Have questions? We're here.
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

Top Lesser Antilles Cruises & Trips

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Filter (40 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Lesser Antilles
A dish created by Chef Ben Robinson
$6,966
EXPLORE

Caribbean Yachting Discovery with Chef Ben Robinson

8 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Relax on Barbuda’s pink-sand beach
  • Discover vibrant town of Gustavia
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / San Juan
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on this 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Start with a welcome reception, join an interactive cooking demo to recreate one of Chef Ben’s dishes, and enjoy his signature multi-course dinner and other special dishes throughout the week. Experience …
Cruise Details
0
Panorama of Les Saintes
$7,190
EXPLORE

Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover quaint island towns
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends:
Bridgetown / Marigot
Activities:
Archaeological Site Visits
Activity Level:
Variable
Set sail on a 7-day Caribbean cruise aboard the luxurious Emerald Azzurra. Begin in Barbados, soaking in vibrant culture and stunning beaches. In Soufrière, indulge in volcanic mud baths and explore scenic volcanic landscapes. At Falmouth Harbour, visit Nelson’s Dockyard, a UNESCO …
Cruise Details
0
Explore colorful Gustavia
$6,340
EXPLORE

Caribbean Enchantment

7 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Visit Fort Napoleon on Les Saintes
  • Visit The Baths on Virgin Gorda
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / Marigot
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, a French-Caribbean archipelago with picturesque towns and the historic Fort Napoleon. Discover Deshaies in Guadeloupe, known for its colorful Creole architecture and beautiful beaches. Visit Virgin …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$8,150
EXPLORE

The Essential of the Caribbean

Fort-de-France Roundtrip - 13 Day Itinerary aboard Le Champlain
  • Cruise in West Indies
  • Visit heritage sites
  • Discover British Virgin Islands
  • Private beach day in Mayreau
Starts / Ends:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Variable
You begin your voyage in St. Kitts, a volcanic island known for its excellent sandy beaches and rich colonial history. Your cruise then docks in Anguilla before continuing west to the British Virgin Islands, which have gorgeous landscapes. Then, sail to Saint Barthelemy and the enchanted setting of …
Cruise Details
0
Pelicans hanging out in the ocean
$9,658
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:
Variable
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 this extraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers …
Cruise Details
0
Explore the famous rock formations of the baths
$7,500
EXPLORE

A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Starts / Ends:
San Juan / San Juan
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Join an 8-day Caribbean journey starting in San Juan, where the city's enduring strength against historic invasions shines through its monumental forts—La Fortaleza, Fort San Felipe del Morro, Fort San Juan de la Cruz, and Fort San Cristóbal—guarding UNESCO World …
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:
Variable
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
Explore the famous rock formations of the baths
$7,990
EXPLORE

Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbour
  • Wander through lively Cruz Bay
Starts / Ends:
San Juan / St. Thomas
Activities:
Archaeological Site Visits, Local Market Visits, Urban Exploration
Activity Level:
Variable
Set sail on an 8-day Caribbean adventure aboard the Emerald Sakara. Discover the vibrant culture and historic charm of San Juan, Puerto Rico, and the lively atmosphere of Saint John in the US Virgin Islands. Enjoy the serene beaches and historic sites of Nevis, and immerse yourself in the …
Cruise Details
0
Relax on the shores of the Caribbean
$6,320
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Fort-de-France - 9 Day Itinerary aboard Le Bellot
  • Visit UNESCO World Heritage sites
  • Visit Portsmouth, Dominica
  • Explore Les Saintes, Guadeloupe
  • See Mayreau's fishes and corals
Starts / Ends:
Les Saintes / Bridgetown
Activities:
Land & Sea Exploration, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Embark on a 9-day cruise through the Caribbean aboard Le Bellot, tailored for travelers seeking cultural immersion. Start in Vieux Fort, St. Lucia, and see the UNESCO-listed Gros and Petit Pitons. Sail to Portsmouth, Dominica, to explore landscapes and local chocolate. Continue to Les Saintes, …
Cruise Details
0
Beautiful beach in Dominica
$8,200
EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Starts / Ends:
Dominica / Anses d'Arlet
Activities:
Scuba Diving, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean cruise aboard Le Ponant. Explore the wild landscapes of Dominica and navigate the mangroves of the Indian River on a local boat, surrounded by green herons and pelicans. Meet the Kalinago people, who share their history and local cuisine, offering insight into their …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,830
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,540
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Star Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Gatun Lock of the Panama Canal
$3,830
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Transit the historic Panama Canal
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Swim in paradise in Bonaire
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
The crystal blue water of Jost van Dyke
$2,720
EXPLORE

Jamaica to Antigua

12 Day Itinerary aboard Star Clipper
  • Swim in Montego Bay's waters
  • Explore Santo Domingo
  • Visit the Treasure Island
  • Hike Virgin Gorda trails
Starts / Ends:
Port Antonio / St. John's
Activities:
Local Market Visits, Small Ship Cruises, Snorkeling, Spa Relaxation
Activity Level:
Variable
Embark on a 12-day Caribbean cruise adventure from Jamaica to Antigua aboard Star Clipper. Explore historical sites like Rose Hall Great House or enjoy activities like snorkeling and zip-lining. Visit Port Antonio, a charming town with lush landscapes, secluded beaches, and attractions like Blue …
Cruise Details
0
Nassau Lighthouse
$23,390
EXPLORE

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown - 13 Day Itinerary aboard Scenic Eclipse
  • Explore beaches on Compass Cay
  • See swimming pigs on Exuma Island
  • Discover Long Island on foot
  • Enjoy the view from Gorda Point
Starts / Ends:
Nassau / Bridgetown
Activities:
Hiking, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Embark on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Discover the hidden gem of Great Exuma Island, with its …
Cruise Details
0
Gaze at the balconies overlooking the breathtaking cathedral in Cartagena, Colombia
$8,565
EXPLORE

Just Drifting Along

Willemstad - Panama - 9 Day Itinerary aboard Sea Cloud Spirit
  • Explore Willemstad's harbor
  • Discover Oranjestad’s culture
  • Sail San Blas Archipelago
  • Stroll Aruba’s pastel streets
Starts / Ends:
Willemstad / Colon
Activities:
Archaeological Site Visits, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on a 9-day cruise aboard the Sea Cloud Spirit. Journey through the vibrant ABC islands, starting in Curacao with its UNESCO-listed capital, Willemstad, known for its "Little Amsterdam" charm. Explore Oranjestad, Aruba, where colorful houses and unique landscapes create its distinct …
Cruise Details
0
Enjoying the landscape of Lencois Maranhenses National Park
$9,080
EXPLORE

Exploring South America

Barbados - Brazil - 21 Day Itinerary aboard SH Vega
  • Explore the Amazon Rainforest
  • Visit Georgetown and Paramaribo
  • Explore Lençóis Maranhenses
  • Explore cultures and wildlife
Starts / Ends:
Bridgetown / Salvador
Activities:
Adventure Options, Archaeological Site Visits, Small Ship Cruises, Wildlife Viewing
Activity Level:
Variable
Embark on a 21-day cruise aboard SH Vega and explore the Atlantic coastline of South America. The adventure takes you from Barbados to Brazil, where you discover the wonders of this diverse region. During the trip, you encounter the rich biodiversity of the Amazon Rainforest, explore the colonial …
Cruise Details
0
The stunning blue coastline of the Canary Islands
$2,490
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Crossing the mighty Atlantic Ocean provides the time to truly appreciate the pure pleasure of the sea. Imagine sailing the Atlantic in the footsteps of legendary explorers, enjoying the Old World family charm and the wonders of the New World. Admire Gran Canaria's exotic vegetation and magical …
Cruise Details
0
19-36 of 40 Results

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By