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Rhapsody of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$869pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,813pp
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!

Grandeur of the Seas
Royal Caribbean
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$609pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 20, 2028 - Mar 27, 2028 (7 Nights)
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
$2,443pp
Jim's Onboard Credit
52% OFF
MSC World Europa
MSC Cruises
Apr 11, 2027 - Apr 24, 2027 (13 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$699pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$1,000pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 21, 2027 - Mar 7, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,366pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Feb 7, 2028 - Feb 19, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,589pp
Jim's Onboard Credit
Allura
Oceania Cruises
Dec 21, 2026 - Jan 7, 2027 (17 Nights)
Miami • Costa Maya • Roatan, Honduras • Harvest Caye, Belize • Cozumel • Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$11,399pp
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!

Hero of the Seas
Royal Caribbean
Nov 13, 2027 - Nov 20, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$1,696pp
Jim's Onboard Credit
40% OFF
Marina
Oceania Cruises
Dec 10, 2026 - Dec 22, 2026 (12 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$2,640pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Feb 5, 2028 - Feb 19, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,639pp
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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