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Choose from one of these hand-picked trips visiting the best beaches in Caribbean. Relax in the sun and sand, or enjoy Snorkeling, Small Ship Sailing, Village Visits, Local Market Visits, and Archaeological Site Visits as you explore Gustavia, Bridgetown, Soufriere, St. Kitts, and Norman Island. Contact one of our Caribbean beach vacation specialists to get started planning your escape in the sun. 
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Relax on the beaches of the Caribbean
from $7,990
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
  • Discover Anguilla’s coral coast
  • Explore Gustavia’s boutiques
  • Wander Nevis seaside buildings
  • Visit Antigua’s English Harbor
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbor’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
Cruise Details
0
Pink beach huts in the Caribbean
from $2,080
SS 25%
EXPLORE

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
0
Take a leisurely stroll through beautiful Bridgetown
from $11,990
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
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
0
Explore colorful Gustavia
from $11,290
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara
  • Explore Soufriere coral reefs
  • Visit Iles des Saintes towns
  • Discover Falmouth Harbor dockyard
  • Experience Charlestown’s Nevis
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Sakara, 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
0
Bright blue waters of the Caribbean
from $2,880
SS 25%
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
0
White Sand Beach in Barbados
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
0
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
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
0
Relax on the beaches of St. Maarten
from $2,010
SS 25%
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
0
Gustavia Harbor in St. Barths
from $1,970
EXPLORE

Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Sail Sir Francis Drake Channel
  • Stroll Norman Island's beach
  • Tour Basseterre's old plantations
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.
Cruise Details
0
Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
EXPLORE

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse
  • Explore Nassau’s vibrant capital
  • Visit Staniel Cay’s beaches
  • Discover San Salvador’s coral reefs
  • Stroll St. Barts iconic Shell Beach
Starts / Ends
Nassau / Bridgetown
Activities
Stand Up Paddle Boarding, Helicopter Tours
Activity Level
Variable
Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
Cruise Details
0
Experience laid-back Marigot
from $15,980
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
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
0
Boats Moored to the Quay at Bridgetown Harbour
from $15,980
EXPLORE

Discover the Pearls of the Caribbean

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Marigot / Bridgetown
Activities
Wildlife Viewing
Activity Level
Variable
Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.
Cruise Details
0
Explore the famous rock formations of the baths
from $21,780
EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Bridgetown / Marigot
Activities
Kayaking
Activity Level
Variable
Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.
Cruise Details
0
Visit beautiful Norman Island
from $9,990
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
0
Gustavia Harbor in St. Barths
from $9,990
EXPLORE

Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla’s coral coastlines
  • Visit Virgin Gorda granite boulders
  • Discover Norman Island's coves
  • Relax on Anegada’s remote sands
Starts / Ends
Marigot / Marigot
Activities
Hiking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
Cruise Details
0
Islands of the Caribbean
from $7,990
EXPLORE

Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbor
  • Wander through lively Cruz Bay
Starts / Ends
San Juan / St. Thomas
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.
Cruise Details
0
Caribbean landscapes and harbors
from $11,990
EXPLORE

Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover Iles des Saintes town
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
Cruise Details
0
Bright blue waters of the Caribbean
from $9,440
EXPLORE

Pearls of the Caribbean

Fort-de-France Roundtrip - 8 Day Itinerary aboard Le Bougainville
  • Wander at Fort-de-France Harbor
  • Discover Union Island Beaches
  • Snorkel at Tobago Cays Reefs
  • Swim Pompierre Beach Les Saintes
Starts / Ends
Fort de France / Fort de France
Activities
Archaeological Site Visits, Rainforest Exploration
Activity Level
Variable
Embark on an 8-day Caribbean cruise from Martinique through the Grenadines aboard Le Bougainville. Explore vibrant towns, secluded beaches, coral reefs, tropical islands, and volcanic landscapes. Snorkel, swim, stroll along scenic shores, and enjoy historic sites.
Cruise Details
0
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