For sailing, catamaran & yacht charter operators

Your charter's booking first mate 

Sail.OS answers guest inquiries instantly, captures their preferences, routes agency bookings straight to you, and keeps everything in one dashboard. Built and running on a real working charter.

No lock-in·Cancel anytime·Chat box, WhatsApp or one inbox — your build
This week aboard
Brittany Wind · March
Sail.OS on duty
14
inquiries answered
3
weeks booked
40s
median reply
Waiting on you · 1 tap to accept
14 – 21 April · 8 guests
Blue Horizon Charters · $6,400
Accept Decline
Confirmed · handled while you sailed
MJ Marta & Jonas · 2–9 Mar · preferences in Deposit paid
FK Familie Krause · 16–23 Mar · menu planned Provisioned
RD Rossi party · 30 Mar–6 Apr · 6 guests Contract sent
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What changes

Your booking desk, handled — while you run the boat.

Same number, same guests. From the first week, the answering, the chasing and the small print happen without you.

Answered in minutes, day or night

Guests hear back while they're still choosing a boat — in their own language, at any hour.

Accept a booking with one tap, from phone or computer

Guest and agency requests land on your own approvals page. Open it, tap accept, and the reply goes out for you.

Guests dialled in before they board

The preferences quiz and the menu planner settle diets, experience and the week's meals in advance. Provisioning gets easy.

One screen for the whole season

Calendar, conversations and confirmed bookings in a single view. Open it with your coffee and you're up to date.

Take over a thread whenever you like

Switch the AI off for one guest and answer in your own words. It keeps handling everyone else, and picks that thread back up the moment you hand it back.

How it works

Three steps, one call, no new app for your guests.

STEP 01
Pick where guests reach you

On the call we wire up the channel you want: a chat box on your site, a WhatsApp line of the boat's own, or both landing in one inbox. Guests write from wherever they found you — there is nothing for them to install.

STEP 02
Your first mate takes the first shift

It answers questions in the guest’s own language at any hour. Once a booking is confirmed it sends on whatever you want built in — transport contacts, house rules, the preferences quiz, the menu planner.

STEP 03
You approve, and the calendar fills

Agency requests are dealt with the same way, and Sail.OS tells you whenever your input is actually needed. One tap to confirm, and the dashboard keeps the season straight. If a guest would rather hear from a human, switch the AI off for that thread and take it over yourself.

Walk through it with us — book 15 minutes →
In action

This is a Tuesday morning with Sail.OS.

Two conversations on the same number. One closes itself while you're at anchor. The other waits for your yes.

MJ
Marta & Jonas · Madrid
Guest inquiry · answered by the first mate
Hola! Is the catamaran free the first week of March? We'd be six adults.
08:42
Hi Marta — yes, 2–9 March is open. Six is comfortable aboard: three double cabins, each with its own head.
08:42
That week runs at our March all-inclusive rate, skipper and cook aboard. Shall I hold the dates for 48 hours while you decide?
08:43
Yes please. One of us is vegetarian, and two have never sailed before.
08:51
Noted, and welcome aboard for a first sail. I've held 2–9 March and sent you a two-minute preferences form so the cook and skipper can plan around it.
08:51
Dates held Preferences form sent You were never woken up
BH
Blue Horizon Charters
Agency · routed straight to you
Do you have 14–21 April open? Client with 8 pax, flexible on the exact islands.
09:05
Agency recognised — no automatic reply sent
Waiting on you
14 – 21 April · 8 guests
Blue Horizon Charters · your April rate applies
Approve & reply
Not available
14–21 April is yours. Contract and deposit link are on their way.
09:12
Approved by you in one tap Calendar updated Contract sent
Automated, with you as the backstop
The first mate works for you. 
Nothing binding, unapproved

Prices, dates, contracts and every agency request wait in your queue until you say yes.

Step in mid-sentence

Take over any thread from your phone and the first mate steps back instantly. Hand it back whenever you like.

Every message kept

Conversations, quotes and preferences are logged and searchable — a written record of the season, backed up off the boat.

Have this conversation yourself → A replayed thread. Sail.OS is live — message it yourself.
What you get

The desk keeps working while you sail.

Built on current frontier language models, not a scripted bot. Around nine in ten guests never work out they were not writing to a person.

Take over whenever you like

Switch the AI off on any thread and write as yourself, from phone or computer. Switch it back on and it picks the thread up where you left it.

AI first mate

Answers guest questions around the clock, in their language, on the channel they already use. Warm, on-brand, never off duty.

Guests handled, agencies to you

Ordinary guest questions get answered on their own. Anything from an agency comes to you first, so you decide before a word goes out. Nothing sits unanswered either way.

Take over whenever you like

Switch the AI off on any thread and write as yourself, from phone or computer. Switch it back on and it picks the thread up where you left it.

Preferences quiz and menu planner

Diets, allergies, sailing experience and the week's meals — guests settle it all in their own browser before they board. Provisioning is decided, and it is waiting for you in the dashboard.

One-tap approvals page

Every inquiry and agency request queues up on a simple web page of your own. Open it, tap accept, and the reply goes out written the way you'd write it.

Take over whenever you like

Switch the AI off on any thread and write as yourself, from phone or computer. Switch it back on and it picks the thread up where you left it.

Owner dashboard

Bookings, conversations and calendar in one clean view. Open it once with your coffee and you know where the season stands.

Text your expenses, get the books

Message the cost from the dock — "diesel 180, ice 12" — or photograph the receipt. Every charter's fuel, food and marina fees add up on their own, and your accountant gets the spreadsheet.

The dashboard

Everything you need to know, in one window.

Three views, and you'll live in all of them. What needs a decision today, where the season stands, and who is actually coming aboard.

Click through the views — this is the real layout.
Swipe to explore
app.sailos.co / wind-dancer
Sat 8 Aug
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Search New booking
Open enquiries
7
3 new since Monday
Awaiting your OK
3
Oldest waiting 40 min
Booked in August
24 / 31 nights
Best month this season
August occupancy
77% 24 of 31 nights
18 booked 6 held 7 open
Next departure
Mon 10
Familie Weber · 6 aboard
August 2026
Booked Held Yard
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24 of 31 nights held or bookedOpen the calendar →
Needs a decision Nothing sends without you
Sunsail Brokers — 12–15 Aug
4 cabins at agency rate, €3,850. Below your floor by €150.
Adjust Approve
Familie Weber — early boarding
Asking to come aboard 09:00 instead of 16:00 on the 10th.
Decline Approve
Marchetti party — quote drafted
7 nights in September, 5 guests, €4,900 with skipper.
Edit Send
Live threads First mate replying
FW
Familie Weber2 min
Können wir Bettwäsche für sechs Personen…
SB
Sunsail Brokers14 min
Confirming the cabin split for the 12th…
LR
Lucía Ramírez31 min
¿El barco lleva tablas de paddle surf?
Answered without you: 31 messages this week.
August 2026
‹ ›
Mon
Tue
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1
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Familie Weber · 6
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Nilsson · 8
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Confirmed charter Held, waiting on your OK Owner block Held dates go back on the market automatically if the broker goes quiet.
All Confirmed Enquiries Repeat guests Has dietary notes
PartyDatesAboardLanguageWhat they told usStatus
FW
Familie Weber
weber.m@web.de
10–17 Aug
6
German
No shellfish, one vegetarian. Two strong swimmers.
Confirmed
SB
Marchetti · via Sunsail
bookings@sunsail-br.com
12–15 Aug
5
Italian
Landing 23:40, needs a late boarding. Agency rate.
Awaiting OK
NP
Nilsson party
e.nilsson@telia.se
17–24 Aug
8
Swedish
Two gluten-free. Third charter with you.
Confirmed
LR
Lucía Ramírez
+34 6•• ••• 214
2–6 Sep
4
Spanish
Wants paddleboards and snorkel gear aboard.
Enquiry
TO
The Okonjos
a.okonjo@gmail.com
9–16 Sep
7
English
Birthday on the third night — cake, quietly arranged.
Deposit paid
DF
Dubois family
c.dubois@orange.fr
20–27 Sep
6
French
Two children under five. Asked about safety nets.
Enquiry
Every line here was filled in by the conversation, not by you.
Built on a real boat

We wrote this between charters,

Sail.OS runs the bookings for Brittany Wind Charters — a 2018 Leopard 40 running private charters in Guna Yala, Panama. Every feature exists because a guest, a broker, or one busy season made us build it.

The first mate learns from a real season, so it gets sharper the same week something comes up. You get software that keeps pace with how charters actually run.

Ask us anything on a 15-min call →
Aerial view of the Brittany Wind Leopard 40 catamaran anchored in turquoise water beside a palm-lined San Blas island
THE BOAT ON THE OTHER END
Brittany Wind Charters
2018 Leopard 40, Guna Yala
8+2
guests aboard
4
cabins, 100% private
8
guest languages

Private all-inclusive charters, booked through the same WhatsApp first mate you're looking at. Whatever language a guest writes in, someone on that crew speaks it — and so does the first mate.

See the charter it runs — brittanywindcharters.com →
Pricing

One recovered booking pays for the year.

Monthly, transparent, cancel anytime. Your channel, your server and your AI are all in the price — nothing else to buy, nothing billed per message.

Where guests reach you
Web chat on your site Included
How many boats
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First boat is in the base price. Every boat after it is $120.
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Get Sail.OS
In every price
—Instant guest replies
—Quotes and 48h holds
—Preferences quiz and menu planner
—Approval queue
—Expense tracking
—Owner dashboard
—Every language a guest writes in
Prices in USD. Server, AI and channel fees are inside the price — there is no second bill and nothing is charged per message. The outright install puts Sail.OS and its model on a machine you own, with no subscription at all; the trade-offs are laid out under Personalized build. Larger fleets and agencies — talk to us on the call.
Your build

A default Sail.OS, or a custom one.

Two choices make your build: where guests reach you, and where the AI thinks. Sail.OS does the same work whichever pair you pick — what changes is who sees the conversations and what it costs. You don't have to decide before the call, and either half can move later.

Part one — where guests reach you
Chat box only

No phone number anywhere. Visitors open a chat on your own site, create an account, and pick the thread back up on any device — and you have an email address for every enquiry before they've asked a single question.

The lightest build. Sensible if your traffic already lands on your site.
WhatsApp number
Most start here

A WhatsApp line of the boat's own, issued through Twilio and live within a day. Put it on your listings, your website and your card. It stays separate from anything personal, so you can hand it to a manager without handing over your phone.

The number and its messages are in the subscription.
Unified inbox

Chat box, WhatsApp and email arriving as one thread per guest. Someone who writes on the site and follows up on WhatsApp stays a single conversation, and a team answers all of it from one view instead of three.

For fleets, agencies and anyone with more than one person answering.
WhatsApp is live today. The chat box and the unified inbox are in build — ask on the call and we'll tell you where they are. Using the number you already carry is possible and we'll try to talk you out of it: your private chats end up in the same account as your bookings, and anything that goes wrong goes wrong in front of your family too.
Part two — where the AI thinks
On your own machine
Maximum privacy

We install Sail.OS once on hardware you own, with a language model that runs on that same box. No provider, no cloud, nothing leaving the building — the conversations, the guest details and the model all sit in your office.

ModelLocal, on your hardware
Cost$3,000 once — no subscription at all
UptimeAs good as that machine and its connection
Trade-offThe machine has to stay switched on for the system to be live, and a local model answers less sharply
A rented server, local model
Private, always on

A VPS is a computer like the one on your desk, except it lives in a data centre and never sleeps. Yours runs Sail.OS and a model of its own — we rent it, patch it and watch it, and no AI provider sees a guest message.

ModelLocal, on the server we manage
CostServer and AI included in the subscription
UptimeAlways on, independent of the boat
Trade-offStill a local model, so still a step behind the cloud one
A rented server, API key
Best and fastest answers

Same managed server, except the thinking is done by a cloud model on our key or one of your own. This is what makes the answers read like a person in whatever language the guest wrote in, and it handles a messy enquiry best.

ModelCloud, our key or yours
CostIncluded, fair use to 3,000 enquiries a month
UptimeAlways on, independent of the boat
Trade-offGuest messages pass through the provider on their way to an answer
Part three — what else we build on top

The booking desk is the same for everyone. Everything below is quoted per boat, because it depends on what you sell and what you already have.

Upsells, offered at the right moment

Diving, a chef's dinner, an extra night, the airport transfer. Sail.OS offers them while the guest is still excited and planning, not in an email they never open — and it stops offering once they have said no.

Usually the first thing that pays for the subscription.
A website worth sending people to

If your site is old, slow or someone else's template, we build a new one around the boat with the chat box already in it. Photos, rates, the season, the enquiry — one page a guest can act on from a phone in bad signal.

Yours to keep, on your own domain and hosting.
Getting found without an agency

Search, maps and the listing sites that actually send charter enquiries, set up properly and in the languages your guests search in. The point is direct bookings, so the 20% an agency takes stays with the boat.

Slow work. Months, not a launch week.
An AI employee, not just a chat box

The same system can chase the review after a charter, remind the guest whose balance is due, answer the agency's paperwork, draft next season's rates from what you actually earned. If a job on your boat is words on a screen, it is worth asking about.

Tell us the job on the call and we will say honestly whether it is ready.
Not sure which pair suits you? That's most of what the fifteen minutes is for.
Straight answers

The questions operators actually ask.

Straight from the chat window on your own website — that route is included. If you add the WhatsApp channel, guests can write to a number we issue for the boat instead, and it goes on your listings, your site and your card. We deliberately don't automate the personal number you already use: your private chats would sit in the same account as your bookings, and that is a bad place for a mistake to happen.
It replies in whatever language the guest writes in. A German family, a Spanish broker and a French couple can all be mid-conversation at once, and each of them is talking to your boat in their own words.
Nothing binding happens without you. Prices, dates and agency requests go to your approval queue, and you can take over any conversation mid-sentence from the dashboard. The first mate handles the first ninety percent; you keep the last word.
One call to set up your channel and tell us about your boat, rates and season. We do the configuration and you are usually live in three to five days, after you have reviewed how it answers.
Your conversations and guest details belong to you. They're used to run your bookings, not sold, shared with other operators, or handed to anyone else. Where the data physically sits depends a great deal on which setup you choose — a managed server, a cloud model on an API key, or a machine aboard the boat all answer this question differently, so compare them under Personalized build and ask for the specifics on the call. If you'd rather nothing left your own hardware at all, the local install does exactly that.
No. If you can run a charter and use WhatsApp, you can run Sail.OS. The dashboard has one job: show you what's booked and what needs a decision.
About us

We run charters. We built the tool we needed.

Sail.OS came out of a working catamaran operation in Guna Yala, Panama — not a software office. Every part of it was written because something on our own boat was being missed: an enquiry that sat unanswered overnight, a dietary note lost between WhatsApp and a notebook, an agency request that arrived while we were three hours from signal. We use it every week of the season. Nothing reaches your boat until it has earned its place on ours.

Guna Yala
Built and tested aboard a Leopard 40 working the San Blas archipelago.
Independent
No investors, no agency ownership, no commission on your bookings.

Five questions and we build your boat’s system.

This is the real thing, not a trial. $130 a month covers the whole system on one channel — extra channels and extra boats are the only things that add to it. Answer five questions and we set yours up.

01 / 05 · YOUR CHANNELS

Where should guests be able to reach you?
02 / 05 · YOUR FLEET

How many boats are you taking bookings for?
03 / 05 · WHERE BOOKINGS COME FROM

Who sends you the most inquiries?
04 / 05 · LANGUAGES

Which languages do your guests arrive in?
05 / 05 · TIMING

When would you like to be live?
READY TO BUILD · 05 / 05

Here is your Sail.OS.

Send this over and we configure it against your rates, season and languages, then hand it to you live. One call, no card until you have seen it running.

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Fleet{{ a1 }}
Bookings from{{ a2 }}
Languages{{ a3 }}
Live by{{ a4 }}
Your price
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And it will handle
—Answering enquiries day and night
—Quoting your rates and holding dates
—Collecting guest preferences
—Sending agency requests to you first
—Planning the week's menu
—Logging expenses by message
Skip the questions, book a 15-min call Try live demo
No card until you have seen it running on your own boat.
SO
Wind Dancer · Leopard 40
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· · ·
·Build one as your boat