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Rotterdam
Holland America Line
Mar 4, 2028 - Mar 18, 2028 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale
Average Starting Price
$3,559pp
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!

Azamara Journey
Azamara
Dec 28, 2026 - Jan 5, 2027 (8 Nights)
Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Charlestown, Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$2,719pp
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!

Crown Princess
Princess Cruises
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$639pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$749pp
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!

Scarlet Lady
Virgin Voyages
Mar 4, 2028 - Mar 11, 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
$973pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • Oranjestad, Aruba • Willemstad, Curacao • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,169pp
Jim's Onboard Credit
Silver Dawn
Silversea
Nov 27, 2027 - Dec 11, 2027 (14 Nights)
Lisbon, Portugal • Funchal, Portugal • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Mindelo, Cape Verde • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$4,500pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 28, 2028 (14 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 • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,154pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Mar 10, 2029 - Mar 25, 2029 (15 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Celebration Key • Fort Lauderdale
Average Starting Price
$2,434pp
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!

Enchanted Princess
Princess Cruises
Dec 13, 2028 - Dec 23, 2028 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Martinique • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,300pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Dec 8, 2026 - Dec 18, 2026 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$609pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Willemstad, Curacao • Oranjestad, Aruba • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,032pp
Jim's Onboard Credit
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