A sailing trip isn't planned on the pontoon but in the months before. Ten steps in the right order, with a timeline, common mistakes and the checklists you need.
In short
The best way to plan a sailing trip is backwards from the departure date: six to nine months before, decide on cruising area, dates and crew and charter the yacht. Three months before, sort out licences, crew list and travel and allocate the cabins. Six weeks before, settle the kitty and provisions and sketch out the route. In the last two weeks, prepare the packing list, safety briefing and check-in. On day one, check-in and safety briefing; after the trip, check-out and settlement. Stick to this order and there's nothing left to sort out on the pontoon.
There are two ways to plan a sailing trip. One starts three weeks before with a WhatsApp group in which twelve people ask at the same time who's actually coming and whether anyone still has a flight. The other starts nine months before with a list. On the pontoon you can tell the difference immediately.
This guide is the list. Ten steps in the order they come up, with a timeline that counts backwards from the departure date, and with links to the detailed checklists for each step. It's written for skippers organising a charter trip with friends, family or fellow club members — and works just as well for training trips.
| When | What |
|---|---|
| 6 to 9 months before | Cruising area and dates, crew, charter the yacht |
| 3 months before | Licences and documents, travel, cabins |
| 6 weeks before | Kitty, provisions, rough route |
| 2 weeks before | Packing list, safety briefing, prepare check-in |
| Day 1 | Check-in and safety briefing |
| Afterwards | Check-out, settlement, recap |
Everything starts with two decisions that shape all the others. The cruising area depends on the crew's experience: Croatia, the Balearics or the Ionian Sea forgive beginners' mistakes and have short legs. The Cyclades in the meltemi summer or the North Sea are for well-practised crews. The dates determine wind, price and how full the harbours are: July and August are expensive and crowded; May, June and September are the better choice for most crews.
Have two alternative dates ready before you ask the crew. Otherwise the group spends weeks discussing weeks when nobody can make it anyway.
The crew comes before the yacht, not the other way round. If you book first and look for people afterwards, you end up with empty berths or a boat that's too small.
What you need to know from everyone: a firm commitment, sailing experience, expectations of the trip. Who wants to sail 40 nautical miles every day, and who mainly wants to lie at anchor in bays? Asking this up front decides whether it'll be a good week. Later come licences, allergies, emergency contacts and cabin preferences.
In practice, this step fails at the collecting stage: commitments come by phone, licences as photos, allergies in a passing remark. In Sailto you send an invite link instead, and each crew member creates their own profile with licences, intolerances and cabin preference. You see on one page who has committed and what's still missing.
With a fixed crew, choosing the yacht is simple: number of cabins equals couples plus solo travellers, size according to cruising area and budget. A 40 to 45-foot yacht with three to four cabins is the standard for six to eight people.
What to look out for in the contract:
The down payment is usually 50 per cent on booking, with the rest due four to six weeks before the trip. Collect the crew's share of the charter before the second instalment is due — that's the trip's first small kitty.
Three months before, things get concrete. The skipper needs the licence the cruising area requires — in Croatia, for example, a recognised licence such as the German Sportbootführerschein See or an ICC, plus a radio certificate, usually the SRC. Check which licences your charter company and the local authorities accept. Do this early: a missing radio certificate can still be obtained in three months, but not in three weeks.
The crew needs ID and a health insurance card, and on training trips also the school's paperwork. At check-in the base will ask for a crew list with the name, date of birth, nationality and ID number of everyone on board; in many cruising areas it is passed on to the authorities. Collect the details now, not the evening before.
And raise the question of insurance: trip cancellation, travel health insurance, skipper liability insurance. Not every crew needs all of them, but every crew should have talked about it once.
Flights in the high season get expensive as soon as the school holidays are fixed. Book once the crew is settled. There's only one important rule: everyone is there on check-in day. Anyone arriving a day later misses the safety briefing and forces the crew to wait in harbour.
Plan the transfer to the marina at the same time. Many bases are an hour from the airport, and a shared taxi for eight people with kitbags needs organising.
Cabin allocation is the step most skippers put off because it gets personal. That's exactly why it belongs before the trip, not on the pontoon. Anyone who finds out while unpacking that they're sharing the forepeak with the snorer starts the week in a bad mood.
What to take into account: couples together, snorers alone if possible or with other snorers, early risers not in the saloon, people with back problems in the aft cabins with the straight berths. Collect preferences early and share the allocation two weeks before — that leaves time for swaps.
In Sailto, each crew member stores their cabin preference and snorer flag in their profile. The cabin planner shows the allocation to everyone, and with the Trip Pass you drag and drop the crew onto the yacht's cabin plan.
Six weeks before, it's about money. Two questions need answering before anyone spends a single euro.
How will you settle up? Does everyone pay as they go and the group settles at the end, or does everyone pay into a pot up front? Both work, but only if the crew knows the system beforehand. We compare the five common models in the article Sharing the kitty fairly.
How much will it be? As a rule of thumb, €25 to €40 per person per day for harbours, diesel, provisions and the odd restaurant visit, plus a 15 per cent buffer. The individual items and a worked example for a week in Croatia are in the article What does a sailing trip cost?
At the same time, the meal plan takes shape: which evenings will you cook, which will you eat out, who has which allergy or diet? That becomes the shopping list for day one. How to manage this without provisioning chaos is explained in meal planning for a sailing trip. With the Trip Pass, the AI meal planner in Sailto creates a suggestion from crew size, duration and intolerances and writes the shopping list for you at the same time.
The route is the part skippers most enjoy working on — and the part that needs the least advance planning. Roughly in advance, in detail each day. For a holiday crew, legs of 20 to 35 nautical miles are comfortable: cast off after breakfast, arrive in the early afternoon, time for a swim. Plan an alternative harbour and anchorage for each day so that strong winds or a full marina don't cause stress.
Two rules have proven themselves: the last day before check-out stays free as a reserve, so the return passage is never a race against the clock. And the longest leg comes in the first half, while the crew is still fresh.
The actual route for the day is decided by the morning weather forecast. Still share the rough plan with the crew in advance, so everyone knows what to expect — and what not to.
Two weeks before, three things go out to the crew and into your own preparation.
The packing list. Soft bag instead of a suitcase, layers instead of outfits, deck shoes with light-coloured soles, sun protection, personal medication. What really has to come and what's already on the yacht is in the sailing trip packing list, including a printable PDF. In Sailto, as skipper you add required items that every crew member has to tick off — so the head torch really does come along.
The safety briefing. It takes 15 minutes, and it needs to be prepared so that nothing is left out: lifejackets, man overboard, fire, gas, seacocks, radio, distress calls. What belongs in it and how to make it stick is in our article on the safety briefing on board.
The check-in checklist. Deck, rig, engine, electrics, bilge, inventory, documenting damage with photos. Print it or set it up in the app so you're not working from memory at the base. The full list: charter check-in checklist.
On day one, the preparation pays off. With a checklist, the check-in takes one to two hours: check every area, photograph every scratch, count the inventory, note defects in the check-in report. Then the safety briefing with the whole crew, before anyone casts off. In Sailto, each crew member confirms the briefing in the app — binding and traceable.
While under way, the kitty, shopping list and logbook run alongside. At the end comes the check-out: full tank, tidied up, with the check-in report in hand so the deposit comes back. And the settlement of the kitty, which with clean records takes two bank transfers instead of twenty.
If you need the sea miles for a licence such as the SKS or SSS, get the trip confirmed now — how that works is explained in the article on the sea miles log.
The ten steps aren't complicated. What makes it complicated is that they're spread across twelve channels: commitments in the chat, licences as photos, cabin preferences on the phone, the kitty in a spreadsheet, the packing list as a PDF, the safety briefing in your head.
Sailto puts these steps in one place. An invite link brings the crew together, each profile holds licences, allergies and cabin preference, and the kitty, shopping and packing lists, safety briefing and check-in all run within the same trip. Organising is free for good, for unlimited trips and with no crew limit. The extras — AI meal planner, drag-and-drop cabin planner, map with track — are unlocked for the whole crew by the Trip Pass.
A well-planned sailing trip starts nine months before casting off with cruising area, dates and crew, gets concrete three months before with documents and cabins, six weeks before with money and provisions, and ends in the last two weeks with the packing list, safety briefing and check-in preparation. Stick to this order and there's only one job left on the pontoon: casting off.
For the Mediterranean high season, six to nine months ahead, because good yachts and cheap flights go early. For the shoulder season or the Baltic, three to four months is enough. Either way, the crew should be settled before the yacht is booked — otherwise the number of cabins won't fit.
A 40 to 45-foot yacht has three to four double cabins and is full with six to eight people. If you want comfort, plan for two people fewer than there are berths. The number of cabins also determines the price per person, because the charter price is divided by the berths.
The skipper needs the licence that is valid for the cruising area — in Croatia a recognised licence such as the German Sportbootführerschein See or an ICC, or higher, plus a radio certificate such as the SRC. The crew doesn't need licences, but does need ID, a health insurance card and, on training trips, the school's paperwork. The base will ask for a crew list with everyone on board at check-in.
Roughly in advance, in detail each day. Legs of 20 to 35 nautical miles are comfortable for a holiday crew, plus one alternative harbour and one anchorage per day. Keep the last day before check-out free as a reserve. The actual route for the day is decided by the morning weather forecast.
Five things: the kitty model and the amount per person, the cabin allocation, how the deposit is handled, how often the crew eats out and who takes on which tasks on board. On top of that comes the safety briefing on day one, which every crew member must have heard.
The charter price divided by the berths, plus the kitty. For a week in Croatia in summer, that's around €550 as your share of the charter and €250 to €450 in the kitty for harbours, diesel, provisions and restaurants, plus travel. If you calculate the kitty in advance and collect it with a buffer, nobody has to top up later.