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Discover the turquoise waters and tranquil island cultures of the Caribbean, on one of these 39 best Caribbean trips for 2024 and 2025 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 Bridgetown, Gustavia, Soufriere, Tobago Cays, and Philipsburg. Our amazing trips to the Caribbean for 2024 feature cruises, small ship cruises, snorkeling, small ship sailing, and beaches, and start from $1,600 for trips of 5 to 29 days. Most of the trips and itineraries below can be customized to meet your precise needs. Contact Adventure Life Caribbean experts for help planning your ideal Caribbean tours and cruises in 2024. 
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Dock going out into the crystal blue ocean
$1,700
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Enjoy Grenada's unique aromas
  • Discover Falmouth Harbour, Antigua
  • Enjoy the beach in ÎIes des Saintes
  • Explore lush St. Lucia Island
Starts / Ends:
St. John's / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Swim and snorkel amidst the beautiful, pristine waters of the Caribbean Sea on this 8-day expedition aboard Royal Clipper. Sail away from your everyday life and find tropical bliss in the islands. From the stunning drama of the spectacular Pitons at St. Luciato the captivating charm of Les Saintes, …
Cruise Details
0
White Sand Beach in Barbados
$1,660
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
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
$11,595
EXPLORE

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb - 15 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts / Ends:
Philipsburg / St. Barth
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
0
Learn about the history of the Caribbean
$6,614
EXPLORE

Embracing Inner Spirit and Thriving Caribbean Cruise

Saint Martin to Barbados - 8 Day Itinerary aboard SH Vega
  • Explore Philipsburg, Sint Maarten
  • Discover the town of Gustavia
  • Explore the village of Deshaies
  • Admire the Pitons in Soufriere
  • Discover Saint-Pierre, Martinique
  • Explore Bridgetown, Barbados
Starts / Ends:
Philipsburg / Bridgetown
Activities:
Archaeological Site Visits, Kayaking, Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Experience the best of the Caribbean with this 8-day itinerary. Start your trip in Philipsburg, Sint Maarten, and soak in the vibrant atmosphere of this Dutch capital. Enjoy the lively beachfront establishments, excellent shopping, and stunning beaches like Great Bay and Little Bay. In Gustavia, …
Cruise Details
0
Pink beach huts in the Caribbean
$1,660
EXPLORE

Windward Islands

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
$1,600
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
0
Beautiful beach in Dominica
$1,600
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
Cruise Details
0
Explore colorful Gustavia
$8,990
Savings
EXPLORE

Hidden Charms of the Caribbean

San Juan - St John's - 8 Day Itinerary aboard Emerald Sakara
  • Discover active reefs in Culebra
  • Experience Vieques Island's charm
  • Indulge in Gustavia's French flair
  • Explore the serene Friars Beach
Starts / Ends:
San Juan / St. John's
Activities:
Urban Exploration, Village Visits
Activity Level:
Relaxed
Set sail on the Emerald Sakara, a contemporary luxury vessel, from San Juan and embark on an exciting Caribbean journey. Explore the diverse marine life and tranquil beaches of Culebra, the bustling waterfront of Esperanza Bay on Vieques Island, and the charming streets of Cruz Bay on St. John …
Cruise Details
0
Relax on the sunny beaches of the Caribbean
$8,890
Savings
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore the azure waters of Tobago
  • Observe the calm waters
  • Discover Eastern Caribbean
Starts / Ends:
Bridgetown / Marigot
Activities:
Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Cruise Eastern Caribbean with St. Barths on this 8-day adventure aboard Emerald Azzurra. Nature and culture aboundinn this mesmerizing tropical exploration of the eastern Caribbean. The azure waters of Tobago Cay National Park teem with wildlife just waiting to be discovered, while …
Cruise Details
0
Scuba diving in Tobago cays
$8,890
Savings
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Eastern Caribbean and Grenadines

8 Day Itinerary aboard Emerald Sakara
  • Visit the Mayreau Island
  • Enjoy picturesque strolls
  • Swim in Tobago Cay National Park
  • Discover Martinique’s history
Starts / Ends:
St. John's / St. John's
Activities:
Local Market Visits, Snorkeling
Activity Level:
Relaxed
Enjoy an 8-day cruise aboard the Emerald Sakara. From Antigua, cruise to the town of Saint-Pierre in Martinique, a cultural and artistic hub nicknamed ‘Little Paris’. Enjoy picturesque strolls and shop in the open-air market of Port Elizabeth, swim in the crystal-clear lagoon of Tobago …
Cruise Details
0
Mountains by the ocean in St Lucia
$5,830
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts / Ends:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Dumont-d'Urville on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its …
Cruise Details
0
Relax on the beaches of St. Maarten
$1,640
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Embark on an 8-day cruise aboard the Star Flyer. With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this unique region, …
Cruise Details
0
Play in the brilliant blue waters of the Caribbean
$8,890
EXPLORE

West Indies Island Hopping with Chef Michael Bonacini

Roundtrip San Juan - 8 Day Itinerary aboard Emerald Sakara
  • Explore Puerto Rico
  • Discover Vieques Island
  • Experience Virgin Gorda
  • Explore St. Barths
  • Explore Jost Van Dyke
Starts / Ends:
San Juan / San Juan
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Embark on this 8-Day West Indies Island Hopping adventure aboard the Emerald Sakara. Departing and arriving from San Juan, this Caribbean cruise takes on a thrilling journey to some of the most breathtaking islands in the region. From the sun-kissed white sand beaches and marine-rich azure waters …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$12,290
EXPLORE

Grenadines & Grenada Adventure

Bridgetown Roundtrip - 8 Day Itinerary aboard Emerald Azzurra
  • Vibrant marine encounters
  • Culinary delights abound
  • Crystal-clear waters for snorkeling
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Local Market Visits, Snorkeling
Activity Level:
Relaxed
Experience the ultimate tropical island adventure aboard Emerald Azzurra on an 8-day cruise through the enchanting Grenadines and Grenada. This extraordinary journey promises to captivate the senses as one traverses a paradise of pristine beaches, vibrant marine life, and captivating cultures. …
Cruise Details
0
Pelicans hanging out in the ocean
$11,830
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
Cruise Details
0
Kayaking in Cuba
$3,390
EXPLORE

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
Activities:
Homestays, Kayaking, Snorkeling
Activity Level:
Easy Active
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves. The country's music and art draw from these diverse influences. Cuba has also exerted an …
Tour Details
0
Explore colorful Bridgetown, Barbados
$5,399
BOGO
EXPLORE

Island Yachting

Bridgetown Roundtrip - 9 Day Itinerary aboard World Voyager
  • Explore The Nature Island, Dominica
  • Enjoy the reggae rhythms of Roseau
  • Relax at Baie de Pompierre
  • Dive in the waters of Mopion’s reef
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Local Market Visits
Activity Level:
Relaxed
Embark on a 9-day cruise from Barbados and back aboard World Voyager. Discover the Nature Island, Dominica, with its lush rainforests, rugged mountain peaks, black-sand beaches, and bubbling hot springs. The thriving capital, Roseau, captivates you with its reggae rhythms and historic streets. …
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
$2,550
EXPLORE

Eastbound Atlantic Ocean Crossing

15 Day Itinerary aboard Royal Clipper
  • Explore the east coast of Barbados
  • Discover Santa Cruz
  • Experience Las Palmas
  • Visit Caldera de Bandama
Starts / Ends:
Bridgetown / Las Palmas
Activities:
Small Ship Cruises
Activity Level:
Relaxed
Join the Royal Clipper on a 15-day cruise departing from Bridgetown, Barbados. Experience the vibrant contrasts of this coastal town, with its red-sand beaches and lively streets. Explore the British-influenced heritage through landmarks like Trafalgar Square and discover traditions like cricket …
Cruise Details
0
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