Connect Claude to Gmail and Booking.com

I had a week of unread email waiting and a trip to book, and I did both the same way I always had: open Gmail, read down the list, decide what matters, then open four hotel tabs and compare them by eye. Neither job is hard. Both eat an afternoon in ten-minute pieces.

Claude can do both, but only after you connect it to the services. A connector is the permission: Gmail for your mail, Booking.com for live hotel prices and availability. Each one takes about four minutes to set up, and neither asks for your password.

On a demo inbox of ten emails, Claude read the unread ones and came back with a ranked list in 33 seconds, and drafted the reply that mattered in 12 seconds more. The hotel shortlist, with per-night maths, took one message once I knew which filters to leave out.

This finding is free. It shows the setup for both connectors on video, the prompts that work, and the two traps that make the Booking.com connector look broken when it is not.

What a Claude connector actually does

A connector signs Claude in to a service the same way a phone app does: you approve the access once, on the service’s own screen, and Claude gets a token rather than your password. You can see every connector you have under Customize, Connectors, and switch one off there in two clicks.

What it does not do is act on its own. With Gmail connected, Claude reads and searches your mail, and writes a reply into the chat. The reply reaches Gmail only when you ask for a draft, and the draft sits in Gmail unsent until you press Send.

Why “summarise my inbox” is not enough on its own

The first prompt everyone tries is “summarise my emails”, and it comes back with a list that mixes an urgent client bug with a newsletter, because nothing in the request says what urgent means to you.

The fix is boring: say which mail to look at (a label, a date range, unread only), and say what the answer is for (“what needs a reply from me today”). The prompts in this finding are written that way, and you can paste them.

Why the Booking.com connector looks broken and is not

Ask for hotels in a city, under a price, with a rating floor, and you get nothing back. I got nothing three times in a row, at two different budgets, and Claude itself concluded the connector was down.

It was not. The same connector, asked for the same city and dates with no price and no rating filter, returned ten properties. Two facts explain it, and both are easy to work around once you know them: the price that comes back is for the whole stay, not per night, and most properties come back with no review score at all, so a rating floor quietly removes them. The finding shows the prompt that works instead.

Quick start

For when you just want both connectors on and one prompt that works.

1. Open claude.ai and sign in. Connectors are set up on the web, and they then work in any chat on any device.
2. Open Customize. It sits in the left menu, under Projects and Artifacts.
3. Open the Connectors tab. Yours lists what you already have, Discover lists everything available.
4. Find Gmail and open it. The page names every tool the connector may use, such as search_threads, create_draft and reply.
5. Press Connect to Claude. Google’s own screen opens.
6. Choose your account and allow the access. Claude receives a token, never your password, and you can withdraw it later from the same page.
7. Search the directory for Booking.com and connect it the same way. It has no sign-in screen, so it finishes in one click.
8. Ask for something narrow. “Summarise my unread emails from the last 7 days, most urgent first” is the one to start with, not “summarise my inbox”.
9. For hotels, leave the filters out. Ask for the city, the dates and the number of guests, then have Claude shortlist by price and rating from what comes back. The reason is in “When it breaks”.

Connecting Gmail, on video

Thirty seconds, from Customize to a connected Gmail. Google’s own approval screen is not filmed, because it shows the address of whoever is signing in; the card in the middle of the video marks where it appears.

What the video does not say out loud: the tool list on the connector page is worth reading before you press the button. Gmail’s includes send_message and trash_message, so it is not a read-only connector, which is why the rest of this finding keeps sending in your hands.

Connecting Booking.com, on video

Twenty-five seconds, and no account screen at all, because the connector searches public availability rather than anything of yours.

What each connector can and cannot do

Gmail can read, search, label and draft. It searches with the same query syntax as Gmail itself, which is why every prompt here scopes the mail first: label:, is:unread, newer_than:7d, from:. It can create a draft in an existing thread, and it can send, but only when you ask in so many words.

Claude answers in the chat first. Ask for a reply and the text appears in the conversation, not in Gmail. That is a feature: you read it before it exists anywhere else. “Save that as a draft in Gmail” is the step that moves it, and the draft then sits unsent until you press Send yourself.

Booking.com can search availability and answer questions about a property. It returns real prices and ratings for real dates. It cannot book, cannot pay and cannot see your Booking.com account or past trips. The booking itself happens on Booking.com, in your browser, with your card.

Using Gmail without handing over your inbox

The demo below ran against a label holding ten messages, so nothing private is in the screenshots. The same prompts work on a real inbox.

Step 1: Scope the mail, then ask

Paste this, changing the label or dropping label: to use the whole inbox:

In label:demo-f003, summarise my unread emails from the last 7 days, most
urgent first. For each one give the sender, one line on what it asks for, and
whether it needs a reply from me today.

1. Read the order, not just the summaries. The answer is a ranking, and the ranking is the useful part: the client whose contact form is broken came first, the expired discount came last.
2. Check one against Gmail. Open the top thread yourself the first time, to see that nothing was invented.
3. Reply in the chat if the order is wrong. “Move anything about money to the top” re-ranks without another search.

In the recorded run this took 33 seconds for eight unread messages.

Step 2: Get the reply written

Draft a reply to Ana's quote request: a five-page site with a cake order form,
$1,400, four weeks, and I can start on 6 October. Friendly and short.

1. Give it the facts it cannot know. Price, scope, dates. Everything else it can take from the thread.
2. Read what comes back for the catch. In the recorded run it flagged, unprompted, that starting on 6 October plus four weeks lands after the launch date the customer had asked for.
3. Fix the wording in the chat. “Shorter, and drop the last paragraph” is faster than editing in Gmail.

Step 3: Move it to Gmail, still unsent

Save that as a draft in Gmail, in the same thread. Do not send.

1. Open Gmail and look at the draft. It sits in the thread it belongs to, with the quoted original underneath.
2. Press Send yourself. This is the only step that puts mail in the world, and it is deliberately yours.

Using Booking.com without empty results

Step 1: Search wide

Find places to stay in Lisbon for 9 to 12 October, two adults. No price or
rating filter. Then shortlist the three best-rated that work out under 150 euros
a night, and show the per-night maths.

1. Leave price and rating out of the search itself. The filters are what empty the results; the shortlist happens afterwards, in the answer.
2. Read the per-night maths. Prices come back for the whole stay, so a “EUR 364” property over three nights is about EUR 121 a night.
3. Expect unrated properties. Small apartments and guest houses often have no review score at all, and they are not necessarily bad.

Step 2: Ask about one property

For Hygge Smart Stays, is breakfast included, is there parking, and what is the
cancellation policy for those dates?

Step 3: Book it yourself

1. Open the Booking.com link from the answer. Prices move, so check the figure on the page before you commit.
2. Book in your browser. Claude has no card, no account and no way to reserve anything.

Ready-made prompts

Sixteen prompts, in the same shape as the ones above: they scope the mail or the dates, ask for one thing, and keep sending and booking manual.

Download connector-prompts.md Download connector-prompts.txt

# Prompts for Claude with the Gmail and Booking.com connectors

Change the parts in CAPITALS. Every prompt says which mail to look at, or which
dates to search, because a vague request is what produces a vague answer.

## Gmail: reading and triage

1. Triage the week

   In label:LABEL, summarise my unread emails from the last 7 days, most urgent
   first. For each one give the sender, one line on what it asks for, and
   whether it needs a reply from me today.

2. Only what needs answering

   Which emails in the last 3 days actually need a reply from me, and which can
   wait until next week? Say why for each.

3. Find one fact

   Find the invoice from SENDER and tell me the amount, the invoice number and
   the due date. Quote the line it comes from.

4. Catch what slipped

   Show me threads from the last 14 days where someone asked me a question and
   I never replied.

5. One sender, one story

   Summarise everything SENDER and I exchanged this month, in order, ending with
   what is still open.

6. Before a meeting

   I have a call with SENDER tomorrow. Summarise our last three threads and list
   the open questions I should be ready for.

## Gmail: writing, without sending anything

7. A reply, in the chat first

   Draft a reply to SUBJECT: I can do SCOPE for PRICE, in TIMELINE, starting on
   DATE. Friendly and short. Do not send it.

8. Move it to Gmail

   Save that as a draft in Gmail, in the same thread. Do not send.

9. A polite no

   Draft a short, warm decline to SUBJECT. No excuses, no long apology, and
   offer DATE as an alternative if that works.

10. Chase without nagging

    Draft a follow-up on SUBJECT. It is the second time I am asking, so keep it
    one short paragraph and make the ask specific.

11. Same answer, many threads

    List the threads from the last month asking about TOPIC, then draft one
    reply I can adapt for each, and say what to change per thread.

## Booking.com: searching

12. The search that works

    Find places to stay in CITY for DATE to DATE, NUMBER adults. No price or
    rating filter. Then shortlist the three best-rated that work out under
    PRICE a night, and show the per-night maths.

13. Near a place, not a district

    Same dates and guests, but near LANDMARK. Give me the walking time from
    each one to LANDMARK.

14. Compare two named hotels

    Compare HOTEL A and HOTEL B for DATE to DATE, NUMBER adults: price for the
    stay, price per night, rating, and what each includes.

15. One question about one property

    For PROPERTY, is breakfast included, is there parking, and what is the
    cancellation policy for those dates?

16. What to do once you are there

    What is worth doing within walking distance of PROPERTY on a Saturday
    morning? Keep it to five, with the walking time from the hotel.

## Rules worth adding to any of them

- Ask for the source: "quote the line you got that from".
- Ask for the gap: "say what you could not find, rather than guessing".
- Keep sending manual: "draft it, do not send it".
- On an empty hotel search: "drop the filters, search again, and filter the
  results yourself".

Paste one into any chat once the connector is on. For the Claude app, the same text works as a project instruction if you use the prompts often.

When it breaks

“I found a few hotel search options” instead of an answer. Claude asks which connector to use when several could serve. Name it in the prompt: “Using the Booking.com connector, find…”.

Every hotel search comes back empty. This is the big one, and it looks like an outage. Asking for Lisbon with a price cap and a rating floor returned nothing three times, at two different budgets, and with the destination named instead of coordinates. The same connector, same city, same dates, with no filters at all, returned ten properties. Two causes: the price that comes back is for the whole stay, not per night, so a nightly cap compares the wrong numbers, and most properties have no review score, so a rating floor removes them silently. Search wide, filter in the answer.

Claude says the connector looks broken. It concluded exactly that during testing, and it was wrong. Before believing it, run one deliberately loose search: city and dates only. If that returns results, the filters were the problem.

The reply never arrives in Gmail. Claude wrote it in the chat, which is where it stays until you ask for a draft. Say “save that as a draft in Gmail”.

“Nothing matches” for mail you can see in Gmail. The search syntax is Gmail’s own. label: wants the label exactly as Gmail spells it, and a label with a space needs quotes: label:"Client work".

The connector was connected and now is not. Tokens expire, and changing your Google password ends them. Open the connector page and press Connect again; the prompts and drafts are unaffected.

Turning a connector off

Not something to do routinely. Disconnect when you stop using it, when you no longer want Claude reading that mailbox, or when an account changes hands.

1. Open Customize, then Connectors.
2. Open the connector.
3. Use the menu beside the button and choose to disconnect. Access ends immediately.
4. For Gmail, remove it at Google too, under Account, Security, Your connections to third-party apps. That is what revokes the token itself.