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Top Caribbean Trips & Tours in October 2026

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Discover Caribbean in October 2026 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of during October 2026 as you enjoy Village Visits, Wildlife Viewing, Local Market Visits, Archaeological Site Visits, and Small Ship Sailing. Prices for trips in October 2026 range from $2,444 to $69,990 for a vacation of 8 to 16 days. Choose any of the below 7 itineraries in October 2026 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Areal view of Old city of Santo Domingo
from $2,443
EXPLORE

Best of Dominican Republic

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Visit coffee factory in Jarabacoa
  • Learn about tobacco production
  • Visit cocoa & chocolate plantation
  • See the beaches of Las Terrenas
Starts / Ends
Punta Cana / Punta Cana
Activities
Hacienda Visits, Volunteering
Activity Level
Relaxed
Visit Dominican Republic and uncover hidden gems, from Jarabacoa coffee farms and cigar factories to coastal escapes in Punta Cana. Our tours include top-rated attractions, immersive cultural visits, and unforgettable nature experiences. Discover the best things to do in the Dominican Republic, from the capital to the coast.
Tour Details
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Cayo Arena Island
from $3,793
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
Archaeological Site Visits
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
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Sunset view by the cliff houses
from $3,400
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
Snorkeling, Local Market Visits, Ziplining, Hiking, Rainforest Exploration
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
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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
Activities
Small Ship Sailing
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
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Aerial View of Halifax Skyline
from $3,199
EXPLORE

Southern Caribbean Yacht Harbors

Halifax - Bridgetown - 9 Day Itinerary aboard Seabourn Venture
  • Tour Citadel Hill
  • Visit Brimstone Hill Fortress
  • Snorkel at Pigeon Island
  • Visit Saint Lucia’s famous Pitons
Starts / Ends
Halifax / Bridgetown
Activities
Spa Relaxation, Kayaking, Photography Seminars
Activity Level
Variable
Cruise from Halifax, Nova Scotia to Bridgetown, Barbados aboard the Seabourn Venture on a 9-day Southern Caribbean Yacht Harbors cruise. Enjoy relaxing days at sea and explore scenic Caribbean islands like Saint Kitts, Montserrat, and Saint Lucia. Visit UNESCO World Heritage Sites, snorkel in clear waters, and experience rich history and culture.
Cruise Details
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Paradise Tropical Island - Bocas del Toro archipelago - Island Colon
from $24,990
2for1
EXPLORE

Pristine Islands of the Bahamas & the Panama Canal

Nassau - Panama City - 11 Day Itinerary aboard Scenic Eclipse
  • Explore Nassau’s colonial streets
  • Visit Staniel Cay’s beaches
  • Discover San Salvador’s coral reefs
  • Meet Cabo de La Vela’s Wayuu people
Starts / Ends
Nassau / Panama City
Activities
Wildlife Viewing, Village Visits
Activity Level
Variable
Join an 11-day cruise from Nassau to Panama City on the Scenic Eclipse, exploring the Bahamas' clear waters and vibrant island cultures. Experience highlights like Pig Beach and the Panama Canal, blending leisure with cultural discovery.
Cruise Details
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Funchal, Madeira, Portugal
from $2,940
EXPLORE

Westbound Atlantic Ocean Crossing

Lisbon - Barbados - 16 Day Itinerary aboard Royal Clipper
  • Explore Lisbon’s vibrant streets
  • Discover Portimão’s historic charm
  • Wander Funchal’s lush landscapes
  • Cruise Barbados’ stunning shores
Starts / Ends
Lisbon / Bridgetown
Activity Level
Variable
Sail across the Atlantic on this 16-day cruise aboard the Royal Clipper, blending culture and adventure. Discover Lisbon’s charm, Portimao’s historical treasures, Madeira’s vibrant nightlife, and Barbados’ stunning shores, with serene days at sea in between.
Cruise Details
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