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.
from $1,299.00 (USD)
Per Person
+ $224.00 taxes/fees
Nights: 4
Ship: SeaDream II
Price Per Night:$324.75 (USD)
(based on double occupancy, for comparison only)
Itinerary: Charlotte Amalie, St. Thomas, Soper's Hole, Tortola, Norman Island, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, North Sound, Virgin Gorda, Charlotte Amalie, St. Thomas
We visit the intimate yachting playgrounds, harbors and ports where large cruise ships cannot go. "It’s yachting, not cruising" and you may never want to go on a cruise ship again.
Other Categories Starting At:
Inside
N/A
Outside
$1,299.00
Cat: YC2
Balcony
N/A
Suite
$2,399.00
Cat: C2
Noumea to Cairns
Cairns, Queensland, Australia to Noumea, New Caledonia
from $1,299.00 (USD)
Per Person
+ $280.00 taxes/fees
Nights: 7
Ship: Wind Spirit
Price Per Night:$185.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Cairns, Queensland, Australia, Noumea, New Caledonia
The Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht. Wind Spirit features wide open, teak decks-quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
Other Categories Starting At:
Inside
N/A
Outside
$1,299.00
Cat: B
Balcony
N/A
Suite
N/A
St. Maarten to St. Maarten
Philipsburg, St. Maarten, Saint Maarten to Philipsburg, St. Maarten
from $1,499.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$214.14 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Charlestown, Saint Kitts, Nevis, Roseau, Dominica, Dominica, Pigeon Island, St. Lucia, Saint Lucia, Les Saintes, Guadeloupe, Guadeloupe, Basseterre, St. Kitts, Saint Kitts, Nevis, Gustavia, St. Barthelemy, St. Barthelemy, Philipsburg, St. Maarten, Saint Maarten
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,499.00
Cat: B
Balcony
N/A
Suite
$3,599.00
Cat: OS
CLASSIC CARIBBEAN
Philipsburg, St. Maarten, Saint Maarten to Philipsburg, St. Maarten
from $1,499.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$214.14 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Roseau, Dominica, Dominica, Pigeon Island, St. Lucia, Saint Lucia, Les Saintes, Guadeloupe, Guadeloupe, Gustavia, St. Barthelemy, St. Barthelemy, Basseterre, St. Kitts, Saint Kitts, Nevis, Charlestown, Saint Kitts, Nevis, Philipsburg, St. Maarten, Saint Maarten
Windstar's Flagship Sailing Ship On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning. Everything about Wind Surf speaks of welcome.
Other Categories Starting At:
Inside
N/A
Outside
$1,499.00
Cat: B
Balcony
N/A
Suite
$3,599.00
Cat: OS
St. Maarten to St. Maarten
Philipsburg, St. Maarten, Saint Maarten to Philipsburg, St. Maarten
from $1,499.00 (USD)
Per Person
+ $130.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$214.14 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Road Bay, Anguilla, Anguilla, SoperS Hole, Tortola, Bvi, British Virgin Islands, Great Harbour, Jost Van Dyke, British Virgin Islands, Virgin Gorda, Bvi, British Virgin Islands, Gustavia, St. Barthelemy, St. Barthelemy, Falmouth Harbour, Antigua, Antigua And Barbuda, Philipsburg, St. Maarten, Saint Maarten
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,499.00
Cat: B
Balcony
N/A
Suite
$3,599.00
Cat: OS
St. Maarten to Colón
Philipsburg, St. Maarten, Saint Maarten to Colon, Panama
from $1,599.00 (USD)
Per Person
+ $308.00 taxes/fees
Nights: 10
Ship: Wind Star
Price Per Night:$159.90 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Virgin Gorda, Bvi, British Virgin Islands, Kralendijk, Bonaire, Bonair, Willemstad, Curacao, Curacao, Oranjestad, Aruba, Aruba, Cartagena, Colombia, Colombia, Colon, Panama
Wind Star is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht. Wind Star features wide open, teak decks-quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
Other Categories Starting At:
Inside
N/A
Outside
$1,599.00
Cat: B
Balcony
N/A
Suite
N/A
St. Maarten to Lisbon
Philipsburg, St. Maarten, Saint Maarten to Lisbon, Portugal
from $1,599.00 (USD)
Per Person
+ $90.00 taxes/fees
Nights: 14
Ship: Wind Surf
Price Per Night:$114.21 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Ponta Delgada, Portugal, Lisbon, Portugal
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,599.00
Cat: B
Balcony
N/A
Suite
$3,399.00
Cat: OS
St. Maarten to Bridgetown
Philipsburg, St. Maarten, Saint Maarten to Bridgetown, Barbados, Barbados
from $1,699.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$242.71 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Basseterre, St. Kitts, Saint Kitts, Nevis, Gustavia, St. Barthelemy, St. Barthelemy, Little Bay, Montserrat, Montserrat, Les Saintes, Guadeloupe, Guadeloupe, Roseau, Dominica, Dominica, Pigeon Island, St. Lucia, Saint Lucia, Bridgetown, Barbados, Barbados
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,699.00
Cat: B
Balcony
N/A
Suite
$4,099.00
Cat: OS
STARS OVER THE AZORES
Miami, Fl, United States to Lisbon, Portugal
from $1,699.00 (USD)
Per Person
+ $90.00 taxes/fees
Nights: 13
Ship: Star Legend
Price Per Night:$130.69 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Fl, United States, Horta, Azores, Portugal, Lisbon, Portugal
Carrying only 312 guests, Star Legend still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure!
Colón to Puerto Caldera
Colon, Panama to Puerto Caldera, Costa Rica
from $1,799.00 (USD)
Per Person
+ $459.00 taxes/fees
Nights: 7
Ship: Wind Star
Price Per Night:$257.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: Colon, Panama, Panama Canal Transit, Cruising, Balboa, Panama, Isla Parida, Panama, Puerto Jimenez, Costa Rica, Quepos, Costa Rica, Puerto Caldera, Costa Rica
Wind Star is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht. Wind Star features wide open, teak decks-quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
Other Categories Starting At:
Inside
N/A
Outside
$1,799.00
Cat: B
Balcony
N/A
Suite
N/A
Puerto Caldera to Colón
Puerto Caldera, Costa Rica to Colon, Panama
from $1,799.00 (USD)
Per Person
+ $459.00 taxes/fees
Nights: 7
Ship: Wind Star
Price Per Night:$257.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: Puerto Caldera, Costa Rica, Quepos, Costa Rica, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama, Panama Canal Transit, Cruising, Colon, Panama
Wind Star is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht. Wind Star features wide open, teak decks-quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
Other Categories Starting At:
Inside
N/A
Outside
$1,799.00
Cat: B
Balcony
N/A
Suite
N/A
Puerto Caldera to Colón
Colon, Panama to Puerto Caldera, San Jose, Costa Rica
from $1,999.00 (USD)
Per Person
+ $380.00 taxes/fees
Nights: 7
Ship: Star Legend
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Colon, Panama, Panama Canal Transit, Cruising, Fuerte Amador, Panama City, Panama, Isla Parida, Panama, Puerto Jimenez, Golfo Dulce, Costa Rica, Quepos, Manuel Antonio Natl Pk, Costa Rica, Puerto Caldera, San Jose, Costa Rica
Carrying only 312 guests, Star Legend still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure!
NEW YORK LIGHTS, WARM CARIBBEAN NIGHTS
Manhattan, New York, United States to San Juan, Puerto Rico
from $1,999.00 (USD)
Per Person
+ $400.00 taxes/fees
Nights: 11
Ship: Star Pride
Price Per Night:$181.73 (USD)
(based on double occupancy, for comparison only)
Itinerary: Manhattan, New York, United States, Hamilton, Bermuda, St GeorgeS Bermuda, Bermuda, Gustavia, St. Barthelemy, St. Barthelemy, Basseterre, St. Kitts, Saint Kitts, Nevis, Virgin Gorda, Bvi, British Virgin Islands, San Juan, Puerto Rico
All Suite Yacht With only 212 guests, a Star Pride cruise will make you feel like you're on board your own private yacht almost as soon as you step aboard. Star Pride is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
Bridgetown to Bridgetown
Roundtrip from Bridgetown, Barbados, Barbados
from $1,999.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Barbados, Barbados, Roseau, Dominica, Dominica, Little Bay, Montserrat, Montserrat, Gustavia, St. Barthelemy, St. Barthelemy, Falmouth Harbour, Antigua, Antigua And Barbuda, Les Saintes, Guadeloupe, Guadeloupe, Pigeon Island, St. Lucia, Saint Lucia, Bridgetown, Barbados, Barbados
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,999.00
Cat: B
Balcony
N/A
Suite
$4,099.00
Cat: OS
Puerto Caldera to Colón
Puerto Caldera, Costa Rica to Colon, Panama
from $1,999.00 (USD)
Per Person
+ $380.00 taxes/fees
Nights: 7
Ship: Star Legend
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Puerto Caldera, Costa Rica, Quepos, Costa Rica, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama, Panama Canal Transit, Cruising, Colon, Panama
All Suite Yacht With only 212 guests, a Star Legend cruise will make you feel like you're on board your own private yacht almost as soon as you step aboard. Star Legend is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
Bridgetown to Bridgetown
Roundtrip from Bridgetown, Barbados, Barbados
from $1,999.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Barbados, Barbados, Roseau, Dominica, Dominica, Little Bay, Montserrat, Montserrat, Gustavia, St. Barthelemy, St. Barthelemy, Falmouth Harbour, Antigua, Antigua And Barbuda, Les Saintes, Guadeloupe, Guadeloupe, Pigeon Island, St. Lucia, Saint Lucia, Bridgetown, Barbados, Barbados
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,999.00
Cat: B
Balcony
N/A
Suite
$4,099.00
Cat: OS
WINDWARD ISLANDS SURF & SUNSETS
Roundtrip from San Juan, Puerto Rico
from $1,999.00 (USD)
Per Person
+ $135.00 taxes/fees
Nights: 7
Ship: Star Pride
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Puerto Rico, St. GeorgeS, Grenada, Grenada, Bequia, Saint Vincent And The Grenadines, Pigeon Island, St. Lucia, Saint Lucia, Les Saintes, Guadeloupe, Guadeloupe, Philipsburg, St. Maarten, Saint Maarten, San Juan, Puerto Rico, St. GeorgeS, Grenada, Grenada, Bequia, Saint Vincent And The Grenadines, Pigeon Island, St. Lucia, Saint Lucia...
All Suite Yacht With only 212 guests, a Star Pride cruise will make you feel like you're on board your own private yacht almost as soon as you step aboard. Star Pride is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
from $1,999.00 (USD)
Per Person
+ $230.00 taxes/fees
Nights: 8
Ship: Wind Star
Price Per Night:$249.88 (USD)
(based on double occupancy, for comparison only)
Itinerary: Colon, Panama, Cartagena, Colombia, Colombia, Nassau, Bahamas
Wind Star is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht. Wind Star features wide open, teak decks-quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
Other Categories Starting At:
Inside
N/A
Outside
$1,999.00
Cat: B
Balcony
N/A
Suite
N/A
Barcelona to Lisbon
Barcelona, Spain to Lisbon, Portugal
from $1,999.00 (USD)
Per Person
+ $180.00 taxes/fees
Nights: 10
Ship: Star Legend
Price Per Night:$199.90 (USD)
(based on double occupancy, for comparison only)
Itinerary: Barcelona, Spain, Motril, Spain, Malaga, Spain, Gibraltar, Gibraltar, Seville, Spain, Cadiz, Spain, Casablanca, Morocco, Lisbon, Portugal
Carrying only 312 guests, Star Legend still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure!
LUSH & LOVELY ISLANDS OF THE LESSER ANTILLES
Philipsburg, St. Maarten, Saint Maarten to Bridgetown, Barbados, Barbados
from $1,999.00 (USD)
Per Person
+ $100.00 taxes/fees
Nights: 7
Ship: Wind Surf
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Saint Maarten, Basseterre, St. Kitts, Saint Kitts, Nevis, Gustavia, St. Barthelemy, St. Barthelemy, Little Bay, Montserrat, Montserrat, Les Saintes, Guadeloupe, Guadeloupe, Roseau, Dominica, Dominica, Pigeon Island, St. Lucia, Saint Lucia, Bridgetown, Barbados, Barbados
On any day, our 310-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Other Categories Starting At:
Inside
N/A
Outside
$1,999.00
Cat: B
Balcony
N/A
Suite
$4,099.00
Cat: OS