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October 2026

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Celebrity Beyond

Celebrity Cruises

Jun 19, 2027 - Jun 27, 2027 (8 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Miami

Average Starting Price

46% OFF

Oct 24, 2027 - Oct 31, 2027 (7 Nights)

Miami • Fun Day at Sea • Grand Turk • Amber Cove, Dominican Republic • Fun Day at Sea • Relaxaway Half Moon Cay • Celebration Key • Miami

Average Starting Price

$564pp

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 17, 2027 - Apr 24, 2027 (7 Nights)

Miami • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Mar 14, 2028 - Mar 24, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • St. Kitts • St John's, Antigua • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

Mar 28, 2027 - Apr 4, 2027 (7 Nights)

Miami • Nassau • George Town, Cayman Islands • Cozumel • Costa Maya • Miami

Average Starting Price

Dec 18, 2027 - Dec 29, 2027 (11 Nights)

Miami • Soper's Hole, Tortola • St. Kitts • Deshaies, Guadeloupe • Fort-De-France, Martinique • St. John • Miami

Average Starting Price

$5,900pp

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!

Silver Ray

Silversea

Jan 15, 2028 - Jan 27, 2028 (12 Nights)

Miami • Cozumel • Limon, Costa Rica • Colon, Panama • Panama Canal, Panama • Manta, Ecuador • Lima, Peru

Average Starting Price

$9,100pp

Jim's Onboard Credit

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Nov 27, 2027 - Dec 7, 2027 (10 Nights)

Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$7,849pp

Jim's Onboard Credit

Norwegian Aura

Norwegian Cruise Line

Sep 18, 2027 - Sep 25, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami

Average Starting Price

Aug 8, 2027 - Aug 11, 2027 (3 Nights)

Miami • Perfect Day Cococay • Miami

Average Starting Price

Dec 6, 2027 - Jan 4, 2028 (29 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

Apr 9, 2027 - Apr 24, 2027 (15 Nights)

Miami • Royal Naval Dockyard, Bermuda • Santa Cruz de la Palma, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Funchal, Portugal • Lisbon, Portugal

Average Starting Price

$3,399pp

Jim's Onboard Credit

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