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Azamara Journey
Azamara
Dec 28, 2026 - Jan 14, 2027 (17 Nights)
Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Charlestown, Nevis • St. Croix • 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
$5,419pp
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!

Star Princess
Princess Cruises
Mar 5, 2028 - Mar 14, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$954pp
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!

Norwegian Pearl
Norwegian Cruise Line
Jan 23, 2027 - Feb 2, 2027 (10 Nights)
Philadelphia • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$629pp
Jim's Onboard Credit
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
Miami • Freeport • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$669pp
Jim's Onboard Credit
Crystal Symphony
Crystal Cruises
Nov 24, 2026 - Dec 3, 2026 (9 Nights)
Fort Lauderdale • St. Thomas • Tortola • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Fort Lauderdale
Average Starting Price
$4,200pp
Jim's Onboard Credit
Silver Nova
Silversea
Dec 3, 2027 - Dec 18, 2027 (15 Nights)
Lisbon, Portugal • Gibraltar • Philipsburg, St. Maarten • San Juan, Puerto Rico • Miami
Average Starting Price
$5,200pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Thomas • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,289pp
Jim's Onboard Credit
Volendam
Holland America Line
Mar 11, 2028 - May 13, 2028 (63 Nights)
Sydney, Australia • Brisbane, Australia • Townsville, Australia • Cairns (Yorkeys Knob), Australia • Scenic Cruising Torres Strait • Darwin, Australia • Slawi Bay, Komodo • Benoa (Bali), Indonesia • Crossing the Equator • Singapore • Singapore • Phuket, Thailand • Colombo, Sri Lanka • Male, Maldives • Port Louis, Mauritius • La Possession, Reunion • Port Elizabeth, South Africa • Cape Town, South Africa • Cape Town, South Africa • Cape Town, South Africa • Luderitz, Namibia • Walvis Bay, Namibia • Crossing Null Island • Sekondi-Takoradi, Ghana • Abidjan, Ivory Coast • Praia, Cape Verde • Mindelo, Cape Verde • San Juan, Puerto Rico • Fort Lauderdale
Average Starting Price
$16,179pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • Samana, Dominican Republic • San Juan, Puerto Rico • Miami
Average Starting Price
$1,040pp
Jim's Onboard Credit
35% OFF
Carnival Vista
Carnival Cruise Line
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$1,084pp
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!

Viking Sea
Viking
Feb 4, 2027 - Feb 14, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$6,799pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 7, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • 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
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