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Showing 36 of 70 sailings

Norwegian · Norwegian BreakawayRepositioning

Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana

Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports

Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana

★ Bucket-list Private Luxury Boston Tour Private Catamaran Sail & Snorkel at Honeymoon Beac…Gros Piton Summit Hike Grenada Private Taxi Tour +4 more

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from $970

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,300

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,131

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Gros Piton Summit Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,084

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,094

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $2,519

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Jan 10 – Jan 17, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Random Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,146

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Royal Caribbean · Odyssey of the SeasRound-trip

Caribbean 11 nights Jan 14 – Jan 25, 2027 from Cape Liberty (Bayonne), New Jersey

Cape Liberty (Bayonne), New Jersey · Philipsburg, St. Maarten · … · Cape Liberty (Bayonne), New Jersey6 ports

Cape Liberty (Bayonne), New Jersey · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Cape Liberty (Bayonne), New Jersey

★ Bucket-list Statue of Liberty & Ellis Island Random Wind 'Paradise Day Sail'Cosol Tours Swim with wild green sea turtles + two shipwrecks… +1 more

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from $1,242

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Jan 24 – Jan 31, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,153

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Royal Caribbean · Odyssey of the SeasRound-trip

Caribbean 12 nights Jan 25 – Feb 6, 2027 from Cape Liberty (Bayonne), New Jersey

Cape Liberty (Bayonne), New Jersey · Labadee (Labadie), Haiti · … · Cape Liberty (Bayonne), New Jersey8 ports

Cape Liberty (Bayonne), New Jersey · Labadee (Labadie), Haiti · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Philipsburg, St. Maarten · Cape Liberty (Bayonne), New Jersey

★ Bucket-list Statue of Liberty & Ellis Island The full 27 jumps at the Damajagua Waterfalls Private Full-Day Boat Charter Private Half-Day Island Adventure & Trunk Bay Beach +2 more

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from $1,427

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Feb 7 – Feb 14, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,205

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Feb 21 – Feb 28, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,439

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Royal Caribbean · Rhapsody of the SeasOne-way

Caribbean 10 nights Mar 6 – Mar 16, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida9 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Random Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +5 more

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from $729

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Norwegian · Norwegian BreakawayRepositioning

Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts

New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports

New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts

★ Bucket-list Steamboat Natchez Stingray City Sandbar Aruba Private Full-Day Curaçao Island Tour with Local Ex… +5 more

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from $1,726

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Royal Caribbean · Vision of the SeasOne-way

Caribbean 10 nights Apr 4 – Apr 14, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +5 more

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from $792

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Royal Caribbean · Grandeur of the SeasOne-way

Caribbean 7 nights Apr 24 – May 1, 2027 from Colon, Panama to San Juan, Puerto Rico

Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico6 ports

Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Panama Canal Full Transit La Soufrière Volcano Summit Hike Cosol Tours Private Half-Day Island Adventure & Trunk Bay Beach +2 more

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from $539

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights May 1 – May 8, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $728

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights May 15 – May 22, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $750

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights May 29 – Jun 5, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $771

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Jun 12 – Jun 19, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $624

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Jun 26 – Jul 3, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $806

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Jul 10 – Jul 17, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $882

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Jul 24 – Jul 31, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $913

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Aug 7 – Aug 14, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $709

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Aug 21 – Aug 28, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $639

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Sep 4 – Sep 11, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $610

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Sep 18 – Sep 25, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $605

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Oct 2 – Oct 9, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $844

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Oct 16 – Oct 23, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $873

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Oct 30 – Nov 6, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $850

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Royal Caribbean · Adventure of the SeasRound-trip

Caribbean Nov 3, 2027 from Port Canaveral, Florida

Port Canaveral, Florida · Perfect Day at CocoCay · … · Port Canaveral, Florida6 ports

Port Canaveral, Florida · Perfect Day at CocoCay · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida

★ Bucket-list Kennedy Space Center Visitor Complex Daredevil's Peak Private Half-Day Island Adventure & Trunk Bay Beach Cosol Tours +1 more

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from $1,011

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Nov 13 – Nov 20, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Tortola, B.V.I. · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Jost Van Dyke Gros Piton Summit Hike Swim with wild green sea turtles + two shipwrecks… +3 more

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from $973

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Royal Caribbean · Grandeur of the SeasRound-trip

Caribbean 7 nights Nov 13 – Nov 20, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Full-Day Boat Charter Buck Island Reef Random Wind 'Paradise Day Sail' +2 more

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from $871

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Norwegian · Norwegian VivaRound-trip

Caribbean 7 nights Nov 14 – Nov 21, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Gros Piton Summit Hike Private Full-Day Curaçao Island Tour with Local Ex… +1 more

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from $1,219

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Norwegian · Norwegian VivaRound-trip

Caribbean 7 nights Nov 21 – Nov 28, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Bridgetown, Barbados · St. Lucia, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Aruba Swim with wild green sea turtles + two shipwrecks…Gros Piton Summit Hike +1 more

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from $1,369

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Norwegian · Norwegian PearlRound-trip

Caribbean 11 nights Nov 27 – Dec 8, 2027 from Philadelphia, Pennsylvania

Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania7 ports

Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · Philadelphia, Pennsylvania

★ Bucket-list The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Private Half-Day Island Adventure & Trunk Bay Beach Gros Piton Summit Hike +1 more

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from $927

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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.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara