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Norwegian Bliss
Norwegian Cruise Line
Dec 22, 2027 - Jan 3, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$2,269pp
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!

Vision of the Seas
Royal Caribbean
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$689pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Harmony of the Seas
Royal Caribbean
Dec 30, 2027 - Jan 8, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,934pp
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!

Rhapsody of the Seas
Royal Caribbean
Dec 31, 2027 - Jan 8, 2028 (8 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • San Juan, Puerto Rico
Average Starting Price
$1,308pp
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!

Eurodam
Holland America Line
Dec 1, 2027 - Dec 22, 2027 (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 • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$4,894pp
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!

Coral Princess
Princess Cruises
Nov 8, 2026 - Nov 18, 2026 (10 Nights)
Fort Lauderdale • St John's, Antigua • Philipsburg, St. Maarten • Dominica • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$739pp
Jim's Onboard Credit
31% OFF
Carnival Horizon
Carnival Cruise Line
Oct 14, 2028 - Oct 28, 2028 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • Fun Day at Sea • Bridgetown, Barbados • St. Lucia • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,360pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$504pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 1, 2027 - Nov 8, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Silver Shadow
Silversea
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Little Bay, Montserrat • St John's, Antigua • Gustavia, St. Barts • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$5,100pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,295pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Aug 14, 2027 - Aug 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$777pp
Jim's Onboard Credit
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