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Cruise Dates

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October 2026

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Vision of the Seas

Royal Caribbean

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

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$599pp

Jim's Onboard Credit

FREE Specialty Dining Meal

31% OFF

MSC World Europa

MSC Cruises

Feb 9, 2027 - Feb 23, 2027 (14 Nights)

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

Average Starting Price

Dec 1, 2026 - Dec 12, 2026 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,924pp

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!

Viking Sea

Viking

Nov 15, 2026 - Nov 25, 2026 (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 19, 2027 (7 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

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

49% OFF

Dec 28, 2027 - Jan 11, 2028 (14 Nights)

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

Average Starting Price

$2,739pp

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!

30% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 8, 2029 - Jan 18, 2029 (10 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • St John's, Antigua • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,378pp

Jim's Onboard Credit

FREE Specialty Dining Meal

21% OFF

MSC World Europa

MSC Cruises

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

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

Average Starting Price

Dec 10, 2028 - Dec 20, 2028 (10 Nights)

Average Starting Price

Dec 27, 2027 - Jan 9, 2028 (13 Nights)

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 • 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

Average Starting Price

$3,760pp

Jim's Onboard Credit

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