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EXPLORA I
Explora Journeys
Dec 5, 2026 - Dec 20, 2026 (15 Nights)
Miami • Cozumel • Costa Maya • Santo Tomas de Castilla, Guatemala • Belize City • Roatan, Honduras • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$7,115pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Nov 9, 2026 - Nov 21, 2026 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,219pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Dec 23, 2026 - Dec 30, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$2,023pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Seabourn Pursuit
Seabourn
Sep 24, 2028 - Oct 2, 2028 (8 Nights)
Halifax, Nova Scotia • Hamilton, Bermuda • San Juan, Puerto Rico • Oranjestad, Aruba
Average Starting Price
$5,088pp
Jim's Onboard Credit
Silver Nova
Silversea
Dec 21, 2026 - Dec 29, 2026 (8 Nights)
Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,200pp
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!

Vision of the Seas
Royal Caribbean
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$875pp
Jim's Onboard Credit
60% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$899pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 21, 2027 - Feb 5, 2027 (15 Nights)
Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami
Average Starting Price
$10,725pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 15, 2027 - Jan 25, 2027 (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
$6,799pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 20, 2028 - Mar 27, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Feb 21, 2027 - Mar 1, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Nassau • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$1,199pp
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!

Grandeur of the Seas
Royal Caribbean
Jul 17, 2027 - Jul 24, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$868pp
Jim's Onboard Credit
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