San Francisco & Chicago in 10 days

Writing this post has been very exciting as for a while I had the luck of living and studying in San Francisco. At the same time, my best friend lived in Chicago for a year and when I visited I was given a very authentic tour (yes, for the first time ever I didn’t planned the trip!)… so this post is based on our best recommendations and our personal experiences. I hope you enjoy as much as we did!

Best time to go: June to September. Definitely avoid the winter as Chicago it is extremely cold and San Francisco is cloudy and foggy during the winter.

Where to stay in San Francisco?

• "Noe's Nest Bed and Breakfast" – a charming Victorian house at Mission District a very cool area with a youthful vibe.

• "Hotel Emblem San Francisco" – in Union Square where most of the hotels are located right in the centre.

Day 1: Golden Gate, Alamo Square and Lombard St

Start the day by renting bikes to do the sightseeing. Recommended bike rental is "Golden Gate Bridge Bike Rentals". Our route for the day is:

1. Presidio of San Francisco park and Vista point: from here you can appreciate the impressive scenic vistas overlooking the Golden Gate Bridge (10 min ride from the bike rental shop).

2. Golden Gate park: if the weather is nice it would be ideal to have a picnic at lunch time at this beautiful park. This is the biggest park in the US (30 min ride from Presidio).

3. Alamo Square: this is one of the most famous pictures of San Francisco with the "Painted Ladies" behind you (20 min ride from Golden Gate park).

4. Lombard ST: the most famous street in San Francisco, very touristic and crowded but a must do as it is actually beautiful (20 min ride from Alamo Square).

At this point you will be 5 min away from the bike rental so you just need to return it.

Suggested dinner at Little Italy – "Seven Hills Restaurant".

Day 2: Union Square, Pier 39 and Sausalito

Our route for this day combines walking, cable car and ferry… a full SF experience.

1. Union square: start the morning going for a walk around Union square where you can find numerous bars, cafes and shops.

2. Cable car: from Union Square you can take the Cable Car (Powell - Hyde line) to get to the Fisherman’s Wharf while enjoying an amazing experience.

3. Fisherman’s Wharf and PIER 39: this a very nice area to walk around and visit during the day. Even though is very touristic, you can have a nice lunch at "Bubba Gump Shrimp Co." enjoying beautiful views.

4. Sausalito: from Pier 39 take a ferry to Sausalito. Sausalito is on the other side of the city after crossing the Golden Gate. This neighbourhood has large numbers of houseboats and it is really picturesque.

Mission District: before going for dinner you can visit Mision Dolores the first building built in San Francisco afterwards, go for dinner at– " Loló" a very nice Mexican restaurant just 10 min from the church.

Day 3: Alcatraz, Chinatown and Financial District

I would definitely visit Alcatraz as it is a super cool and unique experience. I would recommend buying the tickets online, in advance. Departures are usually from Pier 33. Just take into account that the entire experience takes around 3 hours and costs around 40$.

Once you have returned from Alcatraz you can have a nice walk (25 min) to Chinatown. I would definitely recommend exploring the neighbourhood and have lunch there, as there are many nice, authentic Chinese restaurants. Two of our favourites are: "Mister Jiu's" or "Z & Y Bistro s"

After lunch, you can walk from Chinatown to the Financial District which is just 10 minutes away. In the Financial District you must visit the Transamerica Pyramid building, the Colombus Tower and Maiden Lane.

Day 4: Napa Valley

You can either rent a car (my personal preference) or book an online tour that will include pick up from your hotel in San Francisco to visit Napa Valley.

If you rent a car you can start the morning by driving to Twin Picks and, if you get up early enough, you can watch the sunrise from this beautiful hill where you have a fantastic panoramic view of the city.

The drive to Napa Valley takes just 1hour and 15 minutes. You should book the activities that the vineyards offer in advance (wine tasting, cellar visit etc). Two of the recommended vineyards are:

• Luna Vineyards

• V. Sattui

There are just a 20 min drive from each other so if you have time you can visit both.

Suggested hotel to spend the night in Napa is "Candlelight Inn Napa Valley". A very charming hotel very close to Luna Vineyards.

Day 5: Travel Day

Travel day from San Francisco to Chicago that takes around 4 hours.

Where to stay in Chicago?

• "Sonder, Armitage Suite" – at Lincon Park. Located in a very lovely and quiet area that is close to the lake beach. No super centric but is a good, easy commute.

• "The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago" - at River North a very centric but quiet area.

Day 6: Skyscrapers & River Cruise

• The Willis Tower: the skydeck is on the 103rd floor and has retractable glass balconies, overlooking South Wacker Drive. This has become, for obvious reasons, one of Chicago's main attractions. I would recommend to go on a week day and early in the morning, otherwise there is usually a queue. Entry ticket is $26.

• State street (south side): your next stop is the legendary Chicago Theatre. I would suggest getting there by walking down State street as this is one of the popular shopping streets. (approximately 15 min walking from Willis Tower).

• Architecture River Cruise: to get to Chicago Architecture Centre from where you are, you can take the cruise down the Chicago River. This is a must do when visiting Chicago, on the cruise they will provide you with a detailed explanation of the construction and history of over 50 significant buildings. The tour takes around 90 minutes and the prices is approximately $44 but depends on the cruise company.

• Lunch at "Pizzeria Uno", a typical place to try the deep dish-pizza. Take into account that it takes 45 minutes to prepare it

• Magnificent Mile or Michigan North: after the cruise, walk along the Magnificent Mile, the street with all the prominent and very expensive shops (11 minutes' walk from the dock)

• Hancock tower: at the end of Michigan North you can find the Hancock Tower. The good thing about this tower is that you can go to the bar on the 96th floor to have a drink after a long day walking and watch the sunset from there.

Steak for dinner after a long day of walking could be a good idea at "Rosebud Steakhouse".

Day 7: The lake, Parks & Beach

You can start your day visiting the Navy Pier. You can rent a bike at the Navy Pier (suggested rental bike "Bike and Roll Chicago - Navy Pier") to do the following route through the bike line that boarders the river:

• Museum Campus: it is a huge museum park that sits near Lake Michigan and surrounds three of the city's most notable museums. From here you can enjoy a beautiful view of the skyline (20 min cycle).

• Grant Park: a park with amazing views and a very pretty fountain (10 min from Museum Campus).

• Millennium Park: the most famous park in Chicago with 2 very original fountains, the famous bean and the Pritzker Pavilion (5 min cycle from Grant Park).

• Lunch at Nori Sushi, in Lincoln Park it is super nice and they have a 50% off offer at lunch time.

• Lincoln Park: visit the free zoo at the park or go to the beach (25 min cycle from Millennium Park).

Time to return your bike to your starting point that is just 25min away from Lincoln Park.

Dinner at "Bandera" – American food with great burgers and daily live jazz.

Day 8: Wicker Park

Wicker Park is the hipster, charismatic area of Chicago. It is very nice to lose yourself walking around the area. The closest subway station is Damen. Go for lunch at the "Big Star" which is a very cute Mexican restaurant.

After lunch you can walk around Clark street at Lincoln Park as you might not be able explore this beautiful area properly on the bike.

Before dinner go to visit Old Town, underground station Armitage. You can walk around the area and have dinner at "Balena Pop-Up" a very nice Italian restaurant.