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Valiant Lady
Virgin Voyages
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,043pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$731pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$649pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Enchanted Princess
Princess Cruises
Dec 27, 2026 - Jan 6, 2027 (10 Nights)
Fort Lauderdale • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale
Average Starting Price
$1,089pp
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!

EXPLORA IV
Explora Journeys
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami
Average Starting Price
$3,655pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$904pp
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!

Norwegian Bliss
Norwegian Cruise Line
Nov 29, 2026 - Dec 11, 2026 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,529pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 29, 2027 - Feb 12, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico
Average Starting Price
$12,675pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Jan 14, 2029 - Jan 28, 2029 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,714pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Nov 21, 2026 - Nov 28, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Nassau • Perfect Day Cococay • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$1,272pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$5,600pp
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!

Disney Fantasy
Disney Cruise Line
May 6, 2028 - May 13, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$2,085pp
Jim's Onboard Credit
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