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Norwegian Prima
Norwegian Cruise Line
Nov 3, 2027 - Nov 13, 2027 (10 Nights)
Manhattan • Royal Naval Dockyard, Bermuda • Tortola • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,739pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Jul 3, 2027 - Jul 10, 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
$899pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Jan 6, 2028 - Feb 19, 2028 (44 Nights)
Los Angeles • Ensenada • Cabo San Lucas • Acapulco, Mexico • Puerto Quetzal, Guatemala • Puntarenas, Costa Rica • Panama Canal, Panama • Cartagena, Colombia • George Town, Cayman Islands • Miami • Philipsburg, St. Maarten • Fort-De-France, Martinique • Castries, St. Lucia • Grenada • Oranjestad, Aruba • Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Cruising the Straits of Florida • Cozumel • Roatan, Honduras • Harvest Caye, Belize • Costa Maya • Cruising the Straits of Florida • Miami
Average Starting Price
$22,399pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
May 1, 2027 - May 8, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$848pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Resilient Lady
Virgin Voyages
Nov 20, 2027 - Nov 28, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Samana, Dominican Republic • Bimini • Miami
Average Starting Price
$1,032pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Sep 5, 2027 - Sep 12, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,460pp
Jim's Onboard Credit

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!

49% OFF
Carnival Magic
Carnival Cruise Line
Sep 25, 2027 - Oct 3, 2027 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$600pp
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!

49% OFF
MSC Seashore
MSC Cruises
Nov 5, 2027 - Nov 20, 2027 (15 Nights)
Miami • Ocean Cay • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$1,408pp
Jim's Onboard Credit
Allura
Oceania Cruises
Mar 21, 2027 - Mar 31, 2027 (10 Nights)
Miami • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • St. Thomas • Tortola • Miami
Average Starting Price
$5,199pp
Jim's Onboard Credit
57% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Aug 14, 2027 - Aug 21, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$599pp
Jim's Onboard Credit
29% OFF
Carnival Pride
Carnival Cruise Line
Oct 31, 2027 - Nov 14, 2027 (14 Nights)
Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • St. Kitts • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • Grand Turk • Fun Day at Sea • Fun Day at Sea • Baltimore
Average Starting Price
$1,550pp
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!

Icon of the Seas
Royal Caribbean
Jun 5, 2027 - Jun 12, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,700pp
Jim's Onboard Credit
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