Why: Uruguay is a comfortable place to visit, the weather is nice, and not too many tourists go here. Montevideo is a very livable city where you will fell comfortable to walk around and not nearly as large as its neighbor Buenos Aires.
Flights and Car: Montevideo is not the biggest hub in Latin America, however it’s not too tricky to get here. Check for flights on skyscanner.com. I took buses, however renting a car for the few days you spend out of Montevideo would make a lot of sense.
Day 1: Get to Montevideo and head to Buenas Vibras Hostel. Go out and take the free walking tour downtown to get a feel for the area. Head out for some tasty meat for dinner in one of the best places to eat carne in the world!
Day 2: Head out in the morning for a walk, run, or bike ride on La Rambla. This beautiful stretch of the city runs alongside the ocean and is a great outing. Head over to Mercado del Puerto for some tasty lunch. Rent a bike for the afternoon and peddle around the city to check out the different neighborhoods and colorful street art that decorates Montevideo.
Day 3: Head over to Punta del Este for the day and chill on the beach. Check out the famous hand which pops out of the sand. If you are into nightlife and restaurants there are lots of options here. Spend the night at B & B Punta Arenas Hostel.
Day 4: Head up the coast a couple of hours to Punta del Diablo. Stay at Hostal de las Hadas. This a a really chill town which is perfect for relaxing or surfing. As long as you are not here in the middle of summer you will have this town to yourself and about 500 locals who live here.
Day 5: If you have a car stop at La Paloma Beach on your way back down the coast. This will be a big travel day to get you down Colonia de Sacramento. Stay at Hostel Colonia. Get out to walk the cobblestone streets in this pretty little town.
Day 6: Check out the historic quarter in this Unesco Heritage town. Go out for a walk or bike ride on Rambla Costeñera. Enjoy checking out the old cars and if you want some more beach time, get a bus ride out of town.
Day 7: Get a bus back to Montevideo for your flight on to your next flight or take a ferry over to Buenos Aires to start checking out Argentina.