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Vision of the Seas
Royal Caribbean
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$767pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 6, 2028 - Mar 27, 2028 (21 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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 • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$6,873pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Nov 13, 2027 - Nov 27, 2027 (14 Nights)
Barcelona, Spain • Valencia, Spain • Cartagena, Spain • Malaga, Spain • Cadiz, Spain • Tangier, Morocco • Casablanca, Morocco • San Juan, Puerto Rico
Average Starting Price
$815pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 3, 2027 - Dec 10, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,924pp
Jim's Onboard Credit
49% OFF
MSC World America
MSC Cruises
Dec 18, 2027 - Dec 31, 2027 (13 Nights)
Miami • Ocean Cay • Costa Maya • Cozumel • Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$2,009pp
Jim's Onboard Credit

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

Crown Princess
Princess Cruises
Jan 8, 2027 - Jan 15, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,299pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 11, 2029 - Mar 19, 2029 (8 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,125pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Feb 11, 2029 - Feb 18, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$975pp
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!

Vision of the Seas
Royal Caribbean
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$664pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 6, 2028 - Mar 13, 2028 (7 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$3,034pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 26, 2027 - Dec 3, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,654pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,244pp
Jim's Onboard Credit

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

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