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Cruise Dates

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October 2026

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Allure of the Seas

Royal Caribbean

Nov 22, 2026 - Nov 29, 2026 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Mar 13, 2027 - Mar 20, 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 21, 2027 - Jan 29, 2027 (8 Nights)

Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 22, 2028 - Jan 29, 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

Dec 22, 2027 - Jan 2, 2028 (11 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale

Average Starting Price

$3,034pp

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!

38% OFF

Carnival Festivale

Carnival Cruise Line

Feb 5, 2028 - Feb 13, 2028 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

$914pp

Jim's Onboard Credit

Norwegian Bliss

Norwegian Cruise Line

Jan 26, 2028 - Feb 7, 2028 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan

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!

Sonata

Oceania Cruises

Feb 22, 2029 - Mar 15, 2029 (21 Nights)

Miami • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • St. Thomas • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Miami • Cozumel • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Apr 1, 2028 - Apr 8, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami

Average Starting Price

Feb 28, 2027 - Mar 7, 2027 (7 Nights)

Miami • Nassau • St. Thomas • St John's, Antigua • Miami

Average Starting Price

46% OFF

Feb 27, 2027 - Mar 13, 2027 (14 Nights)

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

Average Starting Price

$1,205pp

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!

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