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Caribbean Trips with Village Visits

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Explore remote villages on one of the below 30 unique Caribbean 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, Wildlife Viewing, and Small Ship Sailing and cost from $2,080 for experiences of 7 to 18 days. Tell us about your ideal Caribbean cultural trip and our Caribbean experts will help you plan every detail of your next trip.

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Pink beach huts in the Caribbean
from $2,080
SS 25%
EXPLORE

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
Take a leisurely stroll through beautiful Bridgetown
from $11,990
Save $150
EXPLORE

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
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
0
Relax on the beaches of St. Maarten
from $6,395
Save $150
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Cruising the Leeward Islands

Roundtrip Sint Maarten - 8 Day Itinerary aboard Emerald Sakara
  • Visit Basseterre colonial structure
  • Discover Anguilla marine life
  • Swim in pools at Virgin Gorda
  • Experience Gustavia Creole cuisine
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.
Cruise Details
0
Explore the famous rock formations of the baths
from $6,295
Save $150
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Eastern Caribbean with St. Barths

Bridgetown - Philipsburg - 8 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown rich heritage
  • Enjoy Soufriere sulfur springs
  • See St. John's Nelson's Dockyard
  • Experience Gustavia Creole cuisine
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.
Cruise Details
0
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
Activities
Small Ship Sailing, Snorkeling, Village Visits, Local Market Visits
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
0
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
Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
Save $150
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
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
Experience laid-back Marigot
from $15,980
Save $150
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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
Boats Moored to the Quay at Bridgetown Harbour
from $15,980
Save $150
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Discover the Pearls of the Caribbean

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Marigot / Bridgetown
Activities
Wildlife Viewing, Archaeological Site Visits
Activity Level
Variable
Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.
Cruise Details
0
Explore the famous rock formations of the baths
from $21,780
Save $150
EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Bridgetown / Marigot
Activities
Kayaking
Activity Level
Variable
Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $13,390
Save $150
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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
0
Lush green forests and clear blue waters of the Caribbean
from $13,340
Save $150
EXPLORE

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
0
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