San Pedro de Atacama In the north of the country close to the border with Bolivia is the beautiful desert region of San Pedro de Atacama. This is a spectacular Andes mountain setting that combines desert, hot springs, geysers, and lagoons. I'd recommend renting a car to maximise your time in this region, but there are plenty of companies in the town of San Pedro offering tours. El Tatio is a high altitude field consisting of over 80 geysers which makes it a spectacular spot to visit. Along the same desert road leading you to El Tatio, you'll pass by worthwhile stops like Canyon de Guatin and Puritama, so no diversion is needed. Even the town of San Pedro has it's own charm with cobblestone streets, local markets, and the beautifully unique Iglesia San Pedro Church. Valle de la Luna is the most visited attraction in the region due to its close location to the town and offers a moonlike landscape spreading across the desert.
A great central spot to explore the country as a whole. Regular LATAM flights make it so easy to bounce up and down the country. As for Santiago, it's definitely worth spending a day or two here. The city is home to the highest public observation deck on the continent in the form of Sky Costanera. The centre is relatively compact so you can walk from place to place. Plaza de Armas is the central point where you'll find The Santiago Metropolitan Cathedral and many other colonial buildings. As for a free of charge view point, walk to the highest point inside Santa Lucia Park where you'll get a great view of surrounding skyscrapers. For art lovers, hope on the metro to Departmental and walk a couple of blocks west. You'll find the largest open-air street art museum in the country, with murals covering entire building facades.
Vina Del Mar
For an easy day trip, you can reach Vina Del Mar within 90 minutes of Santiago. It's a coastal resort city known for its blend of gardens, beaches and high rise buildings. There's an Archaeological & History Museum featuring an original moai sculpture from Easter Island. The beaches are peaceful and not over-crowded, so a great place to relax. For those that struggle sitting still, take a walk to the fish market located directly on the seafront. You'll be treated with plenty of seals and seagulls aiming to swipe the left overs.
To maximise time, combine a visit to Valparaiso with Vina Del Mar. It's a colourful port city that's famed for it's clifftop homes and steep funiculars for easy transport. You'll also see street art in abundance, as it's a hotspot for both local and international artists. My advice would be to take the funicular up, walk the streets of the neighbourhood, grab a bite to eat in the many cafes, admire the art, and take a slow gradual walk down to Plaza Sotomayor, which is the central square. For souvenir hunters, there's also plenty of local art galleries and souvenir stores.
Chile has a reputation for producing high quality wine, so you'll see many vineyards during your road trip across the country. Thought it was worthwhile checking one out, so chose to visit was Bodegas RE, which is located in the Casablanca region of Valparaiso. You can book a guided tour to see the full wine making process, or just relax in the many gardens and sample the wines on offer with a vineyard backdrop. In my opinion, even if you're not the biggest fan of wine, this is a great country to experience a vineyard tour.
Easter Island is a "Holy Grail" for many travellers, so there was no chance of me visiting the country without including it. Part of Chile, albeit 3,686km from the mainland, but easily reachable via daily LATAM flights. The island is small in size, but is still home to 887 moai statues, as well as plenty of other worthwhile tourist attractions. The statues range from 3-11 meters in height and some weigh up to 82 tonnes, which makes it even more mystical as to how they were transported across the island. The statues are believed to represent the spirits of great ancestors and there are many archaeological sites spread across the island. In addition to the statues, I'd recommend visiting Orongo to hear all about the Birdman legend, Rano Kau Crater, and Ana Kai Tanata sea cave for coastal views.
Note: I do think it's an island where you're worth using a local guide to fully appreciate the history.
Puerto Montt If you don't have sufficient time to include Patagonia in your itinerary, then a back-up is to include a stop in Puerto Montt, located in the south. The port city is referred to as "The Gateway to the Andes" and although the town itself doesn't offer a great deal, it's the central location for many attractions that draws the appeal. Rent a car and drive around Lake Llanquilhue all the way to Osorno Volcano. This is a beautiful viewpoint where you're able to take a cable car up to a stunning viewpoint of both the lake and volcano itself. Next stop should be Petrohue Waterfalls which has a relaxing boardwalk walking trail through the green surroundings. This is a great spot to snap both the waterfall and volcano in the same shot. Finish off walking the streets in the neighbouring Puerto Varas and grab a bite to eat in the many waterfront cafes and restaurants.
I stayed in some great hotels during my Chile visit, but one I specifically want to recommend is Sommelier Hotel in Santiago. I found many hotels in the city to be expensive, but this hit the spot in terms of a central location with decent facilities. There's many attractions within walking distance, strong WiFi, and newly renovated rooms. The only drawback was the popular rooftop bar open daily, so ask for a low floor to avoid the noise.
If you make it to Valparaiso, be sure to stop off at Cafe del Pintor for lunch. Their home-made burgers are amazing and they also have great options for vegetarians. Prices are reasonable and their home made desserts are a great finisher. It's nice to see so many locally run restaurants and coffee shops, compared to the usual chains seen elsewhere. If you're only visiting Santiago and you're a sushi fan, Badu sushi joint was top class!
For mainland Chile, I genuinely don't think a guide is necessary. You can easily tour the country yourself and there's many tour agencies in all the key cities if you don't have a car rental. The only place I would definitely recommend hiring a tour guide would be Easter Island. The sights are great, but to fully appreciate and absorb yourself in the history of the moai culture and the island itself, hire a local guide. I can 100% recommend Josie as she's very knowledgable, inexpensive, and explains even the deepest history in a simple way. You can reach Josie via Whatsapp on +56 9 8459 1816. Note: To save time, purchase your Easter Island entry permit online ahead of your visit.