Caribbean Offshore Challenge

Caribbean Offshore Challenge

St. Thomas to Grenada
January 15 to 23, 2027

This passage is a true offshore run through the heart of the eastern Caribbean. Departing St. Thomas and finishing in Grenada, we sail the classic southbound trade wind route with a primary landfall in St. Lucia and additional islands passed or approached depending on weather and routing.

This is not island hopping. It is sustained offshore sailing designed to build confidence, judgment, and endurance in real trade wind conditions. Crew members are active participants in every aspect of passage making, from departure planning to offshore watch standing to landfall execution.

 

The Route and the Reality

The route runs south and slightly east out of St. Thomas, committing quickly to open water. After a nonstop offshore leg to St. Lucia, we continue south along the Windward Islands, passing close to St. Vincent and the Grenadines before making our final approach into Grenada.

Depending on conditions, the passage may include close coastal sailing past islands such as Bequia, Canouan, Mayreau, Union Island, and Carriacou, offering valuable navigation experience near land while still operating in an offshore mindset.

Expect long stretches at sea, consistent trade winds, and a steady rhythm of watch keeping that defines real Caribbean passagemaking.

 

St. Thomas to St. Lucia

Committing to offshore

We begin in St. Thomas with a full crew briefing, safety review, and weather analysis before departure. Once clear of the islands, the focus shifts immediately to offshore routines.

This leg is a nonstop passage of roughly two to three days at sea. Crew members settle into the three hours on, six hours off watch rotation and take active roles at the helm, as lookout, and in navigation support. Night sailing is continuous, with radar and AIS used alongside visual targets and traditional situational awareness.

This leg sets the tone for the entire passage. There are no short days and no easy resets. You learn how the boat moves, how your body adapts, and how decisions made early carry forward.

 

St. Lucia to Grenada

Sustained passage through the Windwards

After a short stop in St. Lucia to rest, review weather, and reassess systems, we continue south. From here the passage becomes a mix of offshore sailing and close island navigation.

We run parallel to the Windward Island chain, maintaining offshore discipline while identifying islands visually, managing traffic, and adjusting sail plans for acceleration zones and lee effects. Position fixing, course management, and awareness of current and wind shifts become constant considerations.

As we pass the Grenadines and approach Grenada, attention shifts toward landfall planning, night entry considerations if required, and the transition from passage mode to arrival.

 

Training Focus

What this passage is really about

This passage is built around repetition and responsibility. Skills are not demonstrated once and checked off. They are practiced day after day.

Key focus areas include:

• Offshore passage planning and weather window assessment

• Route selection and contingency decision making

• Practical navigation using GPS, chartplotter, paper charts, radar, and AIS

• Watch keeping discipline including helm, lookout, and log management

• Daily systems checks including engine, bilge, electrical, and safety equipment

• Sail management in steady trade winds including reefing and headsail changes

• Communications using VHF and satellite systems such as Starlink or inReach

• Approach and landfall planning under real world conditions

 

Expected Conditions

January is prime trade wind season in the eastern Caribbean. Conditions are generally consistent but not gentle.

Expect steady easterly to east southeast winds in the fifteen to twenty five knot range. Seas are typically four to eight feet in open water, with steeper chop in island channels and acceleration zones. Squalls are possible but usually brief. Nights are warm with excellent visibility, making them ideal for learning offshore navigation.

Traffic increases near islands, and currents can be variable, particularly in the Windward channels.

 

Why This Passage Matters

This is the kind of passage sailors talk about when they say they have crossed the Caribbean. It builds real offshore miles, reinforces professional watch keeping habits, and exposes you to the decisions that matter when there is no easy exit.

It is especially well suited for sailors preparing to skipper their own boats, planning future Caribbean passages, or looking to move beyond coastal comfort and into true bluewater confidence.

 

You do not just arrive in Grenada. You earn it.