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Sonata
Oceania Cruises
Nov 1, 2028 - Nov 16, 2028 (15 Nights)
Lisbon, Portugal • Portimão, Portugal • Funchal, Portugal • Santa Cruz de Tenerife, Spain • Santa Cruz de la Palma, Spain • San Juan, Puerto Rico • Miami
Average Starting Price
$5,299pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$758pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 2029 (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

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!

Rotterdam
Holland America Line
Feb 13, 2027 - Mar 6, 2027 (21 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • 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
Average Starting Price
$4,109pp
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!

EXPLORA II
Explora Journeys
Mar 19, 2028 - Apr 4, 2028 (16 Nights)
Miami • San Juan, Puerto Rico • St John's, Antigua • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain
Average Starting Price
$7,110pp
Jim's Onboard Credit
35% OFF
Carnival Festivale
Carnival Cruise Line
Apr 1, 2028 - Apr 9, 2028 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$1,016pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale
Average Starting Price
$1,642pp
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!

Azamara Journey
Azamara
Dec 12, 2026 - Dec 28, 2026 (16 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Gustavia, St. Barts • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Scarborough (Tobago), Trinidad and Tobago • Mayreau Island, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$3,979pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 31, 2027 - Feb 14, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,332pp
Jim's Onboard Credit
44% OFF
Carnival Magic
Carnival Cruise Line
Mar 11, 2028 - Mar 19, 2028 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$713pp
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!

Silver Ray
Silversea
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Grenada • Bequia Island, Saint Vincent • Fort-De-France, Martinique • St John's, Antigua • Charlestown, Nevis • San Juan, Puerto Rico
Average Starting Price
$4,500pp
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!

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