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Wind Surf
Windstar Cruises
Feb 27, 2027 - Mar 13, 2027 (14 Nights)
Philipsburg, St. Maarten • 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 • Road Bay, Anguilla • Falmouth (English Harbour), Antigua & Barbuda • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$6,280pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 14, 2028 - Feb 28, 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
$1,522pp
Jim's Onboard Credit
27% OFF
MSC World Europa
MSC Cruises
Dec 29, 2026 - Jan 12, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$2,001pp
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!

Norwegian Prima
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$709pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 27, 2027 - Mar 6, 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
$5,573pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 13, 2027 - Feb 27, 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 • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$6,910pp
Jim's Onboard Credit
51% OFF
MSC Opera
MSC Cruises
Feb 12, 2027 - Feb 26, 2027 (14 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Tortola • Catalina Island, Dominican Republic • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$1,638pp
Jim's Onboard Credit
51% OFF
MSC World Europa
MSC Cruises
Nov 17, 2026 - Dec 5, 2026 (18 Nights)
Marseille (Provence), France • Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Fort-De-France, Martinique
Average Starting Price
$839pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • St. Kitts • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$859pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 6, 2027 - Mar 13, 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
$4,948pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,537pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 11, 2027 - Feb 25, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Tortola • Catalina Island, Dominican Republic • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,658pp
Jim's Onboard Credit
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