The Trip Stories

Trips I've planned. Trips I've taken.

Every trip on this page is real. Some I planned for clients — an anniversary timed to the day, a graduation present, the Paris trip a family had talked about for years. Some are my own, the trips that taught me what good planning feels like from the traveler's side of it. Browse for ideas, find the shape of a trip you like, then make it yours.

Trips I planned for clients — the real itineraries, with names kept to first names and the private details left out.

Find a trip like yours

Filter by destination or season to narrow the list, or browse the whole collection start to finish. Each entry gives the trip, the season, and the one planning detail that made the difference.

The entries

Newest first. Trips already traveled and trips still on the books both live here — each one is labeled, so you always know which is which.

Completed trip · Paris · Darlene + her daughter-in-law JOni · Jul 15–21, 2026

The Trip They'd Always Dreamed Of

Darlene took her daughter-in-law to Paris — the trip they'd always dreamed of taking with her late son. It was JOni's first time out of the country. …

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Completed trip · Scotland & Ireland · Meghan + her father · Jul 25–Aug 4, 2026 · 11 days

Two Generations, Two Countries, Zero Stress

Meghan wanted to take her 80-year-old father to Scotland and Ireland — the heritage trip, done properly, while the walking is still good. The design brief was one line: comfort first, zero-stress transitions. …

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Anniversary cruise · Alaska · Jason & Heidi · Sep 2027 · 12 nights door to door

A 25th Anniversary, Timed to the Day

Royal Caribbean's Anthem of the Seas, Sep 3–10, 2027, balcony midship — then a Denali cruisetour through Talkeetna to Anchorage. Twenty-five years deserved more than a sailing; it deserved a calendar. …

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Multigenerational cruise · Mediterranean · Maria + nephew Aidan · Jun 2027 · 9 days

A Graduation Present, Done Right

Virgin Voyages' Scarlet Lady, Adriatic, Jun 20–27, 2027, Central Sea Terrace — Athens on either side. Maria wanted to give her nephew a graduation present he'd actually remember. …

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Mother-daughter · Ireland self-drive · Mary Lou & Jamie · May 2027 · 10 days

Ireland, Her Way

Dublin → Kinsale → Killarney → Galway, automatic rental car, every hotel quoted three ways. A retirement-year trip, self-driving the southwest, running on one rule set on day one: one bed — king preferred. …

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Family cruise · Alaska · Michael, Meredith + teens 16 & 13 · Jul 2027

Two Rooms, Four People, Zero Guesswork

A family of four means the math matters — two balconies vs. one suite, priced per person, per ship, with the kids' exact ages (they price as adults on some lines, children on others). …

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Couples · Caribbean · Shane + fiancé · Nov & Dec 2026

The Back-to-Back

A November Virgin Voyages sailing, then Christmas week on Disney's Very Merrytime cruise — two trips, one planner, one running conversation.

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Every trip here started with one conversation. Tell me where you want to go, and I will build yours the same way — one trip, planned on purpose.

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