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Carnival Celebration
Carnival Cruise Line
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami
Average Starting Price
$388pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Mar 12, 2028 - Mar 19, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • Gustavia, St. Barts • Fredrikstad (for Oslo), Norway • Ocean Cay • Miami
Average Starting Price
$3,915pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$619pp
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 Dawn
Norwegian Cruise Line
Nov 5, 2027 - Nov 19, 2027 (14 Nights)
Barcelona, Spain • Cadiz, Spain • Casablanca, Morocco • San Juan, Puerto Rico • Jacksonville
Average Starting Price
$1,038pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 7, 2027 - Feb 21, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,436pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
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
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