Trip planning

Some tripsshouldn’t be DIY.

Japan. A safari. Three regions of Italy in ten days. Our advisors plan them with partners who live there, and most hotels book with your member rates and perks.

Trip planning from $550 per trip for two. Advisor support on your bookings is always included with membership.

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.

The Best of Iceland, 7 days

Days 1–2

The Reykjavik EDITION

Reykjavík

City base, an evening ride with Viking horses, and a descent inside a dormant volcano.

Day 3

ION Adventure Hotel

Þingvellir

Snorkeling the Silfra fissure, the gap between two continents.

Day 4

101 Hotel Reykjavik

Hvammsvík

Hot springs at the edge of the fjord, lava-field buggies on the way back.

Days 5–6

ION Adventure Hotel

The South Coast

A private ice-cave tour under the Katla volcano.

Day 7

The Retreat at Blue Lagoon

Blue Lagoon

A retreat-spa day before the flight home.

From recent trips

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 relationships behind the rates

Booked through SKYLARK, you check in as a VIP.

Virtuoso member, part of Ovation (an Amex GBT company), and a preferred partner to the world's leading hotel brands. Booked through us: daily breakfast for two, room upgrades, property credits, and VIP recognition.

Benefits vary by property and stay; upgrades and check-in courtesies are subject to availability.

Start a trip

Start a trip.

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

Trip planning is a member service. Join SKYLARK and take $250 off the planning fee on your first trip, so the membership pays for itself the first time you use it. Explore membership, or if you already have one.

Trip planning from $550 per trip for two. Advisor support on your bookings is always included with membership.