Have questions? We're here.
Explore the Caribbean

Virgin Islands Small Ship Sailing

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Discover the enchanting allure of the Virgin Islands with Adventure Life's array of 9 captivating small ship sailing experiences in 2024. Join us on a sailing adventure to explore the mesmerizing beauty and vibrant cultures of the Caribbean islands. From the turquoise waters of Antigua to the lush landscapes of St. Lucia, each moment offers a unique opportunity to immerse yourself in the wonders of the region. Experience the relaxed pace of small ship sailing as you swim and snorkel amidst the pristine waters, enjoy the French flair of Îles des Saintes, and witness breathtaking sunsets over the horizon. Engage in a variety of activities like snorkeling, wildlife viewing, and discovering hidden beaches, all while surrounded by the natural splendor of the Caribbean. Don't miss this chance to sail away from the ordinary and embark on a journey of a lifetime. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (9 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Virgin Islands
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:
Variable
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. Lucia to the captivating charm of Les …
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
Pink beach huts in the Caribbean
$1,700
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:
Variable
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
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
Tropical waterfall and turquoise pool in lush forest
$1,640
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:
Variable
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
Relax on the beaches of St. Maarten
$8,995
EXPLORE

Barefoot through Balmy January

St Maarten to Barbados - 10 Day Itinerary aboard Sea Cloud
  • Explore St. Maarten’s charm
  • Relax on Bequia beaches
  • Snorkel in Tobago Cays
  • Discover Soufriere’s sulfur springs
Starts / Ends:
Philipsburg / Barbados
Activities:
Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on a 10-day journey through the Caribbean, starting in Philipsburg, St. Maarten. Discover European charm in the heart of the Caribbean, stroll along the Boardwalk, or relax on Great Bay Beach. Visit the island of St. Barths, renowned for its elegant atmosphere and vibrant harbor. In …
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:
Variable
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
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
Gatun Lock of the Panama Canal
$3,640
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
1-9 of 9 Results
TrustScore 4.8 | 372 reviews
TrustScore 4.8 of 5
total score
Based on 372 reviews on
review score
23 hours ago
Very well ececuted. Hily recomended. Great experiance
Nancy Kaierle
review score
2 days ago
Belize adventures I've worked with Adventure Life before in planning trips and appreciate the quality of trips they put together. They use knowledgeable local guides, comfortable lodgings, and assist with transportation. I find trip planning stressful, so am happy to turn it over to them. They work within our parameters of time, budget, activity level, and types of activities to give us great experiences!
Kaesa Footracer
review score
2 days ago
I was reading and it was a good story I need to recommend it
Delilah DeLee
review score
4 days ago
We have been working with Adventure Life for 5 years now and it is very easy to plan out our trips. Our holidays include customization of activities and side trips along with the standard packages available on the Adventure Life website. Kevin, Jess, Mary Rose and their teams have many recommendations that have enhanced our travel.
Joe
review score
1 week ago
We went to the Patagonia on the Chile side and Perito Moreno in El Calafate, Argentina. Eric of San Diego handled our trip with expertise. The preparation went smoothly, despite some changes on our part with scheduling conflicts. He offered great advice which made us feel at ease with all decisions on the trip. It was truly a great experience.
Evelyn and Edwin

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

Jenna Fedyschyn Adventure Life employee profile
Jenna F
Plan My Trip
We love travel, talk with an expert 1.800.344.6118