Itinerary planner

Guests plan their whole stay — before they pay

A day-by-day planner in your checkout: guests browse your experiences and add-ons, place them on the days of their trip, ask for a time, or let AI lay the stay out. You see the itinerary on the reservation. Returning guests are welcomed back with a gift.

See upsells & experiences

What you get

  • A planning step between the dates and the payment, built from your upsell catalog
  • Every offer lands on a day — with a time the guest asks for and you confirm
  • "Plan my stay" lays out the trip in one tap, with every pick explained
  • Returning guests get the gift you choose, pre-added and marked as yours
  • The itinerary lives on the reservation, in the guest portal, and on your phone

An add-on checkbox sells one thing. A plan sells the stay.

Most booking flows offer extras as a list of toggles squeezed above the pay button — no sense of when anything happens, no room to browse, nothing that feels like a trip. Guests skip them. Haven turns that moment into a planner: the days of the stay down one side, your offers in a vivid shop on the other, and a cart that fills as the week takes shape. A guest who has placed breakfast on Saturday and a massage on Sunday has already imagined the trip — and bought it.

How it works

1

Dates in, planner opens

When a guest picks dates and taps Book, Haven opens the planner before checkout: their stay laid out day by day, your experiences and add-ons as searchable, filterable cards with photos, video, and what’s included.

2

Place it on a day, ask for a time

Tap an offer, pick the day it belongs to and — for day-based offers — the time they would like. Timed offers with host slots show the slots and what is still open. The same offer can go on several days, each its own line.

3

Or let AI plan it

"Plan my stay" reads your catalog and the guest’s dates and party, then proposes a plan with a one-line reason for every pick — pickup on arrival, breakfast in the morning, the celebration dinner on the last night. Deterministic guardrails drop anything your catalog cannot honour before the guest sees it.

4

Returning guests find their gift waiting

On any upsell, choose what a repeat guest gets: nothing special, a gift on the house after N stays, or an offer with your note. Haven recognises the guest and pre-adds the gift to their plan — $0, list price struck through, "Gift from your host".

5

The plan carries into checkout and onto the booking

Checkout shows the plan as a summary with an Edit link, prices it from the same pricing pipeline as the stay, and freezes it on the reservation. You confirm requested times, reschedule, or add items to a day from the reservation — on desktop or your phone. Guests see the itinerary in their guest portal and can add more.

Watch a stay get planned

From an empty weekend to a full one — in one screen.

The pickup pins itself to arrival. The guest asks for dinner at seven. AI fills Saturday and Sunday around it. A returning guest finds her breakfast already on the plan, as your gift. You confirm the time from your phone and the whole plan lands on the booking — commission-free.

Plan your stay · The Dock House
Welcome back, Anna

Fri

Arrive

Airport pickup

3:40 pm$85

Sat

Floating breakfast

8:30 am$45$0
Gift from your host

E-bike day

10:30 am$70
Planned by AI

Sun

Couples massage

4:00 pm$190
Planned by AI

Chef dinner

7:00 pm$320
Time requested
Planning the rest of your weekend…
Nothing planned yet$0Continue to checkout
Your reservation · Itinerary

Chef dinner · Sun · 7:00 pm requested

Confirm timeor pick another
Floating breakfast · your gift · 3rd stay$0
Plan sent to your phoneFri 3:40 pickup · Sat 8:30 breakfast, 10:30 e-bikes · Sun 4:00 massage, 7:00 dinner
Extras on this booking+$665 · 0% commission

Key capabilities

Built for

Hosts whose extras are experiences

Floating breakfasts, massages, boat days, chef dinners — things that happen at a time on a day, and sell better when the guest can see the week they are building.

Villas and lodges with arrivals to arrange

Airport pickups and arrival provisioning pin themselves to the check-in day, so the logistics are sold with the stay instead of arranged over text later.

Anyone with regulars

Welcome a third-stay guest with breakfast on the house before they have even paid — and let them see it was from you.

Hosts who want AI to sell, carefully

The planner proposes a sensible stay from your catalog, explains every pick, and never invents an offer, a price, or a time your setup cannot honour.

Because it’s one platform

The planner is a view over the same upsell catalog, pricing pipeline, reservation, and guest portal as the rest of Haven — which is why a planned breakfast is also a priced line, a fulfillment task, and a card in the guest’s portal.

Built from your upsells

Every card in the planner is an experience or add-on you already configured — pricing shapes, inventory, scheduling, and approval rules included.

See upsells & experiences

Delivered through tasks

A planned chef dinner on Sunday at seven becomes a dated, timed task offered to your chef by text, with a Stripe payout when it is done.

See tasks & fulfillment

Kept in the guest portal

The itinerary the guest built at checkout is the one they open on arrival — pinned on the guest portal’s Home and editable from its Offers tab.

See the guest portal

A planner vs. the usual add-on step

Toggles above the pay button

A list of checkboxes with no sense of when anything happens. Guests skip it. The planner makes the extras the shape of the trip.

Arranging extras over text after booking

No record, no payment, no schedule until someone remembers. Planned items are paid, dated, timed, and on the reservation before arrival.

A generic AI concierge

Suggestions with no connection to what you actually sell or when it is available. Haven’s planner only places offers from your catalog, on dates and times you can honour, and shows its reasoning.

Related features

Native Upsells: Experiences & Add-ons

Sell retreats, chef dinners, rentals, late checkout, and provisioning around every stay — with real inventory, scheduling, quotes, and a fulfillment queue. Paid through your Stripe account, 0% Haven commission.

Guest portal & digital guidebook

Haven’s guest portal comes with a built-in vacation rental guidebook — arrival instructions, Wi‑Fi, house rules, and local tips — beside guest ID verification, rental agreements, and upsells, in one branded link. It works on its own, with no Haven booking website required: auto-send it to Airbnb, Vrbo, and PMS guests, and optionally capture emails into your CRM.

Vacation Rental Task Management & Fulfiller Payouts

Turnover cleans and upsell jobs become tasks automatically. Offer them to your cleaner, chef, or driver by SMS, WhatsApp, or email — they reply Y to accept and DONE when finished, no app or login — and pay them through Stripe with one tap.

Guest Loyalty Points

Points guests earn on every stay and spend next time — alongside the gifts you choose for them here.

Related solutions

Grow Your BookingsRepeat Guests & Loyalty
All featuresSolutionsPricingContact

Frequently asked questions

Bookings and booking requests do, when you have at least one offer that can be sold at checkout. If there is nothing to plan, guests go straight to checkout. Inquiries skip it. Guests can also skip the planner with one tap and still see your offers in their guest portal later.

On a day-based offer the guest can request a time. It is saved with the booking as a request, shown on the reservation with a Confirm button, and you can confirm it or set another time. Offers sold as fixed time slots are booked directly into an open slot instead.

It reads your catalog — names, descriptions, scheduling rules — and the guest’s dates and party, then proposes a plan with a reason for each pick. A deterministic validator then removes anything your setup cannot honour: ineligible offers, dates outside the stay, times outside your slots, overlapping timed items, quantity or lead-time limits. The guest reviews the result and can use it, merge it, or try again. The reasoning is saved on the booking so you can see why each item was suggested.

By their prior completed stays with you — matched on their account or the email they book with. You set the threshold per upsell (after one stay, after three, and so on). Gifts are pre-added to their plan at $0 with the list price struck through and marked as a gift from you; "Offer it" shows the item with your note instead.

A gift is a $0 line on the booking; nothing is charged to the guest for it and Haven takes no commission on upsells. You still fulfill it like any other item — it appears on the reservation and in your fulfillment queue, marked as your gift.

Yes. From the reservation, each day has an Add-to-this-day button that opens your catalog or a custom item with a price, date, and time. Items you add go on the guest’s tab and show in their guest portal itinerary.

The pre-checkout planner is part of your direct booking flow. Guests who booked elsewhere still get the itinerary in their Haven guest portal — pinned on Home, with an Itinerary view on the Offers tab where they can add items to any day of their stay.

Next step

Let guests build the trip — and buy it — before they pay.

Turn your checkout into a planner in minutes. It runs from the upsells you already have.

Book a demo