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Crown Princess
Princess Cruises
Mar 7, 2027 - Mar 21, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,688pp
Jim's Onboard Credit
28% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 30, 2028 - Jan 9, 2029 (10 Nights)
Miami • St. Thomas • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,599pp
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!

Brilliant Lady
Virgin Voyages
Dec 14, 2026 - Dec 23, 2026 (9 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Bimini • Miami
Average Starting Price
$891pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Sep 26, 2027 - Oct 3, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,525pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Grandeur of the Seas
Royal Caribbean
Jun 12, 2027 - Jun 19, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$879pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
May 16, 2027 - May 23, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,129pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
May 15, 2027 - May 22, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$911pp
Jim's Onboard Credit
FREE Specialty Dining Meal
33% OFF
Carnival Vista
Carnival Cruise Line
Jun 19, 2027 - Jun 26, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$969pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 21, 2027 - Dec 5, 2027 (14 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$3,329pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Miami • Road Bay, Anguilla • St. Thomas • St John's, Antigua • St. John • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St. Thomas • Disney Castaway Cay, Bahamas • Fort Lauderdale
Average Starting Price
$1,965pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 28, 2027 - Apr 4, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Thomas • St. Lucia • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$1,059pp
Jim's Onboard Credit
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