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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
$6,210pp
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
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
$3,447pp
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!

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
Wind Surf
Windstar Cruises
Nov 5, 2028 - Nov 19, 2028 (14 Nights)
Lisbon, Portugal • St John's, Antigua • Philipsburg, St. Maarten
Average Starting Price
$2,839pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 6, 2029 - Jan 20, 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 • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Bridgetown, Barbados
Average Starting Price
$9,523pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 24, 2028 - Feb 7, 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
Seabourn Ovation
Seabourn
Jan 27, 2029 - Feb 3, 2029 (7 Nights)
Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$5,143pp
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
$6,490pp
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 24, 2028 - Jan 31, 2028 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St. John's • La Romana, Dominican Republic
Average Starting Price
$789pp
Jim's Onboard Credit
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