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Wind Surf
Windstar Cruises
Feb 20, 2027 - Feb 27, 2027 (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
$3,657pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 2, 2029 - Jan 13, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,450pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 31, 2028 - Feb 14, 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
$1,452pp
Jim's Onboard Credit
52% OFF
MSC World Europa
MSC Cruises
Nov 18, 2026 - Dec 5, 2026 (17 Nights)
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
$759pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 29, 2026 - Dec 6, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$919pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 15, 2028 - Jan 22, 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
$4,768pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 23, 2028 - Feb 6, 2028 (14 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 • 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
$3,830pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Feb 13, 2029 - Feb 24, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,500pp
Jim's Onboard Credit
51% OFF
MSC Opera
MSC Cruises
Feb 26, 2027 - Mar 12, 2027 (14 Nights)
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 • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$1,678pp
Jim's Onboard Credit
24% OFF
MSC World Europa
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,282pp
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
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Bridgetown, Barbados • St. Lucia • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,419pp
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
Mar 6, 2027 - Mar 20, 2027 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
$10,008pp
Jim's Onboard Credit
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