How We Plan a Luxury Family Trip Without Losing Our Minds (or Our Budget)

Let me be honest with you: our luxury family travel planning isn’t improvisation. Our trips don’t just happen.

They are planned with intention, with a system, and occasionally with a glass of wine in hand after the kids are in bed. The version of travel you see on The Sawyer Campaign (the boutique hotel mornings, the tables at restaurants we actually wanted to be at, the smooth airport moves with two children in tow) is the result of a planning process I’ve been refining for years.

And people ask me all the time: How do you do it? How do you make it look so easy?

The answer is that I don’t wing it. I have a system. And today I’m sharing the whole thing with you.

Quick Plan

• Dream: Define how you want the trip to feel, shortlist 2–3 destinations, and loop in the kids.
• Research: Lead with lodging, lock priority experiences, and then figure out flights/logistics.
• Lock In: Deploy points strategically, finalize every confirmation in one document or location (I like using my Notes App but have also been transitioning to Obsidian), and of course, insure the trip.
• Extras: Use Amex FHR perks, build a packing list early (or use my FREE ultimate packing list), and schedule check-ins 30/14/7 days out so nothing slips.

Our Luxury Family Travel Planning Phases

I’ve observed that every trip we take moves through three distinct phases, and skipping any one of them is how you end up with a beautiful hotel that’s not actually walkable to anything, or a flight with a four-hour layover because you booked on a whim. Trust me: I’ve learned from both.

Phase 1: Dream

This is the fun part, and it deserves real time. We don’t just open Google and type “best family resorts in Mexico.” We sit with it.

I’ll pull out my travel journal (yes, I have one) or open a new note on my phone and write down everything the feeling of this trip needs to include. Are we chasing culture or relaxation? Do the kids need to run free on a beach, or are we ready to do a more structured city trip? Are we celebrating something? Do we need to decompress, or do we need to be stimulated?

That emotional inventory shapes everything that comes after.

From there, I build a short list of two or three destinations that could deliver that feeling. I look at travel content from creators I trust, I read long-form travel journalism (not just listicles), and I check in with my own bank of experiences. Have we done the Caribbean recently? Maybe we’re due for Europe. Have the kids been asking about a specific place? Is my extended family traveling anywhere we may also want to go? That goes on the list.

What to do in the Dream Phase:

• Define the feeling of the trip before the destination
• Research 2–3 options that match that feeling
• Involve your kids in the early conversation (they will have opinions, and those opinions will surprise you)
• Start a dedicated folder in your phone or bookmarks for inspo

Phase 2: Research

Once we’ve landed on a destination, the research phase begins, and this is where I get genuinely nerdy.

Accommodation first, always. This is a tactic my husband taught me and in the end I’m grateful for. Where you stay is the single biggest variable in whether a family trip feels elevated or exhausting. I start with accommodation before anything else. I’m looking for properties that have been thoughtfully designed, that genuinely welcome children (not just “kids stay free” but actually welcome (think connecting rooms, a pool that’s appropriate for different ages, a breakfast situation that won’t be a circus), and that have reviews from guests whose taste aligns with ours (and aren’t bots).

I look at platforms like Mr & Mrs Smith, Tablet Hotels, and Relais & Châteaux for boutique luxury picks. For larger resort stays, I read reviews on TripAdvisor and Google but I filter ruthlessly because I want reviews from families, not couples, and I read the negative reviews while staying fairly neutral.

Then I build the skeleton of the itinerary. I identify the two or three non-negotiable experiences: the restaurant that requires a reservation three months out, the activity the kids have specifically asked for, the museum or market or neighborhood I will not leave without seeing. Those go on the calendar first. Everything else is flexible.

Flights and logistics last. I know this feels backwards, but I’ve found that building the trip around the experience, not around the cheapest flight, produces better outcomes. Once I know where I want to stay and what I want to do, I find the best flight option to support that itinerary.

What to do in the Research Phase:

• Lead with accommodation, not flights
• Use boutique hotel platforms for elevated options (Mr & Mrs Smith, Tablet Hotels)
• Book any reservation that requires lead time immediately once you’ve confirmed the trip
• Build your itinerary skeleton around 2–3 anchor experiences

Phase 3: Lock In

This is where we commit, and where having a solid points strategy really pays off.

On using points and miles: We use the Amex Platinum as our primary travel card and have for years. The points accumulation, the Fine Hotels + Resorts program, and the airport lounge access alone have fundamentally changed how we experience travel. I am not exaggerating when I say we’ve unlocked rooms and flights we would not have paid for in cash through strategic points use.

A few principles that have served us well:

• Book flights with points during the “sweet spot” window. For international travel, we aim to book 4–6 months out. For domestic, 6–8 weeks is typically the sweet spot. Booking within that window with points often yields significantly better value than cash fares that have already spiked.

• Use Fine Hotels + Resorts for at least one stay per trip. The room upgrades, late checkout, and breakfast inclusion make the per-night value extraordinary on stays you’d be booking anyway.

• Don’t hoard points. This is a mistake I made early on. Points sitting in an account are worth nothing. Points turned into a flight to Paris are worth everything. If you read our Napa girls’ trip itinerary, you’ll see how those perks shaped every decision.

On locking in the details:

Once flights and hotels are booked, I move to the ground level: airport transfers, any necessary travel insurance, activity bookings, restaurant reservations. I keep a running trip doc (I use my Notes App or Obsidian) that has every confirmation number, address, and phone number we might need. This doc lives on my phone, downloaded offline, before we ever leave the house (and shared with at least 2 trusted family/ friends in case of emergency).

What to do in the Lock In Phase:

• Use points strategically — don’t save them, spend them on the trips you care about
• Book flights within the sweet spot window for your destination type (domestic v. international)
• Build a trip doc with all logistics in one place, downloaded offline
• Don’t forget travel insurance, especially for international trips with kids. Coming home with a gigantic hospital bill is no fun.

A Note on “The Budget”

I want to address this directly, because luxury family travel has a reputation for being out of reach that I don’t think tells the whole story.

We are not spending full retail on everything. A significant portion of our travel is subsidized by a points strategy we’ve built over years. Some of the most memorable meals we’ve had were at local spots that cost less than a Applebee’s. We splurge deliberately, usually on accommodation and one or two anchor experiences, and we are strategic everywhere else.

Luxury, to me, is not about spending the most money. It’s about making choices that feel elevated. Choices that consider beauty, culture, service, and the quality of the experience over the number of amenities on the brochure. I consider that to be achievable at almost every budget level if you plan with intention.

Start Planning Now

Summer is closer than you think, and if you’re eyeing Europe, the Caribbean, or anywhere that requires international flights, now is exactly when to start building your plan.

The Dream phase costs you nothing. Open a note on your phone tonight and write down what you want this summer to feel like. Start there.

And if you want a head start on the logistics, download our free Family Travel Planning Checklist below, it walks you through everything from the 6-month mark to the night before departure, so nothing slips through the cracks.

Download the Family Travel Planning Checklist →

Have a trip planning question? Drop it in the comments or reach out on Instagram @thesawyercampaign. I read everything.