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Port: San Juan, Puerto Rico×
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Viking Sky
Viking
Nov 24, 2028 - Dec 4, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 26, 2028 - Mar 4, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$906pp
Jim's Onboard Credit
Azamara Journey
Azamara
Dec 12, 2026 - Dec 18, 2026 (6 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$2,619pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,029pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Jan 31, 2027 - Feb 14, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Celebration Key • Roatan, Honduras • Cozumel • Fort Lauderdale
Average Starting Price
$1,304pp
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!

Norwegian Prima
Norwegian Cruise Line
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,189pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 12, 2027 - Feb 2, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,939pp
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!

Star Princess
Princess Cruises
Feb 17, 2029 - Feb 24, 2029 (7 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$1,025pp
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!

Enchanted Princess
Princess Cruises
Jan 23, 2029 - Feb 3, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,400pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Dec 23, 2026 - Jan 3, 2027 (11 Nights)
Philadelphia • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$1,269pp
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!

Star Legend
Windstar Cruises
Feb 21, 2028 - Mar 13, 2028 (21 Nights)
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 • Funchal, Portugal • Casablanca, Morocco • Lisbon, Portugal
Average Starting Price
$4,271pp
Jim's Onboard Credit
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