Well Gathered.
Well Traveled.
Small trips for women in a season of next — climb, pivot, or leave.
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Not a retreat. Not a workshop.
A pause before the next move.
Here, creativity meets opportunity. Whatever you're building, we're here to help you take the first step with confidence. Driven by curiosity and built on purpose, this is where bold thinking meets thoughtful execution. Let’s create something meaningful together.
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“There's no workbook. No facilitator with a lanyard. No circle of chairs. Waypoint is a small, well-designed trip — built the way every TWW trip is built — for women who happen to be at the same kind of turn. Put the right women in a beautiful place with room to breathe, and the conversation that actually helps tends to happen on its own. We don't call it a program. It isn't one.”
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The woman who's excellent at her career and no longer sure she wants to be. The one weighing whether to keep climbing, step back, or start something of her own. The one who hasn't said any of this out loud yet — and would rather say it over a long dinner than in a performance review.
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A small group, deliberately sized — this only works if the room is right.
Beautifully chosen stays and unhurried pacing (the TWW standard, unchanged).
Long meals, real conversation, and enough open time that things surface naturally.
Zero agenda items with the words workshop, breakout, or action plan.
Join a Waypoint Trip
Paris Is always
a good idea
2027
Coming Soon
New York city
Holiday
2026
Vermont
(SOLD OUT)
London
(past)
Banff
(past)
VENICE
(past)
FAQs
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Not here. If you’re 21+, you’re welcome. Most of our travelers are 40+, and that’s by design—women who know what they like, value comfort, and want travel that feels meaningful (not frantic). Mother–daughter duos are always a favorite, and multi-generational pairs are welcome when it fits the trip.
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Think: grown-woman energy.
Curious, grounded, kind. We’re here for great meals, beautiful spaces, meaningful conversation, and the freedom to be yourself—whether that’s early-to-bed, first-to-the-spa, or last-laugh at dinner -
Either is perfect. Many women come solo and leave with new friends—because we intentionally design these trips to feel warm, easy, and unforced. If you want to bring a friend, sister, or daughter, we love that too.
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You’ll fit right in. TWW itineraries are built with breathing room—a thoughtful rhythm of shared experiences and open time. Join the group when you’re feeling social, wander solo when you’re not, and know that both are completely normal here. No pressure to “perform” the trip.
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Safety is foundational. We work with vetted hotel partners and trusted local guides, monitor travel and weather advisories, and keep a clear, calm communication plan in place before and during the trip. You’ll also have direct access to your host while traveling, plus local support on the ground when needed. Travel should feel expansive—not stressful.
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Yes—travel insurance is mandatory for all TWW group trips. We’ll provide the minimum coverage requirements and help you choose a plan that fits (especially if you want strong cancellation/interruption and medical coverage).
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All booking terms and cancellation details can be found HERE. Because group travel requires contracted reservations secured in advance, cancellation terms can be more structured than individual travel—please review before booking.
