Have questions? We're here.
Tobago Cays

Windward Islands Hiking Trips

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert

Select from one of the below 3 scenic Windward Islands hikes & treks  for 2026-2027. Do you prefer shorter walks or longer treks? Easy strolls or conquering the highest peaks? Windward Islands hiking and trekking trips range from 8 to 11 days in 2026. The Windward Islands hiking & trekking trip planners at Adventure Life can help choose the perfect hikes and then help you to customize them to make your own unique Windward Islands trekking experience. 
 

Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Windward Islands
Relax on the shores of the Caribbean
from $6,800
Save 10%
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot
  • Visit UNESCO World Heritage sites
  • Visit Portsmouth, Dominica
  • Explore Les Saintes, Guadeloupe
  • See Mayreau's fishes and corals
Starts / Ends
Les Saintes / Bridgetown
Activities
Village Visits, Wildlife Viewing
Activity Level
Variable
From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $9,990
OBC
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Soak in Soufriere’s volcanic spring
  • Explore Les Saintes’ French charm
  • Visit Antigua’s Nelson’s Dockyard
  • Stroll Nevis’ Georgian towns
Starts / Ends
Bridgetown / Marigot
Activities
Archaeological Site Visits
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
Cruise Details
0
The crystal blue water of Jost van Dyke
from $2,820
EXPLORE

Antigua to Grenada

Antigua to Grenada - 11 Day Itinerary aboard Star Clipper
  • Explore Gustavia boutiques
  • Swim Norman Island coves
  • Visit Jost van Dyke beaches
  • Relax in St. Kitts landscapes
Starts / Ends
St. John's / St. Georges
Activities
Hiking, Snorkeling
Activity Level
Variable
Set sail on an 11-day Caribbean cruise aboard Star Clipper. Depart from Antigua and explore St. Barts, the British Virgin Islands, St. Kitts, Martinique, Bequia, and Grenada. Discover historic harbors, swim in crystal waters, and relax on world-class beaches.
Cruise Details
0
1-3 of 3 Results
  • 1

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Jason Maynard employee profile
Jason M
Plan My Trip
We love travel, talk with an expert 1.800.344.6118