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

Discover 15-Day Windward Islands Tours

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Experience the captivating beauty and charm of the Windward Islands on a 15-day Caribbean adventure with Adventure Life. Join us on a tour of the Lesser Antilles and set sail to explore the region's hidden gems and unique cultures. Embark on a small ship cruise starting from Bridgetown, Barbados, and meander through the Caribbean islands, snorkeling in crystal-clear waters, marveling at lush wildlife, and immersing yourself in local traditions. Discover the Dutch colonial charm of Curacao, the cultural richness of Grenada, and the stunning landscapes of St. Lucia. Each day promises new adventures and unforgettable memories. Don't miss this opportunity to explore the Windward Islands in 2024 or 2025 - contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (6 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Windward Islands
Take a leisurely stroll through beautiful Bridgetown
$2,550
EXPLORE

Eastbound Atlantic Ocean Crossing

15 Day Itinerary aboard Royal Clipper
  • Explore the east coast of Barbados
  • Discover Santa Cruz
  • Experience Las Palmas
  • Visit Caldera de Bandama
Starts / Ends:
Bridgetown / Las Palmas
Activities:
Small Ship Cruises
Activity Level:
Relaxed
Join the Royal Clipper on a 15-day cruise departing from Bridgetown, Barbados. Experience the vibrant contrasts of this coastal town, with its red-sand beaches and lively streets. Explore the British-influenced heritage through landmarks like Trafalgar Square and discover traditions like cricket …
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
$11,595
EXPLORE

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb - 15 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts / Ends:
Philipsburg / St. Barth
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,540
EXPLORE

Barbados to Panama Christmas Cruise

15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Star Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$4,440
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Gatun Lock of the Panama Canal
$4,440
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Transit the historic Panama Canal
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Swim in paradise in Bonaire
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Amazon River
$26,199
EXPLORE

Wild Guianas to the Amazon Basin

15 Day Itinerary aboard Seabourn Venture
  • Discover Port-of-Spain
  • Explore Bridgetown
  • Experience Paramaribo
  • Witness Devil's Island
Starts / Ends:
Bridgetown / Manaus
Activities:
Hiking, Small Ship Cruises
Activity Level:
Relaxed
Embark on a 15-day cruise aboard the Seabourn Venture. Discover the Caribbean and Amazon starting in Bridgetown, Barbados, boasting British heritage and serene coastlines. Explore Trinidad and Tobago's cultural blend or Caroni Swamp's sunset spectacle. Continue to Suriname's Paramaribo, …
Cruise Details
0
1-6 of 6 Results

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Windward Islands Travel Destinations

Windward Islands Trips by Departure Date

Windward Islands Trips by Duration

Windward Islands Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By