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Harmony of the Seas
Royal Caribbean
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$919pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Viking Sea
Viking
Feb 26, 2028 - Mar 10, 2028 (13 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
Average Starting Price
$3,299pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 14, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • 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
Valiant Lady
Virgin Voyages
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
28% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Nov 20, 2028 - Dec 3, 2028 (13 Nights)
Lisbon, Portugal • Funchal, Portugal • San Juan, Puerto Rico • Miami
Average Starting Price
$7,599pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 6, 2027 - Jan 16, 2027 (10 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale
Average Starting Price
$1,489pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 5, 2027 - Feb 12, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico
Average Starting Price
$7,050pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Feb 26, 2028 - Mar 4, 2028 (7 Nights)
Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$3,820pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$716pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 27, 2027 - Jan 3, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$1,292pp
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
Dec 27, 2026 - Jan 4, 2027 (8 Nights)
Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$7,095pp
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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