The Three Tiers Explained: Choosing Your Planning Level

Most people who find their way to this page aren't comparing Wanderlight, Uncharted Core, and Deep Uncharted for fun. They want to know what they'd actually be getting at each level before deciding where to spend the money. The three tiers explained here are built around a single question: what shape is the trip you're planning?

The tiers aren't a quality ladder. The same taste and the same care go into a long-weekend Wanderlight and a three-week Deep Uncharted. What changes is the deliverable — its scope, its depth, the number of decisions I'm making on your behalf, and the time it takes me to do it well. Picking the right tier means picking the one whose deliverable fits the trip you're actually taking, not the one that sounds most thorough. More isn't always better; appropriate is always better.

If you want the full walk-through of how the planning process works at each stage — intake, review, design, delivery — how the Uncharted planning process works, step by step is the longer read. This post stays focused on the tiers themselves: what's in each, who it fits, and how to pick.

Wanderlight — the long-weekend tier

Wanderlight is designed for trips of 2–3 days. Long weekends. A quick reset. A city you've been meaning to try without the planning overhead eating the weekend before you go.

At $145 with a 3–5 day turnaround, it's the tier that answers a specific question: can I get a thoughtfully planned short trip without it taking more effort than the trip is worth? The answer is yes, and the deliverable is built around that constraint. A clean itinerary with morning, afternoon, and evening structure. Two to three stay options, hand-selected for the trip's style. Four to six restaurant picks. Three to five experience recommendations that mix the obvious and the not-so-obvious. Destination notes to orient you on arrival. Mobile-friendly format so you can navigate from your phone without printing anything. Two live samples of what a Wanderlight deliverable looks like: a one-day plan for Milos and a one-day arrival on St. John.

What Wanderlight isn't is a substitute for Core on a longer trip. The deliverable has a specific carrying capacity — it's designed for a weekend, not a week. If you try to use a Wanderlight framework for a five-day trip, you'll end up with coverage that feels thin, because the tier wasn't built to carry that depth. That's not a knock on the tier; it's a constraint that makes the right trips genuinely good.

Wanderlight fits best when: the trip is genuinely two to three days, you want intentional planning without overwhelming detail, it's a first visit to a destination, or you're planning a quick reset and want the logistics handled without ceremony.

Uncharted Core — the most trips fit here

Uncharted Core is the tier that fits the majority of planned trips. At $395 with a 5–7 day turnaround, it covers 4–10 days and builds a full trip blueprint rather than a condensed itinerary.

The deliverable here is a day-by-day structure with morning, afternoon, and evening flow for each day — not a list of things to do, but a designed sequence with rhythm. Three to five stay options with clear notes on the differences between them. Eight to twelve restaurant recommendations integrated into the flow, not appended as a separate list. Eight to twelve curated experiences that balance the iconic and the less obvious. Transportation guidance between key destinations. One revision round built in. Mobile-friendly delivery that you can use on the ground without carrying a binder.

The difference between Core and a list of recommendations is the structure. Anyone can compile twelve restaurants in Lisbon — the work is in deciding which three to book in advance, which to walk in for, which to save for the slow afternoon, and which to skip because the hour doesn't line up with where you'll be. That sequencing is what the Core deliverable actually contains.

Core is the right tier for a week in one place where every day has to land. It's also the right tier for the trip you've been promising yourself — the one where a disappointing prior trip has raised the bar for what "planned" means. If you've done a week somewhere and come home feeling like you missed what the place actually was, Core is the answer. It's designed to remove the gap between the trip you planned and the trip you lived.

Uncharted Core fits best when: the trip is 4–10 days, you want every day designed rather than outlined, you're traveling to a single destination or a main destination with one or two clear day trips, and you want the restaurants, stays, and experiences sequenced rather than listed.

Deep Uncharted — multi-destination, milestone trips

Deep Uncharted is structurally different from the other two tiers — not just longer, but built differently. At $1,095 and up with a 7–14 day turnaround, it covers 10–21 days and handles trips where multiple destinations, transitions, and sequencing across weeks are all part of the design problem.

The deliverable includes a full day-by-day itinerary across the entire trip, multi-destination flow and routing, 15–25 restaurant and experience recommendations integrated into the travel flow, complete logistics mapping (flights, trains, ferries, transfers), packing and atmosphere guidance specific to the trip's tone, trip narrative flow notes on how the journey evolves emotionally across destinations, and up to two revision rounds. The format is mobile-optimized and interactive, designed to be read rather than scanned.

What makes Deep different isn't the volume — it's the narrative architecture. Each destination, each stay, each transition is designed to build on the last. A honeymoon in two countries should feel like a single journey, not two separate trips stitched at the border crossing. A three-week sabbatical through Japan should have a shape — a pace that starts open and closes contemplative, or moves from high-stimulus cities to quieter rural days. Deep Uncharted designs that shape explicitly. Nothing is random; everything has intention.

This is the tier for honeymoons, milestone anniversaries, sabbaticals, two-week trips across multiple countries — the ones where a wrong transition or a misread tone costs more than inconvenience. It's not Core with more days added on. The deliverable is built to be read before you leave and referred to throughout the trip.

Deep Uncharted fits best when: the trip is 10–21 days, it spans multiple destinations, the stakes are high (honeymoon, once-in-a-decade milestone), and you want every element — logistics, sequence, tone, narrative — deliberately designed.

How to pick the right tier

The tier choice tracks the trip's shape, not the budget. A long weekend in Nashville is Wanderlight whether the hotel is $120 a night or $400. A week in Florence is Core whether you're eating simply or booking ahead everywhere. A two-week trip across Portugal and Morocco is Deep whether you're traveling on a precise budget or with full flexibility.

The cleanest filter is this one: how many days, how many places, and how much do the transitions between them need to be designed? Two to three days and one place: Wanderlight. Four to ten days and one place: Core. Ten or more days and multiple places, or a milestone trip where the shape of the journey matters: Deep.

If you're between tiers, I'll flag it when I review the intake. I'll tell you which way I'd lean and why, and you make the call. I'd rather right-size you than upsell you — the wrong tier produces the wrong deliverable, and that's not something I want to solve in revisions.

For a closer look at what the deliverable actually contains at each tier, the services page has the full breakdown. If you're leaning toward Core and want to understand what a full trip blueprint looks like in practice, Uncharted Core goes into detail on the day-by-day structure.

Add-ons — what extends the tiers

The tiers cover the core planning work. The add-ons extend in specific directions without changing what the tier delivers.

Priority Delivery is the most common. It cuts the turnaround time roughly in half — useful when the calendar is the constraint and you need the deliverable faster than the standard window. It runs $75 to $200 depending on tier.

The Restaurant Strategy Pack adds the reservations layer: booking timing, seating notes, which table to ask for, whether you want me to book directly on your behalf when that's possible. At $45, it's the right addition for travelers who care about food the way they care about stays. The pack goes well with Core and Deep, where the restaurant count is high enough that a strategy document earns its place.

On-Trip Support is $25 per day and gives you same-day access by text — last-minute swaps, weather contingencies, the kind of thing that comes up mid-journey when the plan needs to bend. Most Wanderlight and Core trips don't activate it. Honeymoons and multi-destination Deep trips often do.

Add-ons stack on top of the tier; they don't substitute for depth the tier doesn't include. If you want the restaurant strategy that Core or Deep provides, the add-on works. If you want the full day-by-day structure that Core provides, a Wanderlight with add-ons won't produce it — the tier is the foundation.

What to read next

• How the Uncharted planning process works, step by step — inside each stage of the process, from intake through delivery.
• How curated travel works (and why it beats more research) — what curation actually means versus a longer to-do list.
• Planning a honeymoon without the hype — how the Deep tier applies to milestone trips for two.
• A week of slow travel in Lisbon's Alfama — a look at what a Core-level planned week actually produces in practice.
• The services page lays out all three tiers side by side with full deliverable lists.

When you're ready to start, the intake form is the brief. Fill it out for the trip you're planning — not the trip you wish you were planning — and I'll confirm the tier in my reply. If I'd recommend a different level, I'll explain the reason before you pay anything.