Where to next?
With a toddler, the trip lives or dies on details: cribs that actually work for you, suites where nap time doesn't end the day, beaches you can walk straight onto. I know which hotels mean it when they say family friendly.
This is the golden window. They can hike, swim, and order gelato in bad Italian, and they still want to be around you. These are my favorite trips to plan.
Teenagers need a say and a little slack. A beach club, a boat day, Wi-Fi that works, and one thing that scares them a little. They come home changed in a good way.
Honeymoon, anniversary, or no occasion at all. I book the room with the view you saw online, and I make sure the hotel knows exactly why you're there.
Grandparents, cousins, one very long table. The trick is a villa or connecting suites, one dinner everyone attends, and separate mornings. I can choreograph all of it.
January is for the Caribbean, and for booking summer before everyone else does.
February: warm islands, short flights, and half the lines at the big parks.
March is spring break. If it isn't booked yet, ping me today, not next week.
In April, Europe is waking up. Cities first, coasts soon.
May might be the best month to travel. Warm water, smaller crowds, shoulder-season rates.
June is the sweet spot: school's out, the Med is warm, and the August crowds haven't landed.
July is peak everything. Book the flights first and we'll figure the rest out.
August is for the Alps, the lakes, or anywhere the air is cool and the crowds aren't.
September is the adults' secret: summer weather, and the beaches back to being quiet.
October is Italy at its best. Harvest season, warm afternoons, long dinners.
November is desert sun and quiet deals. Also the month to book next summer.
December books out a year ahead. If the holidays are the plan, we should already be talking.
K.
Shoulder season, somewhere warmOld enough to remember itCliffside, somewhere blueSantorini, GreeceOne very long table Hi, I'm Kristen.
I'm a travel-obsessed wife and mom to three busy kids and a dog, raised in North Carolina, home in Raleigh, and in a more or less permanent state of wanderlust.
I'll admit it: I'm a little hotel-obsessed. I put that obsession to work for you, so the planning is mine and the trip is yours. Most days start with coffee and end with a glass of wine. Your vacation ought to feel just as balanced.
Kristen
More about KristenWhat I plan · 01 / 04
The trips I know by heart.
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Family Travel
The trip everyone remembers. Rest time for little ones and grandparents alike, with room to breathe.
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Honeymoons & Celebrations
Slow mornings, unforgettable meals, and just-for-two moments you'll be talking about for years.
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Multigenerational
Three generations, one seamless itinerary. Choreographed logistics so everyone can relax.
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Europe & Beyond
All-inclusives, cruises, and European itineraries. From the Amalfi Coast to safari and back.
You can't VIP yourself.
Booking through me costs the same as booking the hotel yourself. The difference is what's waiting for you when you walk in.
- Room upgrades, when availableFora X
- Breakfast for two, dailyFora X
- A resort, spa or dining creditVirtuoso
- Early check-in and late check-outFora X
- A welcome that means they know your nameBoth
Through Fora X and Virtuoso, at no extra cost to you, at more than 4,500 hotels worldwide.
Kind words
Real clients, Real feedback-
“Kristen was fantastic, and we’ll definitely work with her again in the future! She was incredibly quick with booking, communicated clearly throughout the process, and was available during our trip whenever I had questions. She also followed up promptly after we returned, which really showed how much she cares about her clients and her commitment to learning from each experience to better help others.”
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“The itinerary was perfection. We had some ideas of what we wanted, but not enough to plan on our own. Got great restaurant recommendations and tour ideas. And a great plus was breakfast included in 2 of the hotels. And a room upgrade at 1. We will continue to book with Kristen on future trips. (Already working on one for December)”
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“Kristen was absolutely amazing when booking our honeymoon. Will be using her for all our trips in the future!”
Questions?
Still curious? Ask me anything- Do I pay more by booking through you?
- No. Same hotels, same rates, sometimes better. The difference is what comes with it: upgrades, breakfast, credits, and a hotel that knows your name before you get there.
- How far out should we start?
- For peak season, big multigenerational trips, and the resorts everybody wants, six to twelve months is the sweet spot. That said, I've pulled together some beautiful trips on short notice, so it never hurts to ask.
- How do we work together?
- Tell me when you can get away and who's coming, and I'll come back with a plan. One point of contact from the first idea to your return home.
- What are Fora X and Virtuoso?
- The networks behind the perks. Fora is the advisor platform I work through. Fora X is its invite-only top tier. Virtuoso is an invitation-only network of the world's best hotels. Together, they're why the front desk greets you with a smile.
Postcards
Follow along at @kristen.pupa.travel"The best memories are the stories you bring home."
No pressure, no obligation. Just a conversation about where you're dreaming of.