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74 Results

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A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados From Montreal, Quebec

Montreal
Quebec City
Saguenay
Saguenay Fjord
Charlottetown
+19 more

Aboard

Azamara Journey

From

Montreal, Quebec

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

16-night Caribbean Voyage: New York, Bermuda & Barbados From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+8 more

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

9-night Bermuda & Caribbean Voyage: New York, Bermuda & St. Maarten From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$1,999

per person*

taxes & fees included

A golden-hour shot of a sandy beach in Portimão, Portugal, with the clear water of the Atlantic Ocean gently washing over the sand and the large, jagged limestone rock formations of the Algarve coast lit by the sun.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

38-night Athens to Miami Grand Voyage From Piraeus (Athens), Greece

Athens (Piraeus)
Olympia
Sarande
Siracusa
Catania
+21 more

Aboard

Azamara Quest

From

Piraeus (Athens), Greece

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+3 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

3 Sailings

Nov 7 - Dec 5, 2026

3 Sailings

Nov 7 - Dec 5, 2026

Published prices from

$1,099

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+9 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

7-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

2 Sailings

Nov 14 - Nov 28, 2026

2 Sailings

Nov 14 - Nov 28, 2026

Published prices from

$779

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

14-night Caribbean Voyage: San Juan, Antigua & Barbados From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+9 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$4,889

per person*

taxes & fees included

Anaga Mountains landscape, Tenerife.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

15-night Transatlantic Cruise: Lisbon to Miami From Lisbon, Portugal

Lisbon
Lanzarote
Santa Cruz de Tenerife
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
+2 more

Aboard

Azamara Quest

From

Lisbon, Portugal

1 Sailing

Nov 23, 2026

1 Sailing

Nov 23, 2026

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

21-night Transatlantic Cruise: Malta, Malaga & Miami From Piraeus (Athens), Greece

Athens (Piraeus)
Katakolon
Siracusa
Valletta
Trapani
+7 more

Aboard

Azamara Quest

From

Piraeus (Athens), Greece

1 Sailing

Nov 26, 2026

1 Sailing

Nov 26, 2026

Published prices from

$6,269

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Maarten From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

Published prices from

$4,859

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

13-night Transatlantic Cruise: Malaga, San Juan & Miami From Malaga, Spain

Malaga
Tangier
San Juan
Miami

Aboard

Azamara Quest

From

Malaga, Spain

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$1,709

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

13-night Caribbean Voyage: San Juan, Antigua & St. Lucia From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+8 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$8,229

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

10-night Eastern Caribbean Cruise: St. Thomas, Saint Kitts & Nevis From Miami, Florida

Miami
Key West
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
+2 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Dec 8, 2026

1 Sailing

Dec 8, 2026

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

6-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+2 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$1,559

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+11 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$5,779

per person*

taxes & fees included

Yellow kayak on sandy beach in Puerto Vallarta, Mexico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

18-night Panama Canal Voyage: Colombia, Costa Rica & Mexico From Miami, Florida

Miami
Cabo Rojo
Cartagena (Colombia)
Panama Canal
Puntarenas
+5 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$3,939

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

10-night Southern Caribbean Voyage: Antigua, St.Barts & Martinique From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
Gustavia
+6 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$1,979

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

18-night Caribbean Holiday Voyage: San Juan, St. Barts & Curacao From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
Gustavia
+11 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$5,879

per person*

taxes & fees included

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

8-night Caribbean Voyage: Curacao, Aruba & St.Lucia From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$2,189

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

17-night Caribbean New Year Voyage: Barbados, Aruba & St. Barts From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+10 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$5,419

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

9-night Southern Caribbean Voyage: St.Barts, Antigua & Tortola From San Juan, Puerto Rico

San Juan
Virgin Gorda
Gustavia
St. Maarten (Philipsburg)
St. John's
+4 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Jan 5, 2027

1 Sailing

Jan 5, 2027

Published prices from

$1,839

per person*

taxes & fees included

A high-angle view of the rugged, rocky coastline of St. John, US Virgin Islands, with the deep blue sea crashing against the cliffs and islands in the distance under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

34-night South America & Antarctica Voyage: Miami To Chile From Miami, Florida

Miami
St. John (U.S.V.I.)
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Charlestown
+18 more

Aboard

Azamara Journey

From

Miami, Florida

1 Sailing

Jan 14, 2027

1 Sailing

Jan 14, 2027

Published prices from

$9,699

per person*

taxes & fees included

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

11-night Eastern Caribbean Voyage: St.Kitts, Antigua & Martinique From Miami, Florida

Miami
St. John (U.S.V.I.)
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Charlestown
+6 more

Aboard

Azamara Journey

From

Miami, Florida

1 Sailing

Jan 14, 2027

1 Sailing

Jan 14, 2027

Published prices from

$4,309

per person*

taxes & fees included

    • Showing results 1 - 24 of 74

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.