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Star Legend
Windstar Cruises
Jan 17, 2028 - Jan 31, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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
$4,014pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$739pp
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!

EXPLORA I
Explora Journeys
Jan 4, 2027 - Jan 20, 2027 (16 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami
Average Starting Price
$11,935pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Apr 15, 2028 - Apr 23, 2028 (8 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,870pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 12, 2027 - Dec 27, 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
$1,448pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,043pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 21, 2027 - Apr 4, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,415pp
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!

Allure of the Seas
Royal Caribbean
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$629pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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!

54% OFF
Carnival Vista
Carnival Cruise Line
Dec 18, 2026 - Dec 26, 2026 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Grand Bahama Island • Port Canaveral (Orlando), Florida
Average Starting Price
$647pp
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!

37% OFF
Carnival Firenze
Carnival Cruise Line
Feb 6, 2028 - Feb 20, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Grand Turk • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • St. Lucia • Bridgetown, Barbados • Martinique • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,006pp
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!

Vision of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$670pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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