Route Planning Calendar — Sail with the Seasons
Why Timing is the Hidden Key to Seamanship
Many new sailors obsess over gear, sails, and provisioning, but underestimate the importance of timing. The truth is that the ocean has rhythms. Trade winds blow in cycles, monsoons arrive and fade, and hurricane seasons define when oceans are safe — or deadly. A sailor who departs at the wrong time may face storms, headwinds, or even cyclones. A sailor who departs in season often enjoys following winds and calm seas.
Route planning is therefore as much about when you sail as it is about where you sail.
The Global Sailing Seasons at a Glance
Below is a Route Planning Calendar that highlights the best departure windows for the three major oceans. It’s simplified, but it gives you the broad strokes most sailors follow to cross oceans safely.
🌍 Sailing Route Planning Calendar
| Ocean Route | Best Departure Window | Why This Season Works |
|---|---|---|
| Atlantic (East → West) | November – January | Trade winds fill in after hurricane season. Boats depart from Canary Islands, Cape Verde, or Azores, bound for the Caribbean. |
| Atlantic (West → East) | April – May | Favorable spring weather before Caribbean hurricane season. Boats head from Caribbean back to Azores or Mediterranean. |
| Pacific (North America → South Pacific) | April – May | Cyclone season ends in the South Pacific, and tradewinds establish. Ideal for passages from Mexico, Panama, or California to French Polynesia. |
| Pacific (South Pacific cruising) | June – October | Safe to explore islands such as Tonga, Fiji, and Vanuatu. Avoids cyclone season. |
| Pacific (To New Zealand or Australia) | November | Boats sail southwest to cyclone refuges before storm season begins. |
| Indian Ocean (SE Asia → South Africa) | September – October | Northeast monsoon fades, and cyclone season has not yet started. Boats cross via Maldives, Chagos, Seychelles, or Mauritius. |
Why This Calendar Matters
Every line of this calendar reflects decades of experience from bluewater sailors. These windows aren’t arbitrary — they are shaped by global weather patterns:
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The Atlantic hurricane season runs June through November, so crossings happen just after it ends.
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The Pacific cyclone season peaks November to April, so sailors move into safe harbors by October and depart again in April.
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The Indian Ocean monsoons dictate timing, with the northeast monsoon easing in September–October, opening the window for westward crossings.
By aligning your plans with the seasons, you drastically reduce your exposure to extreme weather and increase your chances of a comfortable passage.
Turning the Calendar into a Voyage Plan
The calendar gives you the broad picture, but each sailor adapts it to their own route and pace. A circumnavigation might look like this:
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Year 1: Cross the Atlantic in December, spend a season in the Caribbean.
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Year 2: Transit the Panama Canal in spring, cross the Pacific in April, and cruise the South Pacific islands through October before heading to New Zealand.
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Year 3: Depart New Zealand in May, explore the Pacific islands again, then move west to Indonesia and into the Indian Ocean by September.
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Year 4: Cross the Indian Ocean before cyclone season, round South Africa, and sail back into the Atlantic.
This rhythm is the backbone of nearly every world voyage. Individual sailors adapt details, but the seasonal flow remains the same.
Seabound Life Connection
While this calendar provides a useful overview, safe passage planning requires more nuance. That’s where Seabound Life books come in.
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Hidden Islands of the Pacific dives deep into the realities of crossing the Pacific, exploring not just the seasons but the anchorages, cultures, and dangers sailors face.
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Secret Anchorages Around the World combines adventure narratives with practical notes on timing, currents, and weather patterns.
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The Ultimate Beginner’s Guide to World Sailing explains how to integrate seasonal calendars with personal readiness, boat preparation, and safety planning.
The calendar in this article gives you the “when.” The books provide the “how” and the “why.”
Build Your Dream Voyage with Confidence
By aligning your voyages with seasonal windows, you unlock smoother passages, reduce risks, and enjoy the support of hundreds of other sailors traveling at the same time.
👉 Explore Seabound Life Books to go beyond this calendar and gain the practical seamanship wisdom needed to turn timing into a safe and successful voyage.