Surprising Your Significant Other With A Trip

<div class='at-above-post addthis_default_style addthis_toolbox at-wordpress-hide' data-title='Surprising Your Significant Other With A Trip' data-url=''></div><div class='at-above-post-recommended addthis_default_style addthis_toolbox at-wordpress-hide'></div>How to pull off gifting a getaway.<div class='at-below-post addthis_default_style addthis_toolbox at-wordpress-hide' data-title='Surprising Your Significant Other With A Trip' data-url=''></div><div class='at-below-post-recommended addthis_default_style addthis_toolbox at-wordpress-hide'></div>

Ask A Woman: “We’re leaving on a jet plane…where should we go?”

You're hovering a bit there bucko.

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I know how fond you are of gifting experiences rather than just stuff, and since I’m involved with a wonderful woman, I thought heading somewhere nice for the new year (perhaps warm?) would be a perfect gift for the two of us. I recently got a new job and I’m making pretty good money, but I’m no millionaire. As part of the present I would give her a nice travel bag. I’ll put the tickets for our getaway inside her bag and give that to her on Christmas.

But there are a lot of questions that come along with this strategy. Where should we go? Do you have any suggestions? And how do I pull this off while still maintaining the element of surprise? I don’t want to complicate her after-holiday work schedule, or take her out of town when she needs to be in town. Also, I could use a hand with some affordable, but still nice bag suggestions.

Best regards,



Hi Mario,

Wow, what a generous and kind gesture–I think taking your lady on a trip (and getting her a travel bag) is a wonderful idea. And I certainly have my work cut out for me on this question so let’s get started.

Where should you go? That depends on where you are now. If you’re writing from Miami, you probably don’t need to take her to the beach, right? If you’re writing from a rural, sparsely populated area, you probably don’t want to take her to the countryside, right? Take her somewhere different from where the two of you live, so that it feels like a getaway. Also, it depends on how long you want to be away. If you’re going for a week, a sleepy little B&B town is probably not going to provide enough activities to keep you occupied for that long. But for a three-day weekend, it’s perfect.

As for my suggestions…if you want warm, you could always go to a resort–Mexico, Jamaica, the usual suspects, depending on your budget. You probably don’t need my help with those destinations since they’re well-known and easy to book (work with a travel agent if you have specific requirements in mind–they’ve actually checked out all these places so they can give you the inside scoop). For a slightly out of the box destination, La Jolla, California (or any of the small coastal towns in southern California) is a great option. Sleepier and calmer than the party-environment of a beach resort, you can’t beat the natural beauty, restorative atmosphere, and good simple food (bonus if you’re a runner, walker or bike rider–there are tons of trails and paths) of southern California. If you’re open to, um, colder destinations, New York City is a favorite. You can go for a long weekend, or for a whole week. You can do touristy, big-landmark things, or you can walk the streets and discover little cafes and boutiques and bars. Plus, if you go in January, the Christmas decorations will probably still be up. There are so many other options (Southern charm in Savannah! Skiing in Aspen!), depending on your interests.

How do you pull this off? I’ve often wondered how people pull off surprise trips–there are a lot of moving parts. If you want it to be a total surprise, and have it all planned and booked by the time you give it to her as a gift, you might have to get in contact with her boss, to explain what you want to do, and see when would be the best possible time for her to take time off (and then reserve that time for her, through her boss… which might be a little strange). Also, think about other responsibilities she might have that you’d have to account for–if she has a pet, you’ll need to arrange for pet care while she’s gone, etc.

If it’s not possible to book the trip without her knowledge, why not just put a photo of the destination in her travel bag (a view of the beach, Fisherman’s Wharf, a scene of Times Square)? It will still be a big surprise, and then you two can figure out the dates you’ll go together. You’ll probably have to put it off until later (February or even March), but I’m sure she won’t mind. A third option is to tell her ahead of time (now) that her gift is a fabulous trip, which she’ll know nothing about until you exchange Christmas gifts, and then ask what would be the best dates for her to go so that you can book it. She’ll still be thrilled, and she’ll have the next month to look forward to finding out where she’s going.

And now for the the travel bag. I assume you mean a weekender bag, or carry-on bag, not a suitcase, right? Here are some choices:


For a gal with eclectic taste (someone who wears lots of bright colors, bold patterns, etc) the Vera Bradley Weekender – $98 at top left is a nice choice. VB is a much-loved brand; they’re known for their crazy designs and high quality. Available in other patterns. At bottom left is the Everlane Weekender – $95. This would be a good fit for a woman with simple tastes. It’s attractive but functional, very sturdy, with lots of room. Available in other colors. At right we have the Steven BCaprii Leather Tote – $119.94. For a leather bag of this size, this is an exceptional price. Nice and roomy with a couple pockets inside; this bag could also double as a large handbag. One downer is that this bag doesn’t zipper close, it snaps close, so it’s not as secure. This bag has a classic, elegant styling, so it’d fit a lady with the same taste. More options: check out Stella & Dot‘s array of large bags–reasonable prices and on-trend patterns. LeSportSac is another brand with eclectic pattern options; their bags are made out of highly durable nylon. I’ve had one for a decade and it shows no signs of quitting.

So there you have it, Mario. Guys reading, time to share–what are you favorite January vacation spots? Have you ever pulled off a surprise trip for your other half? How did you do it? Mario, listen up, the men are speaking.


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