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Top Caribbean Trips & Tours in October 2025

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Discover Caribbean in October 2025 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of during October 2025 as you enjoy Local Market Visits, Village Visits, Archaeological Site Visits, Wildlife Viewing, and Small Ship Sailing. Prices for trips in October 2025 range from $2,613 to $43,280 for a vacation of 8 to 29 days. Choose any of the below 7 itineraries in October 2025 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Sunset view by the cliff houses
from $3,237
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
Village Visits, Local Market Visits, Wildlife Viewing, Ziplining, Hiking, Rainforest Exploration, Snorkeling
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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Cayo Arena Island
from $3,125
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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Areal view of Old city of Santo Domingo
from $2,612
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
Discover the best of the Dominican Republic's highlights on this 8-day adventure, from the idyllic beaches of Punta Cana to the historic charm of Santo Domingo, the lush landscapes of Jarabacoa, the cultural richness of Santiago de los Caballeros, the bustling streets of San Francisco de Macoris, and the coastal allure of Las Terrenas.
Tour Details
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Enjoying the landscape of Lencois Maranhenses National Park
from $21,580
Air Credit
EXPLORE

Exploring South America

Barbados - Brazil - 21 Day Itinerary aboard SH Vega
  • Explore the Amazon Rainforest
  • Visit Georgetown and Paramaribo
  • Explore Lençóis Maranhenses
  • Explore cultures and wildlife
Starts / Ends
Bridgetown / Salvador
Activity Level
Variable
On this 21-day Exploring South America Cruise from Barbados to Brazil aboard SH Vega, explore South America's Atlantic coast from Barbados to Brazil, encountering the Amazon Rainforest's biodiversity, colonial history in cities like Georgetown and Paramaribo, and natural wonders like Lençóis Maranhenses and the Amazon River mouth.
Cruise Details
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Funchal, Madeira, Portugal
from $2,810
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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Explore the beautiful Canary Islands
from $4,820
EXPLORE

Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer
  • Discover the Rock of Gibraltar
  • Experience Tangier
  • Visit Cadiz
  • Explore Safi
Starts / Ends
Malaga / Philipsburg
Activities
Small Ship Sailing
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
Cruise Details
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Take in the sights, sounds, and colors of Barbados
from $7,120
EXPLORE

Westbound Atlantic Ocean Crossing

Civitavecchia - Bridgetown - 29 Day Itinerary aboard Royal Clipper
  • Explore Bonifacio’s scenic harbor
  • Discover Mahon’s Georgian charm
  • Wander Palma’s markets
  • Unwind on Ibiza’s beaches
Starts / Ends
Civitavecchia / Bridgetown
Activity Level
Variable
Set sail on a 29-day cruise aboard the Royal Clipper, traveling from Civitavecchia to the Caribbean while exploring historic and vibrant locations like Bonifacio, Ibiza, and Malaga. Enjoy days at sea, classic sailing experiences, and onboard activities before reaching Barbados.
Cruise Details
0
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