Small Ship Cruising

(15 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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Dates: Jul 24, 2027 through Sep 24, 2028
Itinerary:
Sicily
Reserve a qualifying Sicily sailing by November 30, 2026, and receive a $500 USD air credit plus a complimentary 3GB WiFi package per cabin.
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Dates: May 15, 2027 through Sep 18, 2027
Itinerary:
Mediterranean
For a limited time, book one of our select 2027 departures by November 30, 2026, and receive up to $500 onboard credit per cabin, plus a complimentary bottle of champagne waiting in your stateroom.
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Dates: Jun 07, 2028 through Sep 15, 2028
Itinerary:
Mediterranean
Reserve a summer 2028 sailing by December 31, 2026, and receive an air credit of up to $700 USD per cabin.
Departing on Feb 27, 2027 on the Star Clipper
Nights: 7
Dates: Feb 27, 2027 through Mar 06, 2027
Ship: Star Clipper
Itinerary:
St. George's, Grenada, Admiralty Bay, Bequia, Grenadines, Tobago Cays, Grenadines, Soufriere, St. Lucia, Beach, Martinique, Cabrits, Dominica, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts, St. John's, Antigua
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Mar 27, 2027 on the Star Clipper
Nights: 7
Dates: Mar 27, 2027 through Apr 03, 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.), Philipsburg, St. Maarten, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), St. John's, Antigua
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Feb 13, 2027 on the Star Flyer
Nights: 7
Dates: Feb 13, 2027 through Feb 20, 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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Mar 13, 2027 on the Star Flyer
Nights: 7
Dates: Mar 13, 2027 through Mar 20, 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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Jan 16, 2027 on the Star Flyer
Nights: 7
Dates: Jan 16, 2027 through Jan 23, 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
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Dec 19, 2026 on the Star Flyer
Nights: 7
Dates: Dec 19, 2026 through Dec 26, 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, Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Feb 20, 2027 on the Star Flyer
Nights: 7
Dates: Feb 20, 2027 through Feb 27, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, 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.), Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Mar 20, 2027 on the Star Flyer
Nights: 7
Dates: Mar 20, 2027 through Mar 27, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Gustavia, St. Barts, 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), Road Bay, Anguilla, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Jan 23, 2027 on the Star Flyer
Nights: 7
Dates: Jan 23, 2027 through Jan 30, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, 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.), Gustavia, St. Barts, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night