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Cruise Dates

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October 2026

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Odyssey of the Seas

Royal Caribbean

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

$1,472pp

Jim's Onboard Credit

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

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!

Crown Princess

Princess Cruises

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

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

$1,244pp

Jim's Onboard Credit

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

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!

Celebrity Constellation

Celebrity Cruises

Mar 20, 2027 - Mar 27, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 16, 2027 - Dec 23, 2027 (7 Nights)

Miami • Labadee, Haiti • Samana, Dominican Republic • St. Thomas • Miami

Average Starting Price

$779pp

Jim's Onboard Credit

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