Sydney is the gateway to Australia as most flights from the US arrive here. You could easily spend your entire vacation in Sydney and the surrounding areas but from my experience, I believe at the very least, 5 days are needed.
Most flights from the US will arrive early in the morning. The jet lag will be insanely difficult but the best thing you can do is caffeinate and push through the tiredness as late as you can. The longer you hold out, the quicker you’ll get adjusted to the new time zone.
Day 1: Explore Circular Quay and the Rocks
Day 2: Explore Sydney’s Harbor via Ferry and go to Manly Beach
Day 3: Day Trip to Blue Mountains
Day 4: Coastal Walk-Bondi to Coogee & explore Watson’s Bay
Day 5: Day Trip to Hunter Valley Wine Region
Day 1: Explore Circular Quay and the Rocks
Circular Quay (pronounced key) is the heart of Sydney. It’s where all of the ferry boats and cruise ships port, and home to the iconic Sydney Opera House with views of the famous Harbor Bridge - which you can climb if you dare! I would highly suggest getting a hotel within this area as you will be within walking distance of the most important features and easy access to public transportation (trains, buses, and ferries). You can read more about public transportation in Sydney here.
Prior to arriving I had scheduled a meet and greet with a Sydney Greeter. This is an incredible organization that runs only on donations. You can be gree
ted by a local and work with them to curate your ideal welcome tour of the city. This is also a great time to get a hands-on learning experience with the public transportation. The tour will not include any ticketed entrances (i.e. tour of the Opera House) so you’ll need to book that separately or go with a more in-depth tour of the city like this one: Private Sydney City Tour with Sydney Opera House, Bondi & Manly
Around Circular Quay and the Rocks, I suggest checking out the following areas
Royal Botanic Gardens
Observatory Hill
Argyle Street
Pitt Street Mall
Pro Tip: Head to Mrs. Macquarie’s Chair, located in the Royal Botanical Gardens, about an hour before the sunset to grab the best seat and some of the best photos of the sun setting behind Sydney’s Opera House.
Day 2: Explore Sydney’s Harbor via Ferry and go to Manly Beach
I cannot speak highly enough about Sydney’s Ferry system. It’s both a transportation and scenic ride as you take on the views of Sydney from the water. I recommend starting your day early because the ferries too Circular Quay will be busy as people come in for the work day but they will be almost empty going to the other ports. Plus, you’ll have epic sunrise lighting on the Opera House and Harbor Bridge for stunning pictures.
Some fun ports to check out:
Pyrmont Bay
Milsons Point (check out Luna Park!)
Barangaroo Wharf
Manly Beach (a must!!)
Pro Tip: Bring a jacket if visiting outside of the summer months; once the ferry speeds up and the wind hits, it can be pretty chilly even on the sunniest of days.
Day 3: Day Trip to the Blue Mountains
After two days of walking around the city, you’ll enjoy the bit of the drive outside of the city to view the Blue Mountains. To compare to something in the US, combine the vastness of the Grand Canyon with the trees and colors of the Blue Ridge Mountains and you’ll have a bit of an idea of Australia’s Blue Mountains.
After extensive research, we chose to book this tour: Late Start Blue Mountains Nature, Waterfalls, Koalas Small Group
I selected it because it had no more than 8 people (we had 5), the fact that it did not stop at Featherdale (you’ll see that on about every other tour), and this tour started later in the day meaning we’d miss most of the crowds and possibly be able to grab some sunset photos before returning, which we did!. The entire trip was about 12 hours and I would highly recommend it to anyone looking for a Blue Mountains tour from Sydney.
If I were to do it again, now that I understand the layout of the Blue Mountains, I would rent a car for the day so that I could have control over my time and stops. I think the tour did an excellent job and every stop we went to, I’d go to again, but I simply like being in control and feel this day trip is not crazy complicated that requires the use of guide. It all depends on your travel style.
Pro Tip: Pack snacks, it’s a long day
Day 4: Coastal Walk-Bondi to Coogee & explore Watson’s Bay
After a day in the car, it’s time to put your walking shoes back on! The coastal walk from Bondi Beach to Coogee Beach is well-known and popular amongst both tourists and locals. If you are ok getting up early, I highly suggest getting to your starting point either right before sunrise for epic views or right after it so that you can at least beat most of the crowds.
For the sake of including Watson’s Bay in this day, I suggest starting at Coogee Beach and ending at Bondi Beach, then catching an Uber or bus up to Watson’s Bay.
However, if traveling during popular beach weather (i.e. summer) Bondi Beach will become even more busy as the day goes on, so you might want to start there instead. It’s all about your personal preference. This walk is perfect for those interested in capturing epic coastline photos, exploring the various beaches along the way, watching surfers, and simply enjoying your surroundings. Some might argue that the walk becomes repetitive so if doing the entire thing doesn’t interest you, I at least encourage you to go from Bondi to Bronte or vice versa as you will see the majority of the highlights.
Once you feel you’ve gotten a good feel for the area, head up to Watson’s Bay for a short stroll to the popular lighthouse viewing. This is a casual spot to simply hang out and catch the breeze. Then you can catch the ferry from Watson’s Bay back to Circular Quay to wrap up your day!
Pro Tip: There aren’t many cafes between Bronte Beach and Coogee so make sure you plan accordingly.
Day 5: Day Trip to Hunter Valley Wine Region
If you like wine at all, you must take a day trip to the Hunter Valley wine region. It’s the oldest wine region in the area with over 150 wineries. The one major pitfall is that it’s about 2 hours from Sydney and public transportation can only get you so close. Thus, your options are to book a tour, hire a private driver, or rent a car and book a hotel stay for a night or two. If I were to do it again, I might look into the hotel option simply because I loved the area and feel it would be fun to have an extended stay here.
There are SO many options for tours that I even got to the point of emailing a few and asking them “Why should I select your tour” - I am not even kidding, haha! The response I got back from one in particular was stellar so we booked and were not disappointed. We had a small group of 6 people and our guide, who is also studying to become a sommelier, is not only passionate about his job but truly invested in your time on the tour. We stopped at 3 boutique wineries and sampled over 30 wines. The tastings were intimate and with the owners so the entire day felt so special. If you are interested in booking this tour, let me know so that I can put you in contact with this exclusive guide. You will not be disappointed.
Pro Tip: Avoid going on the weekends to have a more intimate experience.
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