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Dominican Republic Luxury Travel: A Sample Itinerary

Days 1 - 3

Your opening days in Santo Domingo immerse you in the Americas' first colonial city before ascending to the cool mountain retreat of Jarabacoa, where river valleys offer respite from Caribbean heat.

Day one begins in Santo Domingo's Colonial Zone, designated as the Americas' first UNESCO World Heritage site, where Christopher Columbus's son Diego established the first permanent European settlement in 1496. Walk cobblestone streets where merengue rhythms echo from colonial buildings that housed the first cathedral, university, and hospital in the New World. Experience street music traditions that blend Taíno, African, and Spanish influences while dining on Caribbean flavors.

Your second day explores the Alcázar de Colón, built between 1510-1514 as Diego Columbus's residence, and the Cathedral of Santa María la Menor, completed in 1540 as the Americas' first cathedral, before strolling the Malecón waterfront promenade. Day three brings escape to Jarabacoa, nestled in the Cordillera Central at 500 meters elevation, where Lebanese immigrants established mountain communities in the early 1900s, creating a cultural blend reflected in local cuisine and the cool climate that earned it the nickname "Caribbean Switzerland."

Days 4 - 7

Days four through eight explore from mountain adventures and cultural Santiago to the north coast's cable cars and wind-swept beaches of Cabarete.

Your fourth day in Jarabacoa offers waterfall hikes through cloud forests or optional whitewater rafting on rivers that flow from Pico Duarte, the Caribbean's highest peak at 3,087 meters, while paragliding provides views over valleys where coffee cultivation thrives in the tropical highland climate. Day five features a cultural stop in Santiago, the Dominican Republic's second city founded in 1495, visiting Centro León museum and experiencing the cigar industry that has made Dominican tobacco world-renowned since the 1960s.

Your sixth day brings travel to Puerto Plata, founded in 1502 by Christopher Columbus's brother Bartholomew, where the cable car ascends Mount Isabel de Torres for panoramic views before exploring the Fortress of San Felipe, built in 1577 to defend against pirates who frequently raided Spanish colonial ports. Day seven transitions to Cabarete, transformed from a small fishing village into a world-class windsurfing destination when consistent trade winds and perfect conditions attracted international competitions starting in the 1980s. The eighth day explores El Choco National Park's limestone caves and freshwater Laguna Dudú, formations created over millions of years in this karst landscape.

Days 8 - 12

Your final days shift to the pristine Samaná Peninsula, where humpback whale migrations and palm-lined beaches conclude your Dominican adventure.

Day nine brings travel to Las Terrenas on the Samaná Peninsula, originally settled by escaped slaves and later by European expatriates drawn to beaches consistently ranked among the Caribbean's finest. The peninsula remained relatively isolated until the 1990s, preserving pristine coastlines where coconut palms meet turquoise waters. Your tenth day offers beach exploration at Playa Bonita or Cosón, stretches of white sand backed by coconut groves that have remained largely undeveloped compared to other Caribbean destinations.

Day eleven features the dramatic El Limón waterfall, accessible by horseback through tropical rainforest, or seasonal whale watching opportunities when over 1,500 humpback whales migrate to Samaná Bay between January and March, making it one of the North Atlantic's most important breeding grounds. Your twelfth day provides return journey to Santo Domingo or Las Américas International Airport, perhaps with final reflections on an island that Columbus described as "the most beautiful land human eyes have ever seen" and that continues to blend its Taíno, African, and European heritage into a distinctly Dominican culture.

BEST TIME

TAILORED TRIPS

from £2500 pp, per night

Santo Domingo - Jarabacoa - Las Terrenas

Days 1 - 3

Santo Domingo & Beyond

Days 4 - 7

Waterfalls & Mountains

Days 8 - 12

Peninsula Exploration

Trip Highlights

Begin in Santo Domingo’s Colonial Zone, the first European city in the Americas, where cobblestone streets, 16th-century cathedrals, and Afro-Taíno-Spanish rhythms echo through UNESCO-listed landmarks.

Ascend to Jarabacoa’s mountain cool, where cloud forest hikes, whitewater rafting, and paragliding showcase the highland beauty shaped by Caribbean peaks and Lebanese-Dominican culture.

Visit Santiago’s cultural core, exploring Dominican cigar heritage and museums before heading to Puerto Plata’s colonial fortress and the cable car ascent of Mount Isabel de Torres.

Unwind on Cabarete’s breezy shores, a windsurfing hub backed by limestone caves, freshwater lagoons, and national parks that reveal the island’s ancient karst landscape.

Conclude in Samaná’s untouched paradise, where palm-lined beaches, El Limón waterfall, and seasonal humpback whale migrations offer a serene and spectacular finale.

Day 1

Santo Domingo's Colonial Zone preserves the Americas' first European settlement, where Christopher Columbus's son established institutions that shaped New World civilization.

Your first day explores the Zona Colonial, designated UNESCO World Heritage site in 1990, where Spanish colonists built the Americas' first cathedral, university, and hospital beginning in 1496. These cobblestone streets witness over 500 years of Caribbean history, from Taíno indigenous cultures through Spanish colonization, Haitian occupation, and modern Dominican independence achieved in 1844.

Days 2 - 4

Days two through four transition from colonial architecture to Caribbean paradise, exploring Columbus family legacy and pristine beaches that define Dominican tourism.

Day two visits Alcázar de Colón, the palace built in 1514 for Diego Columbus, Christopher Columbus's son who served as the island's second governor, showcasing Renaissance architecture adapted to tropical Caribbean climate. Parque Colón provides shaded respite where locals gather as they have for centuries in this central plaza. Your third day travels to Punta Cana's white sand beaches along the Caribbean coast, where 32-kilometer stretches of coral sand and palm groves create the postcard-perfect tropical paradise that attracts over 6 million visitors annually to the Dominican Republic. Day four explores Saona Island, part of Del Este National Park, where pristine beaches and coral reefs support marine ecosystems largely unchanged since Columbus first landed in Hispaniola in 1492.

Days 5 - 6

Your final days venture into the Dominican Republic's mountainous interior and northeastern coast, showcasing natural wonders beyond the famous resort beaches.

Day five hikes to El Limón Waterfall in the Samaná Peninsula, where 40-meter cascades tumble through tropical rainforest that supports endemic bird species found nowhere else in the Caribbean. Your sixth day concludes in Las Terrenas, a former fishing village transformed into a cosmopolitan beach town where French and Italian expatriates have created a unique cultural blend while preserving Dominican coastal traditions and pristine Atlantic beaches.

BEST TIME

TAILORED TRIPS

from £2500 pp, per night

Discover Santo Domingo

Day 1

America's First Town

Days 2 - 4

Palaces, Beaches & Islands

Days 5 - 6

Views From The Top

Trip Highlights

Wander Santo Domingo’s Colonial Zone, where the first cathedral, university, and hospital of the Americas stand amid cobblestone streets echoing five centuries of Caribbean history.

Visit Alcázar de Colón, the Renaissance-style palace of Christopher Columbus’s son, and relax in Parque Colón, where centuries of Dominican life converge in shaded plazas.

Bask on Punta Cana’s iconic white-sand beaches, stretching 32 kilometers along the Caribbean coast and drawing millions to the Dominican Republic’s resort capital.

Explore Saona Island’s untouched shores and coral reefs within Del Este National Park, where marine ecosystems remain as pristine as when Columbus arrived in 1492.

Hike to El Limón Waterfall in Samaná’s rainforest, then unwind in Las Terrenas, a coastal haven blending Dominican traditions with European flair along the Atlantic coast.

Best Luxury Hotels in the Dominican Republic: Conte's Picks for 2025

Eden Roc Cap Cana Resort

Cap Cana, Dominican Republic

Eden Roc Cap Cana is a luxurious beachfront resort set in the exclusive Cap Cana area of the Dominican Republic. With Mediterranean-inspired architecture and lush tropical surroundings, this stunning resort offers guests spacious suites, private villas, and unparalleled comfort.

Known for its world-class dining options, the resort also features a tranquil spa, pristine beaches, and a host of outdoor activities including golfing, water sports, and whale watching. Whether seeking a peaceful escape or an adventure-filled getaway, Eden Roc Cap Cana delivers a luxurious and unforgettable experience in one of the Caribbean’s most exclusive locations.

A tropical resort atrium with palm trees, lush greenery, and bamboo accents, surrounded by a serene pool under bright sunlight.

A serene, lit wooden platform in a cave, surrounded by lush greenery and a cascading waterfall, creating a magical atmosphere.

Lush tropical paradise featuring a sparkling pool, palm trees, lounge chairs, and a view of the beach under a bright blue sky.

Luxurious bedroom with a four-poster bed, pastel decor, seating area, and mirrored wardrobe, featuring soft lighting and lush greenery outside.

The St. Regis Cap Cana Resort

Punta Cana, Dominican Republic

The St. Regis Cap Cana Resort is an exquisite getaway located along the pristine shores of the Dominican Republic’s famed coastline. This five-star resort offers an unmatched level of sophistication and luxury, with spacious suites and private villas that exude comfort and elegance.

Guests can enjoy fine dining, relax at the lavish spa, or take part in activities such as golf, water sports, and more. With its lush tropical setting, impeccable service, and personalized experiences, The St. Regis Punta Cana is an idyllic destination for those seeking luxury and tranquility in a Caribbean paradise.

Modern bedroom featuring a plush headboard, stylish bedside table with a marble top, and a chic pendant light overhead.

Elegant dining area with modern decor, featuring plush seating, hanging lights, and lush greenery, creating a warm, inviting atmosphere.

Elegant restaurant with ocean views, featuring dark wood furniture, blue chairs, and lush plants, illuminated by a sunset sky.

Aerial view of a luxurious resort featuring multiple pools, green lawns, and palm trees, surrounded by tranquil water.

Amenera

Playa Grande, Dominican Republic

Amanera is an exclusive luxury resort located in the Dominican Republic, nestled along the serene coast of the Caribbean. This stunning beachfront property offers a perfect balance of nature and refined elegance. With its minimalist design, spacious villas, and private pools, guests experience the ultimate in relaxation and privacy.

Surrounded by lush forests and golden beaches, Amanera invites guests to indulge in world-class dining, rejuvenate at the spa, or explore the vibrant marine life through water activities. Amanera offers a perfect blend of tranquility, adventure, and luxury, making it an exceptional escape in the Dominican Republic.

A serene beach view featuring a palm tree and two lounge chairs with umbrellas overlooking the turquoise sea and sandy shore.

A modern seaside mansion surrounded by lush palm trees on a cliff, overlooking a tranquil beach and ocean in soft sunset hues.

Elegant dining area with a table set for two, framed by large windows showcasing a serene ocean view. Cozy and inviting atmosphere.

Modern villa exterior with a sleek pool, surrounded by lush greenery and featuring a stylish lounge area under a shaded patio.