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Port: Philipsburg, St. Maarten×
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Wind Surf
Windstar Cruises
Jan 9, 2027 - Jan 16, 2027 (7 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
Average Starting Price
$3,097pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 20, 2029 - Feb 3, 2029 (14 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$9,508pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 10, 2028 - Jan 24, 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
$1,572pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Oct 28, 2028 - Nov 19, 2028 (22 Nights)
Barcelona, Spain • Palma de Mallorca, Spain • Cartagena, Spain • Almeria, Spain • Malaga, Spain • Gibraltar • Cadiz, Spain • Lisbon, Portugal • St John's, Antigua • Philipsburg, St. Maarten
Average Starting Price
$6,994pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 10, 2029 - Feb 17, 2029 (7 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,168pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 3, 2028 - Jan 17, 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
$1,712pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 2, 2027 - Jan 9, 2027 (7 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
Average Starting Price
$2,903pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 6, 2029 - Jan 13, 2029 (7 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • 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
55% OFF
MSC Opera
MSC Cruises
Mar 15, 2027 - Mar 22, 2027 (7 Nights)
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
$569pp
Jim's Onboard Credit
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
$6,210pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 30, 2028 - Jan 6, 2029 (7 Nights)
Philipsburg, St. Maarten • Virgin Gorda, British Virgin Islands • St. Kitts • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$5,543pp
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
Jan 17, 2028 - Jan 31, 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
$1,432pp
Jim's Onboard Credit
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