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50% OFF
MSC Opera
MSC Cruises
Dec 27, 2027 - Jan 3, 2028 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$1,559pp
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!

Sky Princess
Princess Cruises
Nov 26, 2028 - Dec 10, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,484pp
Jim's Onboard Credit
Silver Ray
Silversea
Feb 26, 2027 - Mar 10, 2027 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Deshaies, Guadeloupe • Soufrier Bay, St. Lucia • St. Kitts • Philipsburg, St. Maarten • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$6,500pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,009pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 2, 2027 - Jan 23, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,709pp
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!

Norwegian Bliss
Norwegian Cruise Line
Dec 23, 2026 - Jan 4, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Thomas • Tortola • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,899pp
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!

Vision of the Seas
Royal Caribbean
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$664pp
Jim's Onboard Credit
48% OFF
MSC Meraviglia
MSC Cruises
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,505pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

29% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 14, 2028 - Feb 24, 2028 (10 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • 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
$7,199pp
Jim's Onboard Credit
Silver Spirit
Silversea
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$4,600pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
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
$4,768pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$669pp
Jim's Onboard Credit
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