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Cruise Dates

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October 2026

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Celebrity Constellation

Celebrity Cruises

Feb 13, 2027 - Feb 20, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jul 17, 2027 - Jul 24, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

Feb 28, 2027 - Mar 21, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,169pp

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!

Rhapsody of the Seas

Royal Caribbean

Feb 6, 2027 - Feb 13, 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

$608pp

Jim's Onboard Credit

FREE Specialty Dining Meal

26% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Mar 20, 2028 - Apr 1, 2028 (12 Nights)

Miami • Cruising the Atlantic Ocean • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Atlantic Ocean cruising • Atlantic Ocean cruising • Miami

Average Starting Price

Feb 7, 2028 - Feb 17, 2028 (10 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami

Average Starting Price

Jan 23, 2027 - Feb 13, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,029pp

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!

9% OFF

Crystal Symphony

Crystal Cruises

Dec 28, 2027 - Jan 11, 2028 (14 Nights)

Fort Lauderdale • George Town, Cayman Islands • Montego Bay, Jamaica • La Romana, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$7,030pp

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!

Vision of the Seas

Royal Caribbean

Jan 31, 2027 - Feb 7, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$499pp

Jim's Onboard Credit

FREE Specialty Dining Meal

15% OFF

Marina

Oceania Cruises

Feb 23, 2027 - Mar 5, 2027 (10 Nights)

Miami • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Nassau • Miami

Average Starting Price

Feb 19, 2027 - Mar 11, 2027 (20 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Nassau • Miami

Average Starting Price

$11,349pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

Dec 10, 2027 - Dec 20, 2027 (10 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

$1,089pp

Jim's Onboard Credit

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