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Cruise Dates

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October 2026

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Grandeur of the Seas

Royal Caribbean

Jun 5, 2027 - Jun 12, 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

49% OFF

Jul 10, 2027 - Jul 17, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami

Average Starting Price

$1,194pp

Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Harmony of the Seas

Royal Caribbean

Jun 12, 2027 - Jun 19, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

49% OFF

Aug 28, 2027 - Sep 5, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$574pp

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!

Independence of the Seas

Royal Caribbean

Jul 8, 2027 - Jul 17, 2027 (9 Nights)

Cape Liberty • Royal Naval Dockyard, Bermuda • Philipsburg, St. Maarten • San Juan, Puerto Rico • Labadee, Haiti • Cape Liberty

Average Starting Price

35% OFF

Jul 10, 2027 - Jul 17, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida

Average Starting Price

$919pp

Jim's Onboard Credit

59% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

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

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

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

Port Canaveral (Orlando), Florida • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,354pp

Jim's Onboard Credit

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!

Hero of the Seas

Royal Caribbean

Nov 13, 2027 - Nov 20, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami

Average Starting Price

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

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$1,124pp

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!