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Wind Surf
Windstar Cruises
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$6,770pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

51% OFF
MSC Opera
MSC Cruises
Jan 15, 2027 - Jan 29, 2027 (14 Nights)
Fort-De-France, Martinique • St John's, Antigua • Virgin Gorda, British Virgin Islands • La Romana, Dominican Republic • Samana, Dominican Republic • Virgin Gorda, British Virgin Islands • St. Kitts • Philipsburg, St. Maarten • Catalina Island, Dominican Republic • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$1,768pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 26, 2028 - Mar 4, 2028 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,368pp
Jim's Onboard Credit
39% OFF
MSC Opera
MSC Cruises
Jan 18, 2027 - Feb 1, 2027 (14 Nights)
La Romana, Dominican Republic • Samana, Dominican Republic • Virgin Gorda, British Virgin Islands • St. Kitts • Philipsburg, St. Maarten • Catalina Island, Dominican Republic • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • Tortola • La Romana, Dominican Republic
Average Starting Price
$1,170pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,668pp
Jim's Onboard Credit
54% OFF
MSC Opera
MSC Cruises
Jan 18, 2027 - Jan 25, 2027 (7 Nights)
La Romana, Dominican Republic • Samana, Dominican Republic • Virgin Gorda, British Virgin Islands • St. Kitts • Philipsburg, St. Maarten • Catalina Island, Dominican Republic • La Romana, Dominican Republic
Average Starting Price
$559pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$4,748pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Mar 27, 2028 - Apr 10, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$1,292pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$4,743pp
Jim's Onboard Credit
39% OFF
MSC Opera
MSC Cruises
Jan 11, 2027 - Jan 25, 2027 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • Virgin Gorda, British Virgin Islands • La Romana, Dominican Republic • Samana, Dominican Republic • Virgin Gorda, British Virgin Islands • St. Kitts • Philipsburg, St. Maarten • Catalina Island, Dominican Republic • La Romana, Dominican Republic
Average Starting Price
$1,170pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 11, 2028 - Mar 25, 2028 (14 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$10,408pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 14, 2027 - Jan 28, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • Virgin Gorda, British Virgin Islands • La Romana, Dominican Republic • Samana, Dominican Republic • Virgin Gorda, British Virgin Islands • St. Kitts • Philipsburg, St. Maarten • Catalina Island, Dominican Republic • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,508pp
Jim's Onboard Credit
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