Top Caribbean Trips & Tours in December 2026

from $2,080

Air Credit

EXPLORE

Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper

• Explore beaches in Barbados
• See lush island of St. Lucia
• Discover Falmouth Harbour, Antigua
• Visit sophisticated Martinique

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.

Cruise Details

0

from $9,990

EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Soak in Soufriere’s volcanic spring
• Explore Les Saintes’ French charm
• Visit Antigua’s Nelson’s Dockyard
• Stroll Nevis’ Georgian towns

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

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

Cruise Details

0

from $9,990

EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

• Explore Prickly Pear Cays waters
• Admire Nevis’ Georgian buildings
• Visit Soufriere’s volcanic springs
• Wander Bridgetown’s streets

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.

Cruise Details

0

from $2,080

Air Credit

EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper

• Visit one island in Grenadines
• Smell the aroma of Grenada
• Walk and swim at Marigot Bay
• Taste the spicy Creole cooking

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Cruise Details

0

from $2,010

Air Credit

EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Explore Nevis sugar plantations
• Visit Dominica boiling lakes
• Snorkel Terre-de-Haut blue waters
• Swim South Friars Bay clear waters

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.

Cruise Details

0

from $2,010

Air Credit

EXPLORE

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!

Cruise Details

0

from $21,780

EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Bridgetown / Marigot

Activities

Village Visits, Wildlife Viewing, Kayaking

Activity Level

Variable

Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.

Cruise Details

0

from $13,690

EXPLORE

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

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.

Cruise Details

0

from $9,990

EXPLORE

Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

• Explore Saint John's pristine beach
• Stroll Philipsburg's lively markets
• Snorkel Norman Island's caves
• Visit 'The Baths' in Virgin Gorda

Starts / Ends

St. Thomas / St. Thomas

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.

Cruise Details

0

from $9,990

EXPLORE

Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Explore Anguilla’s coral coastlines
• Visit Virgin Gorda granite boulders
• Discover Norman Island's coves
• Relax on Anegada’s remote sands

Starts / Ends

Marigot / Marigot

Activities

Hiking

Activity Level

Variable

Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.

Cruise Details

0

from $11,790

EXPLORE

Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara

• Tour Nelson’s Dockyard
• Explore Nevis Island plantations
• Walk through Gustavia
• Swim Prickly Pear Cays

Starts / Ends

San Juan / St. Thomas

Activities

Urban Exploration

Activity Level

Variable

Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.

Cruise Details

0

from $9,440

EXPLORE

Pearls of the Caribbean

Fort-de-France Roundtrip - 8 Day Itinerary aboard Le Bougainville

• Wander at Fort-de-France Harbor
• Discover Union Island Beaches
• Snorkel at Tobago Cays Reefs
• Swim Pompierre Beach Les Saintes

Starts / Ends

Fort de France / Fort de France

Activities

Archaeological Site Visits, Local Market Visits

Activity Level

Variable

Embark on an 8-day Caribbean cruise from Martinique through the Grenadines aboard Le Bougainville. Explore vibrant towns, secluded beaches, coral reefs, tropical islands, and volcanic landscapes. Snorkel, swim, stroll along scenic shores, and enjoy historic sites.

Cruise Details

0

from $2,210

EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Gustavia French boutiques
• Hike Jost Van Dyke scenic trails
• Tour Tortola to see Soper's Hole
• Explore Basseterre landmarks

Starts / Ends

Philipsburg / Philipsburg

Activities

Snorkeling, Small Ship Sailing

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.

Cruise Details

0

from $2,010

Air Credit

EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Explore Nevis sugar plantations
• Tour Dominica rainforests
• Snorkel Terre-de-Haut waters
• Visit famous Nelson's Dockyard

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Embark on an 8-day roundtrip cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring St. Maarten, Nevis, Dominica, Antigua, and St. Barts. Experience stunning beaches, vibrant culture, and unique natural landscapes across the Leeward Islands.

Cruise Details

0

from $4,330

Air Credit

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