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Celebrity Ascent
Celebrity Cruises
Dec 24, 2026 - Jan 4, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$2,483pp
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!

Rotterdam
Holland America Line
Jan 23, 2027 - Feb 13, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,029pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Eurodam
Holland America Line
Feb 12, 2028 - Mar 4, 2028 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale
Average Starting Price
$5,094pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Viking Sky
Viking
Feb 7, 2028 - Feb 17, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$726pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 6, 2028 - Feb 16, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Nov 7, 2026 - Nov 14, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$608pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Roseau, Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$702pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Tobago • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$6,715pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Nov 20, 2027 - Dec 5, 2027 (15 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • 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 • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$4,845pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$1,049pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Nov 19, 2027 - Nov 30, 2027 (11 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,569pp
Jim's Onboard Credit
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