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Caribbean Tours

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Discover the turquoise waters and tranquil island cultures of the Caribbean, on one of these 75 best Caribbean trips for 2026 and 2027 listed below. When you travel to the Caribbean, you are likely to encounter all the tropical and subtropical beauty that the islands are known for, including lush botanical gardens, swaying palm trees, spectacular beaches with crystal clear waters, and gentle island communities. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Gustavia, Bridgetown, Soufriere, Philipsburg, and St. Kitts. Our Caribbean tour packages for 2026 feature Snorkeling, Village Visits, Small Ship Sailing, Archaeological Site Visits, and Local Market Visits, and start from $2,010 for trips of 5 to 23 days. Most of the trips and itineraries below can be customized to meet your precise needs. Contact Adventure Life Caribbean experts to start planning your ideal Caribbean tours and cruises in 2026. 
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Pink beach huts in the Caribbean
from $2,080
SS 25%
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
Take a leisurely stroll through beautiful Bridgetown
from $11,990
Save $150
EXPLORE

Grenadines & Windwards Yachting

Roundtrip Bridgetown - 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
Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.
Cruise Details
0
Visit beautiful Norman Island
from $9,990
Save $150
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
Relax on the beaches of St. Maarten
from $6,395
Save $150
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Cruising the Leeward Islands

Roundtrip Sint Maarten - 8 Day Itinerary aboard Emerald Sakara
  • Visit Basseterre colonial structure
  • Discover Anguilla marine life
  • Swim in pools at Virgin Gorda
  • Experience Gustavia Creole cuisine
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.
Cruise Details
0
Explore the famous rock formations of the baths
from $6,295
Save $150
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Philipsburg - 8 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown rich heritage
  • Enjoy Soufriere sulfur springs
  • See St. John's Nelson's Dockyard
  • Experience Gustavia Creole cuisine
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $5,000
Up to 40%
EXPLORE

San Juan to San Juan

San Juan Roundtrip - 8 Day Itinerary aboard Silver Dawn
  • Snorkel Trunk Bay reefs in St John
  • Witness Gustavia harbor views
  • Ride horses along Antigua beaches
  • Enjoy swimming at Jost Van Dyke
Starts / Ends
San Juan / San Juan
Activities
Wildlife Viewing, Local Market Visits, Kayaking, Archaeological Site Visits, Rainforest Exploration, Hiking
Activity Level
Variable
Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.
Cruise Details
0
Bright blue waters of the Caribbean
from $2,880
EXPLORE

Aruba to Grenada

Oranjestad - St. George - 11 Day Itinerary aboard Star Clipper
  • Visit Oranjestad to see beaches
  • See Willemstad gabled houses
  • Tour Curacao inland cunucu
  • Swim Charlestown Bay
Starts / Ends
Oranjestad / St. Georges
Activities
Snorkeling, Small Ship Sailing, Village Visits
Activity Level
Variable
Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.
Cruise Details
0
White Sand Beach in Barbados
from $2,080
SS 25%
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
Dock going out into the crystal blue ocean
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.
Cruise Details
0
Relax on the beaches of St. Maarten
from $2,010
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
Tropical waterfall and turquoise pool in lush forest of Dominica
from $2,010
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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!
Cruise Details
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Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
Save $150
EXPLORE

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse
  • Explore Nassau’s vibrant capital
  • Visit Staniel Cay’s beaches
  • Discover San Salvador’s coral reefs
  • Stroll St. Barts iconic Shell Beach
Starts / Ends
Nassau / Bridgetown
Activities
Stand Up Paddle Boarding, Helicopter Tours
Activity Level
Variable
Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
Cruise Details
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1-12 of 75 Results

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