There are trips you take, and then there are trips you remember for the rest of your life.

A milestone trip is the second kind - travel built around a moment big enough to deserve its own story.

What Makes a “Milestone Trip”

A milestone trip isn't defined by the destination. It's defined by why you're going.

It's the 25th anniversary trip you've been promising each other since year five. It's the milestone birthday - 30, 40, 50, 60 - that feels like it should mark something, not just pass by. It's a honeymoon, a retirement, a graduation, a "we finally did it" trip after a hard few years. Sometimes it's quieter than that: a solo trip taken at a turning point, just for you.

Milestone Trips happen only once. There is no redo on a 25th anniversary

A view of the Tiber River, in Rome, Italy

That's exactly why I believe these moments deserve more than a few hours on a booking site.

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Why Work With an Advisor for a Milestone Trip

I've planned enough of these trips to know where they go right and where they quietly go wrong when no one is holding the whole picture.

I protect the moment itself. If there's a proposal, a surprise, or a specific evening that needs to go perfectly, I build the whole itinerary around it - not the other way around.

I know which details actually matter. The right table at the right time of day. The hotel room with the view worth the upgrade. The difference between a "nice" restaurant and the one that becomes the story you tell for years.

I handle what you shouldn't have to think about on this trip. Logistics, timing, backup plans - all of it lives with me, so you're present for the moment instead of managing it.

I've been there. My recommendations come from places I've personally experienced and loved, not a database of listings.

Milestone Trips I’ve Planned

  • Anniversary

    ROME & AMALFI, ITALY

    Twelve days across Rome and Amalfi for the mix of city and coastal experiences. Signature moments in Rome included a private tours of St. Peter’s Basilica (including the dome), the Colosseum, and the Roman Forum, as well as a private cooking class with a local chef. In Amalfi, an arranged tour of one of the oldest lemon groves and a day trip to Ravello.

  • Honeymoon

    MAUI, HAWAII

    For newlyweds, I planned a 10-day Hawaii honeymoon centered on a relaxing Maui getaway with a touch of local experiences from small group snorkeling to experience sea turtles, to a private Luau, an all day Road to Hana experience, and a chartered Catamaran at sunset.

  • Anniversary

    LA FORTUNA & GUANACASTE, COSTA RICA

    An anniversary trip to Costa Rica designed to hit the balance between luxury and adventure. A 5 day stay at a 5-star resort in the jungles of La Fortuna at the base of Arenal volcano, included an anniversary dinner made up of a 14-course tasting menu and private violinist, a tour of the hanging bridges with sightings of toucans and sloths. Another 5 days in Guanacaste to relax and enjoy a slower beach pace.

  • Milestone Birthday

    ASHEVILLE, NC

    For a client marking a milestone 60th birthday, I built out a longer weekend in Asheville, NC including exclusive experiences at The Biltmore Estate, an arranged birthday dinner at a 5-star steak house, and an upgraded suite at The Grand Bohemian.

  • Reunion (Mid-size)

    IRELAND & SCOTLAND

    For a group of four friends, I designed a 14-day reunion trip through Ireland and Scotland, built around core experiences such as a Castle stay in Scotland, a falconry experience, visiting the Cliffs of Moher, a tasting at a distillery, a day trip on the Jacobite Steam Train, and a visit to the Isle of Skye.

  • Reunion (Small)

    LONGBOAT KEY, FL

    An annual girls weekend hosted in Longboat Key, FL and attended by friends who flew in from all over the country. A suite was arranged in addition to added white sand beach and F&B amenities to help make their reunion even more enjoyable and comfortable.

  • Reunion (Large)

    Disney Cruise

    For a large family group of 34, I helped with itinerary selection, room blocking design, booking management, and pre-cruise hotel arrangements.

Let’s Design Yours

If there's a moment coming up that deserves more than an ordinary trip, I'd love to hear about it. Tell me what you're celebrating, and let's build something around it that you'll still be talking about years from now.

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