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Caribbean Trips in 2022

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Relax in the sunny squares of historic Savannah
$5,599
EXPLORE

Boston, MA to Nassau, Bahamas

16 Day Itinerary aboard M/V Victory I
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts/ Ends in:
Boston / Nassau
Activities:
Archaeological Sites, Small Ship Cruise, Urban Exploration, Village Visit
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard M/V Victory I. With stops in Baltimore, Charleston, West Palm Beach, and more, this journey has been handcrafted to sample the Eastern cities of the United States as you head to your final destination …
Cruise Details
0
White Sand Beach in Barbados
$1,580
Savings
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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 in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
0
Bright blue waters of the Caribbean
$1,360
Savings
EXPLORE

Grenadine Islands

7 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Take in Grenada's unique aromas
  • Discover Tobago Cays
  • View Bequia's waterfront
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Snorkeling
Activity Level:
Relaxed
Experience tropical life with a refined twist on this incredible 7-day cruise aboard the tall ship Royal Clipper. Lush mountains, rain forests, volcanic crater lakes, mangroves, beautiful beaches, and delicate coral reefs are hallmarks of this coveted destination. Enjoy a wonderful journey of …
Cruise Details
0
Beautiful beach in Dominica
$1,520
Savings
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
Cruise Details
0
Pink beach huts in the Caribbean
$1,580
Savings
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore lush St. Lucia Island
  • Hike to Trafalgar Falls
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
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Tropical waterfall and turquoise pool in lush forest
$1,520
Savings
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
0
Pelicans hanging out in the ocean
$9,870
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
Cruise Details
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Cuba homes in Havana
$6,795
EXPLORE

Havana to Cienfuegos

11 Day Itinerary aboard Sea Cloud II
  • Stroll the Malecon in Havana
  • Snorkel and swim at Maria la Gorda
  • Explore beautiful Cienfuegos
  • Visit film sets in Jamaica
Starts/ Ends in:
Havana / Cienfuegos
Activities:
Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Experience the incomparable charm of Cuba's colonial heritage paired with Jamaica's relaxed and romantic beach flair onthis 11-day cruise from Havana to Cienfuegos aboard Sea Cloud II. Stroll down the famed Malecon promenade in Havana and soak in the distinctive spirit of the city. Snorkel …
Cruise Details
0
Iconic cars in Havana, Cuba
$6,985
EXPLORE

Havana to Santo Domingo

13 Day Itinerary aboard Sea Cloud II
  • Stroll down the Malecon
  • Snorkel and swim at Maria La Gorda
  • Visit banana farms in Jamaica
  • Marvel at historic Santo Domingo
  • Appreciate Cuban music culture
Starts/ Ends in:
Havana / Santo Domingo
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Warm hospitality, eventful history and lively musical tradition make Cuba and Jamaica two dream destinations in the Caribbean. As different as the two islands are –here, culture, beach and nature go perfectly hand in hand and fit under one hat. Board Sea Cloud II for this 13-day cruise from …
Cruise Details
0
Relax on the beaches of the Caribbean
$4,399
EXPLORE

San Juan to San Juan

via Cruz Bay - 8 Day Itinerary aboard SeaDream II
  • Stroll in the city of San Juan
  • Swim with dolpins at Sandy Ground
  • Relax at White Bay
  • Enjoy the canopy at Tortola Island
Starts/ Ends in:
San Juan / San Juan
Activities:
Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
The Caribbean is known for its opportunities to relax beside crystal blue waters and pristine sands, but there are also exciting activities to enjoy on this 8-day cruise. Embark on the SeaDream II inSan Juan, thelargest city and the capital of Puerto Rico, where you can see theCastillo de San …
Cruise Details
0
Play in the brilliant blue waters of the Caribbean
$3,899
EXPLORE

Charlotte Amalie, St. Thomas to San Juan

via Chrishi Beach Club, Nevis - 8 Day Itinerary aboard SeaDream II
  • Visit the beaches of St. Thomas
  • Explore Great Harbor
  • Dive along the coast of St. Barths
  • See the \"The Baths\" in Virgin Gor
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail the beautiful blue waters of the Virgin Islands on this 8-day Caribbean cruise from Charlotte Amelie to San Juan. Swim and snorkel in one of the most incredible landscapes in the world! Join optional excursions such as an exclusive horseback ride through Nevis Island, hike into the famous …
Cruise Details
0
Mountains by the ocean in St Lucia
$3,620
Save $600
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Dumont-d'Urville on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its …
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
$3,399
EXPLORE

La Romana to Marigot

8 Day Itinerary aboard SeaDream I
  • Visit Isla Saona's beaches
  • Discover marine diversity
  • Enjoy Caribbean's extensive art
  • Explore Caja de Muertos
Starts/ Ends in:
La Romana / Marigot
Activities:
Biking, Land & Sea, Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Set sail to nine of the most incredible and beautiful Caribbean ports from La Romana to Marigot.Embark on SeaDream I to access some of the more intimate, less-traveled ports. Jost Van Dyke, for example, in the British Virgin Islands serves as frequent home to the Signature Champagne & Caviar …
Cruise Details
0
Soak in the sun in colorful Marigot
$2,999
EXPLORE

Marigot to San Juan

via Charlestown, Nevis - 7 Day Itinerary aboard SeaDream II
  • Visit the city of Marigot
  • Enjoy Cades Bay & Nevis's shores
  • Discover Frigate Bay
  • Explore San Juan, Puerto Rico
Starts/ Ends in:
Marigot / San Juan
Activities:
Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Spa & Relaxing, Stand Up Paddle Board
Activity Level:
Relaxed
Explore the Caribbean and enjoy the opportunity to tee off, swim with dolphins, or bike around the islands on this exclusive voyage from Marigot to San Juan via Charlestown, Nevis. Walk along picture-perfect trails & beaches, snorkel among famous reefs, or swim in the clear blue waters as you …
Cruise Details
0
St Barts harbor view
$3,299
EXPLORE

Marigot to San Juan

8 Day Itinerary aboard SeaDream I
  • Visit the city of Marigot
  • Swim with dolphins at Sandy Ground
  • Snorkel at Jost van Dyke
  • Visit Sandy Ground's beaches
Starts/ Ends in:
Marigot / San Juan
Activities:
Biking, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Set sail to ten of the most incredible and beautiful Caribbean ports from Marigot to San Juan.Embark on SeaDream I to access some of the more intimate, less-traveled ports. Jost Van Dyke, for example, in the British Virgin Islands serves as a frequent home to the Signature Champagne & Caviar …
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
$3,299
EXPLORE

Bridgetown to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Admire Mayreau's beauty
  • Snorkel at Tobago Cays
  • Explore Bridgetown
  • Relax and enjoy luxurious amenities
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Feel the unique charm of the Caribbean Islands on this 8-day voyage. Delight yourself in European influence and the ideal weather of this region as you cruise round-trip out of Bridgetown, Barbados. Enjoy playing from the water sports marina as the ship anchors off on different ports. Visit …
Cruise Details
0
Bright blue waters of the Caribbean
$4,140
Savings
EXPLORE

Bridgetown to Fort Lauderdale

9 Day Itinerary aboard Silver Wind
  • See Conception Island's wildlife
  • Visit Devil’s Bay National Park
  • Marvel at Barbuda's frigatebirds
  • Dip in the hot springs of Roseau
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Experience the Caribbean as never before during this 9-day cruise from Bridgetown to Fort Lauderdale. Spend time relaxing on white sandy beaches and enjoying coral reefs and the warm, clear waters of islands such as Dominica, St. Vincent and Antigua. But the Caribbean is so much more: tiny, off the …
Cruise Details
0
Take the time to explore St. Lucia
$3,399
EXPLORE

Bridgetown Roundtrip

8 Day Itinerary aboard SeaDream I
  • Visit Union Island
  • Discover Mayreau
  • Swim and snorkel at Tobago Cays
  • Explore Bridgetown's beaches
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
The natural beauty of the Caribbean, with miles of beaches, private coves, and brilliant turquoise water is brought to life with the casual luxury of the SeaDream I. This 8-day Bridgetown roundtrip cruise is designed to highlight the Caribbean's colorful sightseeing, wonderful dining and …
Cruise Details
0
1-18 of 47 Results

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