Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper

Explore beaches in Barbados
See lush island of St. Lucia
Discover Falmouth Harbour, Antigua
Visit sophisticated Martinique

Starts / Ends: Bridgetown / Bridgetown
Activity Level: Variable

Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.

Cruise Details

Take a leisurely stroll through beautiful Bridgetown

from $11,990

Save $150

EXPLORE

Grenadines & Windwards Yachting

Roundtrip Bridgetown - 8 Day Itinerary aboard Emerald Sakara

Discover Bequia’s secluded beaches
Savor Caribbean dining experiences
Snorkel Tobago Cays' waters
Admire panoramic views from Mayreau

Starts / Ends: Bridgetown / Bridgetown
Activities: Kayaking
Activity Level: Variable

Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.

Cruise Details

Relax on the sunny beaches of the Caribbean

from $9,990

Save $150

EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

Soak in Soufriere’s volcanic spring
Explore Les Saintes’ French charm
Visit Antigua’s Nelson’s Dockyard
Stroll Nevis’ Georgian towns

Starts / Ends: Bridgetown / Marigot
Activities: Hiking
Activity Level: Variable

Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.

Cruise Details

from $9,990

Save $150

EXPLORE

Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

Explore Saint John's pristine beach
Stroll Philipsburg's lively markets
Snorkel Norman Island's caves
Visit 'The Baths' in Virgin Gorda

Starts / Ends: St. Thomas / St. Thomas
Activity Level: Variable

Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.

Cruise Details

Learn about the history of the Caribbean

from $9,990

Save $150

EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

Explore Prickly Pear Cays waters
Admire Nevis’ Georgian buildings
Visit Soufriere’s volcanic springs
Wander Bridgetown’s streets

Starts / Ends: Marigot / Bridgetown
Activity Level: Variable

Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.

Cruise Details

from $6,395

Save $150

EXPLORE

Cruising the Leeward Islands

Roundtrip Sint Maarten - 8 Day Itinerary aboard Emerald Sakara

Visit Basseterre colonial structure
Discover Anguilla marine life
Swim in pools at Virgin Gorda
Experience Gustavia Creole cuisine

Starts / Ends: Philipsburg / Philipsburg
Activity Level: Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.

Cruise Details

Explore the famous rock formations of the baths

from $6,295

Save $150

EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Philipsburg - 8 Day Itinerary aboard Emerald Sakara

Explore Bridgetown rich heritage
Enjoy Soufriere sulfur springs
See St. John's Nelson's Dockyard
Experience Gustavia Creole cuisine

Starts / Ends: Bridgetown / Philipsburg
Activity Level: Variable

Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.

Cruise Details

from $2,880

EXPLORE

Aruba to Grenada

Oranjestad - St. George - 11 Day Itinerary aboard Star Clipper

Visit Oranjestad to see beaches
See Willemstad gabled houses
Tour Curacao inland cunucu
Swim Charlestown Bay

Starts / Ends: Oranjestad / St. Georges
Activities: Snorkeling, Small Ship Sailing, Village Visits, Local Market Visits
Activity Level: Variable

Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.

Cruise Details

from $2,080

SS 25%

EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper

Visit one island in Grenadines
Smell the aroma of Grenada
Walk and swim at Marigot Bay
Taste the spicy Creole cooking

Starts / Ends: Bridgetown / Bridgetown
Activity Level: Variable

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Cruise Details

Dock going out into the crystal blue ocean

from $2,080

EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

Explore Antigua’s vibrant dockyards
Discover Les Saintes’ beaches
Relax on Martinique’s white sands
Stroll Grenada’s aromatic markets

Starts / Ends: St. John's / Bridgetown
Activities: Wildlife Viewing
Activity Level: Variable

Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.

Cruise Details

from $2,010

EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

Explore Nevis sugar plantations
Visit Dominica boiling lakes
Snorkel Terre-de-Haut blue waters
Swim South Friars Bay clear waters

Starts / Ends: Philipsburg / Philipsburg
Activity Level: Variable

Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.

Cruise Details

from $15,980

Save $150

EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra

Explore Anguilla, serene landscapes
Savor Barbados’s cultural delights
Visit Antigua’s historic dockyard
Stroll Nevis’s serene beaches

Starts / Ends: Marigot / Bridgetown
Activities: Archaeological Site Visits
Activity Level: Variable

Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.

Cruise Details

Why Travel With Us?

Rewards That Go Further

Secure your 5% Past Traveler Rewards across a wide range of ships and destinations - not a single brand and not just cruises.

More Value.

Receive personal attention and concierge-level service for the same cost as booking direct. Gain access to exclusive rates, perks, and insider expertise on how to maximize the value for your dollar.