By Jordan Harvey
Updated: July 17, 2019
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Jordan Harvey is a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. He is the co-founder of Knowmad Adventures, which, after being founded in Patagonia, operates exclusively in South America and specializes in high-quality, custom adventures. Below is an example of the type of itineraries he creates. To work with Jordan, you can contact him directly at jordan@knowmadadventures.com.

Day 1: Santiago

Upon arrival you’ll be taken into the capital to enjoy a half-day guided exploration of the city and to rest up. Your private Knowmad guide will highlight Santiago’s most important historical sites, including the downtown area surrounding the Plaza de Armas and the La Moneda Presidential Palace. Pass by the Mercado Central, one of Chile’s largest fresh seafood markets, and stroll by the many bustling stalls to see the tremendous variety available from Chile’s bountiful sea. You’ll also visit some of the lesser-known barrios of Santiago including Republica and Concha y Toro, which were historically privileged neighborhoods and home to Santiago’s high society. There will be time to walk around and take photos of the varied styles of architecture dating back to the 19th and early 20th century. Continuing through the cobblestoned Lastarria neighborhood, you will walk through the Parque Forestal and pass by the Bellas Artes Museum. For a panoramic vista of the city, you will visit the top of Cerro San Cristobal Hill, 984 feet above the city.

Stay: Lastarria Boutique

Days 2-5: Patagonia, Explora Salto Chico Lodge

Flying in the morning, you’ll arrive to Patagonia and embark on a scenic overland transfer into Torres del Paine National Park, the crown jewel of Patagonia. After settling in to Explora Salto Chico Lodge with its unrivaled location and views, you will discuss with your guide Explora’s wide range of excursions in Patagonia and chart out your time in this remote and beautiful land at the bottom of the Earth. These range from more casual driving safaris to demanding full-day hikes near glaciers; glacier boat expeditions to private catamarans on turquoise lakes; introductory horseback rides in striking scenery to galloping through vast grasslands with gauchos; and much more. At Explora Salto Chico, the focus is adventure and an expedition tailored to your interests, while returning to a centrally located lodge of understated elegance. Click to see Explora’s complete list of excursions.

Stay: Explora Salto Chico

Day 6: Patagonia – Santiago

Depart the rugged beauty of Patagonia to fly back north to Santiago. As transfers out of the park take approximately four and a half hours you will not fly out until afternoon or later. You will likely arrive to Santiago in the evening and depart early the following morning for Easter Island. In most cases, it’s advisable to stay at the Holiday Inn across from the airport as opposed to going into the city. If flight times are otherwise, we are happy to suggest an alternative hotel in the city.

Stay: Holiday Inn Aeropuerto

Days 7-9: Santiago – Easter Island

Today you fly four hours into the Pacific to Easter Island, the world’s most isolated inhabited land. While staying at Explora you’ll meander through the picturesque countryside dotted with volcanoes, learn about the mysterious Moai statues erected by the original Polynesian tribes who inhabited the island, relax on deserted, white sand beaches, explore volcanic caves with petroglyphs, and walk the rim of a seaside volcano. Upon arrival, chart out your explorations of the island with a top guide, ensuring a perfect Easter Island trip. In addition to the many hikes and site-seeing excursions, a range of bike rides are offered as well as boat rides, deep-sea fishing, and snorkeling trips. 

Rapa Nui, Explora’s new property, which opened in 2013, is the island’s premier hotel enjoying a privileged location with vast ocean views. It has all the amenities for very comfortable and relaxed evenings after exciting daytime explorations.

Stay: Explora Rapa Nui

Day 10: Easter Island – Santiago – Valparaiso

Departing Easter Island in the afternoon, you’ll arrive to Santiago where you’ll be met and taken an hour and a half to charming accommodations in Valparaiso.

Stay: Casa Higueras

Day 11: Valparaiso

Departing after breakfast today, you'll enjoy a privately guided exploration of Valparaíso, one of the first Chilean cities founded by the Spanish. Declared a UNESCO World Heritage site in 2003 for its architectural and cultural significance, the city is also one of Chile’s most interesting. You will start in the downtown sector, learning about the history of “Valpo” and its importance in South American trade and commerce. Century-old hillside ascensores (elevators) will transport you up into the city’s steep hills, where a labyrinthine of streets reveals brightly colored buildings, bohemian cafes, elegant restaurants, and spectacular views of the harbor below. Your tour will lead you on foot through two of the most famous and eclectic neighborhoods, Cerro Concepción and Cerro Alegre.

Your lunch in Valparaíso will be at one of the city’s top restaurants nestled in the hills. With a privileged vista of the bay and a varied menu paired with a fresh pisco sour or a glass of excellent wine, what could be better? After lunch, you will continue your tour in the resort city of Viña del Mar, also known as “the garden city” for its lush gardens and palm-lined boulevards. You’ll pass by the “Reloj de Flores” (flower clock) and the sandy beaches while learning about the colonial history of the city as well as its contemporary flair.

Stay: Casa Higueras

Day 12: Casablanca Valley

After breakfast, with your bags packed, you will be met by your guide and head back towards Santiago and into the renowned Casablanca Valley. Chile’s move toward cool-climate viticulture began 25 years ago when innovative winemakers dared to suggest planting in the pre-coastal Casablanca region. The valley is now world-famous for its technology and commitment to terroir, producing some of Chile’s best white wines and cool-climate reds.

Your first visit will be to Loma Larga vineyards. Named “Winery of the Year 2011” by Wine & Spirits magazine, Loma Larga continues to represent the best of the Casablanca Valley. Loma Larga sets the bar for quality cold-climate red wines with several award winners and consistent 90+ point ratings by such prestigious publications as Robert Parker’s Wine Advocate. You will enjoy a tour and private tasting of Loma Larga’s distinctive wines.

After your tour and tasting, we will head to HOUSE Casa del Vinofor a special food and wine pairing lunch comprised of three courses, each served with a glass of wine specially selected to accompany the flavors of the dish. After lunch you will visit Viñedos Organicos Emiliana. A true leader in the concepts of biodynamic and organic agriculture, Emiliana aims to create the highest quality wines while promoting sustainability and social responsibility. Emiliana’s wine portfolio is backed by major national and international awards and recognition, and its wineries are certified Fair Trade and Carbon Neutral.

After your amazing day in wine country you will continue on a short bit to the Santiago airport where you will be assisted in checking in for your onward overnight flight home.

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