Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

39 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 $166 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
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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 39 of 39 sailings
11-night Caribbean from MiamiRound-trip
Silversea · Silver Shadow
Suite: above average 15% over usual
Caribbean 11 nights Nov 7 – Nov 18, 2026
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more
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Suite $6,800 pp
Book This Cruise@ Cruisebound
12-night Caribbean from MiamiRound-trip
Silversea · Silver Shadow
Suite: above average 15% over usual↑ 21% suite, 39d
Caribbean 12 nights Nov 18 – Nov 30, 2026
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more
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Suite $7,400 pp
Book This Cruise@ Cruisebound
10-night Caribbean from MiamiRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 10 nights Nov 30 – Dec 10, 2026
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +2 more
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Suite $5,200 pp
Book This Cruise@ Cruisebound
10-night Miami to San JuanOne-way
Silversea · Silver Shadow
Suite: low fare 16% under usual
Caribbean 10 nights Dec 10 – Dec 20, 2026
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico9 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Fort-de-France, Martinique · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
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Suite $4,800 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 11 nights Dec 11 – Dec 22, 2026
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Deshaies, Guadeloupe · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +3 more
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Suite $6,000 pp
Book This Cruise@ Cruisebound
8-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: low fare 12% under usual↓ 10% suite, 39d
Caribbean 8 nights Dec 19 – Dec 27, 2026
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Cruz Bay, St. John, U.S. Virgin Islands · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreBoiling Lake Hike +3 more
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Suite $3,700 pp
Book This Cruise@ Cruisebound
14-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: above average 6% over usual↑ 14% suite, 39d
Caribbean 14 nights Dec 22 – Jan 5, 2027
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida9 ports
Miami, Florida · Grand Turk, Turks and Caicos · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelMt. Liamuiga Volcano Crater HikeAruba +4 more
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Suite $10,800 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: above average 38% over usual
Caribbean 7 nights Dec 27 – Jan 3, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Bequia, Grenadines · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikeSunrise Hike to Le Chameau's Summit Fort +2 more
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Suite $7,050 pp
Book This Cruise@ Cruisebound
8-night San Juan to MiamiOne-way
Silversea · Silver Nova
Suite: above average 99% over usual↑ 54% suite, 39d
Caribbean 8 nights Dec 29 – Jan 6, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Island TourBoiling Lake Hike +3 more
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Suite $8,950 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 7 nights Jan 3 – Jan 10, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsBarbuda's Pink Sand Beach at Dawn, Private & Empty +3 more
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Suite $5,100 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 11 nights Jan 5 – Jan 16, 2027
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Codrington, Barbuda · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +3 more
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Suite $7,900 pp
Book This Cruise@ Cruisebound
12-night Miami to BridgetownOne-way
Silversea · Silver Nova
Suite: above average 18% over usual
Caribbean 12 nights Jan 6 – Jan 18, 2027
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +5 more
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Suite $7,200 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 11 nights Jan 16 – Jan 27, 2027
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Road Town, Tortola, B.V.I. · Anguilla, Caribbean · Port of Charlestown, Nevis, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more
View →
Suite $7,800 pp
Book This Cruise@ Cruisebound
10-night Bridgetown to San JuanOne-way
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 10 nights Jan 20 – Jan 30, 2027
Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailCosol ToursLa Savane des Esclaves +7 more
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Suite $5,900 pp
Book This Cruise@ Cruisebound
12-night Bridgetown to MiamiOne-way
Silversea · Silver Spirit
Suite: above average 12% over usual
Caribbean 12 nights Jan 25 – Feb 6, 2027
Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +5 more
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Suite $5,600 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range↓ 27% suite, 57d
Caribbean 11 nights Jan 27 – Feb 7, 2027
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Anguilla, Caribbean · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more
View →
Suite $8,400 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range↓ 24% suite, 57d
Caribbean 7 nights Jan 30 – Feb 6, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Little Bay, Montserrat, Leeward Islands · Codrington, Barbuda · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Soufrière Hills Volcano Exclusion Zone Helicopter…Barbuda's Pink Sand Beach at Dawn, Private & Empty +3 more
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Suite $5,100 pp
Book This Cruise@ Cruisebound
12-night Miami to BridgetownOne-way
Silversea · Silver Spirit
Suite: typical fare in the usual range
Caribbean 12 nights Feb 6 – Feb 18, 2027
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Aruba +5 more
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Suite $5,000 pp
Book This Cruise@ Cruisebound
12-night Miami to BridgetownOne-way
Silversea · Silver Ray
Suite: above average 18% over usual
Caribbean 12 nights Feb 7 – Feb 19, 2027
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados11 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +7 more
View →
Suite $7,200 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: low fare 12% under usual↑ 7% suite, 39d
Caribbean 7 nights Feb 26 – Mar 5, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
View →
Suite $4,500 pp
Book This Cruise@ Cruisebound
7-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: above average 16% over usual↑ 10% suite, 39d
Caribbean 7 nights Feb 28 – Mar 7, 2027
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Roseau, Dominica · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Open-Top Mini Moke Island Tour of St. BartsTrunk Bay Underwater Snorkel Trail & VI National P… +3 more
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Suite $4,300 pp
Book This Cruise@ Cruisebound
12-night Miami to BridgetownOne-way
Silversea · Silver Spirit
Suite: typical fare in the usual range
Caribbean 12 nights Mar 19 – Mar 31, 2027
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +5 more
View →
Suite $5,000 pp
Book This Cruise@ Cruisebound
14-night Caribbean from MiamiRound-trip
Seabourn · Seabourn Quest
Suite: typical fare in the usual range
Caribbean 14 nights Dec 4 – Dec 18, 2027
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida11 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +6 more
View →
Suite $7,498 pp
Book This Cruise@ Cruisebound
10-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: above average 7% over usual
Caribbean 10 nights Dec 11 – Dec 21, 2027
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +6 more
View →
Suite $4,800 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: low fare 6% under usual↓ 11% suite, 38d
Caribbean 11 nights Dec 18 – Dec 29, 2027
Miami, Florida · Sopers Hole · … · Miami, Florida7 ports
Miami, Florida · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Fort-de-France, Martinique · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeJardin Botanique de Deshaies at Opening Hour +2 more
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Suite $5,900 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 7 nights Dec 21 – Dec 28, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikeCosol Tours +2 more
View →
Suite $3,800 pp
Book This Cruise@ Cruisebound
12-night Caribbean from MiamiRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 12 nights Dec 24 – Jan 5, 2028
Miami, Florida · Exuma Island · … · Miami, Florida9 ports
Miami, Florida · Exuma Island · Santander, Spain · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Sopers Hole · Puerto Plata, Dominican Republic · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Altamira Caves & Santillana del MarWalk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P… +3 more
View →
Suite $5,600 pp
Book This Cruise@ Cruisebound
8-night San Juan to MiamiOne-way
Silversea · Silver Ray
Suite: above average 22% over usual
Caribbean 8 nights Dec 26 – Jan 3, 2028
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Barbuda's Pink Sand Beach at Dawn, Private & EmptyMount Pelée & Saint-Pierre +3 more
View →
Suite $5,500 pp
Book This Cruise@ Cruisebound
7-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 7 nights Dec 28 – Jan 4, 2028
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Boiling Lake Hike +2 more
View →
Suite $4,300 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: above average 8% over usual↓ 9% suite, 38d
Caribbean 11 nights Dec 29 – Jan 9, 2028
Miami, Florida · Key West, Florida · … · Miami, Florida8 ports
Miami, Florida · Key West, Florida · St. Thomas, U.S. Virgin Islands · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkPrivate Catamaran Sail & Snorkel at Honeymoon Beac…The Baths of Virgin Gorda +3 more
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Suite $6,800 pp
Book This Cruise@ Cruisebound
12-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: low fare 27% under usual
Caribbean 12 nights Jan 3 – Jan 15, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more
View →
Suite $6,400 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 9 – Jan 20, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths of Virgin GordaPrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
View →
Suite $6,300 pp
Book This Cruise@ Cruisebound
10-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 10 nights Jan 15 – Jan 25, 2028
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Canouan, St. Vincent · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +5 more
View →
Suite $4,500 pp
Book This Cruise@ Cruisebound
11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 20 – Jan 31, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths of Virgin GordaMt. Liamuiga Volcano Crater Hike +3 more
View →
Suite $6,300 pp
Book This Cruise@ Cruisebound
11-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 11 nights Jan 25 – Feb 5, 2028
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Roseau, Dominica · Canouan, St. Vincent · St. Georges, Grenada, West Indies · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsBoiling Lake Hike +4 more
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Suite $4,800 pp
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 31 – Feb 11, 2028
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida8 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsBarbuda's Pink Sand Beach at Dawn, Private & Empty +3 more
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Suite $6,300 pp
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9-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: low fare 6% under usual
Caribbean 9 nights Feb 10 – Feb 19, 2028
San Juan, Puerto Rico · Spanish Town · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Spanish Town · Anguilla, Caribbean · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Fort-de-France, Martinique · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsSandy Island by Private BoatPrivate Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +4 more
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Suite $3,800 pp
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Feb 11 – Feb 22, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths of Virgin GordaMt. Liamuiga Volcano Crater Hike +3 more
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Suite $6,300 pp
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Feb 22 – Mar 4, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths of Virgin GordaPrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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Suite $6,300 pp
Book This Cruise@ Cruisebound

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