The Greece Collection · Issue No. 01

01

Santorini

The island that introduced the world to Cycladic luxury

In This Guide

Where to Stay My Hotel Picks Three Perfect Days
Santorini · At a Glance

The caldera is only the beginning.

Best For

  • Honeymoons
  • First-Time Greece
  • Luxury Travelers
  • Celebrations

Ideal Stay

  • 3–4 Nights

Best Months

  • May–June
  • September–October

Don't Miss

Sunset Catamaran Cruise

See the caldera from the sea.

Winery Lunch

Taste Santorini's volcanic wines.

Fira to Oia Hike

The island's most iconic walk.

Private Caldera-View Suite

The quintessential Santorini experience.

Getting Around

Private transfers are the easiest way to travel between the airport, ferry port, and your hotel. I also arrange private helicopter transfers through my partnership with Hoper, as well as private boat transfers, for travelers combining Santorini with nearby islands. Rental cars and ATVs provide flexibility, but most luxury travelers won't need one if staying along the caldera.

Keith's Take

Santorini is one of those rare destinations that truly lives up to the hype. The secret isn't seeing more, it's slowing down. Wake up early, linger over long lunches, and enjoy the caldera from your own terrace instead of chasing every viewpoint. With the right hotel and itinerary, it's one of the most unforgettable luxury destinations in Europe.

Where to Stay

Oia

Classic Santorini luxury and iconic sunsets.

Imerovigli

The quietest luxury hotels and best honeymoon setting.

Fira

Restaurants, nightlife, and central convenience.

Canaves Oia Suites — Santorini
Santorini

Canaves Oia Suites

An icon of Oia

Some hotels become famous because of their views. Canaves Oia Suites has those, but it's the feeling of staying here that keeps people coming back. Renovated in 2024, the architecture is timeless, the service is polished without feeling formal, and every suite is designed to make the caldera the center of the experience. For a first luxury trip to Santorini, it's one of my easiest recommendations.

Best For Honeymoons, Celebrations, Luxury Seekers, First Time Greece
Starting Rate From $1,200/night
Room I'd Book Infinity Pool SuiteThe signature Canaves experience with a private infinity-edge pool overlooking the caldera and panoramic views of Oia.
Keith's Notes

Don't assume every room has a pool. Unlike Andronis Boutique, private pools and jacuzzis aren't standard across every room category. If that's part of your Santorini vision, book accordingly.

Request a higher-category suite. The suites higher on the caldera offer more privacy than those below.

Don't underestimate the stairs. Even one of Oia's more accessible luxury hotels involves plenty of climbing. The views are worth it, but you'll definitely get your steps in.

Keith's Take

If someone tells me it's their first trip to Santorini and they want a hotel that's hard to get wrong, Canaves Oia Suites is always near the top of my list. It delivers the classic caldera experience with polished service, beautifully renovated suites, and an atmosphere that feels effortlessly luxurious.

Canaves Oia Suites detail
Andronis Boutique Hotel — Santorini
Santorini

Andronis Boutique Hotel

A caldera classic

Few hotels capture the essence of Santorini quite like Andronis Boutique. Set high above Oia's famous footpath, it combines iconic caldera views with genuinely warm hospitality. The atmosphere feels lively without ever becoming crowded, making it one of the easiest hotels to recommend for travelers experiencing Santorini for the first time.

Best For Honeymoons, Couples, Cliffside Views, Classic Santorini
Starting Rate From $900/night
Room I'd Book Executive Suite with Heated PoolThe sweet spot between privacy, space, and uninterrupted caldera views.
Keith's Notes

Expect a serious workout. Andronis Boutique is spread across the cliffside, with numerous staircases connecting the suites, restaurants, and common areas. If mobility is a concern, this is worth considering before you book.

Reserve dinner at Lycabettus Restaurant. The best tables disappear quickly during peak season.

Not every traveler is looking for the same Santorini. If you'd prefer larger accommodations or a more family-friendly atmosphere, I'd also look at Andronis Arcadia or Andronis Concept. Both maintain the service and design that make the Andronis collection one of my favorites.

Keith's Take

If I'm planning a Santorini honeymoon for younger couples, this is almost always my first recommendation. It delivers the iconic whitewashed architecture, dramatic caldera views, and lively atmosphere people imagine when they picture the island, while still feeling refined and romantic.

Andronis Boutique Hotel detail
Canaves Epitome — Santorini
Santorini

Canaves Epitome

Santorini, reimagined

Located just outside the center of Oia, Canaves Epitome trades the island's busiest footpaths for spacious villas, peaceful surroundings, and some of the best sunsets you'll find anywhere on the island. With everything from one-bedroom villas to expansive two- to five-bedroom residences, it's one of Santorini's strongest options for families and groups traveling together.

Best For Privacy, Sunset Chasers, Families, Repeat Santorini Visitors
Starting Rate From $1,100/night
Room I'd Book One Bedroom Pool VillaThe perfect balance of indoor-outdoor living, privacy, and sunset views without sacrificing proximity to Oia.
Keith's Notes

Book a Pool Villa. The added privacy and indoor-outdoor living define the Epitome experience.

Wander the property's grounds. The gardens are the largest in the Cyclades, and feel a world away from busy Oia.

Make sure to have dinner on property. Omnia was the best meal I had in Greece.

Keith's Take

If Canaves Oia Suites is Santorini's classic icon, Canaves Epitome is its modern evolution. It's the property I recommend for travelers who want the beauty of Oia but appreciate a little more privacy, space, and a slower pace.

Canaves Epitome detail
Santorini · Three Perfect Days

How I'd Spend Three Days Here

How I'd spend three unforgettable days on Greece's most iconic island.

Santorini scenery

Day One | Arrive

Check into your hotel and resist the urge to see everything at once. Spend the afternoon settling into your private terrace, enjoying lunch overlooking the caldera, and unwinding by the pool. End the day with a sunset catamaran cruise followed by dinner with uninterrupted sea views.

Stay: Canaves Oia Suites or Andronis Boutique Hotel
Dinner: Lycabettus Restaurant

Day Two | Explore

Wake early to wander Oia before the village comes alive. Spend the afternoon enjoying a leisurely winery lunch and tasting Santorini's volcanic Assyrtiko before returning to your hotel to relax. Finish the evening with dinner watching the sunset at Omnia at Canaves Epitome.

Don't Miss: Vassaltis Winery
Dinner: Omnia

Day Three | Savor

Enjoy a slow breakfast before hiking the scenic trail between Fira and Oia. Spend your final afternoon relaxing by the pool or at the spa before one last sunset from your own terrace. End your stay with a long farewell dinner overlooking the Aegean.

Keith's Tip

Skip the crowded sunset viewpoints and enjoy golden hour from your hotel instead or via a Private Sunset Cruise.

Want the full hotel-by-hotel breakdown? See Keith's Santorini Hotel Rankings for all 10 properties, ranked.

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