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Cruise Dates

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October 2026

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Viking Sky

Viking

Feb 17, 2028 - Feb 27, 2028 (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

Dec 12, 2027 - Dec 26, 2027 (14 Nights)

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

Average Starting Price

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

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

Average Starting Price

Mar 20, 2027 - Apr 3, 2027 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Cozumel • Fort Lauderdale

Average Starting Price

$1,258pp

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!

32% OFF

Carnival Magic

Carnival Cruise Line

Dec 26, 2027 - Jan 3, 2028 (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

$1,160pp

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!

Disney Fantasy

Disney Cruise Line

May 13, 2028 - May 19, 2028 (6 Nights)

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

Average Starting Price

Feb 5, 2028 - Feb 17, 2028 (12 Nights)

Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Fort-De-France, Martinique • Gustavia, St. Barts • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Nov 28, 2026 - Dec 5, 2026 (7 Nights)

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

Average Starting Price

Nov 17, 2026 - Dec 4, 2026 (17 Nights)

Barcelona, Spain • Las Palmas (Gran Canaria), Spain • Philipsburg, St. Maarten • St. Kitts • Dominica • Bridgetown, Barbados • Saint George • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique

Average Starting Price

46% OFF

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

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

Average Starting Price

$1,345pp

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!

EXPLORA I

Explora Journeys

Dec 5, 2026 - Dec 20, 2026 (15 Nights)

Miami • Cozumel • Costa Maya • Santo Tomas de Castilla, Guatemala • Belize City • Roatan, Honduras • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Nov 5, 2027 - Nov 20, 2027 (15 Nights)

Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten

Average Starting Price

$2,580pp

Jim's Onboard Credit

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