Caribbean Small Ship Sailing Cruises

from $21,340

2for1

EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

• Explore Anguilla’s turquoise waters
• Stroll through Gustavia
• Admire Nevis’ tranquil shores
• Visit Antigua’s Falmouth Bay

Cruise Details

0

from $15,180

2for1

EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

Starts / Ends

Bridgetown / Marigot

Activities

Kayaking

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

• Explore Bridgetown’s capital
• Wander Speightstown’s streets
• Discover Kingstown’s gardens
• Unwind on Bequia Island

Cruise Details

0

from $3,090

EXPLORE

Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.

• Explore St. George’s Fort George
• Discover Charlotteville’s Tobago
• Unwind on Carriacou beach
• Visit Martinique ruins

Cruise Details

0

from $8,050

EXPLORE

Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activities

Village Visits, Snorkeling

Activity Level

Variable

Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.

• Explore St. George’s panoramic view
• Discover Charlotteville coastline
• Unwind at Englishman’s Bay
• Visit Martinique ruins

Cruise Details

0

from $7,590

2for1

EXPLORE

Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

San Juan / Miami

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.

• Explore the pristine beaches
• Snorkel in crystal-clear waters
• Relax on secluded Gordon’s Beach
• Explore Grand Turk’s beaches

Cruise Details

0

from $8,370

EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant

Starts / Ends

Dominica / Anses d'Arlet

Activities

Scuba Diving

Activity Level

Variable

Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.

• Enjoy iconic pitons of Saint Lucia
• Learn about Kalinago culture
• Explore Tobago Cays' coral reefs
• Relax on Marie-Galante's beaches

Cruise Details

0

from $4,350

EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper

Starts / Ends

Bridgetown / Balboa

Activity Level

Variable

Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.

• Explore Bridgetown, Barbados
• Enjoy Grenada's unique aromas
• Discover Dutch colonial Curacao
• Transit the historic Panama Canal

Cruise Details

0

from $4,240

EXPLORE

Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper

Starts / Ends

Bridgetown / Balboa

Activities

Wildlife Viewing

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.

• Explore Bridgetown’s heritage
• Discover St. George’s coastal views
• Admire Kralendijk’s marine life
• Wander Willemstad’s streets

Cruise Details

0

from $3,420

EXPLORE

Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer

Starts / Ends

Philipsburg / Malaga

Activities

Local Market Visits, Small Ship Sailing, Archaeological Site Visits

Activity Level

Variable

Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.

• Explore Philipsburg’s Dutch side
• Experience Marigot’s markets
• Unwind while crossing the Atlantic
• Visit Ponta Delgada’s churches

Cruise Details

0

from $5,610

EXPLORE

Eastbound Atlantic Ocean Crossing

Barbados to France - 29 Day Itinerary aboard Royal Clipper

Starts / Ends

Bridgetown / Nice

Activity Level

Variable

Set sail on a 29-day Eastbound Atlantic Ocean cruise aboard Royal Clipper. Enjoy sailing, historic ports, and scenic coastal landscapes.

• See Ponta Delgada, Azores scenery
• See Malaga, Spain's architecture
• Visit Mallorca’s Gothic cathedral
• Visit Calvi’s coastal citadel

Cruise Details

0

from $4,610

EXPLORE

Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 25 Day Itinerary aboard Star Clipper

Starts / Ends

Malaga / Bridgetown

Activity Level

Variable

Embark on a 25-day cruise aboard the Star Clipper, exploring Spain, Morocco, and the Canary Islands before heading to Barbados. Experience diverse cultures, stunning landscapes, and relaxation at sea on this unforgettable journey.

• Explore Malaga’s Moorish Alcazaba
• Discover Tangier’s culture
• Wander Cadiz’s palm-lined streets
• Visit Safi’s old town

Cruise Details

0

from $2,720

EXPLORE

Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper

Starts / Ends

Las Palmas / Bridgetown

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Cruise Details

0

from $2,850

EXPLORE

Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage all the way to the stunningly beautiful Caribbean Islands.

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Cruise Details

0

from $4,820

EXPLORE

Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer

Starts / Ends

Malaga / Philipsburg

Activity Level

Variable

Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.

• Discover the Rock of Gibraltar
• Experience Tangier
• Visit Cadiz
• Explore Safi

Cruise Details

0

from $7,120

EXPLORE

Westbound Atlantic Ocean Crossing

Civitavecchia - Bridgetown - 29 Day Itinerary aboard Royal Clipper

Starts / Ends

Civitavecchia / Bridgetown

Activity Level

Variable

Set sail on a 29-day cruise aboard the Royal Clipper, traveling from Civitavecchia to the Caribbean while exploring historic and vibrant locations like Bonifacio, Ibiza, and Malaga. Enjoy days at sea, classic sailing experiences, and onboard activities before reaching Barbados.

• Explore Bonifacio’s scenic harbor
• Discover Mahon’s Georgian charm
• Wander Palma’s markets
• Unwind on Ibiza’s beaches

Cruise Details

0