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Wind Surf
Windstar Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • 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 • Philipsburg, St. Maarten
Average Starting Price
$2,658pp
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 Escape
Norwegian Cruise Line
Jan 29, 2027 - Feb 5, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$589pp
Jim's Onboard Credit
46% OFF
MSC World Asia
MSC Cruises
Apr 23, 2028 - May 6, 2028 (13 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France
Average Starting Price
$824pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 30, 2027 (6 Nights)
Fort Lauderdale • Falmouth, Jamaica • George Town, Cayman Islands • Nassau • Fort Lauderdale
Average Starting Price
$640pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Luna
Norwegian Cruise Line
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
Miami • Roatan, Honduras • Harvest Caye, Belize • Costa Maya • Cozumel • Miami
Average Starting Price
$639pp
Jim's Onboard Credit
48% OFF
MSC World Atlantic
MSC Cruises
Nov 4, 2028 - Nov 11, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Ocean Cay • Grand Turk • Puerto Plata, Dominican Republic • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$856pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

49% OFF
MSC Grandiosa
MSC Cruises
Dec 30, 2027 - Jan 9, 2028 (10 Nights)
Port Canaveral (Orlando), Florida • Ocean Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida • Ocean Cay • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$1,515pp
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!

57% OFF
MSC Seaside
MSC Cruises
Mar 29, 2027 - Apr 2, 2027 (4 Nights)
Miami • Nassau • Ocean Cay • Ocean Cay • Miami
Average Starting Price
$378pp
Jim's Onboard Credit
49% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
Apr 1, 2028 - Apr 6, 2028 (5 Nights)
Tampa • Key West, Florida • Progreso, Mexico • Tampa
Average Starting Price
$449pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,244pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Enchantment of the Seas
Royal Caribbean
Apr 29, 2028 - May 6, 2028 (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
$745pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Jan 3, 2028 - Jan 7, 2028 (4 Nights)
Fort Lauderdale • Nassau • Grand Bahama Island • Fort Lauderdale
Average Starting Price
$455pp
Jim's Onboard Credit
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