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Tobago Cays

Windward Islands Trips with Village Visits

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Explore remote villages on one of the below 22 unique Windward Islands cultural experiences for 2026 or 2027. Visit the local village, meet the people, experience local cuisine with a local English speaking guide on your own private tour or small group guided tour. Discover unique local cultures on trips that include activities like Snorkeling, Archaeological Site Visits, Local Market Visits, Small Ship Sailing, and Wildlife Viewing and cost from $2,080 for experiences of 7 to 18 days. Tell us about your ideal Windward Islands cultural trip and our Windward Islands experts will help you plan every detail of your next trip.

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    • Windward Islands
Take a leisurely stroll through beautiful Bridgetown
from $11,990
Save $150
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Grenadines & Windwards Yachting

Roundtrip Bridgetown - 8 Day Itinerary aboard Emerald Sakara
  • Discover Bequia’s secluded beaches
  • Savor Caribbean dining experiences
  • Snorkel Tobago Cays' waters
  • Admire panoramic views from Mayreau
Starts / Ends
Bridgetown / Bridgetown
Activities
Kayaking
Activity Level
Variable
Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.
Cruise Details
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Explore colorful Bridgetown, Barbados
from $9,990
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Grenadines & Windwards Yachting

Bridgetown, Barbados Roundtrip - 8 Day Itinerary aboard Emerald Azzurra
  • Explore historic Kingstown
  • Swim Tobago Cays reefs
  • Discover Mayreau views
  • Relax on Bequia Island
Starts / Ends
Bridgetown / Bridgetown
Activities
Wildlife Viewing
Activity Level
Variable
Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.
Cruise Details
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Explore colorful Bridgetown, Barbados
from $7,195
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Beaches of the Grenadines

Roundtrip Bridgetown - 9 Day Itinerary aboard Emerald Azzurra
  • Tour Soufriere pair of lava domes
  • Experience Bequia Island beaches
  • Enjoy Union Island beaches
  • Visit Tobago Cays to spot turtles
Starts / Ends
Bridgetown / Bridgetown
Activities
Village Visits, Archaeological Site Visits, Urban Exploration
Activity Level
Variable
Set sail on a 9-day Caribbean cruise from Bridgetown on the Emerald Azzurra, exploring charming locations like Speightstown, Kingstown, and Bequia Island. Discover stunning beaches, marine life, and local culture before returning to Bridgetown.
Cruise Details
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St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.
from $3,150
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Grenada Roundtrip

Roundtrip St George - 12 Day Itinerary aboard Star Clipper
  • Tour St. George's Sendall Tunnel
  • Taste Castara Bay Tobago's Creole
  • Stroll Admiralty Bay waterfront
  • View Saint Pierre colonial ruins
Starts / Ends
St. Georges / St. Georges
Activities
Small Ship Sailing, Snorkeling, Local Market Visits
Activity Level
Variable
Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.
Cruise Details
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Enjoy the beautiful blue Caribbean
from $2,880
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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s panoramic view
  • Discover Charlotteville coastline
  • Unwind at Englishman’s Bay
  • Visit Martinique ruins
Starts / Ends
St. Georges / St. Georges
Activity Level
Variable
Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.
Cruise Details
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Relax on the pristine beaches of the Virgin Islands
from $13,390
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Discover Eastern Caribbean & Grenadines

Bridgetown - Philipsburg - 15 Day Itinerary aboard Emerald Sakara
  • Visit Bequia Island sandy beaches
  • See Mayreau Island ocean views
  • Admire Soufriere hot sulfur springs
  • Tour Iles des Saintes Fort Napoleon
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Join a 15-day Caribbean cruise from Bridgetown on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Experience local culture in Speightstown, enjoy water sports in Kingstown, and relax in natural hot springs in Soufriere before returning to Barbados.
Cruise Details
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Bright blue waters of the Caribbean
from $2,880
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Aruba to Grenada

Oranjestad - St. George - 11 Day Itinerary aboard Star Clipper
  • Visit Oranjestad to see beaches
  • See Willemstad gabled houses
  • Tour Curacao inland cunucu
  • Swim Charlestown Bay
Starts / Ends
Oranjestad / St. Georges
Activity Level
Variable
Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.
Cruise Details
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Dock going out into the crystal blue ocean
from $2,080
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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
Starts / Ends
St. John's / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.
Cruise Details
0
Experience laid-back Marigot
from $15,980
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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla, serene landscapes
  • Savor Barbados’s cultural delights
  • Visit Antigua’s historic dockyard
  • Stroll Nevis’s serene beaches
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $13,340
Save $150
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Discover Eastern Caribbean & Grenadines

Philipsburg - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Discover Virgin Gorda The Baths
  • Wander Gustavia wooden houses
  • Visit St. John's Nelson's Dockyard
  • See Soufriere volcanic domes
Starts / Ends
Philipsburg / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Philipsburg on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Visit charming islands like Virgin Gorda, Saint Barthelemy, and Bequia for stunning beaches, local cuisine, and water activities amidst breathtaking views.
Cruise Details
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Caribbean landscapes and harbors
from $11,990
Save $150
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Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover Iles des Saintes town
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
Cruise Details
0
Pink beach huts in the Caribbean
from $2,080
SS 25%
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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.
Cruise Details
0
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