Top Caribbean Trips & Tours in November 2026

from $2,080

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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

• Explore Antigua’s vibrant dockyards
• Discover Les Saintes’ beaches
• Relax on Martinique’s white sands
• Stroll Grenada’s aromatic markets

Starts / Ends

St. John's / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.

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from $2,010

SS 25%

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Treasure Islands

St. Maarten Roundtrip - 8 Day Itinerary aboard Star Flyer

• Visit Virgin Gorda's famous “Baths”
• Enjoy the lifestyle of Soper's Hole
• Walk the streets of Basseterre
• Relax on famous St. Barts

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!

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from $12,490

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Grenadines & Windwards Yachting

Bridgetown, Barbados Roundtrip - 8 Day Itinerary aboard Emerald Azzurra

• Explore historic Kingstown
• Swim Tobago Cays reefs
• Discover Mayreau views
• Relax on Bequia Island

Starts / Ends

Bridgetown / Bridgetown

Activities

Snorkeling, Wildlife Viewing

Activity Level

Variable

Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.

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from $7,590

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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara

• Explore the pristine beaches
• Snorkel in crystal-clear waters
• Relax on secluded Gordon’s Beach
• Explore Grand Turk’s beaches

Starts / Ends

San Juan / Miami

Activities

Kayaking, Local Market Visits

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.

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from $3,590

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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

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.

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from $4,390

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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

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.

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from $4,450

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

• Explore Balboa’s colonial charm
• Transit Panama’s iconic canal
• Discover San Blas culture
• Enjoy Aruba’s clear waters

Starts / Ends

Balboa / St. John's

Activity Level

Variable

Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.

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from $3,890

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Cuba Multisport

8 Day Itinerary

• Bike, kayak, snorkel, and hike Cuba
• Appreciate Cuba's colonial past
• Be immersed in Cuba's culture
• Enjoy excellent wildlife viewing
• Experience Cuban hospitality

Starts / Ends

Havana / Havana

Activities

Biking

Activity Level

Moderate

Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.

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from $2,245

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Classic Cuba

Cars, Rum, and Cigars - 5 Day Itinerary

• Walk the vibrant streets of Havana
• Sample rum and local delicacies
• Tour cigar-rolling factories
• Explore stunning Valley de Vinales
• View Hemingway's former estate

Activities

Hiking, Homestays, Urban Exploration

Activity Level

Relaxed

Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.

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from $3,590

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Cuba Walking Tour

8 Day Itinerary

• Explore Cuba on foot
• Snorkel in Zapata National Park
• Learn about the tobacco industry
• Hike to waterfalls and caves
• Be immersed in Cuba's culture
• Experience Cuban hospitality

Starts / Ends

Havana / Havana

Activity Level

Moderate

Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.

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from $2,970

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Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage all the way to the stunningly beautiful Caribbean Islands.

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from $2,820

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Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Starts / Ends

Las Palmas / Bridgetown

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.

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from $13,695

EBD 30%

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Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Philipsburg - 17 Day Itinerary aboard Sea Cloud Spirit

• Experience Transatlantic Crossing
• See the Gran Canaria landscapes
• Explore Las Palmas old town
• Climb rigging and set sails

Starts / Ends

Las Palmas / Philipsburg

Activity Level

Variable

Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.

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from $13,655

EBD 30%

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Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Bridgetown - 18 Day Itinerary aboard Sea Cloud II

• Experience Transatlantic Crossing
• Sail under full sails
• Visit Santa Ana Cathedral
• Explore Bridgetown, Barbados

Starts / Ends

Las Palmas / Bridgetown

Activities

Small Ship Sailing, Village Visits

Activity Level

Variable

Take part in an 18-day transatlantic cruise aboard Sea Cloud II from Las Palmas, Gran Canaria to Bridgetown, Barbados. Relax under full sails, explore Gran Canaria’s landscapes, and discover Bridgetown’s UNESCO World Heritage colonial architecture and beaches.

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from $4,130

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Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 23 Day Itinerary aboard Star Clipper

• Visit Safi port
• View Arrecife golden sand beach
• See Bridgetown Trafalgar Square
• View Las Palmas volcanic crater

Starts / Ends

Malaga / Bridgetown

Activities

Archaeological Site Visits

Activity Level

Variable

Set sail on a 23-day transatlantic cruise from Malaga to Barbados on the Star Clipper, exploring stunning sites like the Alhambra in Spain, the Hassan II Mosque in Morocco, and the volcanic landscapes of the Canary Islands. Conclude your journey in Bridgetown, Barbados, visiting historic landmarks.

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