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Port: San Juan, Puerto Rico×
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Star Legend
Windstar Cruises
Dec 27, 2027 - Jan 3, 2028 (7 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
Average Starting Price
$2,691pp
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!

Silver Shadow
Silversea
Dec 24, 2027 - Jan 5, 2028 (12 Nights)
Miami • Exuma Island, Bahamas • Samana, Dominican Republic • San Juan, Puerto Rico • St. John • Soper's Hole, Tortola • Puerto Plata, Dominican Republic • Grand Turk • Miami
Average Starting Price
$5,600pp
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!

Disney Dream
Disney Cruise Line
Apr 12, 2027 - Apr 16, 2027 (4 Nights)
Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico
Average Starting Price
$1,304pp
Jim's Onboard Credit
45% OFF
Carnival Venezia
Carnival Cruise Line
Apr 18, 2027 - Apr 25, 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
$584pp
Jim's Onboard Credit
Island Princess
Princess Cruises
Nov 5, 2027 - Nov 15, 2027 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,254pp
Jim's Onboard Credit
Silver Spirit
Silversea
Mar 19, 2027 - Mar 31, 2027 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$5,000pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 21, 2027 - Nov 26, 2027 (5 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados
Average Starting Price
$497pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 14, 2027 - Nov 23, 2027 (9 Nights)
Port Canaveral (Orlando), Florida • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$904pp
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 Bliss
Norwegian Cruise Line
Nov 28, 2027 - Dec 10, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,269pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,213pp
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!

Symphony of the Seas
Royal Caribbean
Nov 20, 2027 - Nov 28, 2027 (8 Nights)
Fort Lauderdale • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Perfect Day Cococay • Nassau • Fort Lauderdale
Average Starting Price
$1,480pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Nov 20, 2027 - Dec 5, 2027 (15 Nights)
Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$1,363pp
Jim's Onboard Credit
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