I am a pretty detailed planner when it comes to almost every part of traveling. I pore over travel guides, blogs, and websites for the best hotels, restaurants, and cultural spots. I make extremely precise itineraries based on both time, location, and ease of travel. I plan out my travel wardrobe based on a color palette and make sure that all my accessories match effortlessly. And then we take the trip that I spent so much time planning, we have a fantastic time, and I never talk about it again.

Seriously, I am the WORST at sharing about my travels. I almost never share pictures (even though I have actual gift cards to Shutterfly burning a hole in my wallet right now) and if people ask about a trip, I generally say, “Yeah, it was super fun!” and leave it at that.

For someone who spends so much time reading, thinking, and dreaming about traveling, you think I would be better at sharing more about it! Thus, this blog series, which is a retelling of some of my favorite adventures, both stateside and international. In the spirit of Throwback Thursday, I’ll be throwing it back each week to share some pictures, reviews, and brief itineraries from some of my favorite trips.

(Read last week’s post about Nashville, TN here!)

This week, we’re quick-tripping to New York City and running through a weekend itinerary for an anniversary celebration that could only happen in the Big Apple!

Having lived in New York for a year during college, I could write a thousand different itineraries of things to do, places to eat, boroughs to visit, etc. I love New York City and if you have longer than a weekend, take advantage of it! There is so much to do all the time!

My husband, however, has only visited the city one time: when we celebrated our first wedding anniversary. The weekend itinerary below is an approximation of that trip. Enjoy!

Friday:

Fly into LaGuardia (flights are always cheaper) and take a cab to Midtown. Find an affordable boutique hotel to stay in for the weekend that is centrally located. We really liked the Hotel Chandler, but they have recently closed. 🙁

Relax in your room, or head out for a late dinner and drinks nearby. If it’s Knicks or Rangers season, head to Madison Square Garden and enjoy the sporting event of your choice! Feel like seeing a show or doing something else a little special? Go for it! This is your anniversary weekend in NYC!

Saturday:

Wake up at your preferred hour of rising (preferably before noon) and head downtown – like, all the way down. You are going to the very bottom of Manhattan, near Battery Park, to board the Staten Island Ferry. Before hopping on the ferry, grab yourself a coffee and a bagel to eat as you ride out into the harbor for some beautiful morning views of the city. While native Manhattanites joke about Staten Island being a lesser borough, the Ferry is one of the best ways to see the city from the water, and best of all: it’s free!

The ride takes about 25 minutes, so enjoy your breakfast and make sure to snap some pictures. You’ll even see the Statue of Liberty on this ride (albeit at a distance). Get off the ferry at Staten Island and immediately walk through the ferry terminal to return to Manhattan.

After exiting your return ferry, walk or take a cab north-east until you find yourself at the foot of the Brooklyn Bridge. (I should caution you here and mention that we walked everywhere in New York, and I do mean everywhere! “It’s 47 blocks away? No problem!” If you have physical restraints, take a cab or public transportation. The subway system is surprisingly easy to figure out, or people are more than willing to help.)

Walking across the Brooklyn Bridge is another of my favorite New York activities, and one I made everyone that came to visit me do. The views of the city are amazing and just walking on the bridge itself is a fantastic experience. Although it’s a little over a mile, when you reach the Brooklyn side, you will be rewarded with some of the best ice cream of all time at the Brooklyn Ice Cream Factory. (Seriously, it’s amazing. I highly recommend the Peaches and Cream.) Open at noon each day, the Factory only takes cash, so make sure you come with your wallet stocked.

If you are recharged after your sugar fix, walk back across the bridge. If your legs are starting to ache, take a subway back into Manhattan and get off at Rockefeller Center. Home of NBC television shows like Saturday Night Live, there is an NBC Studio Tour for television buffs, or a more general Rockefeller Studio Tour that takes you through some of the businesses and gardens that make up 30 Rock. There are countless shops and restaurants to spend some time in as well.

The real attraction here is Top of the Rock, an observation deck at the very top of Rockefeller Center that will give you breathtaking views of the city no matter what time of day or time of year you visit. (Open 8am-Midnight daily.) I consistently chose Top of the Rock over the Empire State Building because their queue is shorter and much better organized and managed, and because when you are in the Empire State building, you don’t get pictures of the Empire State building in your photos of the city! (And tickets to Top of the Rock are just a hair cheaper at $34/adult compared to the Empire State’s $37.)

After snapping your fill of photos, head back to the subway and head downtown a bit, to 14th Street to be exact. Get off at Union Square and you’ve found yourself in one of my favorite areas. Walk just a block or two out of the subway to the Strand Bookstore, home to 18 miles of books. Arguably the greatest bookstore ever, the Strand could occupy your time for the rest of the day. For a fun twist, challenge your partner (or friend or family member) to choose a book for you and you choose one for them. Whatever you choose, the other person has to read. This is how B and I chose each other’s anniversary gifts and he ended up choosing a book that I loved that turned out to be almost prophetic. (But more on that later…)

Once you’re satisfied with your book choices, cross the street for a late dinner at Max Brenner. Billed as a chocolate restaurant, this place has a menu that is full of delicious items of all sorts: salads, sandwiches, savory pastas, you name it, it’s all delicious. Obviously you must save room for dessert, or splurge a lot and have a dinner that is entirely made up of desserts. I highly recommend splitting (or not) the Banana Split Waffles. I’ve enjoyed them on a number of occasions. But really, any dessert you get here will be phenomenal. Have a drink to cap off your night before heading back to your hotel for some well-deserved rest.

                          Sunday:

Sundays are made for Central Park. You’ve planned ahead and made reservations for brunch at the Loeb Boathouse this morning, and while brunch will be a little pricey, it’s always delicious, and the views more than make up for it.

While at brunch, you’ll check your email to see that you’ve won the ticket lottery for an afternoon matinee on Broadway! (Whatever style of show you are into, check the lottery policies before you arrive in NYC. Most shows have a lottery you can enter, whether in person or digitally, and the odds of winning are generally pretty good. I’ve seen at least ten Broadway shows from the front row for less than $40 per ticket. Lotteries should absolutely be your first choice if you want to see a show! Playbill does a roundup of the policies for each show that is super user-friendly. Check that out HERE.)

You have a few hours before you need to head to Times Square, so stroll through some of the park. My list of can’t-miss attractions includes: the Shakespeare Garden, Bethesda Fountain, Strawberry Fields, Belvedere Castle, and the Mall (the only straight path in the entire park). My personal favorite spot is the Alice in Wonderland statue, while B really liked Hans Christian Andersen.

Continue to walk downtown until you exit the park at 5th Avenue and 59th Street. Head east on 59th about five blocks, or until you find yourself outside of Serendipity 3. If you’ve never seen the movie, it’s no big deal. Just know that you are headed inside to share a frozen hot chocolate with your companion as a reward for all that strolling.

Finish your dessert, and depending on how your legs recovered from yesterday’s walk, and your time schedule, walk or take a subway to Times Square, which is only slightly quieter on Sunday afternoons. Take in a matinee of a Broadway show with the tickets that you won previously in the lottery or head to TKTS to score some heavily discounted tickets. After the show, grab a drink at one of the nearby bars (The Mean Fiddler was a favorite of mine in college) or get a slice of the “World’s Most Fabulous” cheesecake or other refreshment at Junior’s.

That’s it for your jam-packed weekend itinerary. It made for a fantastic and romantic anniversary for us, but it would be just as fun for a group of friends or a family with just a few small adjustments. Let me know if you decide to try it out, or what your favorite NYC attractions and locales are!

Honorable Mention: If you are a Packers fan and are in town during football season, we highly recommend you check out Kettle of Fish bar! It is a little piece of Wisconsin in the middle of New York City and we had an excellent time watching a preseason game here.

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