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October 2026

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Seven Seas Mariner

Regent Seven Seas Cruises

Nov 7, 2028 - Nov 17, 2028 (10 Nights)

Miami • Tortola • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • Miami

Average Starting Price

Feb 22, 2027 - Mar 4, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami

Average Starting Price

Jan 3, 2028 - Jan 10, 2028 (7 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Jan 29, 2027 - Feb 5, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Nov 21, 2026 - Dec 5, 2026 (14 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • San Juan, Puerto Rico

Average Starting Price

Feb 14, 2027 - Mar 6, 2027 (20 Nights)

Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami

Average Starting Price

$4,444pp

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!

Island Princess

Princess Cruises

Mar 18, 2028 - Apr 3, 2028 (16 Nights)

Fort Lauderdale • St. Thomas • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • St. Lucia • Bridgetown, Barbados • Grenada • Willemstad, Curacao • Oranjestad, Aruba • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

$1,599pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

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

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

Average Starting Price

Mar 29, 2028 - Apr 7, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

Dec 5, 2027 - Dec 12, 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

$709pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

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

Miami • St John's, Antigua • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami

Average Starting Price

Nov 27, 2027 - Dec 12, 2027 (15 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami

Average Starting Price

$1,408pp

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!

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