Trip planning

Some tripsshouldn’t be DIY.

Japan. A safari. Three regions of Italy in ten days. Our advisors craft your dream trip with partners who live there; your member rates and perks included.

An infinity pool cut into red desert cliffs at a remote luxury retreat.

How it works

Describe your trip

Tell us where, when, who, and what a great trip would look like to you.

We build it

Your advisor drafts an itinerary with our on-the-ground partners at the destination.

Book with your perks

Most hotels book through SKYLARK: member rates, upgrades, credits, breakfast.

Your advisors

People who’ve actually been.

The destinations each advisor can plan in their sleep, and what they look for in a hotel once they get there.

Teddy Balestro

Italy · Greece · Spain · Saint Barths

I pack for trips the way I live: big appetite, bigger sense of adventure, always room for spontaneity.

Bucket list: Rwanda, Japan, or Patagonia.
Favorite hotels: Singita Boulders Lodge, Il San Pietro di Positano, Forestis, and Nihi Sumba.
What makes a hotel special: The details you didn't think to ask for, a staff member who becomes a character in the story, a sense of place, and how it makes you feel leaving, not just arriving.
Zodiac: Aries.

Trips we’ve built

Kenya & Mauritius, 15 days

With our East Africa partners

Days 1–4

Segera Retreat

Laikipia

The Laikipia wilderness from a private villa retreat.

Day 5

Giraffe Manor

Nairobi

Afternoon tea with the resident Rothschild giraffes.

Days 6–8

Sala's Camp

Masai Mara

The quiet southern corner of the Mara, and a hot-air balloon safari at dawn.

Days 9–10

Angama Mara

Masai Mara

Two nights perched on the edge of the Great Rift Valley, the Mara spread out below.

Days 11–15

Shangri-La Le Touessrok

Mauritius

Five nights on a private-islet beachfront to close out the trip, dinner tables set each night.

An Italian Summer, 10 days

With our Italy partners

Days 1–4

Villa TreVille

Positano

An afternoon in Ravello with a sunset dinner, a beach-club lunch at Le Sirenuse, and a private boat day along the coast.

Days 5–6

Jumeirah Capri Palace

Capri

Across by boat for a cooking class and a slow island day.

Day 7

Grand Hotel Excelsior Vittoria

Pompeii & Naples

The ruins with a private guide on the drive north.

Days 8–10

Bvlgari Hotel Roma

Rome

The Colosseum and Roman Forum by day, the Vatican after the doors close.

China & the Philippines, 18 days

Days 1–3

The Peninsula Beijing

Beijing

The Forbidden City, a calligraphy lesson in the hutongs, and the Great Wall at Mutianyu.

Days 4–5

Sofitel Legend People's Grand Hotel Xi'an

Xi'an

The Terracotta Warriors, then a dumpling banquet at De Fa Chang.

Days 6–7

The Upper House Chengdu

Chengdu

In by first-class high-speed train, then the pandas early, while they're still awake.

Days 8–10

Amandayan

Lijiang

The UNESCO old town on foot and a cableway up Jade Dragon Snow Mountain.

Days 11–12

Mandarin Oriental Manila

Manila

Intramuros by horse-drawn kalesa, then a Filipino feast with traditional dance.

Days 13–18

El Nido Resorts Lagen Island

El Nido

Five nights in a water villa on Bacuit Bay, with lagoons and kayaks at the jetty.

User Reviews

Real reviews we’ve gotten from our users.

Hover over a hotel photo to show the review.

The manor house and lit fountain courtyard at Rosewood Miramar Beach at dusk — “Not only did we pay less than the direct hotel rate, we also received perks that really elevated the trip — daily breakfast credit, a resort credit, and a room upgrade. Everything felt seamless from start to finish, and the added value was very real.”
Rosewood Miramar Beach · Montecito

The château at Domaine Les Crayères above its formal gardens in evening light — “The hotel is truly beautiful, and everyone has been incredibly kind and attentive. Thanks to your help, the hotel kindly offered us complimentary champagne and breakfast, which was such a thoughtful gesture.”
A note to Katrina · Domaine Les Crayères, Champagne

A suite terrace at Four Seasons Resort Maui, palms and the ocean beyond — “Our trip to Maui was fantastic. Thank you for helping us with the room change, it made a big difference. The breakfast credit was also much appreciated, especially by our daughters! We'd like to do exactly the same thing again for 2026.”
Four Seasons Resort Maui at Wailea

The lantern-lit courtyard entrance of Rosewood Mansion on Turtle Creek at twilight — “Thank YOU for our wonderful stay last week, you truly made it so easy and seamless. The hotel was fabulous and my colleagues were so happy with the accommodations.”
A note to Jack · Rosewood Mansion on Turtle Creek, Dallas

A suite bedroom at Mandarin Oriental Mayfair beneath a sculptural gold chandelier — “Just a note to thank the Skylark team for making the trip easy to administer. A few changes along the way, these were handled smoothly and professionally, and I realised tangible benefits. Looking forward to the next trip.”
A note to Teddy · Mandarin Oriental Mayfair, London

A toile-papered room at Le Normandy in Deauville, the bed dressed in cream and rose — “Just checked in and I want to thank you for the lovely note and gift! The hotel is absolutely amazing and we can't wait to explore Deauville.”
Hôtel Barrière Le Normandy · Deauville

Start a trip

Start a trip.

Tell us about your dream trip and your advisor will be in touch to set up a call.

Note: Trip planning is a member service. Join SKYLARK for $250/year and take $250 off your first planning fee. Planning starts at $550 per trip for two. Explore membership, or .