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Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape
from $6,995
EXPLORE

Pirate Islands With A Yachtie Vibe

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Gustavia harbor
  • Visit Shirley Heights, Antigua
  • Explore The Baths, Virgin Gorda
  • Sail Sir Francis Drake Channel
  • Experience Virgin Islands fun
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.
Cruise Details
0
Kayaking in Cuba
from $3,590
EXPLORE

Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities
Homestays, Kayaking
Activity Level
Easy Active
Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.
Tour Details
0
Sunset view by the cliff houses
from $4,438
EXPLORE

Dominican Republic: North Coast Expedition

8 Day Itinerary
  • Enjoy canyoning in Puerto Plata
  • See the landscape using 4x4 buggy
  • Visit the Los Pepines murals.
  • Learn about tobacco production
  • See the lovely bay of Rio San Juan
  • Zip line over the Laguna Dudu
Starts / Ends
Puerto Plata / Puerto Plata
Activities
Hiking, Rainforest Exploration, Ziplining
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
Tour Details
0
Cayo Arena Island
from $4,000
EXPLORE

Dominican Republic: Culture and Cocktails

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Visit coffee factory in Jarabacoa
  • Visit Los Pepines murals
  • Swim in azure waters of Cayo Arena
  • Visit cocoa & chocolate plantation
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Cooking Classes
Activity Level
Easy Active
This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.
Tour Details
0
Enjoy the beautiful blue Caribbean
from $2,880
EXPLORE

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
Activities
Snorkeling, Local Market Visits
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
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
Wildlife Viewing, 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
Bicycle on Cuban street
from $4,390
EXPLORE

Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Activities
Biking
Activity Level
Moderate
A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where the island's rich history isn't just remembered—it is lived every day. It reveals Cuba’s greatest resource and truest legend: its people.
Tour Details
0
Boats Moored to the Quay at Bridgetown Harbour
from $4,450
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
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
The vivid colors of the San Blas Islands
from $4,330
NO SS
EXPLORE

Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown’s heritage
  • Discover St. George’s coastal views
  • Admire Kralendijk’s marine life
  • Wander Willemstad’s streets
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.
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
Archaeological Site Visits, Village Visits, 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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Shannon Fischer-Kendro Adventure Life employee profile
Shannon K.
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