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Caribbean Princess
Princess Cruises
Dec 1, 2028 - Dec 8, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$1,563pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 28, 2028 - Jan 6, 2029 (9 Nights)
Miami • Grand Turk • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,522pp
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!

Norwegian Pearl
Norwegian Cruise Line
Dec 23, 2026 - Jan 3, 2027 (11 Nights)
Philadelphia • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$1,319pp
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!

Celebrity Apex
Celebrity Cruises
Feb 24, 2029 - Mar 3, 2029 (7 Nights)
Port Canaveral (Orlando), Florida • Key West, Florida • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$873pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Mar 17, 2027 - Mar 21, 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
$1,741pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Dec 17, 2028 - Dec 24, 2028 (7 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Fort-De-France, Martinique • Bridgetown, Barbados • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$585pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Jan 26, 2028 - Feb 4, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • St John's, Antigua • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,117pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
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 • 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
$4,320pp
Jim's Onboard Credit
Celebrity Xcel
Celebrity Cruises
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
Miami • Nassau • St. Thomas • St John's, Antigua • Miami
Average Starting Price
$897pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 7, 2029 - Jan 14, 2029 (7 Nights)
Tampa • Key West, Florida • Grand Bahama Island • Nassau • Tampa
Average Starting Price
$728pp
Jim's Onboard Credit
Norwegian Joy
Norwegian Cruise Line
Dec 14, 2026 - Dec 18, 2026 (4 Nights)
Miami • Great Stirrup Cay • Nassau • Miami
Average Starting Price
$249pp
Jim's Onboard Credit
Disney Magic
Disney Cruise Line
Dec 13, 2026 - Dec 17, 2026 (4 Nights)
Galveston • Progreso, Mexico • Galveston
Average Starting Price
$860pp
Jim's Onboard Credit
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