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Celebrity Reflection
Celebrity Cruises
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,870pp
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!

Silver Nova
Silversea
Jan 9, 2028 - Jan 20, 2028 (11 Nights)
Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St. Kitts • St John's, Antigua • St. John • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
26% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 7, 2027 - Dec 18, 2027 (11 Nights)
Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$8,499pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,113pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$637pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 24, 2028 - Feb 5, 2028 (12 Nights)
Cape Liberty • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Philipsburg, St. Maarten • Cape Liberty
Average Starting Price
$1,785pp
Jim's Onboard Credit
Explorer of the Seas
Royal Caribbean
Nov 18, 2026 - Nov 27, 2026 (9 Nights)
Port Canaveral (Orlando), Florida • St John's, Antigua • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$642pp
Jim's Onboard Credit
Oosterdam
Holland America Line
Dec 11, 2027 - Dec 22, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,739pp
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!

Silver Dawn
Silversea
Dec 11, 2027 - Dec 21, 2027 (10 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Gustavia, St. Barts • Fort-De-France, Martinique • Grenada • Bequia Island, Saint Vincent • Castries, St. Lucia • St John's, Antigua • St. John • San Juan, Puerto Rico
Average Starting Price
$4,800pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Dec 3, 2027 - Dec 13, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,245pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Nov 21, 2027 - Dec 22, 2027 (31 Nights)
Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Costa Maya • Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$8,649pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Mar 6, 2027 - Mar 27, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,949pp
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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