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October 2026

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Adventure of the Seas

Royal Caribbean

Dec 1, 2027 - Dec 10, 2027 (9 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

Jan 2, 2028 - Jan 13, 2028 (11 Nights)

Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty

Average Starting Price

71% OFF

Mar 27, 2027 - Apr 4, 2027 (8 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

Nov 13, 2027 - Nov 21, 2027 (8 Nights)

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

Average Starting Price

$1,829pp

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!

Norwegian Pearl

Norwegian Cruise Line

Mar 28, 2027 - Apr 8, 2027 (11 Nights)

Philadelphia • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • Tortola • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Philadelphia

Average Starting Price

46% OFF

May 23, 2027 - May 30, 2027 (7 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

Dec 12, 2027 - Dec 22, 2027 (10 Nights)

Port Canaveral (Orlando), Florida • San Juan, Puerto Rico • St. Kitts • St. Lucia • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 22, 2027 - Jan 8, 2028 (17 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

$4,794pp

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!

Enchanted Princess

Princess Cruises

Dec 14, 2027 - Dec 24, 2027 (10 Nights)

Fort Lauderdale • St. Thomas • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Dec 19, 2027 - Dec 28, 2027 (9 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$1,017pp

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!

56% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

Apr 3, 2027 - Apr 10, 2027 (7 Nights)

Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$579pp

Jim's Onboard Credit

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