Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

10 sailings across 23 cruise lines, each one priced and planned end to end: the ports it calls at, the one unmissable thing to do at each, and the flights and nights either side. A balcony averages about $165 a night on Carnival and about $414 on Disney, per person with taxes in — what a night costs on every line. Leaving within three weeks?

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines
Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Showing 10 of 10 sailings
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA III
Suite: low fare 19% under usual↓ 55% suite, 40d
Caribbean 7 nights Nov 8, 2026
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico7 ports
Miami, Florida · Providenciales, Turks & Caicos · Puerto Plata, Dominican Republic · La Romana, Dominican Republic · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefThe full 27 jumps at the Damajagua WaterfallsSaona Island Private Speedboat & Natural Pool Day +3 more
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Suite $4,385 pp
Book This Cruise@ Cruisebound
14-night Caribbean from San JuanRound-trip
Explora Journeys · EXPLORA III
Suite: typical fare in the usual range
Caribbean 14 nights Jan 29, 2027
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Providenciales, Turks & Caicos · Key West, Florida · Miami, Florida · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint John/cruz Bay · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandPrivate Half-Day Island Adventure & Trunk Bay BeachIguana Island & Reef +5 more
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Suite $12,185 pp
Book This Cruise@ Cruisebound
7-night San Juan to BridgetownOne-way
Explora Journeys · EXPLORA III
Suite: above average 92% over usual
Caribbean 7 nights Mar 7, 2027
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Bridgetown, Barbados11 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +7 more
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Suite $10,400 pp
Book This Cruise@ Cruisebound
15-night Miami to BridgetownOne-way
Explora Journeys · EXPLORA III
Suite: low fare 54% under usual↑ 7% suite, 26d
Caribbean 15 nights Mar 14, 2027
Miami, Florida · Providenciales, Turks & Caicos · … · Bridgetown, Barbados6 ports
Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Half-Day Island Adventure & Trunk Bay BeachDeath in Paradise Filming Locations & Botanical Ga… +2 more
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Suite $5,100 pp
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8-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: typical fare in the usual range
Caribbean 8 nights Nov 5, 2027
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico7 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint John/cruz Bay · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsDeath in Paradise Filming Locations & Botanical Ga… +2 more
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Suite $4,480 pp
Book This Cruise@ Cruisebound
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: typical fare in the usual range
Caribbean 7 nights Feb 26, 2028
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico6 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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Suite $3,820 pp
Book This Cruise@ Cruisebound
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: above average 5% over usual
Caribbean 7 nights Mar 11, 2028
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico6 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · St. John's, Antigua · Road Bay, Anguilla · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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Suite $4,020 pp
Book This Cruise@ Cruisebound
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: typical fare in the usual range↓ 9% suite, 38d
Caribbean 7 nights Mar 25, 2028
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico6 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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Suite $3,655 pp
Book This Cruise@ Cruisebound
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: low fare 7% under usual
Caribbean 7 nights Apr 8, 2028
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico6 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · St. John's, Antigua · Road Bay, Anguilla · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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Suite $3,545 pp
Book This Cruise@ Cruisebound
7-night Miami to San JuanOne-way
Explora Journeys · EXPLORA IV
Suite: typical fare in the usual range
Caribbean 7 nights Apr 22, 2028
Miami, Florida · Providenciales, Turks & Caicos · … · San Juan, Puerto Rico6 ports
Miami, Florida · Providenciales, Turks & Caicos · Gustavia, St. Barts · St. John's, Antigua · Road Bay, Anguilla · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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Suite $3,640 pp
Book This Cruise@ Cruisebound

Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.