Custom NYC Plans: Date Nights, Family Days & Trips

Your NYC planning desk

Be the person
with the great plan.

A date night that feels thoughtful. A kids’ day with room for snacks and breaks. A first visit that flows. Tell us your people, budget and kind of good time—we’ll connect the dots.

Personal planning from $39 · one-time fee. Explore the sample before choosing a package.

One-time planning feesUp to 4 peopleBook at least 7 days aheadLove Your Plan Guarantee
Manhattan skyline seen from the Brooklyn waterfront at dusk
New York after sunset. Photo: Toni Tan / Unsplash. Reference photography; conditions vary.

A preview of what you’re buying

Less “what should we do?”
More “that was a great date.”

This is how a simple request becomes a connected afternoon. An illustrative sample, not a real customer order or a booked experience.

Chelsea Market sign on the brick exterior of the market
01 / Chelsea MarketPhoto: Crystal Jo / Unsplash
Visitors walking through the landscaped High Line at The Spur
02 / The High LineReference view of The Spur, a different section from the sample stroll. Photo: Akshat Jhunjhunwala / Unsplash
Little Island park rising above the Hudson River on sculptural concrete supports
03 / Little IslandPhoto: Structural Photography / Unsplash

Reference photography for inspiration. Seasons and conditions vary.

SAMPLE BRIEF · TWO ADULTS · ONE AFTERNOON

Your afternoon, connected

3:00 PM / EAT FIRST

Start with Chelsea Market.

Meet at 75 Ninth Avenue, between West 15th and 16th Streets. Choose a casual bite together and leave room for something sweet. Allow about an hour, including browsing and possible queues.

4:15 PM / TAKE THE SCENIC ROUTE

A short High Line stroll.

Walk toward the West 16th Street access and follow the southern stretch toward Gansevoort Street. Allow 30–45 minutes for the walk, photos and pauses, rather than trying to cover the whole park.

5:15 PM / LEAVE ROOM TO LINGER

Finish by the river at Little Island.

Allow about 15–20 minutes to reach Pier 55, with time for street crossings. Wander the park, enjoy the river views and take a breather. The public park is free; ticketed performances are separate. Stay around 45 minutes, or head home when you’re ready.

Sample timing allows breathing room. Opening hours, entrances, elevator service, weather and vendor availability must be checked for the actual outing date.

Put the plan on your phone

Three places. One little pocket of New York.

Explore the sample stops in Google Maps, then keep the written itinerary handy for the scenic High Line section.

Open the sample walking map ↗

The walking map connects Chelsea Market, the High Line’s Gansevoort entrance and Little Island. Google may choose street-level paths rather than the elevated park; use the written plan for the suggested West 16th Street-to-Gansevoort stroll. Check opening hours, entrances and current conditions before setting out.

The TTDNY Touch

The little things we’d add for you.

A good date needs a little room to be a date. Here’s how we’d make this afternoon feel more thoughtful, without filling every minute or spending your whole budget.

A small surprise for each other.

Before you leave Chelsea Market, each pick a small treat for the other person, keeping their food preferences in mind. Save the reveal for your river stop. Nothing elaborate—just a little “I saw this and thought of you.” Keep it within your food allowance.

A piece of old New York to notice.

At Little Island’s South Bridge entrance, look for the old steel archway. It’s a surviving piece of the Cunard–White Star building. Pause for a photo and a little waterfront history before you head into the park—it’s an easy detail to miss when you’re just following a pin.

Save your money for the good bits.

Little Island’s public park is free to visit, so you can put more of your budget toward food or a treat you’ll enjoy together. Performances in The Amph are separately ticketed. We’d leave some breathing room in your budget, too, so the afternoon feels relaxed.

That’s the idea behind the TTDNY Touch: a thoughtful surprise, a detail worth noticing and a useful way to make your budget go further. In your own plan, we’d choose the little extras around you. Any available discounts would be checked for your dates and eligibility.

Little Island’s archway history and admission details: official visitor FAQ, checked October 19, 2026. Treat purchases are optional and paid separately.

The money plan

A possible split of that $100 target: $60 for casual food, $20 for dessert or drinks and $20 as a buffer. These are spending allowances, not verified menu prices. Check menus before choosing; tax and tips need to fit within your allowance.

Getting there

For Chelsea Market, the A, C, E or L to 14th Street / Eighth Avenue is a useful starting point. Check service for your date. Tell us your actual starting area and walking preferences so your own route fits you.

If the weather turns

Skip the exposed park walks. Make Chelsea Market the indoor food-and-browsing anchor and use your remaining budget for a longer café stop, after checking the venue’s hours and seating. In your paid plan, the backup is selected around your date and preferences.

Why this fits the brief

One compact area, food before the walking, no need to chase a full-day checklist, and a waterfront finish. Your paid plan is built around your own people—not copied from this example.

One-time planning fee. Food, tickets and transport are separate. Choose your package, then tell us what would make it yours.

Official references checked October 17, 2026: Chelsea Market visitor information · High Line 2026 map (PDF) · Little Island visitor FAQ. This is a sample excerpt, not a reservation or a guarantee of access.

Know what comes with your plan

A plan you can actually use.
Not another list of places.

Your custom itinerary is a written plan sent by email, with links you can open on your phone. The sample above shows the style; your own dates, people, budget and preferences shape the result.

✓ Your route✓ Map links✓ Food ideas✓ Weather backup✓ Revision or refund

01 / YOUR ROUTE

Your day, in a sensible order.

A day-by-day schedule with suggested timing, up to five main stops per day, map links and practical travel notes. One day can mean a date night instead.

02 / THE USEFUL DETAILS

Food, budget and a backup.

Food ideas, useful provider links, spending guidance and a weather alternative. You choose and book activities directly; tickets, meals and transport are separate.

03 / ROOM TO REFINE

One small revision round.

Up to three activity or food swaps for the same dates, group and trip length, requested within seven days of delivery. Larger changes are quoted separately.

Want to talk it through before paying?

Ask about your ideas, scope or delivery date first. We can confirm the arrangements and send a payment link if you decide to go ahead. There is no charge to inquire.

Ask before ordering →

Standard checkout is for outings at least seven days away. Delivery timing is confirmed after review; if you need an agreed deadline before payment, use the inquiry option above. Priority Planning is available by request.

Not just for tourists

What would you love
someone else to figure out?

You bring the occasion. We turn it into a manageable route with nearby stops, food ideas, useful booking links and a backup for the weather.

A couple looking toward the New York waterfront and bridge
Photo: Theo Laflamme / Unsplash
01 / FOR TWO

Date nights & anniversaries

Go beyond “where should we eat?” Pair dinner with something to do, sensible travel and the right pace for your evening.

Autumn trees and Manhattan buildings beside the water in Central Park
Photo: Paul Huisman / Unsplash
02 / FOR YOUR CREW

Kids’ days & family outings

Age-appropriate ideas, manageable travel, food breaks and an indoor alternative. Less bouncing across the city.

A candlelit dinner table at Metrograph in New York City
Photo: Yimeng Zhao / Unsplash
03 / MAKE IT AN OCCASION

Birthdays & small celebrations

A thoughtful outing for up to four people. For a bigger group or a full event, ask for a separate scope first.

Manhattan skyline and the Brooklyn waterfront at dusk
Photo: Toni Tan / Unsplash
04 / FIRST NYC MOMENTS

A trip that fits together

Connect the sights you came for with neighborhoods, meals and enough time to enjoy them.

Rowboats and trees on the Lake in Central Park
Photo: Harry Gillen / Unsplash
05 / HOST WITHOUT THE TABS

Friends & family visiting

Show guests a New York that feels like you. Build around their must-dos and your actual starting neighborhood.

A landscaped walkway along the High Line at The Spur
Photo: Akshat Jhunjhunwala / Unsplash
06 / DO SOMETHING DIFFERENT

Solo days & friend catch-ups

A museum afternoon, a food neighborhood, a park-to-dinner route or a fresh way to spend a free day.

Rowboats on the Lake in Central Park

The small details make the day

Not just where to go.
How the day comes together.

A good plan remembers the meal, the travel, the pause—and what to do if the weather changes.

Illustrative planning: an easy park loop, a nearby lunch and one afternoon activity. Your plan is tailored to your own dates, group and preferences.

Photo: Harry Gillen / Unsplash. A reference image, not a booked activity.

The Love Your Plan Guarantee

Love your plan.
Or get your planning fee back.

We want you to feel good about the plan you receive. If it is not right for you, you can choose a revision or your money back.

Make it more you.Choose your included round of small revisions.
Or get a full refund.You do not have to try a revision first.

Contact us within seven calendar days of receiving your itinerary. The full refund covers your TTDNY itinerary-planning fee, including any Priority Planning fee. If you choose the revision and still are not happy, you can request a refund within seven calendar days of receiving that revision.

To use the guarantee, email hello@thingstodony.com with your order number and tell us whether you would like a revision or a refund. This guarantee covers our planning service; tickets, meals, transport, hotels and other purchases from outside providers are separate and are not covered.

Explore the planning packages →

Choose your planning time

One evening. A weekend.
A whole little escape.

Ready to make it yours? Every package covers one shared plan for up to four people. Choose your occasion and package below. Next, you will enter your outing details and review the total at checkout before paying.

Online ordering is being refreshed. Send us a planning request while we finish.

Your fee covers planning—not the activities. Tickets, meals, hotels, transit and reservations are separate. You book and pay providers directly. This service does not include childcare, venue booking or on-site event coordination.

Choose a first outing date at least seven days away. We confirm scope and delivery after reviewing your paid request. If we cannot accept it, your planning fee is refunded. For sooner dates, larger groups or a different scope, ask before paying.

Less back-and-forth

From “we should do something”
to a plan.

01 / CHOOSE

Pick the right package.

A day or evening, two days or three. Choose your occasion and continue to secure checkout.

02 / TELL US + PAY

Keep it in one order.

Add your date, group, starting area, budget and preferences. Pay with PayPal, card or an available digital wallet.

03 / LOOK FORWARD TO IT

We connect the dots.

We review your request, confirm scope and delivery by email, then create your plan. Your brief stays with your order.

Make a tradition of it

“Let’s do this
every month.”

We’re exploring recurring personal planning for date nights and family days. Help shape a service you would actually use.

Explore the NYC Plans Club →

Interest list only. No subscription, payment or automatic renewal.

A fresh reason to go out.

  • Monthly Date Night: an evening built around the two of you.
  • Monthly Family Day: an outing shaped around your children’s ages and interests.
  • Pricing and final scope shared before anyone joins.

Clear plans. Clear expectations.

A few things to know.

Can I order a date night instead of a full tourist day?

Yes. The $39 package covers one evening or one day. Choose date night at checkout and tell us your available hours, food preferences and kind of atmosphere. The fee is the same for either format.

Can you help with kids’ activities or birthdays?

Yes, as an outing-planning service. Tell us children’s ages, interests, budget, travel comfort and food or rest needs. Standard packages cover up to four people total. Bigger birthdays, parties or events need a separate agreed scope; childcare and on-site coordination are not included.

When will I receive my plan?

Book at least seven days before your first outing. After reviewing your paid request, we confirm the planning scope and delivery date by email. Please ask before ordering if you need a plan sooner. If we cannot accept the request, we refund the planning fee.

Can I get my plan sooner?

Priority Planning is an optional $29 one-time addition to any package, subject to availability. Request availability first and tell us your outing date and when you need your plan. If we can accept it, we confirm an exact deadline before payment and send a payment link. Delivery is within three calendar days after acceptance, payment and receipt of your complete brief. Please do not use standard checkout for an outing less than seven days away unless we have confirmed the arrangements in writing. Rush planning does not include tickets or guarantee activity availability.

What is the Love Your Plan Guarantee?

Contact us within seven calendar days of receiving your itinerary. Choose the included revision or a full refund of your TTDNY itinerary-planning fee, including any Priority Planning fee. If you try the revision and still are not happy, request a refund within seven calendar days of receiving that revision. Email hello@thingstodony.com with your order number. Tickets, meals, transport, hotels and other purchases from outside providers are not covered.

What changes are included?

One round of small changes: up to three activity or food swaps for the same dates, group and trip length, requested within seven days of delivery. New dates, extra days or a full redesign are quoted separately before further work.

Does paying reserve tickets, a table or a venue?

No. You are paying for planning. You make reservations and buy tickets directly from providers, subject to their availability, prices and terms. A recommendation does not guarantee a reservation or opening time.

Is this a subscription?

All three packages above are one-time purchases. NYC Plans Club is an interest list for a possible future recurring service; joining the list does not start billing.

What if I need to change or cancel my request?

Email hello@thingstodony.com with your order number as soon as possible. Tell us what changed so we can check the stage of work and discuss the next step.

A conversation before a commitment

Ask us before you order.

Not sure which package fits, or want scope and delivery agreed before payment? Tell us your outing date, group size, budget and what you would love help with. This is also the place for larger groups, nearer dates and special requests. There is no charge to inquire, and submitting this form does not place a paid order.

How TTDNY works: We mix public/community listings with bookable experiences. We label dates, prices and availability based on what we can verify. Some booking links are affiliate links, which may earn TTDNY a commission at no extra cost to you. Affiliate status does not determine recommendation ranking.