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Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 21, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • 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
Volendam
Holland America Line
Mar 28, 2028 - May 13, 2028 (46 Nights)
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
$10,954pp
Jim's Onboard Credit
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
$1,159pp
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!

56% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$569pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$4,020pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$903pp
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!

Celebrity Constellation
Celebrity Cruises
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,124pp
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!

Emerald Princess
Princess Cruises
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$739pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 3, 2028 - Jan 9, 2028 (6 Nights)
San Juan, Puerto Rico • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$823pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Dec 23, 2026 - Jan 4, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Thomas • Tortola • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,899pp
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!

Caribbean Princess
Princess Cruises
Nov 18, 2028 - Dec 3, 2028 (15 Nights)
Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,714pp
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!

Harmony of the Seas
Royal Caribbean
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$781pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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