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Emerald Princess
Princess Cruises
Mar 5, 2028 - Mar 19, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,908pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$489pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Aura
Norwegian Cruise Line
Aug 26, 2028 - Sep 2, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,299pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$3,027pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 22, 2028 - Jan 2, 2029 (11 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados
Average Starting Price
$1,870pp
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 Aqua
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$509pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 28, 2029 - Feb 11, 2029 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,856pp
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!

Harmony of the Seas
Royal Caribbean
Dec 12, 2026 - Dec 19, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Nassau • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$642pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Rhapsody of the Seas
Royal Caribbean
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$794pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 10, 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
$1,938pp
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 Escape
Norwegian Cruise Line
Dec 11, 2026 - Dec 18, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$509pp
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!

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