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59% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jun 5, 2027 - Jun 12, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$799pp
Jim's Onboard Credit
Viking Sky
Viking
Jan 8, 2028 - Jan 18, 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
4% OFF
Carnival Vista
Carnival Cruise Line
Feb 6, 2027 - Feb 14, 2027 (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
$757pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 14, 2027 - Jan 25, 2027 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Cape Liberty
Average Starting Price
$1,869pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Viking Sea
Viking
Mar 6, 2027 - Mar 19, 2027 (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
$3,499pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jan 29, 2027 - Feb 6, 2027 (8 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort-De-France, Martinique • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,352pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Feb 7, 2028 - Feb 17, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,390pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 3, 2028 - Jan 17, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • 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
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
48% OFF
MSC Seashore
MSC Cruises
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,098pp
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!

Azamara Journey
Azamara
Dec 5, 2026 - Dec 18, 2026 (13 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$5,729pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 20, 2027 - Feb 5, 2027 (16 Nights)
Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$9,000pp
Jim's Onboard Credit
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