HIGHWIND FIELD OFFICE / 2026THE GRENADINES / ROUTE 07LOCAL WIND / LOCATING…
HIGHWINDSUPPLYALL TRIPS
Tobago Cays aerial route viewROUTE / 0712.63°N / 61.36°W

THE GRENADINES / DEC—JUN

TOBAGO CAYS

A moving Caribbean basecamp: sleep aboard, read the trades at breakfast and reach protected anchorages without repeating a shoreline.

DURATION8 DAYS / 7 NIGHTSGROUP4—8 RIDERSRIDER LEVELINTERMEDIATE—ADVANCEDWIND / WATERENE TRADE / ISLAND HOPS

DESTINATION EXPERIENCE

A ROUTE, NOT A PACKAGE.

This route uses the yacht as a mobile equipment room, hotel and launch platform. Each day can begin in a new anchorage, with the captain and guide matching exposure, water state and distance to the riders onboard.

BASE
CREWED PERFORMANCE CATAMARAN
ACCESS
YACHT-BASED ROUTE
CONDITIONS
ISLAND-HOPPING TRADES
BEST WINDOW
DEC—JUN
Tobago Cays field view 1
07.1 / DESTINATION VIEW
Tobago Cays field view 2
07.2 / DESTINATION VIEW
Tobago Cays field view 3
07.3 / KITE FRAME / REFERENCE

ROUTE HIGHLIGHTS / 04

WHAT DEFINES THE WEEK.

  1. 01

    Crewed yacht and tender support

  2. 02

    Multiple islands in one route

  3. 03

    Downwind and flat-water options

  4. 04

    Private anchorages and chef service

SAMPLE PRIVATE ITINERARY

8 DAYS / 7 NIGHTS

DAY 01

ARRIVE + ALIGN

Private arrival, local briefing, equipment check and first forecast read.

DAYS 02—03

BUILD THE BASELINE

Guided sessions selected around rider level, wind quality and water state.

DAYS 04—06

OPEN THE ROUTE

Remote access, downwind or boat-supported days when the forecast lines up.

DAY 08

LAST WATER + DEPART

Final session window, equipment reset and coordinated departure.

This is a route blueprint, not a fixed departure. Every Highwind itinerary is rebuilt around the riders, dates, forecast, access and non-rider needs.

CONTINUE THE FIELD GUIDE

FIND THE ROUTE THAT FITS YOUR WATER.

VIEW ALL TEN TRIPS