Tips, Please.

One time in high school,
my friends and I were bored on a Friday night.

We didn't really have anything better to do,
so I, the ever-ready opportunist, suggested an activity:
We could stand on the street corner with signs
and ask people for money.

Not that we really needed money, 
as our 16 year-old suburban needs were met
quite well by our parents.

But it was more of an experiment to see if we could get people to give us money.

So we held up signs and asked people 
to pay for our prom dresses.

Our friends came and sat on the grassy hill by the intersection
and watched the spectacle. 

It was a party.

We made over $100 in 45 minutes
until the police made us leave
because they didn't think it was safe.

{Editor's Note: My 28 year-old self would scoff at them and keep hustling.}

My friends' parents were appalled and made them donate their money to charity.

My parents had never been so proud of me.

Eh, to each their own.

Anyway, getting stuff for free is great.

I like getting it when I can.
I like giving it to others when I can.

This summer, I have been replying to travel emails
like it was my job.

Manhattan, NY

{The street corner gig paid better, btw.}

I really do love getting to help people plan their vacations
and maximize their special trip.

Civita Di Bagnoregio, Italy

But after everyone has come back home
and is reveling in the post-vacation glow,
I'm left to wonder:

Did you like any of my advice?
If you don't mind, I'd love to hear any travel tips
that you have used from my site
and hear what you thought.


Was it as awesome as I promised?
What did you love that you wouldn't have tried otherwise?

London, UK

Or was there a problem that I should know?

Vernazza, Cinque Terre

I don't want to recommend bum advice,
so help a sister out!

*all images original to Aspiring Kennedy


  1. i just laughed OUT LOUD at the hustling part of this post..and your parents being proud. my parents would of definitely been the ones in the proud group is i managed to get 100 bucks off of people for not doing anything but standing on a street corner..

    that came out wrong.

  2. Ha! Good idea...maybe I should try that? :)
    When I was little, a Friend & I thought we could trick passing cars into thinking we were statues. I'm SURE it worked.
    Eat Cake

  3. So you're the reason I don't give money to people...partially kidding, partially serious. LOL. And If I ever have time to travel (writing that makes me want to slam my head into my desk) I will surely email you for tips and then let you know what we thought!

  4. My parents definitely would have made me give the money back. But they would have laughed their asses off first. I particularly love the cops telling you to leave because it wasn't safe - I wonder what they thought of you two?

    Sadly, my travels have been limited and so I haven't had a chance to use any of your advice. But, for what it's worth, I'm living vicariously through you every time you go somewhere new!

  5. As your former high school French teacher, I have to say that A) I am not one bit surprised that YOU came up with this idea, but B) I am SHOCKED that you convinced your friends to do this. Also, I am laughing my head off at the mental picture.


    Love you tons, sister.


  6. I haven't yet, but that doesn't mean I will! The next time I go abroad, I am definitely searching through all your posts to find what to do.

  7. I know this doesn't answer your question, but that story is amazing and my parents would have done the same thing!

  8. Will let you know next week when I go here:, for homemade profiteroles!

  9. Lauren - You are spot on with your travel posts! I love the way you describe the places you visit and your original photographs. Your recommendations are always insighful (and I have visited many of the same places and agree with you wholeheartedly). Check out my new travel blog ( and see what you think!! Keep up the amazing work!

  10. your story about high school was so creative and fun! i wonder how that would work out for me today...
    i recently gave a list of must-do's to a co-worker of mine visiting miami for the first time. i can't wait to here which ones she tried and which ones she loved. one thing is for sure, it's great to be able to share great finds with others, not only because they can try them, but because it's almost like you're revisiting them each time!

  11. Despite the fact that I've been to Paris before I still followed your advice for things to do - everyone has vastly differing experiences in the same cities - and I paid heed to your tips on visiting the Louvre (I haven't been there for nearly 10 years. Things have moved on a bit...). So, (a little belatedly) thank you! More please!

  12. yes ma'am we love it all and love you for answering our travel questions and taking us along for your adventures :) :) keep on keepin on!!! xoxo jillian:: cornflake dreams

  13. ohmygosh -- i bet every person thinks to email you when they take a trip! we're considering croatia for next spring, and of course I thought, 'I need to email Lauren..I know she's been.' (remember you guest posted about it for me in my old One Way Ticket series. I'm sure you've never given bum advice! You are the perfect blend of traveler...budget savvy, food lover, live like the locals. I hate when people suggest the Ritz...well duh, of course that's a nice choice, but now tell me where I can really stay!!?? wow -- where'd that come from?

    anyway...funny story about your we need a pic of you in said prom dress

    1. this made me laugh out loud... i think the same thing. duh. of course i want to stay in the most expensive place! i think that isn't advice... real advice comes from people finding great places that aren't obvious (and reasonable for the average joe's budget.)

  14. That is easily one of the most awesome stories ever on how to pay for your prom dress. I love it! If you get a sec, I'd love to hear your thoughts on my latest posts!

  15. I definitely use your blog as my own personal travel site. I emailed you earlier about a long trip to Paris, London and Amsterdam, and we havent taken the trip yet (1 month away!) but, I promise to let you know what we think. The hotel suggestions were SPOT.ON. though, so I already appreciate your wonderful blog.

  16. Wow, I just found this blog! It is awesome!

  17. i love these photos! your blog is fabulous!

    xxClassic & Bubbly

  18. just so you know, the prom dress story has always been one of my favorites.

  19. haha that's so great! when i was little, my friend and i went door-to-door singing for quarters. such dorks. i seriously need to catch up on your blog, it's been too long and i have some travels planned in the coming months/year! xoxo

  20. That is so classic. I bet all the "tippers" were of the male variety when they saw a bunch of good looking girls!! xo

  21. You should totally set up a travel business online... an e-service type thing where you schedule out trips for people. Then you could buy a FEW prom dresses ; ) You can thank me later. And cut me in for 10%.

    1. at least 10%, michelle... at least thats what my pimp tells me. :)

  22. I used your directions for Neuschwanstein castle word for word and they were PERFECT. I will also never forget your awesome recommendation for Le Coupe Chou in Paris! Now I hand that rec out all over the place - it was so good! I can't even remember all the times I've taken your travel advice, but I know every time it has been nothing short of amazing - keep it coming!!

    1. awww.... thanks liz! good reinforcement to hear a big traveler like you approves. i'll do my best to keep italy in check, too! xo


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