Dolomites + Milan

About This Trip

Our marquee international trip takes you to the Italian Dolomites, a UNESCO World Heritage site and co-host of the 2026 Winter Olympics. Ride the legendary Dolomiti Superski circuit under jagged alpine peaks, then unwind in Milan with curated cultural experiences, world-class dining, and Italian fashion. This is the trip of a lifetime.

The Mountain

Dolomiti Superski — Cortina d'Ampezzo

January 17 — 22, 2027 · 6 days skiing

Six days of skiing across the iconic Dolomiti Superski circuit with access to Cortina, Kronplatz, and Alta Badia. Expect dramatic limestone spires, perfectly groomed corduroy, long cruising runs, and legendary Italian mountain cuisine.

Lodging: Hotel Cristallo

Historic 4-star mountain hotel with panoramic Dolomite views, ski storage, and wellness spa.

The City

Milan

January 23 — 26, 2027 · 3 nights

Explore the Duomo, Galleria Vittorio Emanuele II, and the Brera art district. Enjoy curated group dinners, a guided fashion district tour, and free time to discover one of Europe's most stylish cities.

Lodging: NYX Hotel Milan

Contemporary art-focused boutique near Milano Centrale with rooftop bar.

What's Included

✓ Group transfers between Venice/Milan airports and Cortina

✓ 5 nights mountain hotel in Cortina (double occupancy)

✓ 3 nights boutique hotel in Milan (double occupancy)

✓ Welcome dinner in Cortina

✓ Farewell dinner in Milan

✓ Guided Milan walking tour

✓ Duomo rooftop terrace access

✓ Aperitivo social evening

✓ Trip photographer

✓ AWWLAND swag bag

What's NOT Included

✗ International flights to Venice (VCE) / from Milan (MXP)

✗ Lift tickets (Ikon Pass accepted; otherwise ~€300-350)

✗ Travel insurance (required for international trips)

✗ Gear rental (available as add-on)

✗ Lessons (available as add-on)

✗ Meals not listed as included

✗ Personal expenses and shopping

✗ Italy tourist visa if required

Ikon Pass Info

Dolomiti Superski is on the Ikon Pass — Ikon Pass holders get 7 days, Ikon Base Pass holders get 5 days. If you have an Ikon Pass, you are covered. Otherwise, a 6-day Dolomiti Superski pass costs approximately €300-350 and grants access to 1,200+ km of runs across 12 ski areas.

Payment Schedule

Oct 15, 2026

$500 — Deposit

Secures your spot

Dec 1, 2026

$1,100 — Second Payment

Dec 31, 2026

$1,100 — Third Payment

Jan 5, 2027

$1,100 — Final Payment

Cancellation Policy

Full refund (minus $100 admin fee) if cancelled 90+ days before departure
50% refund if cancelled 60-89 days before
25% refund if cancelled 30-59 days before
No refund within 30 days of departure

11 days · Intermediate

Dates Jan 15 — 26, 2027

Duration 11 days

Mountain Days 6 days

City Days 3 nights

Skill Level Intermediate

Capacity 20 participants

Spots Left 8 spots

Deposit $500

Ikon Pass ✓ Accepted

Free account required to register. Deposit due Oct 15, 2026.