The Five On It Start My Custom Five
Custom Trip Planning

Your getaway,
built just for you.

Girls trips, honeymoons, date nights, celebrations, or whatever you're dreaming up. Tell us where you're going and the trip you want, and we'll build a personalized plan around it, with the neighborhoods, restaurants, experiences, timing, and insider details tailored just to you.

Start My Custom Five See a Sample Plan
✓ Personalized to your trip✓ Delivered in 3–5 business days✓ Starting at $50✓ No sponsored recommendations✓ Built by real travelers

What's inside your Custom Five?

A personal, mobile-friendly guide built entirely around your trip, not a template.

✓Personalized itinerary
✓Neighborhood recommendations
✓Restaurants & bars
✓Activities & experiences
✓Where to stay
✓Transportation guidance
✓Reservation recommendations
✓Interactive map
✓Booking links
✓Insider tips
✓Mobile-friendly guide
✓Timing for every day

A peek inside.

An example of what a Custom Five looks like, this one built from a real request.

The request · Example

Three nights in New York

  • Two friends
  • Cocktails
  • Great food
  • Shopping
  • One iconic experience
Custom Five · Example

Sarah & Mia's New York Weekend

3 nightsWest Village baseCocktails + foodElevated budget
Saturday · planned to the hour
10:30aCoffee at Maman, then a boutique route through SoHo, ordered so you never double back.
1:00pLunch at Balthazar, order the seafood plateau and ask for a banquette.
4:30pGolden hour across the Brooklyn Bridge, start Manhattan-side so you walk into the skyline.
8:00pDinner at Rezdôra. Reserve 30 days out at 9am, we'll remind you the morning of.
10:30pNightcap at a hidden bar, a 4-minute walk from dinner.
A couple of the insider tips inside Balthazar's back room is quieter and takes walk-ins before noon. Start the bridge at 4:30 sharp to beat the golden-hour crowds.
Your full plan also includes
+Friday & Sunday, planned the same way +Your hotel pick, plus two backups +Two Broadway shows, matched to you +Rainy-day & late-night alternatives +Every reservation, with when to book +An interactive map, saveable to Google Maps

Start My Custom Five Just a taste, yours is built from scratch.

Simple, transparent pricing

Indicative packages to show scope. We confirm the exact price by email before any payment.

Most popular

The Custom Weekend

$50 starting at
Skip the 40 open tabs. A full weekend, personally researched and planned around you, ready to use, for less than the cost of one dinner out.
Best for: 2–3 day trips, couples, friends, first-time visits, birthday or celebration weekends
  • Personalized daily itinerary
  • Restaurants, bars, and activities
  • Neighborhood recommendations
  • Suggested timing and sequencing
  • Reservation guidance
  • Direct booking and map links
  • Insider tips
  • Mobile-friendly plan
Start My Custom Weekend

The Extended Trip

$85 starting at
Best for: 4–5 day trips, travelers who want a fuller itinerary, trips combining multiple neighborhoods or day trips
  • Everything in the Custom Weekend, plus
  • A complete 4–5 day itinerary
  • Multiple neighborhoods & day-trip options
  • Where-to-stay guidance
  • Transportation & logistics notes
  • Backup recommendations for every day
Start My Extended Trip

Full Trip Planning

Custom Quote
Best for: trips longer than five days, large groups, multi-city travel, international itineraries, special occasions, and complex dietary, accessibility, or scheduling needs
  • Everything in the Extended Trip, plus
  • Multi-city & international logistics
  • Group coordination
  • Special-occasion planning
Request a Quote

Just need one day? Focused planning, one perfect day, date night, a celebration, or a single-neighborhood itinerary, starts around $25–$35.

Final pricing is confirmed before payment based on trip length, group size, destination, and complexity. These packages are examples to help you understand scope.

Complete Guide or Custom Five?

Both do the research for you. Here's how to pick.

Complete Guides

Perfect when
  • You're visiting one of our guide cities
  • You want ready-made plans
  • You need instant access
  • You want the most affordable option
Browse Guides

Custom Five

Perfect when
  • You have unique preferences
  • Your destination isn't covered
  • You're planning a celebration
  • You have accessibility or dietary needs
  • You want a plan built around your exact trip
Start Custom Planning

How it works

1

Tell us about your trip

  • Destination
  • Dates
  • Travelers
  • Budget
  • Preferences
2

We research & curate

  • Neighborhoods
  • Logistics
  • Reservations
  • Timing
  • Experiences
3

Receive your Custom Five

  • Personalized guide
  • Interactive map
  • Booking links
  • Insider tips
4

Book your favorites

  • Reserve directly using the included booking links
  • Your plan, ready to go

What's included, and what's not

Clear scope, so you know exactly what you're getting.

Included

  • Research
  • Recommendations
  • Personalized planning
  • Booking links
  • Neighborhood guidance
  • Interactive map
  • One reasonable revision after delivery

Not included

  • Booking your flights
  • Making reservations on your behalf
  • Real-time concierge support
  • Guaranteeing pricing or availability

Start your Custom Five

Tell us about your trip. We'll reply within one business day with the recommended package, pricing, and next steps.

No payment now. We confirm scope and price by email first.

Questions, answered

How much does it cost?

The Custom Weekend starts at $50, the Extended Trip at $85, and Full Trip Planning is a custom quote. One-day focused planning starts around $25–$35. We confirm the exact price by email before any payment, based on trip length, group size, destination, and complexity.

How long does it take?

Most Custom Fives are delivered within 3–5 business days of confirming your request and details.

Can you plan cities not on your website?

Yes. Custom planning isn't limited to our guide cities, tell us where you're headed and we'll build it.

Do you make reservations?

We include booking links and reservation recommendations, but you book directly, so you stay in control of your own accounts and cards.

Can you help with hotels?

Absolutely. We recommend the neighborhood and specific places to stay matched to your trip, with booking links.

Can I request revisions?

Every Custom Five includes one reasonable revision after delivery. Additional revisions are quoted separately.

Are recommendations sponsored?

Never. Everything is independently curated, with no sponsored placements, built only around your trip.

Can you plan for large groups?

Yes, large groups and special occasions are a great fit for full trip planning. Tell us the details and we'll quote it.