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

Windward Islands Cultural Trips

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Filter (24 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Windward Islands
Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
2for1
EXPLORE

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse
  • Explore Nassau’s vibrant capital
  • Visit Staniel Cay’s beaches
  • Discover San Salvador’s coral reefs
  • Stroll St. Barts iconic Shell Beach
Starts / Ends
Nassau / Bridgetown
Activities
Village Visits, Wildlife Viewing, Small Ship Sailing, Snorkeling, Kayaking, Stand Up Paddle Boarding, Helicopter Tours
Activity Level
Variable
Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
Cruise Details
0
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
  • Explore Malaga’s Moorish Alcazaba
  • Discover Tangier’s culture
  • Wander Cadiz’s palm-lined streets
  • Visit Safi’s old town
Starts / Ends
Malaga / Bridgetown
Activities
Local Market Visits, 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.
Cruise Details
0
Funchal, Madeira, Portugal
from $2,810
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
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
Mountains by the ocean in St Lucia
from $8,490
EXPLORE

Panama, Colombia & Caribbean Islands

Colon to Fort-de-France - 13 Day Itinerary aboard Le Champlain
  • Sail through the Central America.
  • See San Blas, Bonaire & Grenadines
  • Experience swim and snorkel.
  • Learn traditions of the Kuna people
  • Dive with an experienced instructor
Starts / Ends
Colon / Fort de France
Activities
Land & Sea Exploration
Activity Level
Variable
Join Le Bellot for an exceptional 13-day cruise sailing from Colón to Fort-de-France. This itinerary gives you the opportunity to appreciate the richness and diversity of Afro-Caribbean cultures, an azure blue sky, and white-sand beaches. Visit stunning ports, including Portobelo, Cartagena, Santa Marta, Mayreau Island, and Soufriére.
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
  • Explore Bonifacio’s scenic harbor
  • Discover Mahon’s Georgian charm
  • Wander Palma’s markets
  • Unwind on Ibiza’s beaches
Starts / Ends
Civitavecchia / Bridgetown
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.
Cruise Details
0
Aerial View of Halifax Skyline
from $3,199
EXPLORE

Southern Caribbean Yacht Harbors

Halifax - Bridgetown - 9 Day Itinerary aboard Seabourn Venture
  • Tour Citadel Hill
  • Visit Brimstone Hill Fortress
  • Snorkel at Pigeon Island
  • Visit Saint Lucia’s famous Pitons
Starts / Ends
Halifax / Bridgetown
Activities
Photography Seminars, Spa Relaxation
Activity Level
Variable
Cruise from Halifax, Nova Scotia to Bridgetown, Barbados aboard the Seabourn Venture on a 9-day Southern Caribbean Yacht Harbors cruise. Enjoy relaxing days at sea and explore scenic Caribbean islands like Saint Kitts, Montserrat, and Saint Lucia. Visit UNESCO World Heritage Sites, snorkel in clear waters, and experience rich history and culture.
Cruise Details
0
19-24 of 24 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