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55 Night Star Collector Grand Caribbean Adventure

From Philipsburg (St. Maarten) to Philipsburg (St. Maarten)

Wind Surf

Windstar Cruises
5 Stars
  • Cruise #: 13942772
  • Departs: Sun, Jan 4, 2026
  • Returns: Sat, Feb 28, 2026
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    Oceanview
    Call to Book1-800-543-1915
    Suite $43,691
    *Prices are per person based on double occupancy
    Includes taxes & fees
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    Itinerary Summary

    Day by Day Details

    Cruise Segment of Itinerary

    Sunday - Jan 4, 2026
    Day
    1
    Philipsburg (St. Maarten), Netherlands Antilles
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Depart: 19:00:00
    Monday - Jan 5, 2026
    Day
    2
    Falmouth Harbour, Antigua/Barbuda
    • Falmouth Harbour, Antigua/Barbuda
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Tuesday - Jan 6, 2026
    Day
    3
    • Road Bay, Anguilla
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Wednesday - Jan 7, 2026
    Day
    4
    • Sopers Hole, Virgin Islands - British
    • Arrive: 08:00:00
    • Depart: 18:00:00
    • Great Harbour, British Virgin Islands
    • Arrive: 19:00:00
    Thursday - Jan 8, 2026
    Day
    5
    Great Harbour, British Virgin Islands
    • Great Harbour, British Virgin Islands
    • Depart: 22:00:00
    Friday - Jan 9, 2026
    Day
    6
    Prickly Pear, British Virgin Islands, British Virgin Islands
    • Prickly Pear, British Virgin Islands, British Virgin Islands
    • Arrive: 08:00:00
    • Depart: 17:00:00
    Saturday - Jan 10, 2026
    Day
    7
    Gustavia, St. Barts, Saint Barthelemy
    • Gustavia, St. Barts, Saint Barthelemy
    • Arrive: 08:00:00
    • Depart: 22:00:00
    Sunday - Jan 11, 2026
    Day
    8
    Philipsburg (St. Maarten), Netherlands Antilles
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Arrive: 06:00:00
    • Depart: 19:00:00
    Monday - Jan 12, 2026
    Day
    9
    Basseterre, St. Kitts & Nevis
    • Basseterre, St. Kitts & Nevis
    • Arrive: 08:00:00
    • Depart: 21:00:00
    Tuesday - Jan 13, 2026
    Day
    10
    Gustavia, St. Barts, Saint Barthelemy
    • Gustavia, St. Barts, Saint Barthelemy
    • Arrive: 08:00:00
    • Depart: 22:00:00
    Wednesday - Jan 14, 2026
    Day
    11
    St John's, Antigua and Barbuda
    • St John's, Antigua and Barbuda
    • Arrive: 08:00:00
    • Depart: 22:00:00
    Thursday - Jan 15, 2026
    Day
    12
    Iles des Saintes, Guadeloupe
    • Iles des Saintes, Guadeloupe
    • Arrive: 08:00:00
    • Depart: 21:00:00
    Friday - Jan 16, 2026
    Day
    13
    Pigeon Island, Saint Lucia
    • Pigeon Island, Saint Lucia
    • Arrive: 08:00:00
    • Depart: 17:00:00
    Saturday - Jan 17, 2026
    Day
    14
    Kingstown, St. Vincent & The Grenadines
    • Kingstown, St. Vincent & The Grenadines
    • Arrive: 07:00:00
    • Depart: 14:00:00
    Sunday - Jan 18, 2026
    Day
    15
    Bridgetown, Barbados
    • Bridgetown, Barbados
    • Arrive: 05:00:00
    • Depart: 18:00:00
    Monday - Jan 19, 2026
    Day
    16
    Anse Mitan, Martinique
    • Anse Mitan, Martinique
    • Arrive: 09:00:00
    • Depart: 23:00:00
    Tuesday - Jan 20, 2026
    Day
    17
    Castries, St. Lucia
    • Castries, St. Lucia
    • Arrive: 08:00:00
    • Depart: 16:00:00
    • Pigeon Island, Saint Lucia
    • Arrive: 18:00:00
    Wednesday - Jan 21, 2026
    Day
    18
    Pigeon Island, Saint Lucia
    • Pigeon Island, Saint Lucia
    • Depart: 18:00:00
    Thursday - Jan 22, 2026
    Day
    19
    Bequia, St. Vincent & The Grenadines
    • Bequia, St. Vincent & The Grenadines
    • Arrive: 08:00:00
    • Depart: 22:00:00
    Friday - Jan 23, 2026
    Day
    20
    Mayreau, St. Vincent & The Grenadines
    • Mayreau, St. Vincent & The Grenadines
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Saturday - Jan 24, 2026
    Day
    21
    St George's, Grenada
    • St George's, Grenada
    • Arrive: 07:00:00
    • Depart: 14:00:00
    Sunday - Jan 25, 2026
    Day
    22
    Bridgetown, Barbados
    • Bridgetown, Barbados
    • Arrive: 06:00:00
    • Depart: 18:00:00
    Monday - Jan 26, 2026
    Day
    23
    • Man of War Bay, Trinidad and Tobago
    • Arrive: 08:00:00
    • Depart: 17:00:00
    Tuesday - Jan 27, 2026
    Day
    24
    Mayreau, St. Vincent & The Grenadines
    • Mayreau, St. Vincent & The Grenadines
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Wednesday - Jan 28, 2026
    Day
    25
    Soufriere , Saint Lucia
    • Soufriere , Saint Lucia
    • Arrive: 08:00:00
    • Depart: 16:00:00
    Thursday - Jan 29, 2026
    Day
    26
    At Sea
    • At Sea
    Friday - Jan 30, 2026
    Day
    27
    Bonaire, Netherlands Antilles
    • Bonaire, Netherlands Antilles
    • Arrive: 13:00:00
    • Depart: 22:00:00
    Saturday - Jan 31, 2026
    Day
    28
    Willemstad (Curacao), Netherlands Antilles
    • Willemstad (Curacao), Netherlands Antilles
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Sunday - Feb 1, 2026
    Day
    29
    Oranjestad, Aruba
    • Oranjestad, Aruba
    • Arrive: 06:00:00
    • Depart: 18:00:00
    Monday - Feb 2, 2026
    Day
    30
    At Sea
    • At Sea
    Tuesday - Feb 3, 2026
    Day
    31
    Santa Marta, Colombia
    • Santa Marta, Colombia
    • Arrive: 07:00:00
    • Depart: 18:00:00
    Wednesday - Feb 4, 2026
    Day
    32
    Cartagena, Colombia
    • Cartagena, Colombia
    • Arrive: 08:00:00
    • Depart: 15:30:00
    Thursday - Feb 5, 2026
    Day
    33
    At Sea
    • At Sea
    Friday - Feb 6, 2026
    Day
    34
    Bocas Del Toro, Panama
    • Bocas Del Toro, Panama
    • Arrive: 12:00:00
    • Depart: 17:30:00
    Saturday - Feb 7, 2026
    Day
    35
    At Sea
    • At Sea
    Sunday - Feb 8, 2026
    Day
    36
    Colon, Panama
    • Colon, Panama
    • Arrive: 07:00:00
    Monday - Feb 9, 2026
    Day
    37
    Colon, Panama
    • Colon, Panama
    • Depart: 16:00:00
    Tuesday - Feb 10, 2026
    Day
    38
    Bocas Del Toro, Panama
    • Bocas Del Toro, Panama
    • Arrive: 10:00:00
    • Depart: 16:00:00
    Wednesday - Feb 11, 2026
    Day
    39
    • San Andres Island, Colombia
    • Arrive: 13:00:00
    • Depart: 19:00:00
    Thursday - Feb 12, 2026
    Day
    40
    At Sea
    • At Sea
    Friday - Feb 13, 2026
    Day
    41
    At Sea
    • At Sea
    Saturday - Feb 14, 2026
    Day
    42
    Roatan, Honduras
    • Roatan, Honduras
    • Arrive: 09:00:00
    • Depart: 17:00:00
    Sunday - Feb 15, 2026
    Day
    43
    Belize City, Belize
    • Belize City, Belize
    • Arrive: 09:00:00
    • Depart: 19:00:00
    Monday - Feb 16, 2026
    Day
    44
    Costa Maya, Mexico
    • Costa Maya, Mexico
    • Arrive: 08:00:00
    • Depart: 17:00:00
    Tuesday - Feb 17, 2026
    Day
    45
    Cozumel, Mexico
    • Cozumel, Mexico
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Wednesday - Feb 18, 2026
    Day
    46
    At Sea
    • At Sea
    Thursday - Feb 19, 2026
    Day
    47
    Georgetown , Cayman Islands
    • Georgetown , Cayman Islands
    • Arrive: 08:00:00
    • Depart: 18:00:00
    Friday - Feb 20, 2026
    Day
    48
    • Cayman Brac, Cayman Islands
    • Arrive: 07:00:00
    • Depart: 13:00:00
    Saturday - Feb 21, 2026
    Day
    49
    Port Antonio, Jamaica
    • Port Antonio, Jamaica
    • Arrive: 12:00:00
    • Depart: 18:00:00
    Sunday - Feb 22, 2026
    Day
    50
    At Sea
    • At Sea
    Monday - Feb 23, 2026
    Day
    51
    Santo Domingo, Dominican Republic
    • Santo Domingo, Dominican Republic
    • Arrive: 13:00:00
    • Depart: 22:00:00
    Tuesday - Feb 24, 2026
    Day
    52
    La Romana, Dominican Republic
    • La Romana, Dominican Republic
    • Arrive: 07:00:00
    • Depart: 17:00:00
    Wednesday - Feb 25, 2026
    Day
    53
    At Sea
    • At Sea
    Thursday - Feb 26, 2026
    Day
    54
    Great Harbour, British Virgin Islands
    • Great Harbour, British Virgin Islands
    • Arrive: 08:00:00
    • Depart: 23:59:00
    Friday - Feb 27, 2026
    Day
    55
    Prickly Pear, British Virgin Islands, British Virgin Islands
    • Prickly Pear, British Virgin Islands, British Virgin Islands
    • Arrive: 08:00:00
    • Depart: 17:00:00
    Saturday - Feb 28, 2026
    Day
    56
    Philipsburg (St. Maarten), Netherlands Antilles
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Arrive: 06:00:00


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