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Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,738pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$860pp
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!

Wind Surf
Windstar Cruises
Mar 27, 2027 - Apr 19, 2027 (23 Nights)
Philipsburg, St. Maarten • Funchal, Portugal • Porto Santo (Madeira), Portugal • Lisbon, Portugal • Cadiz, Spain • Gibraltar • Malaga, Spain • Almeria, Spain • Cartagena, Spain • Palma de Mallorca, Spain • Barcelona, Spain
Average Starting Price
$5,919pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,413pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

28% OFF
MSC World Europa
MSC Cruises
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$996pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 6, 2027 - Mar 20, 2027 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$10,008pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$817pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$959pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 3, 2026 - Dec 17, 2026 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Martinique • Dominica • St. Lucia • Port of Spain, Trinidad • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$2,179pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 22, 2028 - Jan 2, 2029 (11 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados
Average Starting Price
$1,870pp
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!

46% OFF
MSC Meraviglia
MSC Cruises
Jan 2, 2027 - Jan 16, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,175pp
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!

Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,938pp
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!

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