Same destination, different departure cities?

February 2, 2006 6:50 PM

Two people travelling from two different departure cities on the cheap.

My husband is in San Francisco and I'm in Toronto, Canada; I'm waiting for my visa and it isn't easy for me to go down there to visit him. So instead we'd like to go on a vacation together. We'd preferably rather spend less money than more, so a package of some sort with air+hotel would be great; we'd love to go somewhere interesting in Canada or to Europe (the Caribbean would be okay also). I'm having no luck, however, finding deals that have departures from both the Bay Area and Canada; are there any particular websites that would be useful? Alternatively, have you ever done this type of trip before, and where did you book, and how did you arrange the meeting-up? Talking to a travel agent is my plan for tomorrow, but I'd love some ideas first.

posted by livii to Travel & Transportation (7 answers total)

I'd suggest looking at getting a package for one person that will allow you to add a second person just to the hotel portion. Then simply find a cheap flight for the other person to the destination. Something like Travelocity's Last Minute Deals (though you may not want last minute) would probably allow for this. The per person price is higher for one than two, to cover the single person in the hotel room, but that won't matter if you're ultimately sharing the room anyway.

Consider also cruises, if they're within your budget, as they do this sort of thing all the time, and you simply meet up on the ship once you both arrive.
posted by jacquilynne at 7:08 PM on February 2, 2006

Best answer: I've had a hell of a time finding cheap flights to Europe lately, so I'm thinking your best options are Canada, the Carribbean (or maybe Mexico or Costa Rica).

A big portion of the cost depends on how long you're staying (days? weeks? months?). Someplace like Costa Rica is going to be more expensive to get to (probably) but is a fairly inexpensive destination once you're there.

My current favorite flight website is Kayak, though I'm sure other people will list other aggregators as well.

I've done this sort of trip many times, and would make a few recommendations:
-Have one person book everything, all at once.
-Pick a destination with plenty of carrier service.
-Don't fly out on the last flights of the day, if at all avoidable.
-Have fun!
posted by I Love Tacos at 7:38 PM on February 2, 2006

Oh, and as long as your destination isn't an all-inclusive resort^*, it's absolutely no problem to book a package for one, and then add the second person at the front desk.

Some places want a little extra money/night for that, but it's usually been free, and it's never been outrageous.

^* It might work at all-inclusives too, but I've never tried it at one, so don't want to state that their pricing would be fair.
posted by I Love Tacos at 7:41 PM on February 2, 2006

Best answer: Site59.com has a two departure cities, one destination search. Toronto and SF are both on the list of possible departure cities.
posted by xueexueg at 6:57 AM on February 3, 2006 [1 favorite]

Response by poster: Thanks for the answers; in particular Site59.com is very useful.

If anyone's still reading the next day, I should have clarified that we are looking last-minute (we'd like to go within the next two weeks) and it will only be for one week. Also, cruises would make it easier but I can't leave from a U.S. port of call.

Thanks again!
posted by livii at 8:14 AM on February 3, 2006

I'd also endorse Site59.com, which works exactly the way it should, though it does have a pretty crappy and limited selection of Departure Cities -- some of the biggest ones in North America, not to mention Europe, are annoyingly missing.

Still, if your cities are covered, it's hard to beat the convenience of three-way booking. I wish all the travel search sites did that. How on earth does anyone book a reunion, family event, business meet-up or get-together using those one-source, one-destination searches?
posted by j-dub at 3:03 PM on March 22, 2006

It should also be noted, I suppose, that old-fashioned travel agents (yes, they still exist) work for free. Call seven of them with your requirements and wait to see if anyone finds a good deal.
posted by j-dub at 3:04 PM on March 22, 2006