Top Caribbean Trips & Tours in November 2025

from $2,020

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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 $1,960

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Leeward Islands

8 Day Itinerary aboard Star Flyer

• Visit Dominica Island
• Snorkel at Iles des Saintes
• Sail across Rivière Salée
• Enjoy Gustavia's unique charm

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.

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from $1,960

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Treasure Islands

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 $8,390

2for1

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Grenadines & Windwards Yachting

8 Day Itinerary aboard Emerald Sakara

• Discover Bequia’s secluded beaches
• Savor Caribbean dining experiences
• Snorkel Tobago Cays' waters
• Admire panoramic views from Mayreau

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich islands aboard Emerald Sakara. Enjoy pristine beaches, vibrant local cultures, and water activities like swimming and snorkeling.

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from $8,390

2for1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

Starts / Ends

Bridgetown / Marigot

Activities

Wildlife Viewing

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.

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from $15,180

2for1

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

• Experience Falmouth's historic port
• Discover Soufriere's Sulfur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

Starts / Ends

Bridgetown / Marigot

Activities

Small Ship Sailing

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

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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 Cuba’s history may not have been made, but where it was lived every day. It reveals to you to Cuba’s true resource, its true legend: its people.

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from $4,350

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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.

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from $4,240

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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

Activities

Local Market Visits

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.

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from $4,350

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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 $4,840

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Natural Sanctuaries & Heritage of the Caribbean

Willemstad - Colon - 8 Day Itinerary aboard Le Champlain

• See sites in Cartagena & Willemstad
• Explore Santa Marta & Sierra Nevada
• Discover San Blas Islands' beaches
• Visit and explore Fort San Lorenzo
• Witness wildlife and ecosystems

Starts / Ends

Willemstad / Colon

Activities

Hiking, Snorkeling, Archaeological Site Visits, Village Visits

Activity Level

Variable

Explore the Caribbean on this 8-day Natural Sanctuaries & Heritage of the Caribbean cruise from Willemstad to Colon aboard the Le Champlain. Walk through UNESCO-listed cities, snorkel in the San Blas Islands, and meet the Kuna people. Visit Santa Marta’s mountains and the Fort San Lorenzo in Panama. Discover coral reefs, mangroves, and wildlife.

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from $2,850

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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 $4,610

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Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 25 Day Itinerary aboard Star Clipper

• Explore Malaga’s Moorish Alcazaba
• Discover Tangier’s culture
• Wander Cadiz’s palm-lined streets
• Visit Safi’s old town

Starts / Ends

Malaga / Bridgetown

Activity Level

Variable

Embark on a 25-day cruise aboard the Star Clipper, exploring Spain, Morocco, and the Canary Islands before heading to Barbados. Experience diverse cultures, stunning landscapes, and relaxation at sea on this unforgettable journey.

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from $2,720

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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 $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, Kayaking

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

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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