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Tobago Cays

Windward Islands Trips with Village Visits

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    • Windward Islands
Tropical waterfall and turquoise pool in lush forest of Dominica
from $7,995
OBC $200
EXPLORE

Caribbean Flair Away from the Everyday

St. Maarten Roundtrip - 9 Day Itinerary aboard Sea Cloud Spirit
  • Visit historic Saint-Pierre ruins
  • Watch the crew hoist the sails
  • Snorkel the clear Tobago Cays
  • Explore St. Lucia's twin Pitons
  • Wander through Charlestown, Nevis
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing
Activity Level
Variable
Embark on a 9-day Caribbean cruise aboard the Sea Cloud Spirit. You depart from St. Maarten and visit Martinique, the Tobago Cays, St. Lucia, Dominica, and Nevis, then explore historic ruins, volcanoes, and reefs.
Cruise Details
0
Caribbean landscapes and harbors
from $11,990
EXPLORE

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
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
Beautiful beach in Dominica
from $8,710
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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
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
0
Relax on the shores of the Caribbean
from $12,295
EXPLORE

Grenadines, Colombia & Panama Canal Transit

Bridgetown - Panama City - 12 Day Itinerary aboard Emerald Azzurra
  • Explore Bequia Caribbean lifestyle
  • Admire Cartagena Old Town
  • See San Blas Islands nature
  • Navigate the Panama Canal
Starts / Ends
Bridgetown / Panama City
Activity Level
Variable
Set sail on a 12-day Caribbean cruise from Bridgetown aboard the Emerald Azzurra, exploring islands like Bequia and Mayreau. Conclude your journey in Panama City after traversing the historic Panama Canal and enjoying vibrant local cultures and stunning coastal views.
Cruise Details
0
Bustling port of Fort de France, Martinique
from $6,940
EXPLORE

Panama, Colombia & Caribbean Islands

Fort-de-France - Colon - 10 Day Itinerary aboard Le Bellot
  • Uncover lush Minca
  • Stroll through Port Elizabeth
  • Admire colorful Willemstad
  • Visit historic Santa Marta
Starts / Ends
Fort de France / Colon
Activities
Snorkeling, Village Visits, Scuba Diving, Archaeological Site Visits, Local Market Visits
Activity Level
Variable
Set sail on a 10-day cruise aboard the Le Bellot to explore the stunning Caribbean, including the vibrant towns and rich history of Panama and Colombia. Swim in turquoise waters and snorkel in marine reserves while discovering unique cultures and ecosystems.
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $9,990
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore beaches in Bridgetown
  • Hike nature trails in Soufriere
  • Discover forts in Les Saintes
  • Visit the dockyard in Falmouth
Starts / Ends
Bridgetown / St. Martin
Activities
Hiking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Azzurra, starting from Barbados. Explore stunning destinations like Soufrière, Falmouth Bay, Iles des Saintes, Gustavia, and end in lively Marigot, where vibrant culture and delicious local cuisine await.
Cruise Details
0
Learn about the history of the Caribbean
from $9,990
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Prickly Pear Cays waters
  • Admire Nevis’ Georgian buildings
  • Visit Soufriere’s volcanic springs
  • Wander Bridgetown’s streets
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.
Cruise Details
0
Explore the famous rock formations of the baths
from $6,295
EXPLORE

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
Snorkeling
from $7,910
No SS
EXPLORE

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
Wildlife Viewing, Rainforest Exploration
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
0
Sunset over Cartagena, Colombia
from $12,295
EXPLORE

Panama Canal Transit, Colombia & the Grenadines

Panama City - Bridgetown - 12 Day Itinerary aboard Emerald Azzurra
  • Explore Cartagena walled Old Town
  • Discover Santa Marta oldest city
  • Tour Willemstad Queen Emma Bridge
  • See Mayreau Island Station Hill
Starts / Ends
Panama City / Bridgetown
Activities
Urban Exploration
Activity Level
Variable
Set sail on a 12-day Caribbean cruise from Bridgetown aboard the Emerald Azzurra, exploring islands like Bequia and Mayreau. Conclude your journey in Panama City after traversing the historic Panama Canal and enjoying vibrant local cultures and stunning coastal views.
Cruise Details
0
City of Basseterre and Frigate Bay from the Timothy Hill viewpoint in St. Kitts.
from $12,690
EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Sint Maarten - 15 Day Itinerary aboard Emerald Sakara
  • Visit Soufriere mud baths
  • Tour Iles des Saintes Fort Napoleon
  • See St. John's Nelson’s Dockyard
  • Observe Anguilla beaches
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Barbados aboard the Emerald Sakara, visiting Saint Lucia for its mud baths, Antigua's historic dockyard, and Anguilla's vibrant coral reefs. Conclude your journey in Philipsburg, Sint Maarten, enjoying the region's rich culture and cuisine.
Cruise Details
0
13-24 of 29 Results

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Erin Correia
Erin C.
Tobago Cays
Caribbean

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