Start Here
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A Collaborator With a Point of View
Most travel-buying falls into two camps: the order-taker who books what you described, and the expert who already decided what you should want. I'm building something different. A collaborator with a point of view.
April 2026 -
A Trip Has Chapters
If your trip plan walks into the room as a list, the only story it tells is "we did the things." "We did the things" is not a story; it's a receipt. Here's the four-act arc I work from — and why the order matters more than the chapters.
May 2026 -
Finding Your Thread
I move through the world as a gay man and a Jew by choice, and I've stopped pretending it doesn't change how I travel. This is about that lens — and why I want every traveler to have a thread of their own to follow.
May 2026
Stories from the Road
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The Secret in the Itinerary: Behind Bonnie & Shelby's Switzerland & Italy
Shelby texted me out of the blue: there was a plan, and it needed a co-conspirator. Eight weeks later, in a valley of seventy-two waterfalls, Bonnie said yes. Here's the trip with a secret folded inside it.
May 2026 -
A Solo Thanksgiving on the Danube
Sometimes you need to be somewhere else entirely — somewhere that has no memory of who you usually are at the table. The Danube, it turned out, was the right kind of somewhere else.
March 2026 -
16 Days on a Panama Canal Cruise: A Trip Report
I'd recommended the Panama Canal crossing to clients before I ever took it myself. Then I booked 16 days on a Princess cruise — alone, no agenda — and arrived somewhere I hadn't expected.
November 2025 -
Holding Someone's Becoming
She wasn't looking for a vacation. She was looking for permission to disappear — and then maybe come back a little different. Here's how we built 45 days around that.
November 2025 -
Seven Days at Sea: Why You Cross Instead of Fly
There is no flight that competes with the feeling of crossing the Atlantic by sea. Here’s what a Cunard transatlantic crossing is actually like—from someone who’s done it.
June 2025
Rivers & Small Ships
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Which Alaska cruise is right for you? Seven kinds of trip, and the line I'd book for each
The real choice in Alaska isn't which cruise line. It's which kind of trip you're after. Here are the seven I see most, and the line I reach for in each.
October 2026 -
Two Valleys, One Harvest: The Douro or Bordeaux by River
One river line sails both of Europe's great wine valleys — the Douro and Bordeaux. Readers picked the Douro for my own 2027 sailing; here's the honest case for each, so you can pick the one that's actually yours.
August 2026 -
AmaWaterways vs. Viking: How to Choose Your River Cruise Line
Two of the best river cruise lines on the water, and they're built for different travelers. Here's the honest, side-by-side breakdown — and how I'd help you pick.
August 2026 -
The Danube Educates. The Rhine Enchants. The Douro Slows You Down. Here's How to Pick Your River.
The three great European river cruise routes are all beautiful and completely different. Here's how I help clients pick — Educator, Romantic, or Intimate.
April 2026 -
What Is River Cruising (And Is It Right for You)?
River cruising is not ocean cruising in miniature. It's a fundamentally different way to move through the world — and once you understand the difference, it's very hard to go back.
March 2026 -
Bordeaux River Cruising: A Week on the Garonne, the Way I'd Plan It
A week on the Garonne is the wine-region cruise I'd send a serious traveler on this year — château by château, oyster bar by oyster bar. Here's what the rhythm of it actually feels like.
October 2025 -
European Holiday Markets River Cruise: What to Expect
The holiday markets river cruise is one of my most-requested itineraries, and for good reason. Here's what the experience is actually like—beyond the mulled wine photos.
October 2025 -
Fall Wine Country River Cruising: The Season I'd Choose
Fall is when wine country river cruising is at its best—harvest festivals, vineyard colors, and the sense that you've arrived at exactly the right moment.
September 2025 -
The Best Time for a European River Cruise, Month by Month and River by River
The month decides what's happening on shore. The river decides what the water is likely to do. Here's the whole calendar, month by month and river by river.
March 2025 -
The Best AmaWaterways Itinerary for First-Timers
Of all the AmaWaterways itineraries, the Romantic Danube is the one I send first-timers to. Iconic cities, manageable pacing, easy flights, and the kind of week that turns one river cruise into the first of many.
December 2024 -
Choosing Your AmaWaterways Cabin: French Balcony, Twin Balcony, and the Suites
The Twin Balcony cabin is AmaWaterways' signature for a reason. Here's the breakdown of every cabin category — what each one really gets you, and which one I'd book for your trip.
October 2024 -
Small Ship vs. Mega Ship Cruising: Which Is Right for You?
Mega ships and small ships are both cruises the way a Marriott and a boutique inn are both hotels. Here's how to tell which one is actually you.
May 2024 -
UnCruise vs the other small ships in Alaska — how the field actually compares
Small-ship Alaska covers everything from a 20-guest yacht to a 170-guest coastal ship. They are not competing for the same traveler. Here's the field as it stands in 2027, and where UnCruise sits in it.
March 2024
Honeymoons & Milestones
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What Couples Always Forget on Their Honeymoon
The things couples consistently overlook. Don't be that couple.
April 2026 -
Solo Celebration Travel: Post-Divorce, Post-Promotion, Post-Retirement
Celebrating alone is serious. Here's how to plan it.
March 2026 -
How to Plan a Honeymoon Without Losing Your Mind
Honeymoon planning doesn't have to be chaos. Here's what actually matters.
February 2026 -
The Honest Truth About Honeymoon Budgets: What Each Tier Actually Buys
Price transparency without judgment. What your honeymoon budget actually buys.
January 2026 -
When to Start Planning Your Honeymoon: The Month-by-Month Timeline
The single biggest predictor of whether a honeymoon comes together well isn't the budget. It's the timeline. Here's the month-by-month version, working backward from your wedding date.
January 2026 -
The Calm Babymoon: A Final Adult Trip Before the Sleep Disappears
This is the last trip before parenting. Plan it accordingly.
May 2025 -
Hawaii Honeymoon vs. Abroad: When the Domestic Answer Is the Right One
The honest comparison most honeymoon guides skip: when Hawaii is actually the right call over Europe, the Caribbean, or Asia — and when it isn't.
July 2024 -
All-Inclusive Resorts: An Honest Take
I recommend all-inclusive resorts to clients regularly — and I also talk people out of them regularly. Here's the honest framework, and when each answer is right.
January 2024
Groups & Celebrations
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Travel With Me: What It Means, and What It Doesn't
Every 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.
September 2026 -
The Ringleader's Reward
Every friend group has one — the person who gathers everyone. Here's how to keep the part you're good at and hand off the rest, and why filling the trip often earns you your own seat.
July 2026 -
Bachelorette Without the Sashes: How I Plan These for Adults
The bachelorette you want to remember isn't the one in matching shirts.
April 2026 -
The 40th, 50th, 60th: Milestone-Birthday Trips That Earn the Hype
Not every birthday gets a group trip. The milestone ones do. Here's how to plan them right.
February 2026 -
Reunion Travel: When Your College Roommates Want to Go to Tuscany
Reunion trips have their own rhythm. Here's how to honor the history without forcing the intimacy.
January 2026 -
Girls Trips That Actually Work When Eight People Try to Agree
Coordinating eight people is a puzzle. Here's the structure that solves it.
May 2025 -
Multigenerational Travel: How to Plan a Trip Everyone Actually Shows Up For
Multigenerational travel is a different puzzle than a regular group trip. Here's how to solve it so nobody feels bored, rushed, or left behind.
April 2025 -
How to Plan a Group Trip Without Losing Your Friends
The 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.
January 2025 -
Celebration Trips for Adults: A Guide for the Group That Wants to Plan One Once
Not every celebration trip needs sashes. Here's how adults actually plan them.
January 2024
Wild Places & Luxury Lodges
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Aurora 101: What the Northern Lights Actually Are (and How to See Them)
What the northern lights actually are, why Fairbanks is the canonical aurora city, and the math that separates a trip where you'll almost certainly see them from a coin flip.
September 2025 -
How to Pack for -20°F (And Actually Enjoy It)
Interior Alaska in winter runs from -20°F at night to 20°F in the afternoon. Here's the actual packing list — what you need, what to leave home, and how layering works when the temperature swings 40 degrees in a day.
January 2025 -
Safari Lodges, Camps, and Private Reserves: What's the Difference?
A permanent lodge with a wine cellar is a completely different experience than waking to lion sounds in a tented camp. Here's how to understand what you're actually choosing between.
August 2024 -
What Is Luxury Lodge Travel?
Luxury lodges are not hotels that happen to be remote. They're a specific kind of experience built around place, access, and a level of service you can't replicate anywhere else.
June 2024 -
What Is Expedition Travel?
Expedition travel isn't a destination — it's a category defined by place-first design, expert guides, and itineraries built around conditions instead of clocks.
May 2024
The Reading Route
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The Reading Route
Reading is how you travel before you go, and how you keep traveling after you're home. A new series: one book that earns a trip, the route it demands, and a drink to start it with tonight.
August 2026 -
Six Days Without Land: Waugh and the Crossing
A crossing is a suspension: no ports, no arrivals, nowhere to be. Which makes it the best place on earth to finish a four-hundred-page novel about a house you'll never own.
September 2026 -
Wilde's Last Address
Everybody has read Dorian Gray. The book that earns this trip is the one almost nobody reads — fifty thousand words written from a prison cell, in which the wit drops out from under you.
August 2026 -
The Drake Is the Whole Point
The thing standing between most people and the trip of their life is not money and not time. It's a two-day stretch of water they read about on the internet at midnight. Semple built a whole novel on it.
August 2026 -
The Traveller's Portugal: Saramago on the Douro
Saramago drove around his own country refusing to say 'I' — he calls himself 'the traveller' for four hundred pages. It is the strangest and best travel book I know, and the Douro is where his method pays out.
August 2026 -
Quoyle's Coast: The Shipping News in Newfoundland
The best novel I know about the specific dignity of being no good at things — and one island off Newfoundland where the story of the book and the story of the place have gone on to rhyme.
August 2026 -
Mongibello Doesn't Exist
Highsmith invented the village and put it on a coast that doesn't have it. Three screen versions went looking anyway, and not one of them filmed in the town she was actually staring at.
August 2026 -
The Flag They Fly So Nobody Boards
Two people in their seventies board a riverboat, run the cholera flag up the mast so nobody can board and nobody can land, and keep going. The finest thing any writer has ever done with a boat.
August 2026 -
Snowbound: Christie and the Train
A blizzard buried the Orient Express near Çerkezköy in 1929 and held it for the best part of a week — a train full of wealthy strangers with nothing to do but look at each other. Christie only had to add a body.
August 2026 -
Everyone Aboard Has a Motive
Most murder mysteries make a place look dangerous. This one makes the Nile look like the most civilised way anyone has ever travelled — which, annoyingly, expensively, correctly, it still is.
August 2026 -
The Rooms Baldwin Wrote In
He was advised, in so many words, to burn it. He published it instead. Seventy years on, Giovanni's Room is still a slightly shocking book — not for the content but for the nerve.
August 2026 -
Reading Twain Down the Mississippi
Twain spent four hundred pages teaching you that a river is a text. Then you want to be on it, moving at its speed, learning it a bend at a time — Memphis to New Orleans, at reading pace.
August 2026 -
Two Acts: Isherwood From the West End to Berlin
A book you can see staged in one city and true in another. The only pairing on the route with an intermission — the West End's Kit Kat Club, then the Schöneberg street where it was written.
August 2026 -
My Brilliant Friend, Your Next Trip
Four 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.
August 2026 -
Walking Into Winter: Fermor on the Danube
In December 1933 an eighteen-year-old set out to walk from the Hook of Holland to Constantinople. The book he made of it is the best prose ever written about moving slowly through Europe.
August 2026 -
The View From Fontana Vecchia
In 1950 Capote left New York for a hillside villa above the sea and did the best quiet work of his early life there. A writer nobody could shut up, gone happily quiet — and the trip that earns.
August 2026 -
Somewhere in Northern Italy
Read it again as travel writing and you notice what the swooning reviews skipped: nobody has written the pace of Italy in July better — the way a day can hold almost nothing and be the fullest day of your life.
August 2026
Field Guides & Destinations
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Kahal Kadosh Beth Elohim: Charleston's Jewish Story, and How to Fit It Into a Weekend
A congregation from 1749, a petition from 1824, an organ installed after the fire of 1838, and a sanctuary from 1841 that's still in use. Here's the story behind Kahal Kadosh Beth Elohim, and the practical shape of a visit, including the one day of the weekend it won't work.
October 2026 -
Following the Thread Through Andalusia: Sephardic Spain
The golden age, the rupture, and the thread that runs north from Córdoba to a ritual bath under a Catalan street. How I plan the slow Sephardic arc through Spain — with the pacing, the operators, and the kosher logistics that make it land.
August 2026 -
I'm Married. I Still Travel Alone.
Solo travel has been sold as a transformation. It isn't one. It's a skill, and a pleasure, and the most honest way I know to find out what you actually like. Here's how I do it, where I've gone alone, and the one hour nobody warns you about.
August 2026 -
What's a Repositioning Cruise? (And Why the Crossing Is the Whole Point)
A repositioning cruise is the trip most people scroll past — a ship moving between seasons, sold cheap by the night, with days at sea that are the whole reason to go. It's also the smartest way to sample a luxury line you've never dared book.
June 2026 -
Choosing the Right River Cruise: An Honest Guide
Most 'best river cruise' lists answer the wrong question. There's no best one — there's the right river, line, cabin, and week for you. Here's how I match them.
May 2026 -
Jewish Heritage Travel: Following the Thread, Not Just the Sites
An advisor's lens on Sephardic Spain, Ashkenazi Europe, Israel, and the trips that earn the depth. How I plan Jewish heritage travel — the destinations, the archetypes, the operators, and why the work is different when the lens is right.
May 2026 -
Italy Destination Weddings: What You Actually Need to Know
Italy destination weddings are glorious and logistically demanding in equal measure. Here's what I've learned planning trips around them—and what makes the difference between beautiful and chaotic.
January 2026 -
Eating Italy Like You Live There: A Pragmatic Guide
Italian cooking is not haute cuisine. It's the food Italians eat at home. Here's how to find the restaurants worth your reservations — and how to order in a country where the menu hierarchy actually means something.
April 2025 -
When to Go to Italy: A Region-by-Region Seasonal Guide
"When to go to Italy" depends entirely on where in Italy you're going. Here's the region-by-region version of the answer, plus the windows nobody tells you to avoid.
February 2025 -
Italy in Five Itineraries: Which One Is Yours?
Italy isn't one trip. It's at least five distinct kinds of trip wearing the same name. Here's how to tell which one you actually want — and which destinations build it.
January 2025
Why I Recommend
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Is the British Pullman worth it? And which seat to ask for
The British Pullman is the day version of the great train trip: 1920s Pullman carriages out of London Victoria, lunch in the countryside, home by evening. The decision isn't really whether to go. It's which journey, which table, and whether the Coupé is worth paying for.
October 2026 -
Is Queen Mary 2 worth it? What I tell my clients about the transatlantic crossing
Queen Mary 2 is the only ocean liner still crossing the Atlantic on a schedule. I've made the crossing with my husband. Here's what it actually is, what it costs in each stateroom tier, and the traveler I'd put on it. Some people shouldn't book it, and I'll say who.
September 2026 -
When to go to Southeast Alaska — the week matters more than the month
Earlier buys weather; later buys wildlife. The weather it buys is far smaller than people think, and the wildlife it costs is total. Here's the week-by-week case, sourced properly.
September 2026 -
What an UnCruise sailing actually costs — and how to read the number
The sticker price on an UnCruise sailing looks high next to a big-ship Alaska fare. Then you add back everything the big ship charges separately, and the gap narrows more than you'd expect. Here's the honest math.
September 2026 -
UnCruise reviews: the complaints worth reading before you book
UnCruise sits at 4.5 out of 5 across 211 Cruise Critic reviews, and the complaints inside that number are specific, consistent, and worth reading before you book. Here they are, and here's which ones matter.
September 2026 -
Which UnCruise Alaska itinerary is right for you — all nine, compared
Two of the itineraries with 'Glacier Bay' in the title don't go into the bay proper. That is the fork that decides this trip, and the booking page won't tell you about it. Here are all nine, sorted by that fork.
September 2026 -
Is Canyon Spirit worth it? What I tell my clients about the Rockies to the Red Rocks
Canyon Spirit is the new name on a route Rocky Mountaineer used to run — a daylight-only luxury train from the Colorado Rockies to Utah's red rocks. Here's what it actually is, what it costs, and the traveler I'd put on it.
August 2026 -
Why I Started With Belmond
Most luxury hotel collections are a logo stretched over properties that have nothing to do with each other. Belmond is the rare exception. Here is why I built the first TWE landing page around Cap Juluca — and what I am putting under the rest of the collection, property by property.
May 2026 -
Why I Keep Recommending the Sea of Cortez
Jacques Cousteau called it "the aquarium of the world." Sea lions at Los Islotes, gray whales in Bahía Magdalena, dolphins from the skiff, and the kind of expedition pace that lets the trip find you. Most travelers don't know to plan for it.
December 2025 -
Is UnCruise Adventures Worth It? What I Tell My Clients
UnCruise has been running expedition routes for thirty years in places most operators can't access. Here's an honest assessment of whether it's worth the price — and who it's actually for.
August 2025 -
The Anti-Resort Hawaii: UnCruise Hawaiian Seascapes
Most Hawaii trips involve a resort. The UnCruise Hawaiian Seascapes itinerary is what happens when you skip all of that — 36 guests, a small expedition ship, and coastline most visitors never see.
October 2024 -
Virgin Voyages for Couples Who Don't Want Kids on the Ship
An adults-only cruise isn't about disliking kids. It's about choosing the kind of vacation where the pool deck stays calm at noon and dinner doesn't start at 5:30.
August 2024 -
Why I Recommend Virgin Voyages
Virgin Voyages isn't trying to be every cruise line. It's trying to be the one for adults who want design, food, and a transparent fare — and that focus is exactly why I keep recommending it.
April 2024 -
Why I Recommend AmaWaterways: A Family-Founded River Cruise Line, Up Close
AmaWaterways isn't the only river line I recommend, but it's the one I've sailed and keep recommending. Here's what makes the family-founded approach show up in the actual ship.
February 2024
Before You Book
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Is a private arrival transfer worth it? The one thing I never skip, even for myself
Every trip has a moment where it either starts well or starts badly, and it's not the flight. It's the twenty minutes after you clear customs. Here's why I pre-book a car for that moment on every trip I take, which kind of car for which trip, and where you can book your own.
October 2026 -
The Expensive Way to Save Money
I spend a fair amount of my working life untangling trips that were planned sensibly. Not badly — sensibly. Here's the difference between what a trip costs and what it's worth, told through six trades that looked smart on paper and weren't.
October 2026 -
Adults-Only at Sea: Which Line Is Yours?
Only three of these five lines are adults-only by rule, and the other two still come up every time a couple asks me for a grown-up ship. Here's who each one suits, and who'd be happier on something else.
October 2026 -
The Two Clocks: When Your Trip Actually Goes on Sale (and When It Sells Out)
Most people plan a trip around one date: theirs. But every trip runs on a second clock — the market's — and it decides whether you get more trip for your money or pay the late tax. Here's the calendar I'm already watching for you.
August 2026 -
How Travel Advisors Actually Get Paid (and How to Choose a Good One)
The money question most people are too polite to ask: how does a travel advisor get paid, does it cost you anything, and how do you tell a good one from a bad one? Here's the honest version.
August 2026 -
Dear Travelers, Some of You Are Doing This Wrong
Somebody who loves travel needs to say the blunt thing out loud. Nine instincts that feel like freedom and quietly cost you the trip — from someone who's made most of them himself.
August 2026 -
What Does a Planning Fee Actually Get Me?
Clients sometimes hesitate at a planning fee. Here's what it actually buys you — broken down honestly, without the sales pitch.
October 2025 -
What Is a Travel Consortium (And Why It Matters for Your Trip)?
When advisors talk about being "consortium members," most clients nod politely and have no idea what it means. Let me explain — because it directly affects the value an advisor brings.
February 2025 -
Do I Really Need a Travel Advisor?
The question I get asked more than any other. Here's my honest answer — including the cases where I'll tell you that you probably don't need me.
January 2025 -
When Should You Start Planning Your Trip?
The most common mistake I see is starting too late. Here's how to think about booking timelines by destination type — and what you actually lose by waiting.
November 2024 -
Travel Insurance: An Honest Guide
Travel insurance is the thing most people buy wrong or skip entirely. Here's how to think about it correctly — and why the cheapest policy is almost always the worst deal.
September 2024