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Cruise Dates

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October 2026

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Rhapsody of the Seas

Royal Caribbean

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

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

Average Starting Price

$1,172pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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!

Crown Princess

Princess Cruises

Mar 5, 2027 - Mar 12, 2027 (7 Nights)

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

Average Starting Price

44% OFF

Jun 11, 2027 - Jun 18, 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

$967pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 15, 2026 - Nov 22, 2026 (7 Nights)

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

Average Starting Price

Jan 16, 2028 - Jan 23, 2028 (7 Nights)

Philipsburg, St. Maarten • St John's, Antigua • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

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

Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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

Average Starting Price

Jan 22, 2029 - Feb 5, 2029 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

$1,874pp

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!

49% OFF

MSC Opera

MSC Cruises

Sep 17, 2027 - Sep 24, 2027 (7 Nights)

Average Starting Price

Feb 26, 2027 - Mar 5, 2027 (7 Nights)

Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados

Average Starting Price

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

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

Average Starting Price

$1,949pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Dec 20, 2026 - Dec 27, 2026 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico

Average Starting Price

Mar 6, 2027 - Mar 20, 2027 (14 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 • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

$6,280pp

Jim's Onboard Credit

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