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October 2026

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Viking Sea

Viking

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

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

Average Starting Price

Nov 12, 2027 - Nov 16, 2027 (4 Nights)

San Juan, Puerto Rico • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

$1,230pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

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

San Juan, Puerto Rico • Tortola • St. Lucia • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Dec 9, 2027 - Dec 19, 2027 (10 Nights)

Average Starting Price

Jan 20, 2028 - Jan 31, 2028 (11 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • St. Kitts • Gustavia, St. Barts • St John's, Antigua • St. John • Miami

Average Starting Price

Nov 23, 2027 - Dec 4, 2027 (11 Nights)

Miami • San Juan, Puerto Rico • Saint Barthelemy, Gustavia • Little Bay, Montserrat • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

37% OFF

Jul 31, 2027 - Aug 7, 2027 (7 Nights)

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

Average Starting Price

36% OFF

Jul 3, 2027 - Jul 11, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$964pp

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!

Harmony of the Seas

Royal Caribbean

Sep 25, 2027 - Oct 2, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 12, 2027 - Mar 21, 2027 (9 Nights)

Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,834pp

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!

Sirena

Oceania Cruises

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

Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

39% OFF

Jan 27, 2028 - Feb 5, 2028 (9 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

$909pp

Jim's Onboard Credit

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