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Top Caribbean Tours & Cruises in 2028

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City of Basseterre and Frigate Bay from the Timothy Hill viewpoint in St. Kitts.
from $13,090
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
Enjoy the beautiful blue Caribbean
from $13,190
EXPLORE

Discover the Pearls of the Caribbean

Sint Maarten - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Experience Soufriere mud baths
  • See St. John's Nelson’s Dockyard
  • Discover Charlestown beaches
  • Visit Gustavia painted houses
Starts / Ends
Philipsburg / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean cruise aboard the Emerald Sakara, visiting islands like Anguilla for snorkeling and Virgin Gorda for stunning rock formations. Explore vibrant Gustavia in Saint Barthelemy, enjoy the charm of the Iles des Saintes, relax in Saint Lucia's hot springs, and experience the colonial beauty of Barbados.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $13,390
EXPLORE

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
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
Learn about Spanish colonial history in Old San Juan
from $7,045
EXPLORE

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Kaia
  • Visit Culebra Flamenco Beach
  • Tour St. John Mongoose Junction
  • Discover Cruz Bay bustling bay
  • Walk Philipsburg street markets
Starts / Ends
San Juan / St. John's
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring Vieques, Cruz Bay, and Jost Van Dyke's stunning beaches. Visit Gustavia in Saint Barthelemy, experiencing its unique French culture before concluding the journey in St. John's, Antigua.
Cruise Details
0
Learn about Spanish colonial history in Old San Juan
from $7,045
EXPLORE

Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Kaia
  • Discover Basseterre architecture
  • See Iles des Saintes Fort Napoleon
  • Walk Gustavia painted wooden houses
  • Tour Virgin Gorda granite boulders
Starts / Ends
St. John's / San Juan
Activities
Village Visits
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $5,000
EXPLORE

San Juan to San Juan

San Juan Roundtrip - 8 Day Itinerary aboard Silver Dawn
  • Snorkel Trunk Bay reefs in St John
  • Witness Gustavia harbor views
  • Ride horses along Antigua beaches
  • Enjoy swimming at Jost Van Dyke
Starts / Ends
San Juan / San Juan
Activities
Wildlife Viewing, Rainforest Exploration, Kayaking, Hiking
Activity Level
Variable
Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.
Cruise Details
0
Stroll along the beaches of Puerto Rico
from $9,295
EXPLORE

Paradise Beaches from the U.S. Virgin Islands to The Bahamas

San Juan - Miami - 10 Day Itinerary aboard Emerald Kaia
  • Tour Grand Turk lighthouse
  • Wander Gordon's Beach
  • Walk Nassau bustling Straw Market
  • Dive San Salvador Island
Starts / Ends
San Juan / Miami
Activities
Local Market Visits, Snorkeling, Archaeological Site Visits
Activity Level
Variable
Set sail on a 10-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring the beautiful Turks and Caicos Islands and vibrant marine life in The Bahamas. Enjoy fresh local seafood and conclude your journey in the lively metropolis of Miami, blending cultural discovery with natural beauty.
Cruise Details
0
Beautiful beach in Dominica
from $8,370
EXPLORE

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
Enjoy the beautiful blue Caribbean
from $5,590
EXPLORE

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
Activities
Scuba Diving
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
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
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
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