Group travel, actually planned
Group travel lives or dies on the logistics underneath it. Rooms that actually sleep the cousins. A restaurant that can seat thirty without losing the evening. A ship that holds the whole party without feeling cavernous. I plan the group from the guest list up — who's coming, what they can handle, what they'll remember — and then choose the destination, property, or vessel that serves it.
What I plan
Five group formats, one method — start with the people, end with the itinerary.
Destination Weddings
Rehearsal dinner to send-off brunch, handled. See also the destination-wedding planning guide.
Multigenerational Family Trips
One itinerary that works for a 4-year-old, a 14-year-old, and an 84-year-old. See also the multigenerational planning guide.
Milestone Reunions
40ths, 50ths, college reunions, sibling trips — everyone under one roof. See also reunion travel for college friends and celebration trips for adults.
Curated Group Cruises
Small-ship and river-cruise charters for 20–50 travelers — heritage itineraries, wine weeks, interest-led voyages. See also Rivers & Small Ships.
Chosen-Family Getaways
Queer-affirming destinations and friend-group weeks, booked through partners who'll celebrate the whole table.
Trip shapes I'm planning right now
Five group formats in motion this season — pick the one that sounds like yours, take the quiz if it doesn't.
A Girls' Trip Eight People Agree On
The shapes that hold when you've got eight opinions and one calendar. No sashes required.
Read the dispatch →︎ Multi-gen · 7–10 nights · Year-roundA Multi-Gen Reunion That Doesn't Crater
Three generations, one property that handles all of it. The planning model that keeps everyone in their corners.
Read the dispatch →︎ Reunion · 4–7 nights · FlexibleA Reunion of College Friends
Twenty years later, the same six people, a destination that earns the airfare.
Read the dispatch →︎ Small group · 7 nights · 2027–28A Colombia Group Trip
Cartagena, the coffee region, and a curated group of travelers who'll feel like friends by Day 3.
See the interest page →︎What I do for groups
I plan like a logistician; I write like a host.
Room blocks, dietary needs, rehearsal dinners, shore excursions, airport transfers — managed in the background so the experience reads effortlessly to the guests.
One point of contact for the planning, not a clipboard.
Whether it's 8 travelers or 80, you get me directly. No call center, no intake form between you and the decision.
Group leverage where it actually matters.
The relationships behind these trips — direct hotel and cruise-line partners, plus the trade contacts I keep current through conferences and supplier meetings — give me real room to work on group pricing, private-event holds, and property buyouts. I apply them where they meaningfully improve the trip, not as a line item to justify the booking.
For group cruise charters — AmaWaterways for the rivers, UnCruise for small-ship wilderness →︎
Trips like these are planned on a fee that scales with their complexity — here's what it actually buys →︎
Why the logistics ARE the craft — the manifesto →︎
Who this is for
Couples planning a wedding away from home. Families trying to get everyone in the same country for one week a year. Friend groups marking a 40th or a 60th. Alumni circles, book clubs, wine clubs, congregations. Chosen families carving out a week that's theirs. Anyone who wants group travel to feel less like a project and more like the point.
Bringing the group together yourself? Here's how I make you the host →︎
Keep Reading
More from the Journal
Travel With Me: What It Means, and What It Doesn'tEvery so often I put a departure in front of you and say: come with me. The operator runs the trip; I'm your advisor before you go and a fellow passenger once you're there. Here's why that split works in your favor.Read the dispatch →︎
How to Plan a Group Trip Without Losing Your FriendsThe group trip paradox: the more excited everyone is at the start, the more exhausted someone is by month two of planning. Here's how to avoid it.Read the dispatch →︎
Celebration Trips for Adults: A Guide for the Group That Wants to Plan One OnceNot every celebration trip needs sashes. Here's how adults actually plan them.Read the dispatch →︎
The 40th, 50th, 60th: Milestone-Birthday Trips That Earn the HypeNot every birthday gets a group trip. The milestone ones do. Here's how to plan them right.Read the dispatch →︎
Bachelorette Without the Sashes: How I Plan These for AdultsThe bachelorette you want to remember isn't the one in matching shirts.Read the dispatch →︎
My Brilliant Friend, Your Next TripFour books means your club has lived with these women for a year before you land. Naples and Ischia host eight to twelve people almost suspiciously well — this is the greatest book-club trip on earth.Read the dispatch →︎
