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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

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Select one of the below 11 best Lesser Antilles trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Lesser Antilles. Our Lesser Antilles trips for 2026 feature Small Ship Sailing, Snorkeling, Archaeological Site Visits, Village Visits, and Wildlife Viewing, and start from $2,010 for trips of 8 to 18 days. Contact Adventure Life's Lesser Antilles trip planning experts to start planning your next seamless trip.

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    • Lesser Antilles
Pink beach huts in the Caribbean
from $2,080
NO SS
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
Panama's turquoise waters
from $4,450
NO SS
EXPLORE

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.
Cruise Details
0
White Sand Beach in Barbados
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
Snorkeling
from $7,910
No SS
EXPLORE

Panama, Colombia & Caribbean Islands

Colon - Fort-de-France - 11 Day Itinerary aboard Le Bellot
  • Cartagena colonial old town
  • Visit Santa Marta and Sierra Nevada
  • Visit Bonaire reef marine park
  • Visit Fort-de-France landmarks
Starts / Ends
Colon / Fort de France
Activities
Scuba Diving
Activity Level
Variable
Set sail on an 11-day cruise through Panaman, Colombia and Caribbean Islands aboard Le Bellot. Visit Cartagena and Santa Marta with guided historic and cultural excursions. Explore the San Blas Islands for beaches, snorkeling, and Kuna culture. The voyage combines nature, culture, and Caribbean island experiences.
Cruise Details
0
St Barts harbor view
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
The vivid colors of the San Blas Islands
from $4,330
NO SS
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
Relax on the white sandy beaches of the Caribbean
from $2,010
Air Credit
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
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
View of Mount Pelée overlooking Saint-Pierre, northwest Martinique, French Caribbean island
from $6,995
EBD 30%
EXPLORE

Sun-Drenched Sailing Days

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Philipsburg beaches
  • Visit Saint-Pierre ruins
  • Uncover St. Lucia’s Pitons
  • Discover Dominica’s jungle
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.
Cruise Details
0
Visit Las Palmas’ Santa Ana Cathedral, a central landmark in the city
from $13,695
EBD 30%
EXPLORE

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.
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
from $13,655
EBD 30%
EXPLORE

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.
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
Archaeological Site Visits, Local Market Visits, Wildlife Viewing, Hiking, Rainforest Exploration, Kayaking
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
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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
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