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Silver Ray
Silversea
Jan 16, 2027 - Jan 27, 2027 (11 Nights)
Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Tortola • Road Bay, Anguilla • Charlestown, Nevis • Miami
Average Starting Price
$7,800pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Feb 14, 2027 - Mar 6, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami
Average Starting Price
$4,444pp
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!

Resilient Lady
Virgin Voyages
Nov 8, 2026 - Nov 16, 2026 (8 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • Bimini • Miami
Average Starting Price
$872pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Nov 28, 2027 - Dec 10, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,269pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Nov 26, 2027 - Dec 3, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$819pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Nov 27, 2027 - Dec 5, 2027 (8 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$824pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$804pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Apr 9, 2027 - Apr 16, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$739pp
Jim's Onboard Credit
Disney Dream
Disney Cruise Line
Jan 22, 2027 - Jan 29, 2027 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Tortola • Fort Lauderdale
Average Starting Price
$1,591pp
Jim's Onboard Credit
36% OFF
Carnival Firenze
Carnival Cruise Line
Apr 16, 2028 - Apr 30, 2028 (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 • Tortola • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,045pp
Jim's Onboard Credit
Vista
Oceania Cruises
Feb 7, 2029 - Feb 16, 2029 (9 Nights)
Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$4,299pp
Jim's Onboard Credit
Norwegian Dawn
Norwegian Cruise Line
Dec 9, 2027 - Dec 18, 2027 (9 Nights)
Jacksonville • Grand Bahama Island • Great Stirrup Cay • San Juan, Puerto Rico • Tortola • Puerto Plata, Dominican Republic • Jacksonville
Average Starting Price
$969pp
Jim's Onboard Credit
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