Have questions? We're here.
Clear waters of the Caribbean sea

Caribbean Small Ship Cruise Tours

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
Talk with an expert Ask a Question
Filter & Sort (91 Results)
Show Filter

1-18 of 91 Results
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Caribbean
St Barth Island, Caribbean
$7,230
EXPLORE

Golf and Pro-Am in the Caribbean

11 Day Itinerary aboard Le Champlain
  • Cruise with Figaro Golf
  • Enjoy a golf cruise
  • Access world-renowned golf courses
  • Treat yourself to quality excursion
Starts/ Ends in:
Santo Domingo / Fort de France
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
This 11-day cruiseallows you to choose between two options, “Competition Pro-Am” with 5 rounds orThe option “Leisure” including 5 golf courses and 2 optional tournaments.The most experienced among you will be able to participate in thePro-Am tournament, in the company of …
Cruise Details
Pelicans hanging out in the ocean
$8,990
Savings
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud (LI)
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Sailing Schooner, Small Ship Cruise, 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
Pink beach huts in the Caribbean
$1,500
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore lush St. Lucia Island
  • Hike to Trafalgar Falls
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Activities:
Sailing Schooner, Small Ship Cruise, 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
St George's Harbor - Grenada
$3,400
EXPLORE

Pearls of the Caribbean

8 Day Itinerary aboard Le Champlain
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Champlain on its 8-day cruise combining long, white-sand beaches and the easy Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its garrison. Visit …
Cruise Details
Tobago
$8,190
EXPLORE

Caribbean and Amazonia

13 Day Itinerary aboard Le Dumont-d'Urville
  • Visit Saint Vincent
  • Discover beautiful landscapes
  • Explore underwater life in the Gren
  • Admire Cayenne´s tropical beauty
Starts/ Ends in:
Fort de France / Cayenne
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling, Spa & Relaxing, Wildlife Viewing
Activity Level:
Relaxed
Set sail on an incredibly diversecruise, taking in Caribbean beaches and excursions into tropical rainforests aboard Le Dumont-d’Urville, from Fort-de-France to Cayenne.Embarking in Martinique, sail to the idyllic beaches ofSaint Vincent and the Grenadines, renowned for the richness of their …
Cruise Details
Beautiful beach in Dominica
$2,240
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
Activities:
Sailing Schooner, Small Ship Cruise, 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
The Pitons in St Lucia
$1,649
EXPLORE

Sail to St. Lucia

7 Day Itinerary aboard Mandalay
  • Enjoy morning coffee at sunrise
  • Snorkel & swim in Caribbean waters
  • Sip a rum swizzle
  • Relax on the top deck
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the S/V Mandalay crew on this 7-day roundtrip sailing adventure starting and ending in St. Lucia, an island known for its beaches and reef-diving sites. Enjoy the winds of the Caribbean, take a turn at the helm, and partake in raising the vessel sails. Experience daily island visits for …
Cruise Details
Bustling port of Fort de France, Martinique
$2,110
EXPLORE

Ocean Voyage: Fort-de-France - Ponta Delgada

9 Day Itinerary aboard Le Champlain
  • Observe endless horizons
  • Enjoy the comfort of this ship
  • Keep fit in the spa
  • Discover sailing techniques
Starts/ Ends in:
Fort de France / Ponta Delgada
Activities:
Small Ship Cruise, Spa & Relaxing
Activity Level:
Relaxed
On this 9-day cruise, you can admire the waves from the upper deck, keep fit in the spa and make good use of the pool or the gym, share the daily life of the crew, discover sailing techniques and instruments, and enjoy a break from the hectic pace of life. From Fort-de-France, Martinique to Ponta …
Cruise Details
Gatun Lock of the Panama Canal
$4,160
EXPLORE

Panama Canal: 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 in:
Barbados / Balboa
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
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
Caribbean beach bar
$1,799
EXPLORE

British Virgin Islands

7 Day Itinerary aboard Mandalay
  • Look for bird life
  • Snorkel in crystal waters
  • Gaze at the night sky
  • Relax with your favorite book
Starts/ Ends in:
St. Martin / Tortola
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the S/V Mandalay in St. Maartenand make your way to Tortola for a 7-day Caribbean sailing adventure. Besides being one of the most scenic islands in the Caribbean, Tortola offers a decidedly cultural and historical side. Visit a selection of islands including, Anguilla, Jost Van Dyke, Norman …
Cruise Details
Dock going out into the crystal blue ocean
$2,800
EXPLORE

Grenada Round Trip

14 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night
  • Learn to raise the ship's sails
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. This fabulous 14-day voyage offers you an authentic sailing experience giving you the chance to learn how to raise the sails, take a turn at the helm, or just relax on deck! …
Cruise Details
The beautiful waters of the Caribbean
$1,799
EXPLORE

St. Maarten Round Trip

7 Day Itinerary aboard Mandalay
  • Watch the sunrise from the deck
  • Snorkel in crystal waters
  • Enjoy lunch ashore
  • Join in on the Mandalay Masquerade
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the S/V Mandalay for a once-in-a-lifetime experience that fewothers ever see or even dream of. Partake in raising the sails, take a turn at the helm, or just enjoy the winds of the Caribbean sea filling the sails with new friends aboard. The choice is yours! Visit locations such asSt. …
Cruise Details
Dock going out into the crystal blue ocean
$2,340
EXPLORE

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
Activities:
Sailing Schooner, Small Ship Cruise
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
Gatun Lock of the Panama Canal
$4,160
EXPLORE

Panama Canal: 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:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
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
Charlestown, Nevis
$2,999
EXPLORE

Charlotte Amalie to San Juan via St. John

8 Day Itinerary aboard SeaDream II
  • Relax on St. Thomas' beaches
  • Enjoy incredible food on board
  • Scuba dive the waters of Nevis
  • Swim with dolphins at Anguilla
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Delight yourself with all the European charm of the Caribbean on this wonderful 8-day cruise that mixes adventure and relaxation perfectly. From your small ship, the SeaDream II, you have the opportunity to join some incredible land excursions and practice different water sports to let out the …
Cruise Details
Explore beautiful Jost van Dyke
$7,985
EXPLORE

Caribbean: Philipsburg to Bridgetown

11 Day Itinerary aboard Sea Cloud
  • Visit beautiful islands
  • See St Barths' luxurious lifestyle
  • Observe incredible sunsets
  • Discover The Baths at Virgin Gorda
Starts/ Ends in:
Philipsburg / Bridgetown
Activities:
Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 12-day round-trip cruise from Philipsburg in St. Maarten. As you sail, visit the charming port cities and remote coves of Gustavia, Virgin Gorda and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly …
Cruise Details
Beach, harbor and village of Terre-de-Haut
$7,945
EXPLORE

Caribbean: Bridgetown to Bridgetown

12 Day Itinerary aboard Sea Cloud
  • Visit the Old Hegg Turtle Sanctuary
  • Visit Cabrits National Park
  • Stroll in the town of Gustavia
  • Discover volcanic sulphur springs
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Small Ship Cruise, Wildlife Viewing
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 12-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Port Elizabeth, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly locals. …
Cruise Details
Relax on the shores of the Caribbean
$4,400
EXPLORE

Bridgetown Round-trip

10 Day Itinerary aboard Silver Whisper
  • Explore Bridgetown
  • Visit St.Georges, the Isle of Spice
  • Stroll through Oranjestad
  • Discover Willemstad
  • Admire Bequia's virgin beaches
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
If it is vibrant color from turquoise seas to lush verdure that you want, then look no further than the Caribbean. Hop from one island to the next, taking in Grenada’s spicy scents, Aruba’s pastel architecture and St. Lucia’s gleaming beaches. Set against a canopy of palm trees …
Cruise Details
1-18 of 91 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News