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Relax on the beaches of the Caribbean

Leeward Islands Small Ship Cruises

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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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Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
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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
Wildlife Viewing, Kayaking, 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
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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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
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Beautiful beach in Dominica
from $8,370
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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Relax on Grande Anse Beach
  • Snorkel Tobago Cays Reefs
  • Visit Port Elizabeth waterfront
  • Discover Portsmouth landscapes
Starts / Ends
Anses d'Arlet / Marie Galante
Activities
Scuba Diving
Activity Level
Variable
Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.
Cruise Details
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Soufriere bay, St Lucia
from $6,495
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Relax The Caribbean Way

Roundtrip Bridgetown - 8 Day Itinerary aboard Sea Cloud II
  • Snorkel in the Tobago Cays
  • Discover Grenada’s spices
  • Explore Saint-Pierre, Martinique
  • View Gros and Petit Piton
Starts / Ends
Bridgetown / Bridgetown
Activities
Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding
Activity Level
Variable
Experience an 8-day voyage aboard Sea Cloud II roundtrip from Bridgetown, Barbados, through the Lesser Antilles & Grenadines. You snorkel in the Tobago Cays, explore spice-rich Grenada, visit Saint-Pierre in Martinique, admire St. Lucia’s Pitons, and enjoy Caribbean sunsets at sea.
Cruise Details
0
White Sand Beach in Barbados
from $2,080
SS 25%
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Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.
Cruise Details
0
Snorkeling
from $7,910
No SS
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Panama, Colombia & Caribbean Islands

Colon - Fort-de-France - 11 Day Itinerary aboard Le Bellot
  • Cartagena colonial old town
  • Visit Santa Marta and Sierra Nevada
  • Visit Bonaire reef marine park
  • Visit Fort-de-France landmarks
Starts / Ends
Colon / Fort de France
Activities
Rainforest Exploration, Hiking
Activity Level
Variable
Set sail on an 11-day cruise through Panaman, Colombia and Caribbean Islands aboard Le Bellot. Visit Cartagena and Santa Marta with guided historic and cultural excursions. Explore the San Blas Islands for beaches, snorkeling, and Kuna culture. The voyage combines nature, culture, and Caribbean island experiences.
Cruise Details
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Enjoy the beautiful blue Caribbean
from $5,590
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 8 Day Itinerary aboard Le Champlain
  • Visit scenic Les Saintes
  • Swim at Pompierre Beach
  • Relax on Mayreau Island
  • Explore historic Bridgetown sites
Starts / Ends
Les Saintes / Bridgetown
Activity Level
Variable
Embark on an 8-day cruise aboard Le Champlain and explore Saint Lucia, Dominica, Les Saintes, Bequia, Mayreau Island, Tobago Cays, and Barbados. Snorkel coral reefs, swim in turquoise lagoons, discover historic towns, visit beaches, and encounter marine life across the Caribbean.
Cruise Details
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Explore colorful Bridgetown, Barbados
from $7,195
Save $150
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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
Archaeological Site Visits, Village 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
0
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
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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Panama's turquoise waters
from $4,450
SS 25%
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Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Starts / Ends
Balboa / St. John's
Activity Level
Variable
Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
Cruise Details
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