Have questions? We're here.
Tobago Cays

16-Day Windward Islands Tours & 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 one of these 3 highly-recommended 16-day Windward Islands tours. Explore worry-free with your bilingual guide on a small group or private Windward Islands tour where you will enjoy Small Ship Sailing, and Archaeological Site Visits during the day and stay in hotels with decidedly local flavor at night. Our 16-day Windward Islands trips and vacation packages range from $2,820 to $6,660. Contact one of Adventure Life's Windward Islands travel specialists for help planning every detail of your dream trip. 

Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Windward Islands
Funchal, Madeira, Portugal
from $2,940
EXPLORE

Westbound Atlantic Ocean Crossing

Lisbon - Barbados - 16 Day Itinerary aboard Royal Clipper
  • Explore Lisbon’s vibrant streets
  • Discover Portimão’s historic charm
  • Wander Funchal’s lush landscapes
  • Cruise Barbados’ stunning shores
Starts / Ends
Lisbon / Bridgetown
Activities
Archaeological Site Visits
Activity Level
Variable
Sail across the Atlantic on this 16-day cruise aboard the Royal Clipper, blending culture and adventure. Discover Lisbon’s charm, Portimao’s historical treasures, Madeira’s vibrant nightlife, and Barbados’ stunning shores, with serene days at sea in between.
Cruise Details
0
The stunning blue coastline of the Canary Islands
from $2,970
EXPLORE

Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
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 all the way to the stunningly beautiful Caribbean Islands.
Cruise Details
0
The stunning blue coastline of the Canary Islands
from $2,820
EXPLORE

Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Starts / Ends
Las Palmas / Bridgetown
Activities
Small Ship Sailing
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.
Cruise Details
0
1-3 of 3 Results
  • 1

Relax. We've got this.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Kassandra Magruder Adventure Life employee profile
Kassandra M.
Tobago Cays
Caribbean

Chat Windward Islands with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
1.800.344.6118

Where is your next adventure?

Contact Chat Call
More Reasons

Why Travel With Adventure Life

All News

Recognized By

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

Kassandra Magruder Adventure Life employee profile
Kassandra M
Plan My Trip
We love travel, talk with an expert 1.800.344.6118