Small Ship Cruising

(20 offers included)
Small Ship Cruising offers high crew to passenger ratios, unparalleled service, and access to destinations unreachable by large cruise ships.
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Some Horizons Are Worth Chasing
Dates: Jan 01, 2027 through Dec 31, 2028
Itinerary:
Caribbean, Mediterranean
For a limited time, select 2027 and 2028 departures include: $500 USD Air Credit per cabin plus one bottle of champagne in your cabin upon arrival.
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Caribbean Winter Sailings
Dates: Dec 05, 2026 through Mar 31, 2028
Itinerary:
Caribbean
Reserve now and receive two complimentary Shore Excursions per cabin plus Prepaid Gratuities.
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Sail Croatia in 2027
Dates: Jun 01, 2027 through Jul 31, 2027
Itinerary:
Croatia, Italy, Albania, Greece, Montenegro
Croatia has become one of the most requested regions in the Mediterranean. These 2027 sailings place you directly along its coastline.
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Sailing Makes Us Different
Dates: May 31, 2027 through Jan 31, 2028
Itinerary:
Europe, Caribbean
Book select departures by September 30, 2026, and receive Up to $300 USD Onboard Credit per cabin plus a complimentary bottle of champagne waiting in your stateroom.
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The Greek Isles Are Calling
Dates: May 01, 2027 through Sep 15, 2027
Itinerary:
Greece
Book by September 30, 2026, and you may also receive Up to $500 Onboard Credit per cabin plus a complimentary bottle of champagne waiting in your stateroom.
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Next Summer Starts Now
Dates: Apr 17, 2027 through Oct 27, 2027
Itinerary:
Mediterranean
Once aboard, enjoy $300 USD Shipboard Credit per cabin toward experiences such as shore excursions, drinks or spa time. Pre-paid gratuities are also included, adding ease and peace of mind throughout your sailing.
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More Reasons to Cross the Ocean
Dates: Apr 03, 2027 through Dec 31, 2027
Itinerary:
Atlantic Ocean
Reserve a qualifying Ocean Crossing sailing departing through Dec. 31, 2027 and receive: $800 USD Air Credit per cabin plus two massages per person.
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The Southern Caribbean
Dates: Feb 01, 2027 through Dec 31, 2027
Itinerary:
Caribbean
Book select Southern Caribbean sailings aboard Star Clipper and receive: $400 USD Air Credit per cabin plus one bottle of champagne waiting in your cabin upon arrival.
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Star Pride New York
Windstar Cruises Logo
Quick Getaways: Seaside Charms & Dutch Waterways
Departing on May 10, 2027 on the Star Pride
Nights: 3
Dates: May 10, 2027 through May 13, 2027
Ship: Star Pride
Itinerary:
LONDON / HMS BELFAST, CRUISING THAMES RIVER, OOSTENDE, BRUGES, HARLINGEN, AMSTERDAM
from
$1,432.00
(USD)
Per Person
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Suite
$1,432.00
Cat: SP
$477.33/Night
Star Legend Caribbean
Windstar Cruises Logo
Quick Getaways: Balearic Islands and Port Vendres Escape
Departing on Jun 24, 2027 on the Star Legend
Nights: 4
Dates: Jun 24, 2027 through Jun 28, 2027
Ship: Star Legend
Itinerary:
BARCELONA, ALCUDIA, MALLORCA, MAHON, PORT VENDRES, BARCELONA
from
$1,444.00
(USD)
Per Person
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Suite
$1,444.00
Cat: SP
$361.00/Night
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Sicily & Greece
Departing on Oct 30, 2026 on the Star Clipper
Nights: 5
Dates: Oct 30, 2026 through Nov 04, 2026
Ship: Star Clipper
Itinerary:
Piraeus (Port of Athens), Greece, Monemvasia, Greece, Pilos, Greece, Syracuse - Sicily, Italy, Valletta, Malta
from
$1,740.00
(USD)
Per Person
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Inside
$1,740.00
Cat: Category 6
$348.00/Night
Outside
$1,880.00
Cat: Category 5
$376.00/Night
Star Pride New York
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Quick Getaways: St. Malo Getaway
Departing on May 18, 2027 on the Star Pride
Nights: 4
Dates: May 18, 2027 through May 22, 2027
Ship: Star Pride
Itinerary:
LONDON / HMS BELFAST, CRUISING THAMES RIVER, ST. MALO, LONDON / HMS BELFAST
from
$1,798.00
(USD)
Per Person
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Suite
$1,798.00
Cat: SP
$449.50/Night
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Leeward Islands
Departing on Jan 02, 2027 on the Star Flyer
Nights: 7
Dates: Jan 02, 2027 through Jan 09, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Deshaies, Guadeloupe, Terre-de-Haut, Iles des Saintes, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
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Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Leeward Islands
Departing on Feb 27, 2027 on the Star Flyer
Nights: 7
Dates: Feb 27, 2027 through Mar 06, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Treasure Islands
Departing on Nov 28, 2026 on the Star Flyer
Nights: 7
Dates: Nov 28, 2026 through Dec 05, 2026
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Leeward Islands
Departing on Dec 05, 2026 on the Star Flyer
Nights: 7
Dates: Dec 05, 2026 through Dec 12, 2026
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Leeward Islands
Departing on Jan 30, 2027 on the Star Flyer
Nights: 7
Dates: Jan 30, 2027 through Feb 06, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Antigua roundtrip
Departing on Mar 13, 2027 on the Star Clipper
Nights: 7
Dates: Mar 13, 2027 through Mar 20, 2027
Ship: Star Clipper
Itinerary:
St. John's, Antigua, Gustavia, St. Barts, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Sopers Hole - Tortola, British Virgin Islands (BVI, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, White Bay, Jost van Dyke (B.V.I.), Road Bay, Anguilla, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), St. John's, Antigua
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Treasure Islands
Departing on Jan 09, 2027 on the Star Flyer
Nights: 7
Dates: Jan 09, 2027 through Jan 16, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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Treasure Islands
Departing on Dec 12, 2026 on the Star Flyer
Nights: 7
Dates: Dec 12, 2026 through Dec 19, 2026
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
More Details Contact Us
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night