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October 2026

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Vista

Oceania Cruises

Feb 7, 2029 - Feb 16, 2029 (9 Nights)

Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Aug 13, 2027 - Aug 16, 2027 (3 Nights)

Miami • Perfect Day Cococay • Nassau • Miami

Average Starting Price

Dec 5, 2027 - Dec 19, 2027 (14 Nights)

Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami

Average Starting Price

$1,098pp

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!

71% OFF

MSC Meraviglia

MSC Cruises

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

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

Average Starting Price

May 22, 2027 - May 29, 2027 (7 Nights)

Miami • George Town, Cayman Islands • Cozumel • Costa Maya • Perfect Day Cococay • Miami

Average Starting Price

35% OFF

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

Miami • Celebration Key • Nassau • Relaxaway Half Moon Cay • Fun Day at Sea • Amber Cove, Dominican Republic • Fun Day at Sea • Miami

Average Starting Price

$962pp

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!

20% OFF

Allura

Oceania Cruises

Feb 5, 2027 - Feb 12, 2027 (7 Nights)

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

Average Starting Price

$3,320pp

Jim's Onboard Credit

Norwegian Jewel

Norwegian Cruise Line

Dec 20, 2027 - Dec 30, 2027 (10 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$1,559pp

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!

Zuiderdam

Holland America Line

Apr 7, 2027 - Apr 17, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Miami

Average Starting Price

$2,004pp

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 Viva

Norwegian Cruise Line

Apr 18, 2027 - Apr 25, 2027 (7 Nights)

Miami • Roatan, Honduras • Harvest Caye, Belize • Cozumel • Great Stirrup Cay • Miami

Average Starting Price

46% OFF

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

Miami • Fun Day at Sea • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • Amber Cove, Dominican Republic • Fun Day at Sea • Miami

Average Starting Price

Mar 29, 2027 - Apr 3, 2027 (5 Nights)

Miami • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

$795pp

Jim's Onboard Credit

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