have alone time wandering the parks or sitting for a quick drink or meal and simply engross myself in reading something, checking out my phone, reviewing my photos, etc in a way that makes it clear I'm not looking to chat up anyone, but not in an unfriendly way. Other times, just by sitting at a bar, or in a line, or on a bench with my eyes up and looking open, more often than not others will engage me first and we'll chat about where we're from, the trip, the weather, rides, how to get around, or whatever strikes up. Amazingly I rarely have to start the conversations.

To the poster that asked about staying at Caribbean - I think you'll be fine...as really with any resort. It's a big place, but the 'hub' is easily accessible from any section, and is a nice spot to congregate if you are feeling like you want to be around people. The bar there is great - open but covered, music, party atmosphere, very beachy-islandy vibe - and usually quite friendly to chat up others. That's kind of the key at any of the resorts - plenty of grounds to spend your own time, but the pool bars and main building bars are usually great spots to be around others and talk.

For cruising - I haven't done a Disney cruise, but have cruised many times - some solo, others with family or friends. Regardless, I choose tables for 6-8 whether I'm solo or with people. I find it's generally easy to get seated with decent people - the cruises do a reasonable job of finding similar aged folk...and even when they don't, I have only had maybe 1-2 tables ever out of 30+ cruises where there was a poor match at a table - in those situations, it was usually one person or one couple that was not really a match for the rest - so the other folks would just get along and either try to include them to open them up, or they'd end up requesting to move tables within the first day or so. Most of the time, I've left cruises with e-mails and contacts from other table mates that got along great - some we lightly kept in touch a few times after, others faded away - and still others have remained friends to this day. I've got 3 cruise friends that will still come and visit and stay at my house, plan trips to Disney, etc despite living in other states and even other countries, going on 20 years since we met.

I'm going to be at Disney World the 2nd week of June, this time with a friend - which will be nice and we'll do mostly whatever she wants to do because she doesn't go as often - in September, I'll be there again, but likely solo, then another trip in December where I'm traveling solo but meeting up with a large group for an annual meet-up photography event. I was last there in February, so you can see I like to mix it up and definitely like to include some solo trips whenever possible each year.
 

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