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25% OFF
Seven Seas Voyager
Regent Seven Seas Cruises
Dec 19, 2027 - Jan 13, 2028 (25 Nights)
Miami • Tortola • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$13,149pp
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!

20% OFF
Seven Seas Splendor
Regent Seven Seas Cruises
Dec 11, 2026 - Dec 28, 2026 (17 Nights)
Galveston • Montego Bay, Jamaica • Port Royal, Jamaica • Cap Cana (Punta Cana), Dominican Republic • San Juan, Puerto Rico • Tortola • St John's, Antigua • Gustavia, St. Barts • Philipsburg, St. Maarten • George Town, Cayman Islands • Galveston
Average Starting Price
$13,099pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,125pp
Jim's Onboard Credit
Insignia
Oceania Cruises
Nov 24, 2026 - Dec 19, 2026 (25 Nights)
Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Miami
Average Starting Price
$13,249pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Dec 10, 2027 - Dec 19, 2027 (9 Nights)
San Juan, Puerto Rico • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • Gustavia, St. Barts • Tortola • Fort Lauderdale
Average Starting Price
$3,660pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 2, 2027 - Feb 23, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$4,249pp
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!

Brilliant Lady
Virgin Voyages
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
$1,191pp
Jim's Onboard Credit
Azamara Journey
Azamara
Jan 5, 2027 - Jan 14, 2027 (9 Nights)
San Juan, Puerto Rico • St. John • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$3,009pp
Jim's Onboard Credit
Celebrity Xcel
Celebrity Cruises
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$957pp
Jim's Onboard Credit
15% OFF
Allura
Oceania Cruises
Feb 19, 2027 - Feb 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami
Average Starting Price
$3,740pp
Jim's Onboard Credit
Silver Ray
Silversea
Jan 5, 2027 - Jan 16, 2027 (11 Nights)
Miami • San Juan, Puerto Rico • St. John • St. Kitts • Deshaies, Guadeloupe • St John's, Antigua • Tortola • Miami
Average Starting Price
$7,900pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Dec 3, 2027 - Dec 10, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$819pp
Jim's Onboard Credit
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