Windward Islands
Wind
15-25 knots
Water Temp
26°C (January) to 29°C (September)
Best Season
December to May
Difficulty
Intermediate
Julia Högner
Charter Coordinator"I know this destination well — let me help you plan the perfect itinerary."
12+ years experience · Speaks English, German, French
Overview
The Windward Islands offer a quintessential Caribbean sailing experience, with lush volcanic landscapes, pristine beaches, and a rich cultural heritage. From the iconic Pitons of St. Lucia to the spice-scented air of Grenada, this is a destination that will captivate your senses.
Sailing insights
Expect consistent trade winds and open-water passages between islands, making for exhilarating sailing. The waters are generally calm, but can be choppy in open channels. This is an ideal destination for sailors with some experience looking for a bit of adventure.
The Windward Islands offer a more authentic and less crowded sailing experience compared to other parts of the Caribbean. You'll find a mix of lively towns and secluded anchorages, with plenty of opportunities for hiking, diving, and exploring ashore. Be prepared for some open-water sailing between islands, which can be a thrilling experience.
Wind Conditions
Consistent easterly trade winds, typically stronger in the winter months.
Base Ports
Martinique, Grenada, St. Lucia
Peak Months
December, January, February, March, April, May
How to get there
The Windward Islands are easily accessible via international flights to St. Lucia (UVF), Grenada (GND), and Martinique (FDF). From the airport, it's a short taxi ride to the main charter bases.
UVF
Hewanorra International Airport
GND
Maurice Bishop International Airport
FDF
Martinique Aimé Césaire International Airport
Highlights
The iconic Pitons in St. Lucia
The spice markets of Grenada
The Tobago Cays Marine Park
The pristine beaches of Bequia
The vibrant culture of Martinique
World-class diving and snorkeling
Exploring secluded anchorages
Points of interest
The Pitons
Gros Piton and Petit Piton are two majestic volcanic plugs that are a UNESCO World Heritage Site. You can hike Gros Piton for breathtaking views.
St. George's
The capital of Grenada is one of the most picturesque cities in the Caribbean, with a beautiful harbor and colorful colonial architecture.
Tobago Cays Marine Park
A stunning collection of five uninhabited islands with crystal-clear water, vibrant coral reefs, and abundant marine life, including sea turtles.
Bequia
A charming island with a rich maritime history, beautiful beaches, and a relaxed atmosphere. Don't miss the model boat builders of Port Elizabeth.
Anse Mitan
A popular beach in Martinique with calm waters, white sand, and a variety of restaurants and bars.
Mount Gay Rum Distillery
Visit the world's oldest rum distillery in Barbados (a nearby island) and learn about the history of rum production in the Caribbean.
Sample itineraries
1 Week Itinerary
7 days · ~154 NM total
Martinique → St. Lucia
Sail to Rodney Bay and enjoy the beautiful beach and lively atmosphere.
21 NMSt. Lucia → The Pitons
Anchor between the iconic Pitons and enjoy the stunning scenery.
15 NMThe Pitons → St. Vincent
Sail to Wallilabou Bay, the filming location for 'Pirates of the Caribbean'.
45 NMSt. Vincent → Bequia
Explore the charming island of Bequia and its rich maritime history.
8 NM2 Week Itinerary
14 days · ~283 NM total
Grenada → Carriacou
Explore the laid-back island of Carriacou and its beautiful beaches.
35 NMCarriacou → Union Island
Visit the lively town of Clifton and enjoy the vibrant kite-surfing scene.
8 NMUnion Island → Tobago Cays
Spend the day snorkeling and swimming with sea turtles in the Tobago Cays.
4 NMTobago Cays → Mayreau
Anchor in Salt Whistle Bay and enjoy the beautiful beach and stunning views.
2 NMWeather & climate
| Month | Air Temp | Water Temp | Wind (Bft) | Rainy Days |
|---|---|---|---|---|
| January | 26°C | 26°C | 4-6 | 13 |
| February | 26°C | 26°C | 4-6 | 10 |
| March | 27°C | 27°C | 4-6 | 9 |
| April | 28°C | 27°C | 4-5 | 8 |
| May | 28°C | 28°C | 3-5 | 10 |
| June | 28°C | 28°C | 3-5 | 14 |
Practical tips
Book your charter well in advance, especially during the peak season.
Pack light, quick-drying clothing and plenty of sunscreen.
Be prepared for some open-water sailing between islands.
Provision wisely, as some of the smaller islands have limited options.
Don't forget your snorkeling and diving gear.
Be respectful of the local culture and customs.
Always check the weather forecast before setting sail.
Windward Islands
7-day sailing forecast
Sunny
13 kn
SE Wind
1.2m
Waves
16°
Sea Temp
Excellent
Visibility
Availability Calendar
Windward Islands — 2026 Season Overview
Jan
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Feb
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Mar
€
Apr
€
May
€€
Jun
€€€
Jul
€€€€
Aug
€€€€
Sep
€€€
Oct
€€
Nov
-
Dec
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Peak Season (Jul–Aug)
Book 6–12 months in advance for the best yacht selection. Popular models sell out fast.
Best Value: May & October
Great weather, fewer crowds, and early-bird or last-minute discounts available.
Price Trend
€ = Low season rates · €€€€ = Peak season premium. Contact us for exact pricing.