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Cruise Dates

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November 2026

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Star Princess

Princess Cruises

Mar 3, 2029 - Mar 10, 2029 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$1,025pp

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!

Star Pride

Windstar Cruises

Mar 6, 2028 - Mar 27, 2028 (21 Nights)

Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Apr 15, 2028 - Apr 22, 2028 (7 Nights)

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

Average Starting Price

49% OFF

Sep 3, 2027 - Sep 10, 2027 (7 Nights)

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique

Average Starting Price

$629pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Apr 1, 2028 - Apr 8, 2028 (7 Nights)

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

Average Starting Price

Feb 27, 2028 - Mar 12, 2028 (14 Nights)

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

Average Starting Price

Jan 5, 2027 - Jan 15, 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

Feb 14, 2027 - Feb 28, 2027 (14 Nights)

Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$1,449pp

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!

Wind Surf

Windstar Cruises

Jan 3, 2028 - Jan 16, 2028 (13 Nights)

Philipsburg, St. Maarten • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

29% OFF

Dec 2, 2026 - Dec 15, 2026 (13 Nights)

Bridgetown, Barbados • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Jan 24, 2027 - Jan 31, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,413pp

Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Seabourn Ovation

Seabourn

Jan 29, 2028 - Feb 12, 2028 (14 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados

Average Starting Price

$10,808pp

Jim's Onboard Credit

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