Onboard Star Pride
Roundtrip · San Juan
Wed, Oct 28 2026
San Juan, St. Barts, St. Kitts, Antigua, Les Saintes, Guadeloupe, Rodney Bay, Grenada, Jost Van Dyke Isl., Virgin Gorda, San Juan, San Juan
Rates Starting At
$3,310
per person
$301 per person per day
Onboard Star Pride
Boston → San Juan
Tue, Oct 20 2026
Hamilton/BERMUDA, Hamilton/BERMUDA, St. George's/BERMUDA, St. George's/BERMUDA, San Juan, San Juan
Rates Starting At
$2,444
per person
$306 per person per day
Onboard Star Legend
Barbados → Aruba
Fri, Dec 4 2026
Barbados, Rodney Bay, Bequia, Mayreau, Grenada, Curacao, Aruba, Aruba
Rates Starting At
$2,700
per person
$338 per person per day
Onboard Star Legend
Roundtrip · Barbados
Fri, Nov 27 2026
Barbados, Anses D'arlet, Martinique, Rodney Bay, Rodney Bay, Casablanca/MOROCCO , Mayreau, Grenada, Bequia, Barbados, Barbados
Rates Starting At
$2,419
per person
$346 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Mar 6 2027
St. Maarten, Jeju Isl./S. KOREA, Dominica, Mayreau, Les Saintes, Guadeloupe, St. Kitts, St. Barts, St. Maarten, St. Maarten
Rates Starting At
$2,467
per person
$352 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Jan 2 2027
St. Maarten, Antigua, Road Bay, Anguilla, Sopers Hole, British Virgin Islands, Jost Van Dyke Isl., Jost Van Dyke Isl., Virgin Gorda, St. Barts, St. Maarten, St. Maarten
Rates Starting At
$2,483
per person
$355 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Mar 20 2027
St. Maarten, Jeju Isl./S. KOREA, Dominica, Mayreau, Les Saintes, Guadeloupe, St. Kitts, St. Barts, St. Maarten, St. Maarten
Rates Starting At
$2,537
per person
$362 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Nov 22 2026
San Juan, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marmaris/TURKEY, San Juan, San Juan
Rates Starting At
$2,606
per person
$372 per person per day
Onboard Star Legend
Barbados → Aruba
Fri, Nov 27 2026
Barbados, Anses D'arlet, Martinique, Rodney Bay, Rodney Bay, Casablanca/MOROCCO , Mayreau, Grenada, Bequia, Barbados, Barbados, Rodney Bay, Bequia, Mayreau, Grenada, Curacao, Aruba, Aruba
Rates Starting At
$5,757
per person
$384 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Dec 19 2026
St. Maarten, St. Barts, Antigua, Road Bay, Anguilla, Sopers Hole, British Virgin Islands, Jost Van Dyke Isl., Jost Van Dyke Isl., Virgin Gorda, St. Maarten, St. Maarten
Rates Starting At
$2,693
per person
$385 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Dec 20 2026
San Juan, Grenada, Bequia, Mayreau, Marmaris/TURKEY, San Juan, San Juan
Rates Starting At
$2,761
per person
$394 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Jan 30 2027
St. Maarten, Road Bay, Anguilla, Sopers Hole, British Virgin Islands, Jost Van Dyke Isl., Jost Van Dyke Isl., Virgin Gorda, St. Barts, Antigua, St. Maarten, St. Maarten
Rates Starting At
$2,763
per person
$395 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Feb 27 2027
St. Maarten, Sopers Hole, British Virgin Islands, Jost Van Dyke Isl., Jost Van Dyke Isl., Virgin Gorda, St. Barts, Road Bay, Anguilla, Antigua, St. Maarten, St. Maarten
Rates Starting At
$2,798
per person
$400 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Dec 26 2026
St. Maarten, St. Barts, Jeju Isl./S. KOREA, Dominica, Mayreau, Les Saintes, Guadeloupe, St. Kitts, St. Maarten, St. Maarten
Rates Starting At
$2,817
per person
$402 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Nov 29 2026
San Juan, St. Barts, St. Kitts, St. Maarten, Jost Van Dyke Isl., Virgin Gorda, San Juan, San Juan, Grenada, Bequia, Mayreau, Marmaris/TURKEY, San Juan, San Juan
Rates Starting At
$5,656
per person
$404 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Nov 22 2026
San Juan, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marmaris/TURKEY, San Juan, San Juan, St. Barts, St. Kitts, St. Maarten, Jost Van Dyke Isl., Virgin Gorda, San Juan, San Juan
Rates Starting At
$5,656
per person
$404 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Dec 6 2026
San Juan, Grenada, Bequia, Mayreau, Marmaris/TURKEY, San Juan, San Juan
Rates Starting At
$2,831
per person
$404 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Nov 15 2026
San Juan, St. Kitts, St. Barts, St. Maarten, Jost Van Dyke Isl., Virgin Gorda, San Juan, San Juan, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marmaris/TURKEY, San Juan, San Juan
Rates Starting At
$5,976
per person
$427 per person per day
Onboard Wind Surf
Roundtrip · St. Maarten
Sat, Feb 20 2027
St. Maarten, Jeju Isl./S. KOREA, Dominica, Mayreau, Les Saintes, Guadeloupe, St. Kitts, St. Barts, St. Maarten, St. Maarten
Rates Starting At
$3,062
per person
$437 per person per day
Onboard Star Pride
Roundtrip · San Juan
Sun, Nov 29 2026
San Juan, St. Barts, St. Kitts, St. Maarten, Jost Van Dyke Isl., Virgin Gorda, San Juan, San Juan
Rates Starting At
$3,178
per person
$454 per person per day