So unless you're a Count, or Oprah, this is an idea that you might use only for a special occasion, or after you have come into a bit of extra cash - a tax refund, a bonus, a jewel heist, etc.
The idea is to give someone the gift of a surprise trip. I have done this twice; once with a close friend, and another time for my current boyfriend. You can either make it a complete surprise, if you're positive the person will be available, or you can let them know about the "mystery trip" and make sure they keep the dates clear, but not reveal the details.
The first time I did this was for my friend Roxann. I took her to New York. Neither of us had ever been, and she didn't know for sure where we were going until we got to the airport and printed out our boarding passes. Part of the reason I chose New York was that Paul McCartney was playing at Madison Square Garden that weekend.
Something funny happened as soon as we arrived in the city. I had planned the trip partially based on the McCartney concert, which my friend had no idea was going on. When we exited the subway, literally the first thing we saw was an enormous billboard advertising the concert. It was literally festooned across an entire side of a high rise building, just outside the subway exit. I thought my friend would notice and the jig would be up, but she made no mention of it.
I printed out the itinerary I had come up with (Statue of Liberty boat cruise, lunch at Tavern on the Green, MSG concert, getting on the list at a hot club, etc) and covered the destinations with post-it flags. A few hours before each event, I would have my friend pull off one of the flags and reveal our next destination. It was a fun game and a memorable trip.
Here we are on a windy and hot boat cruise that ended with Roxy looking wistful in front of the statue.
The smallest person to ever visit Times Square...
A couple of years later, I decided to do a similar thing for Kyle. We had been dating for about a year and I wanted to take him somewhere special for a weekend. He had never been to New York, so once again I used that as my mystery trip destination (what can I say? It's a cheap, short flight, and there's lots to do there!). I took him to different places (a Broadway show, an expensive French restaurant, a Brooklyn bar for beer enthusiasts) and once again employed the post-it flag trick for our itinerary. We had a grand time!
For some reason, Kyle decided to act like a real New Yorker and look furious in every picture.
On the way to a fancy restaurant and feeling either melancholy or resentful about it.... but still catching a great lean against that wall.
Tips - Make sure the person you want to take on a trip is available and doesn't mind traveling. Make it a short weekend trip - 3 days is ideal. Plan the itinerary around your travel companion's interests, and have a "surprise" for every day. It doesn't have to be expensive - museums are cheap and sometimes free, and so are landmarks. Sometimes the simplest things can be the most memorable - eating a messy and delicious meatball sandwich at a street corner NYC deli, discussing controversial art at a famous museum, having a frosty beverage at a place with a view. There is something truly rewarding about planning the perfect trip for someone else and seeing the look on their face as they discover what you have organized. I highly recommend it, if that jewel heist goes off without a hitch. Good luck!