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Showing 36 of 82 sailings

Oceania · Oceania VistaRepositioning

Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida

New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports

New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida

★ Bucket-list Manhattan Helicopter Tour Private Full-Day Boat Charter Jost Van Dyke Private Half-Day Island Adventure & Trunk Bay Beach +6 more

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from $3,412

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Nov 9 – Nov 21, 2026 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $1,127

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Oceania · Oceania VistaRound-trip

Caribbean 14 nights Nov 11 – Nov 25, 2026 from Miami, Florida

Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida10 ports

Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City Sandbar Blue Hole & Secret Falls Aruba +5 more

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from $3,605

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Norwegian · Norwegian PrimaRound-trip

Caribbean 7 nights Nov 15 – Nov 22, 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. · St. John's, Antigua · 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 Private Half-Day Island Adventure & Trunk Bay Beach Swim with wild green sea turtles + two shipwrecks… +3 more

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from $1,423

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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 GemRound-trip

Caribbean 12 nights Nov 28 – Dec 10, 2026 from Tampa, Florida

Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida9 ports

Tampa, Florida · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida

★ Bucket-list Clearwater Beach Private Luxury Charter Walk El Morro & Old San Juan's City Walls Jost Van Dyke Mt. Liamuiga Volcano Crater Hike +4 more

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from $941

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Nov 29 – Dec 11, 2026 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $945

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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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Oceania · Oceania MarinaRound-trip

Caribbean 12 nights Dec 10 – Dec 22, 2026 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · St. John's, Antigua · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Private Half-Day Island Adventure & Trunk Bay Beach Mount Pelée & Saint-Pierre +3 more

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from $2,697

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Dec 11 – Dec 23, 2026 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $887

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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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Oceania · Oceania AlluraRound-trip

Mexico 17 nights Dec 21 – Jan 7, 2027 from Miami, Florida

Miami, Florida · Costa Maya, Mexico · … · Miami, Florida12 ports

Miami, Florida · Costa Maya, Mexico · Roatan, Honduras · Harvest Caye, Belize · Cozumel, Mexico · Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Chacchoben Mayan Ruins Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Lamanai Mayan Ruins +5 more

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from $10,049

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Oceania · Oceania MarinaRound-trip

Caribbean 14 nights Dec 22 – Jan 5, 2027 from Miami, Florida

Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida10 ports

Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City Sandbar Martha Brae River Bamboo Rafting Aruba +5 more

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from $3,915

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Dec 23 – Jan 4, 2027 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $1,860

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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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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Dec 28 – Jan 7, 2027 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +1 more

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from $6,649

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Jan 4 – Jan 16, 2027 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $1,157

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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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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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Oceania · Oceania AlluraRound-trip

Caribbean 9 nights Jan 27 – Feb 5, 2027 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida6 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +1 more

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from $4,349

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Feb 1 – Feb 13, 2027 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac… +3 more

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from $1,305

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Oceania · Oceania MarinaRound-trip

Caribbean 12 nights Feb 1 – Feb 13, 2027 from Miami, Florida

Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida9 ports

Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Aruba Private Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +3 more

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from $3,899

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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 14 – Feb 21, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Tortola, B.V.I. · 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 Swim with wild green sea turtles + two shipwrecks…Mt. Liamuiga Volcano Crater Hike +2 more

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from $1,092

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Oceania · Oceania AlluraOne-way

Caribbean 8 nights Feb 19 – Feb 27, 2027 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports

San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike Private Half-Day Island Adventure & Trunk Bay Beach +2 more

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from $2,970

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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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Oceania · Oceania MarinaRound-trip

Caribbean 10 nights Feb 23 – Mar 5, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Random Wind 'Paradise Day Sail' +3 more

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from $2,760

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Mar 1 – Mar 13, 2027 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $1,379

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Mar 11 – Mar 21, 2027 from Miami, Florida

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports

Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat Charter Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +1 more

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from $3,899

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Norwegian · Norwegian PrimaRound-trip

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

San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · 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… +2 more

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from $1,264

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Oceania · Oceania AlluraRound-trip

Caribbean 10 nights Mar 21 – Mar 31, 2027 from Miami, Florida

Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Miami, Florida7 ports

Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Mt. Liamuiga Volcano Crater Hike Random Wind 'Paradise Day Sail'Private Full-Day Boat Charter +1 more

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from $3,735

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Oceania · Oceania SirenaRepositioning

Caribbean 27 nights Oct 25 – Nov 21, 2027 from Montreal, Quebec to Miami, Florida

Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida21 ports

Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Suez Canal, Egypt · Miami, Florida

★ Bucket-list Old Québec Private Walking Tour with Expert Local…Mingan Archipelago BridgeClimb Sydney Peggy's Cove & Lunenburg +10 more

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from $8,749

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Norwegian · Norwegian PrimaOne-way

Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico

New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports

New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Manhattan Helicopter Tour Private Island Wrap-Around Van Tour of Bermuda Jost Van Dyke Mt. Liamuiga Volcano Crater Hike +5 more

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from $1,554

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Oceania · Oceania SirenaRepositioning

Caribbean 15 nights Nov 6 – Nov 21, 2027 from New York, New York to Miami, Florida

New York, New York · Tortola, B.V.I. · … · Miami, Florida10 ports

New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida

★ Bucket-list Manhattan Helicopter Tour Jost Van Dyke Private Half-Day Island Adventure & Trunk Bay Beach Mt. Liamuiga Volcano Crater Hike +5 more

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from $4,199

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Norwegian · Norwegian BlissRound-trip

Caribbean 12 nights Nov 8 – Nov 20, 2027 from New York, New York

New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports

New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York

★ Bucket-list Manhattan Helicopter Tour The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike +3 more

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from $1,140

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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