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57% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
May 22, 2027 - May 29, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$629pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Jul 31, 2027 - Aug 7, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,920pp
Jim's Onboard Credit
Azamara Onward
Azamara
Dec 22, 2027 - Jan 5, 2028 (14 Nights)
Miami • Nassau • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St. Pierre • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Miami
Average Starting Price
$4,099pp
Jim's Onboard Credit

Jim's Ship Pick
One of my absolute favorite ships! Small, simple, and luxurious without feeling stuffy - and perfect for immersive, port-intensive cruises!

Viking Mars
Viking
Feb 23, 2028 - Mar 14, 2028 (20 Nights)
Fort Lauderdale • Sail the Caribbean Sea • Sail the Caribbean Sea • 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 • Sail the Mediterranean Sea • Barcelona, Spain • Barcelona, Spain • Sete, France • Marseille (Provence), France • Monte Carlo, Monaco • Livorno, Italy • Livorno, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$7,298pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Dec 27, 2027 - Jan 10, 2028 (14 Nights)
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 • 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
Average Starting Price
$4,504pp
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 III
Explora Journeys
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • St. Thomas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami
Average Starting Price
$10,725pp
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!

35% OFF
Carnival Firenze
Carnival Cruise Line
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • St. Lucia • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,135pp
Jim's Onboard Credit
Island Princess
Princess Cruises
Nov 5, 2027 - Nov 15, 2027 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,254pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 21, 2027 - Nov 26, 2027 (5 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados
Average Starting Price
$497pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Nov 13, 2027 - Nov 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$833pp
Jim's Onboard Credit
15% OFF
Marina
Oceania Cruises
Feb 23, 2027 - Mar 5, 2027 (10 Nights)
Miami • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$3,527pp
Jim's Onboard Credit
50% OFF
MSC Meraviglia
MSC Cruises
Apr 10, 2027 - Apr 27, 2027 (17 Nights)
Miami • Philipsburg, St. Maarten • Ponta Delgada (Azores), Portugal • Lisbon, Portugal • Cadiz, Spain • Malaga, Spain • Palma de Mallorca, Spain • Marseille (Provence), France • Tarragona, Spain
Average Starting Price
$953pp
Jim's Onboard Credit
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