This past weekend was a double whammy because it was Father’s Day and my birthday. Now as someone who loves a good experience almost as much as they love a good drink, I knew I had to find the perfect plan of attack for the weekend festivities. Personally, I think the activities you’re about to read below are perfect for anyone, regardless of age (though most would be suited for our 21+ friends – always check for age limits before booking any of these) and minimal walking is required. So get ready to relax, drink up, and take in some amazing views of the beautiful city of Boston – by land or by sea.

Day 1: Sky High & Sauced
For the first day of our Boston weekend, I took my dad into the city where we traveled almost 750 feet to the top of the Prudential Center. Why? Because there’s an amazing spot there called View Boston. This newly renovated attraction is very different from what I remember visiting on a field trip in middle school. In full honestly, it’s on par with what you’d see in Disney. Top notch special effects, a stunningly clean area, and the best view Boston.

We took a super quick elevator ride to the observation area of the building. There, you can traverse the 360 degree, panoramic views that extend well beyond the Boston lines into the North and South Shores as well as out to sea and West. I’ve been to View Boston twice – both times on weekends – and there’s never been an unbearable crowd there. I think that the multiple floors of the attraction are so large that everyone is spread out. Or maybe we timed it right.

My dad loved the views of Fenway Park, while I loved looking at the sailboats on the Charles River. After walking around the main observation floor, with floor to ceiling windows, we descended a floor to visit View Boston’s bar, Stratus. We grabbed drinks and headed outside to sit and take in the views.

I made only one mistake when planning this day out. I didn’t plan enough time at View Boston. I had only allowed for an hour and a half (you can stay as long as you like but I had made reservations elsewhere for lunch) and I should have planned on staying for at least two hours. Pro tip: if you plan to have lunch at the attraction, you can come and go between floors as you please. Next time, that’s what I’ll be doing.

Now time for the “sauced” part of the day. No I don’t mean sauced in that way. Okay maybe it’s a bit of a double entendre. Sure we had our fill of drinks but the real meaning of the “sauced” part of the day was the fact that we had reservations at Eataly’s La Pizza & La Pasta. A very short walk from the exit of View Boston (I’m talking probably 100 feet), Eataly is an Italian food lover’s dream. As someone who is half Italian, I know good Italian food. This was it. The Prosciutto, the olives, the pasta, and the burrata – I have no words. After the meal, we perused through the shop – again, I’m a sucker for a good Italian grocery store – and finished my dining experience with some hazelnut gelato.

Another pro tip: If you park at the Prudential and you buy something at one of the shops, make sure you share your parking ticket with the cashier because they’re able to validate a portion of your parking expense. Obviously be sure to check at the time of your visit if this policy is still being honored.

Day 2: Tan Lines & Table Wines
My birthday. I ventured back into Boston to the Waterfront for another day of views and vibes. I had no idea Boston even had Tiki Cruises until a search for things to do on TikTok, and let me tell you, I’m here for it. Also, the dock was conveniently located directly across from my birthday restaurant of choice, The Palm.

I was lucky to have a beautiful, sunny day to go on the 90 minute boat ride. There were also only 10 travelers in total, which gave me plenty of room to move around to a new spot when I felt the urge to do so. I started the trip bellied up to the bar and finished it in the uncovered seating area of the boat. Yes, I officially got my first sunburn of the summer. Please pack sunscreen and be prepared for a cool breeze.

The drink selection spanned several menu pages and there were mocktails for those who choose to go alcohol-free. We sailed from the waterfront to Charlestown and the Zakim Bridge before turning around and returning to the dock. Pro tip to getting a good seat – make sure you are lined up in front of the boat a good 15 minutes before boarding. For us, they boarded 5 minutes prior to departure. There are 12 seats at the bar and another bench-style area that fits about 12 passengers. Note that this area is fully in the sun. If you want to avoid sun exposure, make sure to sit at the bar. In case of rain, there are curtains that are rolled down to keep you dry.

After our adventure, we crossed the street to The Palm. This is the perfect restaurant if you value service, atmosphere, and food quality. Pricey, a little but I believe that you get what you pay for. If you go for lunch, it’s worth trying their Power Lunch menu option so that you can have a three course selection of some of their most popular menu items. In the summer you can sit outside but I prefer to remain indoors and soak up the dark wood and red marble interior as well as the various caricatures that grace the restaurant walls.

And with that, my birthday/Father’s Day weekend concludes. Until next year…