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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
Nieuw Statendam
Holland America Line
Mar 28, 2027 - Apr 4, 2027 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,539pp
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!

26% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 28, 2027 - Jan 7, 2028 (10 Nights)
Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$8,499pp
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!

Disney Believe
Disney Cruise Line
Feb 7, 2028 - Feb 12, 2028 (5 Nights)
Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • Nassau • Fort Lauderdale
Average Starting Price
$1,822pp
Jim's Onboard Credit
Disney Wish
Disney Cruise Line
Nov 12, 2027 - Nov 16, 2027 (4 Nights)
San Juan, Puerto Rico • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,230pp
Jim's Onboard Credit
46% OFF
MSC Opera
MSC Cruises
Jul 16, 2027 - Jul 23, 2027 (7 Nights)
Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$1,147pp
Jim's Onboard Credit
Disney Dream
Disney Cruise Line
May 24, 2027 - May 28, 2027 (4 Nights)
Port Canaveral (Orlando), Florida • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,800pp
Jim's Onboard Credit
Celebrity Reflection
Celebrity Cruises
Jul 2, 2027 - Jul 5, 2027 (3 Nights)
Fort Lauderdale • Key West, Florida • Grand Bahama Island • Fort Lauderdale
Average Starting Price
$451pp
Jim's Onboard Credit
51% OFF
MSC Grandiosa
MSC Cruises
Jul 31, 2027 - Aug 7, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$720pp
Jim's Onboard Credit
Norwegian Getaway
Norwegian Cruise Line
Aug 27, 2027 - Aug 30, 2027 (3 Nights)
Miami • Nassau • Great Stirrup Cay • Miami
Average Starting Price
$359pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Jun 7, 2027 - Jun 11, 2027 (4 Nights)
Fort Lauderdale • Nassau • Perfect Day Cococay • Fort Lauderdale
Average Starting Price
$618pp
Jim's Onboard Credit
Enchantment of the Seas
Royal Caribbean
Sep 18, 2027 - Sep 25, 2027 (7 Nights)
Tampa • Costa Maya • Cozumel • Roatan, Honduras • Tampa
Average Starting Price
$632pp
Jim's Onboard Credit
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