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Cruise Dates

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October 2026

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Rhapsody of the Seas

Royal Caribbean

Feb 27, 2027 - Mar 6, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$588pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Celebrity Apex

Celebrity Cruises

Feb 27, 2027 - Mar 6, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida

Average Starting Price

Jan 13, 2027 - Jan 29, 2027 (16 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$11,600pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

Jan 28, 2028 - Feb 4, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

Apr 15, 2028 - Apr 22, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 11, 2029 - Jan 30, 2029 (19 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami • Cozumel • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,884pp

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!

Azamara Onward

Azamara

Nov 25, 2027 - Dec 22, 2027 (27 Nights)

Athens (Piraeus), Greece • Valletta, Malta • Syracuse (Sicily), Italy • Catania, Sicily, Italy • Salerno, Italy • Salerno, Italy • Rome (Civitavecchia), Italy • Trapani, Italy • La Goulette, Tunisia • Alger, Algeria • Cartagena, Spain • Motril, Spain • Malaga, Spain • Tangier, Morocco • St. Thomas • Miami

Average Starting Price

$5,429pp

Jim's Onboard Credit

Jim's Ship Pick
One of my absolute favorite ships! Small, simple, and luxurious without feeling stuffy - and perfect for immersive, port-intensive cruises!

Star of the Seas

Royal Caribbean

Jul 4, 2027 - Jul 11, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,775pp

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!

45% OFF

MSC Meraviglia

MSC Cruises

Feb 21, 2027 - Mar 7, 2027 (14 Nights)

Miami • Nassau • Ocean Cay • Grand Turk • Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

$1,155pp

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!