Site icon Magpie by Jen Shoop

How Do You Plan a Great Vacation?

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A few weeks ago, one of my girlfriends described our Magpie community as “strategic.” She was so right — I am constantly delighted and informed by the thoughtful ways you approach everything, from meal planning to skincare while traveling. I routinely pick up tiny, well-considered insights in the comments section. (Just this morning, I pulled up a Magpie comment from a few weeks ago with recommendations on where to eat in Charlottesville, VA! Thank you Hayden!) We’re just returning from a quick overnight trip there (we stayed at Keswick Hall, seen above), and the visit spurred lengthy conversations on the subject of travel and travel preferences, as we find ourselves with more time and inclination to get away, just the two of us, or as a family. (I found traveling with two young children over-intimidating, and we largely avoided it, for better or worse, for the past few years. Yet another reminder that the only constant is change.) Knowing how strategic and informed Magpies are on the subject of travel (fascinating Magpie tips on better travel days here), I wanted to toss out some nosy questions on how you approach and plan travel for leisure:

01. How do you decide where to visit? Do you keep a spreadsheet of ideas? Is it driven by ticket prices, or seasonality? By recommendations of friends or trusted travel resources? (And what are those resources?)

02. Are you more likely to spend on accommodations or destination/attractions? Why?

03. What are you more likely to splurge on: a convenient travel time, upgraded airplane seats, or upgraded accommodations? Why?

04. How do you select a hotel? Are you committed to one loyalty program / hotel group? Do you have a chain that you tend to prefer? What resources do you use to learn about and vet a hotel? Are there categories of accommodation that you routinely avoid (e.g., bed and breakfasts / AirBnBs / chains), and why?

05. How do you plan an itinerary? A girlfriend of mine recently said that Facebook Groups are a gold mine for this kind of information. Mr. Magpie and I tend to lean on Reddit. But how else do you plan what to do in a given destination?

06. How do you balance structured/planned activities with downtime for R&R?

07. What is the ideal length of trip? (This is probably going to be different if traveling with young children, no children, etc?)

08. Any other guiding principles for planning a great vacation?

09. Is there anywhere you have visited in the past year or two that you found truly exceptional? I’d love to compile a list of “Magpie approved” destinations / hotels / resorts, especially if you can include a quick note, e.g., “Great for family,” “The most romantic place you’ll ever visit,” etc.

10. Where are you traveling next?

I should mention that my perspectives on all of these questions are half-formed at best and am looking forward to being taken to school in your responses. The only element that I have found myself consistently drawn to and happy with: splurging on an exceptional hotel. I find that the amenities, finely appointed rooms, gracious common areas, and typically exceptional service frequently “make” a trip for me and play the largest role in the feeling of getting away and being cared-for.

I also wanted to mention that I recently discovered the travel Substack Yolo Intel and have been obsessing over its posts! I’ve only read a few posts but know I will be mining it for intel!

Please share your thoughts!

Post-Scripts.

+On the magic and mayhem of traveling with young children. I think about the comments on this post a lot. One of you made the point that traveling as a family unit (without extra friends, families, etc) makes a world of difference when your children are young, as you aren’t balancing the needs and routines and moods of your children with those of others. You can eat dinner at 5 without apology, call an audible and quit mini-golf early, stay an extra hour at the pool, etc. We’ve since traveled just as our immediate family and it really does make an enormous difference — feels much easier!

+ Notes on a recent successful family trip to Deep Creek Lake and a fabulous trip with just Mr. Magpie to Napa Valley.

+The saltings of motherhood.

+One thing I love about traveling with just Mr. Magpie: it brings me back to “the befores.” Laying in a hotel bed with no definitive endpoint, no place to be, no drop off to get to, feels like such a delicious luxury at this phase of my life. Of course, we’re always ready to get back to the babies, but it is a really wonderful break, with the tap fully off.

Let’s Go Shopping.

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+I wore these $60 mules all weekend long — they were the only shoes I packed for Charlottesville despite three very different outfits (one for wine tasting, one for dinner and a concert, one for wandering around Grounds), and they suited every moment! They look much more expensive than their $60 price tag suggests!

+Another quiet luxury find: this Soldout.NYC “everything shirt.” OMG. The quality is insane — the fabric/material is unlike anything I’ve ever touched, with a silky satiny finish. The top runs oversized/boxy — you can size down, if you can snag one in your size! (Selling fast!)

+Run — my favorite Vitamin C product has finally been restocked. I ordered so fast!

+Have we talked about Glamsquad recently? I know I yapped about them last fall after a string of great experiences, but I find it so convenient to have a blowout at home, and not *that* much more expensive than going to a DryBar (especially if you factor in parking / the time you spend in transit / etc) — plus I find the quality more consistent. I think it ends up being around $80 for an at-home blowout (including tip) versus $70ish at a Drybar. (PS, do you remember when it used to cost $35 to get one?!). I’d happily pay an extra $10 to have it done in my home. Anyway, I’m thrilled because Glamsquad is offering us a discount code: $20 off for new users with code JenniferS and $15 for returning users with code JenniferS15. I will absolutely be using this code myself, as it makes the blowout that much more reasonable. Treat yourself the next time you’re heading out for dinner, have a big meeting, etc. I think it was Mally Goldman who said that (paraphrasing) a good blowout makes your outfit look better. I couldn’t agree more — when my hair is done, I feel like a different woman.

+Speaking of beauty: Emese Gormley has been raving about this splurgey bronzer and I’m totally bought in. I am nearly done with my most recent order of Guerlain’s Terracotta powder (which I have used and loved for probably a decade now) and think I’ll test this one next.

+Recently spotted this cropped trench on the ever chic Lilly Sisto and think I need it!!! I had my eyes on this lace-inset trench style coat from VB but I don’t know…now I might need the Rails one instead.

+I think I need these for the Easter table.

+These little skirt and top sets from Julia Amory are adorable. Like vintage Lilly!

+I received a handful of questions about my hair strengthening routine over on Instagram. I have been using Mielle’s rosemary oil and Anablue’s treatment oil (15% off with code JEN15) every few days — basically if I’m going to exercise or know I plan to take a shower early in the day, I’ll wake up and apply a dropper full of each to my scalp, then massage into my hair and apply a tiny bit to the ends, too. This is heavy duty oil and you are really not in any shape to be interfacing with the public while wearing it — ha! — so I will then tie my hair back and put on a baseball cap for my run. Then I get home and shower it all out. I think this has been really helpful as I try to grow my hair out. I was also using Vegamour’s shampoo and conditioner but the scent was not for me, so I’ve been skipping. (BTW, Katie at Beach Reads and Bubbly recently shared these genius terry cloth scrunchies for use while applying a hair mask or hair oils. Really holds hair in place, and won’t stain like my satin scrunchies do. Ordered them immediately.)

+Have heard such good things about these “Find It” capsules for young children — such a clever activity! I have this earmarked as a gift for car travel or maybe just for my son’s fifth birthday.

+We’re all in an indigo mood right now — so many Magpies have bought my Gabriella dress (see me in it here), and these flared “Mer” jeans have also been majorly trending. I have codes for both: 20% off the dress with JEN-20 and 10% off the jeans with MAGPIE10. (Codes also work sitewide.). More great denim finds here.

+Finally, on the denim point: I wore this little denim jacket over this slip dress to go to a concert and it was PERFECT. The unfinished hem dressed things down but has a great, snug, stretchy fit that made me feel still pulled together. I also love this iconic denim jacket from La Ligne!

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