The Five On It • New York City Guide

Five New York City guide plans, already made.

Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.

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What's inside

Five guides, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
The Timeless RomanticA 1767 carriage house, candlelight, and live piano, the classic proposal night.
02
The Skyline SplurgeDinner sixty floors up, then cocktails even higher, the whole city at your feet.
03
The Cool DowntownA buzzy wine-bar dinner, then a knock on an unmarked speakeasy door.
04
Dinner & a ShowA checkered-tablecloth classic, then the curtain goes up on Broadway.
05
The Brooklyn Bridge DateWalk the bridge at golden hour to a Michelin dinner under it.
The first of five · a first taste
7:00 PM
One if by Land, Two if by Sea West Village

Widely called the most romantic restaurant in New York, a candlelit former carriage house on a quiet Barrow Street corner, with brick fireplaces, a baby grand piano, and a secluded garden.

Revealed inside

A five-minute walk away, descend into Smalls (or its sister room Mezzrow), an intimate West Village basement jazz club that's been the real thing for decades.

+ 1 more
Revealed inside

Low pressure, easy to talk, and full of places to duck into if the conversation's good, which, if you played the other five right, it will be.

Planning a guide like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.

5 complete guides, every one chosen and mapped, yours for $5.

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A note from us

From us to you

We've done every one of these guides ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting New York City. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the guides we recommend to the people we care about most.

Now go enjoy it,

The Five On It
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