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Port: San Juan, Puerto Rico×
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Norwegian Prima
Norwegian Cruise Line
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,309pp
Jim's Onboard Credit
Silver Shadow
Silversea
Jan 10, 2027 - Jan 20, 2027 (10 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • Les Saintes, F.W.I. • St. Kitts • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados
Average Starting Price
$4,850pp
Jim's Onboard Credit
9% OFF
Crystal Grace
Crystal Cruises
Jan 11, 2029 - Jan 19, 2029 (8 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • St. Kitts • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$4,900pp
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!

Silver Dawn
Silversea
Feb 10, 2028 - Feb 19, 2028 (9 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Gustavia, St. Barts • St. Kitts • Deshaies, Guadeloupe • Fort-De-France, Martinique • St John's, Antigua • St. John • San Juan, Puerto Rico
Average Starting Price
$3,800pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
Miami • St. John • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,760pp
Jim's Onboard Credit
Viking Sea
Viking
Mar 6, 2027 - Mar 26, 2027 (20 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Cadiz, Spain • Sail the Strait of Gibraltar • Valencia, Spain • Barcelona, Spain • Barcelona, Spain • Sete, France • Marseille (Provence), France • Monte Carlo, Monaco • Livorno, Italy • Livorno, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$7,098pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 29, 2027 - Feb 5, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$5,025pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,930pp
Jim's Onboard Credit
Viking Sky
Viking
Jan 28, 2028 - Feb 7, 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
$4,299pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Dec 28, 2027 - Jan 3, 2028 (6 Nights)
Fort Lauderdale • George Town, Cayman Islands • Montego Bay, Jamaica • La Romana, Dominican Republic • San Juan, Puerto Rico
Average Starting Price
$3,820pp
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!

Zuiderdam
Holland America Line
Feb 14, 2027 - Mar 6, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami
Average Starting Price
$4,444pp
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!

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