Plan your Sail with AI - Sea TV

Plan your Sail with AI






Plan Your Sail with AI — A Skipper’s 2026 Toolkit | SeaTV



SeaTV Toolkit · 2026 Edition

A Skipper’s AI Toolkit for 2026

I’m planning my June 2026 charter from Sardinia to Corsica using AI. Here’s the toolkit that actually works for sailors — and where every tool will quietly lie to you.

In June 2023 I wrote about ChatGPT and a planning tool called MindMap. MindMap is gone. ChatGPT is still here — but it’s no longer the only game in town, and using it the way I used to is leaving real value on the table.

Here’s the honest update. AI is genuinely useful for sailing — but only if you understand what each tool is good for, and where it will fabricate things that get you in trouble.

⚠ Reality check: AI will confidently invent marina depths, mooring fees, and even non-existent harbours. Every detail that touches your boat — depths, hazards, VHF channels — needs a second source. That’s where SeaTV comes in. More on that below.

The Three Layers of Sailing Planning

Stop asking one tool to do everything. Different AIs are good at different things. I think of trip planning in three layers — and I use a different tool for each.

Layer 1

Research & Discovery

Understanding the cruising area before you commit. Best for: Perplexity, Claude, NotebookLM.

Layer 2

Itinerary & Budget

Building a day-by-day plan and pricing it. Best for: ChatGPT, Claude, Google Gemini.

Layer 3

Weather & Routing

Decisions that affect the boat. Best for: PredictWind AI, Windy, SeaLegsAI.

Layer 1 — Research the Cruising Area

Before you book a charter, before you draw a single mile on a chart, you need to understand the place. Wind patterns. Anchorage protection. Local regulations. Marine reserves. Distances. This is where AI saves you days of forum scrolling.

Perplexity — for sourced answers

Perplexity is the only AI I trust with current factual questions, because every answer comes with a footnote linking to the source. Ask it “What are the marine reserve regulations for the Bouches de Bonifacio in 2026?” and you’ll get an answer with three or four citations from official sources. You verify in 30 seconds.

⚓ Claude — for digesting cruising guides

Claude has a much larger context window than ChatGPT, which means you can paste an entire 80-page cruising guide PDF and ask: “List every anchorage on the south coast with depth under 8 m, sand bottom, and protection from NW winds.” It will actually read the document and give you a structured answer. ChatGPT loses track. Claude doesn’t.

NotebookLM — for turning your library into a chatbot

Google’s NotebookLM lets you upload up to 50 sources — PDFs, websites, YouTube videos — and turns them into a research notebook you can query. Drop in your charter contract, three cruising guides, and the marina’s website. Now you have a single brain that knows everything about your trip and won’t hallucinate beyond what you fed it.

Layer 2 — Build the Itinerary

This is where my original 2023 prompt still earns its keep — but I’ve upgraded it. The new version forces the AI to think like a skipper, not a tourist: distances in nautical miles, daily sailing time, prevailing wind direction, anchorage protection.

Copy this prompt

Act as an experienced charter skipper familiar with [REGION]. I’m planning a [X]-day sailing trip starting from [START PORT] in [MONTH/YEAR]. Crew: [NUMBER, EXPERIENCE LEVEL]. Boat: [LENGTH, MONOHULL/CAT, DRAFT].

Build me a day-by-day plan with the following for each leg:

• Distance in nautical miles + estimated sailing hours at 5 kn average

• Prevailing wind direction & strength for that month

• Anchorage or marina with bottom type, depth range, and which winds it’s exposed to

• Approximate berthing fee (high season)

• One specific shore activity worth the stop

• A safety note specific to that leg

Then give me a total budget breakdown: marina fees, fuel estimate, provisioning, dining ashore, contingency. Flag any leg over 6 hours of sailing as a long day.

Run this in ChatGPT and Claude separately. Compare the answers. Where they agree — strong signal. Where they disagree — that’s where you dig deeper.

Layer 3 — Weather & Routing

This is the layer where AI changed the most since 2023, and the layer with the highest stakes. We’re now past the era of “ChatGPT, will it be windy on Tuesday?” Real weather AI is here, and it’s good.

PredictWind AI Polars

PredictWind now uses AI to learn how your specific boat sails. Plug in their DataHub, sail normally for a few weeks, and it builds a personalized polar diagram — including how you sail at night versus day. Result: weather routing that actually matches what your boat will do, not what a generic 40-footer would do. This was professional-navigator territory two years ago.

Windy AI wind forecast

Windy added a 24-hour AI wind prediction at every weather station, plus their EXP3 coastal model — an AI-powered model that captures wind shadows behind cliffs and headlands. For Mediterranean coastal sailing, where the funneling effect of mountains can double the wind in a kilometer, this is the closest thing we have to local knowledge encoded in software.

SeaLegsAI — Go / Caution / Avoid

If you don’t want to interpret raw GRIBs, SeaLegsAI runs 12+ weather models and gives you a single recommendation for your trip: Go, Caution, or Avoid. It’s not a replacement for skipper judgment — but as a sanity check before leaving harbour, it’s a fast second opinion.

Layer 4

What AI Still Can’t Do

No AI on this list has ever sailed into the marina you’re about to enter. They’ve never seen the rocks at the harbour mouth. They don’t know that the inner pontoon at Bonifacio gets flushed by ferry wash, or that the southern approach to Santa Teresa has a sandbar that shifts every winter.

That’s the missing layer — and it’s why SeaTV exists.

We physically visit every location, film the approach from the sea and from the air, and document what the chart can’t show: where to actually drop the hook, what the bottom looks like, where the showers are, who runs the marina office, and what time the ferry comes through.

Use AI to plan the trip. Use SeaTV to know what you’re sailing into.

My Actual Workflow — Sardinia to Corsica, June 2026

Here’s how the layers stack up in practice. This is what I’m doing right now to prep my own charter:

1
Perplexity — research current marine park regulations between Sardinia and Corsica. Save the source links.
2
Claude — feed it my cruising guide PDFs and ask for anchorages with NW protection in late June.
3
ChatGPT — run the skipper prompt above. Get a draft itinerary and budget.
4
SeaTV — cross-check every marina and anchorage on the AI itinerary against our visual pilot library. Adjust where reality differs from the AI’s confidence.
5
PredictWind + Windy — start tracking conditions two weeks out. Build a sense of the pattern, not just the day.
6
Skipper’s brain — final decision. Always. AI is the assistant, not the captain.

Bottom Line

AI in 2026 is a fundamentally better planning partner than it was in 2023. It’s also more dangerous — because it’s confident enough that you stop questioning it. The trick is using each tool for what it’s good at, and never letting any of them make a decision that the boat will pay for.

Plan with AI. Verify with SeaTV. Decide with your own eyes.

Up next on SeaTV

We’re building a structured visual pilot data layer — the kind of detail no AI can hallucinate, designed to plug into the navigation apps you already use. If you’re a charter agent, broker, or app developer, have a look here.

Planning a Mediterranean charter? Start with our regional pages: Sardinia · Corsica · Ionian Islands · Sporades.


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