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Wind Surf
Windstar Cruises
Jan 9, 2027 - Jan 23, 2027 (14 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • 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 • Gustavia, St. Barts • Falmouth (English Harbour), Antigua & Barbuda • Philipsburg, St. Maarten
Average Starting Price
$5,860pp
Jim's Onboard Credit
36% OFF
MSC Opera
MSC Cruises
Jan 25, 2027 - Feb 8, 2027 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • Tortola • La Romana, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Tortola • Catalina Island, Dominican Republic • La Romana, Dominican Republic
Average Starting Price
$1,320pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 13, 2027 - Feb 20, 2027 (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
$5,173pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
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
$3,552pp
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!

49% OFF
MSC Opera
MSC Cruises
Mar 20, 2028 - Mar 27, 2028 (7 Nights)
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
$779pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 19, 2028 - Feb 26, 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
$5,343pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 2, 2027 - Jan 16, 2027 (14 Nights)
Philipsburg, St. Maarten • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$5,580pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Mar 13, 2028 - Mar 27, 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
$1,392pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 6, 2027 - Feb 13, 2027 (7 Nights)
Bridgetown, Barbados • St. Kitts • St. Pierre • Roseau, Dominica • Terre de Haut, Guadeloupe • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$5,963pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 26, 2026 - Jan 9, 2027 (14 Nights)
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 • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$6,280pp
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!

49% OFF
MSC Opera
MSC Cruises
Mar 20, 2028 - Apr 3, 2028 (14 Nights)
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 • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$1,492pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 4, 2028 - Mar 18, 2028 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
$9,408pp
Jim's Onboard Credit
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