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Our Greater Antilles Trips & Vacation Packages

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Discover the vibrant and diverse Greater Antilles with our 16 unique trips for 2027. Join us on one of these top-rated vacation packages, carefully curated to showcase the rich cultural tapestry and stunning landscapes of this Caribbean region. From the historic streets of Havana to the lush jungles of the Dominican Republic, each adventure offers a mix of cultural immersion, wildlife viewing, and beach relaxation. Engage in local market visits, archaeological site explorations, and snorkeling excursions, all while surrounded by the natural beauty that defines the Greater Antilles. Whether you're interested in food & wine experiences, urban exploration, or active adventures like hiking and kayaking, there's something for every type of traveler on these trips. With trips ranging from in length, there's no better time to start planning your next Caribbean getaway. Contact one of our Caribbean specialists for help planning your next seamless trip.
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    • Greater Antilles
Nassau Lighthouse
from $7,590
EXPLORE

Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara
  • Explore the pristine beaches
  • Snorkel in crystal-clear waters
  • Relax on secluded Gordon’s Beach
  • Explore Grand Turk’s beaches
Starts / Ends
San Juan / Miami
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.
Cruise Details
0
Stroll along the beaches of Puerto Rico
from $9,295
EXPLORE

Paradise Beaches from the U.S. Virgin Islands to The Bahamas

San Juan - Miami - 10 Day Itinerary aboard Emerald Kaia
  • Tour Grand Turk lighthouse
  • Wander Gordon's Beach
  • Walk Nassau bustling Straw Market
  • Dive San Salvador Island
Starts / Ends
San Juan / Miami
Activities
Local Market Visits
Activity Level
Variable
Set sail on a 10-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring the beautiful Turks and Caicos Islands and vibrant marine life in The Bahamas. Enjoy fresh local seafood and conclude your journey in the lively metropolis of Miami, blending cultural discovery with natural beauty.
Cruise Details
0
Panoramic views on the climb to Pico Duarte
from $2,299
EXPLORE

Mountain Adventure in the Caribbean Highlands

Self Drive Tour - 8 Day Itinerary
  • Trek to the Pico Duarte summit
  • Hike to towering waterfalls
  • Explore the historic Zona Colonial
  • Rappel down into lush canyons
  • Drive steep mountain roads
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Ziplining, Camping
Activity Level
Challenging
Pick up your 4x4 and set off into the Dominican Republic's central mountains for an active 8-day adventure. You drive over high mountain passes, explore coffee plantations, and rappel down canyons. The trip culminates in a challenging 2-day trek to the summit of Pico Duarte, the highest peak in the Caribbean.
Tour 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
Horse-drawn carriage passes Santiago's Monument to the Heroes of the Revolution
from $3,932
EXPLORE

Dominican Republic: Nature, Culture & History

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Mountain plantation tour
  • Cayo Arena snorkeling
  • Discover Los Haitises caves
  • Relax on Cayo Levantando beach
Starts / Ends
Santo Domingo / Santo Domingo
Activity Level
Relaxed
This 8-day tour crosses the Dominican Republic, blending historic city exploration with lush mountain landscapes and pristine coastline. Wander the colonial streets of Santo Domingo, visit thriving highland plantations, and snorkel the coral reefs of Cayo Arena. Uncover local history and relax on white sand beaches along the way.
Tour Details
0
Socoa Falls and natural pool
from $3,013
EXPLORE

Exotic Samaná Peninsula

Self Drive Tour - 15 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Swim Salto Socoa waterfall
  • Secluded eco-lodge stay
  • Los Haitises boat tour
  • Cayo Levantado beaches
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Wilderness Lodge Exploration
Activity Level
Relaxed
Experience a 15-day exploration of the Dominican Republic, from the historic streets of Santo Domingo to the remote shores of the Samaná Peninsula. Wander the oldest colonial city in the Americas before driving north to discover secluded beaches, vibrant marine life, and lush national parks. Retreat to eco-lodges and pristine coastal villages.
Tour Details
0
Learn about Spanish colonial history in Old San Juan
from $6,845
EXPLORE

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Kaia
  • Visit Culebra Flamenco Beach
  • Tour St. John Mongoose Junction
  • Discover Cruz Bay bustling bay
  • Walk Philipsburg street markets
Starts / Ends
San Juan / St. John's
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring Vieques, Cruz Bay, and Jost Van Dyke's stunning beaches. Visit Gustavia in Saint Barthelemy, experiencing its unique French culture before concluding the journey in St. John's, Antigua.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $5,000
EXPLORE

San Juan to San Juan

San Juan Roundtrip - 8 Day Itinerary aboard Silver Dawn
  • Snorkel Trunk Bay reefs in St John
  • Witness Gustavia harbor views
  • Ride horses along Antigua beaches
  • Enjoy swimming at Jost Van Dyke
Starts / Ends
San Juan / San Juan
Activities
Wildlife Viewing, Kayaking, Rainforest Exploration
Activity Level
Variable
Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.
Cruise Details
0
Rocky banks and flowing waters of the Jimenoa River
from $7,134
EXPLORE

Dominican Republic Explorer in Depth

15 Day Itinerary
  • Cayo Arena snorkeling
  • Santo Domingo city tour
  • Explore Los Haitises National Park
  • Relax at Las Galeras beaches
  • Choose your adventure in Jarabacoa
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Snorkeling, Village Visits
Activity Level
Relaxed
Travel with a private driver-guide across the Dominican Republic for 15 days of nature, history, and coastal relaxation. Explore the colonial center of Santo Domingo before heading inland to the mountains of Jarabacoa. Discover hidden beaches, snorkel vibrant coral reefs, and rest each night in comfortable eco-lodges and boutique hotels.
Tour Details
0
Tropical Dominican Republic beach with palm trees
from $2,660
EXPLORE

Dominican Republic North Coast Beaches

Self Drive Tour - 15 Day Itinerary
  • Cayo Arena snorkeling
  • Santo Domingo history tour
  • 27 Waterfalls canyoning
  • Cabarete beach kayaking and surfing
  • Samana Peninsula beaches
Starts / Ends
Santo Domingo / Santo Domingo
Activity Level
Easy Active
Spend 15 days driving the Dominican Republic's north coast, from the colonial streets of Santo Domingo to the fishing village of Punta Rucia, the surfer town of Cabarete, and the beaches of Las Terrenas on the Samana Peninsula. This self-drive tour combines a guided city tour, snorkeling, and open coastal roads with free time at each stop.
Tour Details
0
Ziplining through the mountains
from $3,564
EXPLORE

Dominican Republic Active Island Experience

Self Drive Tour - 15 Day Itinerary
  • Tour the historical Colonial Zone
  • Drive through the mountainous
  • Hike to a towering waterfall
  • Choose your adventure
  • Hike to seven secluded beaches and
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Archaeological Site Visits, Biking, Hiking
Activity Level
Moderate
This 15-day self-drive tour crosses the Dominican Republic from Santo Domingo's Colonial Zone to the cool highlands of Jarabacoa, the surf town of Cabarete, and the beaches of the Samaná Peninsula. Along the way, you raft rivers, hike to waterfalls, bike through history, and explore secluded coves reachable only by boat.
Tour Details
0
Relax on the sunny beaches of the Bahamas
from $24,990
EXPLORE

Sounds of Discovery: New York to the Bahamas

New York - Nassau - 13 Day Itinerary aboard Scenic Eclipse
  • Explore Buenos Aires’ districts
  • Admire Ushuaia’s landscapes
  • Navigate Beagle Channel
  • Witness Antarctic wildlife
Starts / Ends
New York City / Nassau
Activities
Whale Watching
Activity Level
Variable
Experience a 13-day cruise from New York City to Nassau aboard the Scenic Eclipse, featuring stops in Bermuda, Turks and Caicos, San Salvador, Bimini, and Miami. This journey blends culture, history, and relaxation.
Cruise Details
0
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The looming fort walls of San Juan
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