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Experience the stunning shades of blue as you sail through the Caribbean

Guadeloupe Beach Trips

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Embark on an incredible journey to the breathtaking beaches of the Caribbean's Virgin Islands with one of these 12 hand-picked beach vacations and tours offered in 2025 and 2026. Relax on secluded islands, explore lively villages, or take a stroll along picturesque coastlines - the possibilities are limitless. Enjoy discovering the unique beauty of each destination, such as Guadeloupe's stunning mountain views and lush tropical rainforest. So why wait? Contact one of our Caribbean beach vacation specialists today and start planning your dream escape to paradise!
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    • Guadeloupe
Explore colorful Gustavia
from $7,990
2for1
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
St Barts harbor view
from $7,990
2for1
EXPLORE

Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Starts / Ends
St. John's / San Juan
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
Cruise Details
0
Enjoy the beautiful blue Caribbean
from $8,050
EXPLORE

Grenada to Antigua

St. George - St. John - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s harbor
  • Experience Charlotteville coast
  • Relax at Englishman’s Bay
  • Wander through Admiralty Bay
Starts / Ends
St. Georges / St. John's
Activities
Village Visits
Activity Level
Variable
Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
from $8,390
2for1
EXPLORE

Caribbean Yachting Discovery

St John - St Thomas - 8 Day Itinerary aboard Emerald Azzurra
  • Visit Barbuda's pink-sand beaches
  • Explore Norman Island hidden caves
  • Sail luxury yacht through Caribbean
  • Relax on Virgin Gorda beaches
Starts / Ends
St. John's / St. Thomas
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop.
Cruise Details
0
Explore the famous rock formations of the baths
from $7,990
2for1
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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
Soufriere bay, St Lucia
from $5,520
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Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Bellot
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts / Ends
Fort de France / Fort de France
Activities
Scuba Diving
Activity Level
Variable
Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
Cruise Details
0
Relax on the shores of the Caribbean
from $6,800
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot
  • Visit UNESCO World Heritage sites
  • Visit Portsmouth, Dominica
  • Explore Les Saintes, Guadeloupe
  • See Mayreau's fishes and corals
Starts / Ends
Les Saintes / Bridgetown
Activity Level
Variable
From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.
Cruise Details
0
Pink beach huts in the Caribbean
from $2,020
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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
The vivid colors of the San Blas Islands
from $4,350
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Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Starts / Ends
Balboa / St. John's
Activity Level
Variable
Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $11,600
EXPLORE

Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit
  • Explore top Caribbean islands
  • Visit Bequia and Iles des Saintes
  • Explore Gustavia’s historic harbor
  • Experience the Caribbean culture
Starts / Ends
Bridgetown / Bridgetown
Activities
Wildlife Viewing, Local Market Visits, Archaeological Site Visits, Small Ship Sailing, Spa Relaxation
Activity Level
Variable
Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.
Cruise Details
0
Dock going out into the crystal blue ocean
from $2,020
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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
Enjoy the natural beauty of the Caribbean
from $5,270
EXPLORE

Caribbean Flair Away from the Everyday

9 Day Itinerary aboard Sea Cloud Spirit
  • Fort Napoleon island lookout
  • Hike Tet Paul, St. Lucia springs
  • Snorkel Tobago Cays reefs
  • Dominica hikes and river tours
Starts / Ends
Philipsburg / Philipsburg
Activities
Snorkeling, Hiking, Stand Up Paddle Boarding
Activity Level
Variable
Sail roundtrip from St. Maarten on a 9-day Sea Cloud Spirit cruise through the Lesser Antilles. Visit Îles des Saintes, St. Lucia, Union Island, Bequia, and Dominica. Highlights include volcanic hikes, rainforest tours, snorkeling in Tobago Cays, and tall ship sailing days with sunset views and sea air.
Cruise Details
0
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