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

Best Small Ship Caribbean Cruises

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 (111 Results)
Show Filter

73-90 of 111 Results
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Caribbean
Explore the small island of Virgin Gorda as you sail the Caribbean
$7,515
EXPLORE

Philipsburg Round Trip

10 Day Itinerary aboard Sea Cloud Spirit
  • Visit the charming Virgin Islands
  • Explore stunning White Bay
  • Discover magnificent Isla Culebrita
  • Tour Cruz Bay known as ‘Love City’
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Sea Cloud Spirit takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Philipsburg, St. Maarten. As you sail, visit the British Virgin Islands with heavenly bays, gorgeous beaches, idyllic anchoring spots, smart yacht clubs, and …
Cruise Details
Explore the famous rock formations of the baths
$4,099
EXPLORE

San Juan to San Juan

10 Day Itinerary aboard SeaDream II
  • Stroll in the city of San Juan
  • Swim with dolpins at Sandy Ground
  • Relax at White Bay
  • Enjoy the canopy at Tortola Island
Starts/ Ends in:
San Juan / San Juan
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
The Caribbean is known for its opportunities to relax beside crystal blue waters and pristine sands, but there are also exciting activities to enjoy on this 10-day cruise. Embark on the SeaDream II in San Juan, the largest city and the capital of Puerto Rico, where you can see the Castillo de …
Cruise Details
St Barth Island, Caribbean
$4,199
EXPLORE

Philipsburg to Marigot

9 Day Itinerary aboard SeaDream I
  • Experience shopping in Philipsburg
  • Relax on Antigua's beaches
  • Explore Gustavia by hike or bike
  • Visit the famous Foxy’s Bar
Starts/ Ends in:
Philipsburg / Marigot
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean on this incredible9-day cruise through the islands of Saint Martin, Montserrat, Antigua and Barbuda, Anguilla, St. Barths, Jost van Dyke, and Virgin Gorda. Enjoy water sports, leisurely tours, land adventures and hiking options to make the most of your Caribbean adventure.
Cruise Details
Explore the colorful streets of Marigot
$3,199
EXPLORE

Marigot to Castries St. Lucia

8 Day Itinerary aboard SeaDream I
  • Enjoy the scenic Saba Island
  • Bike around Gustavia
  • Relax on beautiful beaches
  • Experience Iles des Saintes
Starts/ Ends in:
Marigot / Mayreau
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Embark SeaDream I for a spectacular 8-day journey across the Caribbean. Explore the beautiful town ofMarigot, where itscolonial houses stand beside cafés and bistros, pastry shops and luxury boutiques. Enjoy an incredible hike to a scenic overview of Saba Island. Many beautiful places are …
Cruise Details
Jost Van Dyke, British Virgin Islands
$3,199
EXPLORE

Castries, St. Lucia to San Juan

8 Day Itinerary aboard SeaDream I
  • Dive along the coast of St. Barts
  • Enjoy a unique dolphin encounter
  • Enjoy the sulfur springs at Soufrie
  • Visit the Spanish fortress
Starts/ Ends in:
Bequia / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the beautiful blue waters of the Virgin Islands on this 8-day Caribbean cruise. See the fascinating islands of the area, including Castries St. Lucia, Port Elizabeth, Bequia, Soufriere Bay and and many more.Swim and snorkel in one of the most incredible landscapes in the world or dive to your …
Cruise Details
Mountains by the ocean in St Lucia
$3,199
EXPLORE

Castries to San Juan

8 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Bike around Gustavia
  • Experience Iles des Saintes
  • Enjoy Saint Lucia
Starts/ Ends in:
Bequia / San Juan
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
On this once-in-a-lifetime Caribbean adventure, join SeaDream on an 8-day exploration.Enjoy an incredible hike as well as an exciting water sport in different islands. Many beautiful places are waiting for you to visit, explore and to discover!
Cruise Details
Peaceful seclusion in the Caribbean
$3,299
EXPLORE

Marigot to Bridgetown via St. Lucia

8 Day Itinerary aboard SeaDream I
  • Discover spectacular natural beauty
  • Enjoy the Rodney Bay
  • Explore Bridgetown's beaches
  • Swim and snorkel at Tobago Cays
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
SeaDream anchors off in different places and offers an exciting adventure.Discover what the underwater looks like with the “sit on top “double clear bottom kayaks. It’s the best thing to Snorkeling or Scuba Diving. Then, travel through the quaint town of red-tiled roofs, and spice …
Cruise Details
Tropical Caribbean Beach in Martinique
$3,299
EXPLORE

Bridgetown to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Explore Bridgetown
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Start your journey in the port city of Bridgetown.It's famous for its British colonial architectureand horseracing track. Then sail to one of the popular beaches in Martinique, theGrande de Anse. You can also enjoy clear bottom kayaking, snorkeling, and scuba diving. There are still a lot of …
Cruise Details
Beautiful beach, Tobago Cays
$3,399
EXPLORE

Marigot to Bridgetown

8 Day Itinerary aboard SeaDream II
  • Visit Union Island
  • Discover Mayreau
  • Swim and snorkel at Tobago Cays
  • Explore Bridgetown's beaches
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Hiking, Small Ship Cruise
Activity Level:
Relaxed
SeaDream II anchors off in different places and offers an exciting adventure.Discover beautiful and magnificent beaches in the Caribbean. Embark the ship in the four streets wide city of Marigot and take time to go around it. One of these days, you will visit Tobago Cays and the Tobago Cays Marine …
Cruise Details
Peaceful seclusion in the Caribbean
$3,099
EXPLORE

Marigot to Marigot

8 Day Itinerary aboard SeaDream I
  • Relax on beautiful beaches
  • Hike or bike around the islands
  • Discover the town of Marigot
  • Visit Gustavia
Starts/ Ends in:
Marigot / Marigot
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Explore the Caribbean on this incredible journey full of land adventures for you to discover the islands from sea or land. Embark and disembark in Marigot,the main town and capital on the French side of Saint Martin, an area well known for its elegant stores with the latest in European designer …
Cruise Details
St Barts harbor view
$4,599
EXPLORE

Marigot to San Juan via St. Kitts

8 Day Itinerary aboard SeaDream II
  • Explore Saba's natural beauty
  • Enjoy the breeze at Leverick Bay
  • Enjoy water sports at Soper's Hole
  • Stroll through historic San Juan
Starts/ Ends in:
Marigot / San Juan
Activities:
Biking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean on this incredible journey full of land adventures for you to discover the islands from sea or land. Embark in Marigot,the main town and capital on the French side of Saint Martin, an area well known for its elegant stores with the latest in European designer fashions and fine …
Cruise Details
Tranquil shores on your Virgin Islands cruise
$10,295
EXPLORE

Caribbean: Bridgetown - Colon

15 Day Itinerary aboard Sea Cloud II
  • Observe incredible sunsets
  • Visit the ABC islands
  • Sail through Panama Canal
  • Discover Bequia's turtle sanctuary
  • Snorkel at Tobago Cays
Starts/ Ends in:
Bridgetown / Colon
Activities:
Sailing Schooner, Small Ship Cruise
Activity Level:
Relaxed
Join the Sea Cloud ll on this 15-day sailing adventure from Bridgetown to Colon. Clear your mind in this paradisaical destination that mixes adventure and relaxation perfectly.Discover the unique range of flora and fauna in Colon, experience sailing through Panama Canal where it connects the …
Cruise Details
Snorkeling in the Caribbean with a starfish
$8,355
EXPLORE

Philipsburg Round Trip

11 Day Itinerary aboard Sea Cloud Spirit
  • Spend two days at Nature Isle
  • Visit charming Terre-de-Haut
  • Enjoy touring Moskito Island
  • Explore St. Barthélemy
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Sea Cloud Spirit on this 11-day experience-of-a-lifetime Caribbean cruise. This voyage which starts at Philipsburg, St. Maarten will take you to exquisite places. Visit the charming main town of Terre-de-Haut, explore the unspoiled beauty of the Winward Islands -Dominica, immerse in the …
Cruise Details
Take the time to explore St. Lucia
$3,800
EXPLORE

Bridgetown to Fort Lauderdale (Florida)

11 Day Itinerary aboard Silver Whisper
  • Visit Scarborough's botanic gardens
  • Ride Basseterre's scenic train
  • Explore Jost Van Dyke
  • Enjoy shopping and dining
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Be amazed by the Caribbean’s distinctive charms as you travel everywhere from the “Nature Island” to the “Isle of Spice.” The landscapes you’ll see are sure you leave you in breathless appreciation—beautiful waterfalls, towering mountains, fertile green …
Cruise Details
Clear water in the bay
$3,199
EXPLORE

Marigot to Philipsburg

7 Day Itinerary aboard SeaDream I
  • Explore the town of Marigot
  • Visit beaches, resorts and restaura
  • Swim with dolphins
  • Hike, snorkel and scuba dive
Starts/ Ends in:
Marigot / Philipsburg
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover the Caribbean's beauty on this amazing 7-day cruise sailing across enchanting and unique islands. Explore Sandy Ground by biking around the island.Enjoy some great hiking opportunities as well as snorkeling and scuba diving in different places.
Cruise Details
Unspoiled beaches and pristine coves in the Caribbean
$2,899
EXPLORE

Marigot to Marigot

7 Day Itinerary aboard SeaDream I
  • Explore the city of Marigot
  • Be welcomed at Montserrat
  • Relax in Gustavia
  • Visit Foxy’s Bar at Great Harbour
Starts/ Ends in:
Marigot / Marigot
Activities:
Hiking, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
The start and end of this 7-day journey are in Marigot. Itis the main town and capital in the French Collectivity of Saint Martin. Then, SeaDream sails toMontserrat and visit Little Bay. You will have an opportunity to swimwith dolphins or for the energetic, bike around the island of Sandy Ground. …
Cruise Details
Soufriere bay, St Lucia
$3,800
EXPLORE

Bridgetown to Bridgetown

10 Day Itinerary aboard Silver Whisper
  • See the pastel colors of Road Town
  • Admire Martinique's landscapes
  • Visit Grenada, the Isle of Spice
  • Explore markets in Port Elizabeth
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Spa & Relaxing, Wine Tasting
Activity Level:
Relaxed
Traverse the Caribbean’s shallow, sparkling waters, and tick off envied destinations at the same time! The swaying palms of Castries will set the scene for the next 10 days that will see colorful streets in Road Town, chic boutiques in St. Barts, volcanic slopes in St. Kitts, and sprawling …
Cruise Details
Spectacular views over the crater lake
$3,299
EXPLORE

Bridgetown to Lisbon

13 Day Itinerary aboard SeaDream I
  • Sit back and relax on board
  • Discover tranquility offshore
  • Enjoy perfect views of Lisbon
  • Visit the Azores
Starts/ Ends in:
Bridgetown / Lisbon
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Crossing the Atlantic in a small ship is an experience that leaves a lasting impression. For 13 days sail across the Atlantic Ocean, making your way from Barbados to the enchanting city of Lisbon. Sit back and relax, surrounded by vast horizons and perfect tropical weather conditions as you leave …
Cruise Details
73-90 of 111 Results

Why Travel With Adventure Life

More Reasons

Awards and Accolades

All News