We're a late-30s couple celebrating our 10th wedding anniversary in late May. Our top priorities are great food and great entertainment. He likes jazz and classical music, architecture & beer; I'm a fan of Billy Joel, drama, modern art and cocktails. We've put together a preliminary plan, but have a couple of holes as well as only pending plans at restaurants that we won't be able to reserve until April. I also want to leave some time just for walking and people-watching. This isn't our first trip to NY and I realize that the number of shows/concerts we have planned might not appeal to everyone, but we're super excited about them all.

Would love any feedback on our plans as well as a couple of recommendations. We'll purchase 7 day Metro cards and will also probably rely on uber as needed. I'm also not planning anything in the mornings before 10:30am since we'll be out late each evening. Thoughts?

First Day - Wed, May 27
- Arrive LGA early-afternoon; Carmel Limo from LGA to Hilton Midtown
- Early dinner at Gato
- "Sleep No More" at the McKittrick Hotel in Chelsea
- Looking for a place to have drinks after the show - ideally near the venue or near our hotel.

Thu, May 28
- MoMA & Lunch at The Modern Bar Room
- Leaving time open in the afternoon for Tonight Show with Jimmy Fallon (fingers crossed I can score tickets when they're available in April if he's filming this day; if not we'll probably try to do a tour of the UN instead)
- Billy Joel at Madison Square Garden (8pm)
- Late dinner & drinks at The NoMad Bar
- Empire State Building - I know it's touristy and locals tend to recommend TOR over ESB, but the we've never been to ESB together and I think the late night saxophonist there will be a nice touch given that it's our anniversary.

Fri, May 29
- late breakfast at Barney Greengrass
- Cathedral of St John the Divine Vertical Tour (12pm tour - 1 hour)
- NY Philharmonic at Lincoln Center (2pm concert)
- Dinner at Babbo (pending reservations)
- Yellowjackets at The Blue Note (a full circle moment as our first date was to a Yellowjackets concert)
- Maybe Comedy Cellar afterwards???

Sat, May 30
- East River Ferry from 34 St/Midtown to N 6th St/N Williamsburg
- Williamsburg Smorgasburg
- Brooklyn Brewery Tour & Tasting Room
- Brooklyn Botanic Garden (uber from Brooklyn Brewery)
- Early dinner at Roberta’s (uber from BBG)
- Jazz at Lincoln Center concert in Rose Hall (8pm)
- Post-concert drinks at the Mandarin Oriental Lobby Lounge

Sun, May 31 (Anniversary)
- Brunch at the Sarabeth’s Central Park South - or someplace else recommended
- The Frick
- "The Audience" matinee at the Gerald Schoenfeld Theatre (3pm)
- Anniversary Dinner at Per Se or Eleven Madison Park (pending reservations)

Departure Day - Mon, June 1
- 9/11 Museum & Memorial
- Early lunch at Motorino or Momofuku Ssam
- Carmel Limo Hotel Pickup for late afternoon flight

Looks like a lot of fun. Your quickest route from St John to Lincoln Center will be the 1 train - You may feel rushed...

Sat - I don't know where Roberta's is but you are packing a lot into this day. Be flexible and decide what is important ahead of time.

Sun - If you are looking for alcohol with your brunch it won't happen until noon. The Frick will be crowded during their 11-1 pay what you want time so you should do it first.

Enjoy!

Happy 10th!! Looks awesome! Good luck with Jimmy Fallon - we did get tickets to David Letterman (Jimmy wasn't there yet) and it was very cool!

If you want/need a back up reservation for Eleven Madison Park day make it Jean Georges. Also I personally have enjoyed my meals at Le Bernardon more than Eleven Madison since their big overhaul. I dined there in September and just found it a bit overwhelming. You won't mind a 6:30 reservation there one bit.

Thanks, @Doug. Would you pick Jean Georges or Le Bernadin over Per Se as well?

Per Se is brilliant - but prices are really sky high - way higher than any of the other upscale places you are looking at. We have done twice with clients and once for ourselves for a special occasion - but I still have trouble when I think what else I could do with so much money ($800 per couple with good wines).

I'm not sure what you mean @nytraveler. Per Se and Eleven Madison Park are comparable pricewise and yes it's a splurge, but I'm not looking for other options to spend the money on instead. We want an unforgettable dining experience for our anniversary dinner and those are the two restaurants that seem to fit the bill. I'm interested in knowing if @doug prefers his two suggestions over Per Se as well as EMP.

Instead of Babbo, I would consider dining at Marea so you can experience the cooking of Michael White and his team. These are the premier pasta cooks in the city right now. Babbo is consistently good, but there are others that you might enjoy more..

I would also try to dine at The Modern Dining Room for one of your dinners. They seem to be at the top of their game right now. I'd put this on a par with EMP and Jean Georges; the three of these are among my favorites for celebratory meals.

ps. Agree with your choice of Gato. We try to get there a couple of times a month when we are at home in Manhattan....never disappointing! On the same level, you might consider Estela, a half block away.

Hope you have enough time between events to enjoy NY.

Thank you @ekscrunchy. I've gone back and forth between Marea & Babbo. Your recommendation of Marea may push me in that direction. I've enjoyed reading your contributions on Fodors as I've been researching this trip. Thanks for chiming in.

Interesting comment, @IMDonehere. For us, the "events" will only add to our enjoyment of NY! We've come before with kids and not done any shows or concerts due to their ages. This trip is all about adult options and frankly is the main reason we chose NY. As I mentioned in my original post, I realize that the number of shows/concerts we have planned might not appeal to everyone, but we're super excited about them all. To each their own

If you like seafood, then I think Le Bernardino is more enjoyable to me than EMP. I found my last meal at EMP remarkable but also remarkably exhausting. But it's a singular experience and a wonderful restaurant. I have not eaten at Per Se. It's never appealed to me, so it's hard for me to compare. I think Jean George's is really outstanding, but it's not as elaborate a presentation as either Per Se or EMP. But the food is every bit as good. But I still favor Le Bernardin. Marea's menu is predominately seafood, so I probably wouldn't do both it and Le Bernardino on the same trip. I hope that helps.

We have traveled a bit ourselves and some of the best memories were things that were serendipitous. Getting lost and finding a beautiful street, a restaurant, or a shop.

This is clearly well-researched and organized, down to the mode and time of transportation and some of the hippest and latest. To me, it is a symptom of modern society, where it is like a business agenda with built in take aways, rather than a time to exhale and enjoy this great city.

Any recommendations for cocktails near the McKittridge Hotel in Chelsea or somewhere else for Sunday brunch besides Sarabeth's (between the HIlton Midtown and the Frick). We don't want anything too heavy or too late since we'll be doing a tasting menu for dinner. Also, Roberta's was recommended by friends for pizza in Brooklyn. Any other suggestions besides Roberta's?

Hubby is a classically trained percussionist who plays in a jazz combo in addition to his 9-5 job in the hotel biz. He was stoked when I told him that the Jazz at Lincoln Center concert "The Artistry of Max Roach with Ali Jackson" coincided with our trip. We have tickets for everything except "Sleep No More." I'm not 100% certain that we would enjoy it given what I've read, so we might end up looking for something else on Broadway for the first night.

Cafe Boulud serves brunch, and it's not far from the Frick. I've never had brunch there, but the food is great generally.

I'm ordinarily not at all a fan of Sarabeth's. I had one of the worst dinners I can remember from the past year there (the location on the Upper East Side). However, they do a consistently good brunch.