Have questions? We're here.
Vivid blue waters of the Caribbean

Top Windward Islands Tours & Cruises in 2025

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
Filter (21 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Windward Islands
Enjoy the clear blue waters of the Canary Islands
from $4,610
EXPLORE

Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 25 Day Itinerary aboard Star Clipper
Starts / Ends
Malaga / Bridgetown
Activities
Local Market Visits, Wildlife Viewing, Small Ship Sailing, Archaeological Site Visits
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Clipper, exploring Spain, Morocco, and the Canary Islands before heading to Barbados. Experience diverse cultures, stunning landscapes, and relaxation at sea on this unforgettable journey.
  • Explore Malaga’s Moorish Alcazaba
  • Discover Tangier’s culture
  • Wander Cadiz’s palm-lined streets
  • Visit Safi’s old town
Cruise Details
0
The stunning blue coastline of the Canary Islands
from $2,720
EXPLORE

Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper
Starts / Ends
Las Palmas / Bridgetown
Activity Level
Variable
Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Cruise Details
0
Take in the sights, sounds, and colors of Barbados
from $7,120
EXPLORE

Westbound Atlantic Ocean Crossing

Civitavecchia - Bridgetown - 29 Day Itinerary aboard Royal Clipper
Starts / Ends
Civitavecchia / Bridgetown
Activities
Village Visits
Activity Level
Variable
Set sail on a 29-day cruise aboard the Royal Clipper, traveling from Civitavecchia to the Caribbean while exploring historic and vibrant locations like Bonifacio, Ibiza, and Malaga. Enjoy days at sea, classic sailing experiences, and onboard activities before reaching Barbados.
  • Explore Bonifacio’s scenic harbor
  • Discover Mahon’s Georgian charm
  • Wander Palma’s markets
  • Unwind on Ibiza’s beaches
Cruise Details
0
19-21 of 21 Results

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

Erin Correia
Erin C
Plan My Trip
We love travel, talk with an expert 1.800.344.6118
GOT IT!
We use cookies to give you the best experience on our website. Continue browsing the site if you're ok with this. For more info, please see our privacy policy.