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Viking Sea
Viking
Mar 1, 2029 - Mar 22, 2029 (21 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 • Sail the Atlantic Ocean • Casablanca, Morocco • Cadiz, Spain • Sail the Strait of Gibraltar • Valencia, Spain • Barcelona, Spain • Barcelona, Spain • Sete, France • Marseille (Provence), France • Monte Carlo, Monaco • Livorno, Italy • Livorno, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$7,798pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Celebration Key • Roatan, Honduras • Cozumel • Miami
Average Starting Price
$1,569pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Star of the Seas
Royal Caribbean
Feb 7, 2027 - Feb 14, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,404pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Wind Surf
Windstar Cruises
Dec 27, 2027 - Jan 3, 2028 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,432pp
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!

42% OFF
MSC World Europa
MSC Cruises
Nov 18, 2026 - Dec 2, 2026 (14 Nights)
Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$769pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,048pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 8, 2028 - Jan 22, 2028 (14 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$9,038pp
Jim's Onboard Credit
Azamara Quest
Azamara
Jan 24, 2028 - Mar 22, 2028 (58 Nights)
Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Sailing In The Chilean Fjords • Sailing In The Chilean Fjords • Punta Arenas, Chile • Punta Arenas, Chile • Ushuaia, Argentina • Sailing Snow Island • Sailing Bransfield Strait • Sailing Gerlache Strait • Sailing Paradise Bay • Sailing Wilhelmina Bay • Sailing Penguin Island • Sailing King George Island • Port Stanley, Falkland Islands • Punta del Este, Uruguay • Montevideo, Uruguay • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Saint George's, Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$26,859pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 23, 2027 - Jan 30, 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
$547pp
Jim's Onboard Credit
FREE Specialty Dining Meal
45% OFF
MSC Meraviglia
MSC Cruises
Jan 16, 2027 - Jan 30, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,055pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 17, 2026 - Dec 27, 2026 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,179pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Scarlet Lady
Virgin Voyages
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
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