Alaska — June 1

Day 1 Mon, Jun 1

Boston → Anchorage

Travel day Anchorage

AMFly BOS → ANC (1 stop, ~10–12 hrs total via SEA or MSP)
PMLand Anchorage. Pick up rental SUV (Turo or Avis at ANC)
EVEDinner: 49th State Brewing or Moose's Tooth. Sleep early — sun won't set until ~11:30 PM

Tip: Book a hotel near downtown (Hotel Captain Cook, Lakefront, or an Airbnb in South Addition). Grab groceries at Fred Meyer for the road.

Day 2 Tue, Jun 2

Drive Seward Highway → Seward

Drive ~2.5 hrs Scenic Seward

AMDepart Anchorage. Stop at Beluga Point (whale spotting), Bird Point, Girdwood
MIDDetour: Alyeska tram or Crow Creek Mine. Lunch in Girdwood (Jack Sprat)
PMContinue over Turnagain Pass. Stop at Tern Lake junction
LATEArrive Seward. Walk waterfront, dinner at The Cookery or Ray's

Don't miss: Alaska SeaLife Center for an evening rainy-day option. The Seward Hwy is rated one of America's most scenic drives — give it 4–5 hrs with stops.

Day 3 Wed, Jun 3

Kenai Fjords Glacier Cruise 🧊

Icebergs Whales Book ahead

7:30Boarding — Major Marine Tours or Kenai Fjords Tours
8–4Full-day Northwestern or Aialik Glacier cruise (8.5 hrs). Calving glaciers, orcas, humpbacks, sea otters, puffins, Steller sea lions
PMBack in Seward. Soak at the harbor, beer at Seward Brewing Co.

Pick the long cruise (8.5 hrs, not 6). The shorter ones don't reach the calving glaciers. Bring layers — it's cold on deck even in June. Dramamine ahead of time if you're prone to seasickness.

Day 4 Thu, Jun 4

Kayak Among Icebergs 🛶

Kayak Icebergs Book ahead

AMTop pick: Liquid Adventures — Bear Glacier ice-field paddle (helicopter or water-taxi in, paddle through a lagoon of icebergs the size of houses)
ALTSunny Cove Sea Kayaking — Aialik Bay water-taxi + glacier paddle (full day)
EZMellow option: Resurrection Bay 3-hr guided paddle from Lowell Point
EVETonsina Point hike (4 mi RT) for a sunset stretch, dinner in Seward

The Bear Glacier trip is the headline kayak experience in Alaska. ~$500–800/person but unforgettable. Book months ahead. If weather scrubs the helicopter, water taxi is the fallback.

Day 5 Fri, Jun 5

Exit Glacier → Anchorage

Hike Drive ~2.5 hrs

AMExit Glacier — choose: Harding Icefield Trail (8.2 mi RT, 3,500 ft, 6–8 hrs, world-class views) or Edge of the Glacier (2 mi easy)
PMPack up, drive back toward Anchorage. Stop in Hope or at Portage Glacier visitor center
EVEAnchorage overnight — easier launch toward Denali tomorrow

Harding Icefield is a top-5 day hike in Alaska. Snowshoes may still be needed on the upper section in early June — check the ranger station the day before.

Day 6 Sat, Jun 6

Anchorage → Talkeetna → Denali

Drive ~5 hrs Talkeetna stop Denali

AMDepart Anchorage on Parks Hwy
MIDDetour to Talkeetna (quirky river town, Denali viewpoint, brewery). Lunch at Denali Brewing
OPTIf clear skies: Talkeetna Air Taxi flightseeing + glacier landing (1.5–2 hrs). This is THE flight to take
PMContinue to Denali (Healy or McKinley Park area). Check in, easy walk near visitor center

Flightseeing weather is the constraint. If Day 6 is clear, fly today and skip Day 8's flight. June has long days — flights run as late as 9 PM.

Day 7 Sun, Jun 7

Denali — Bus Into the Park

Wildlife Book ahead All day

AMTransit bus deep into the park (Toklat River turnaround, ~6.5 hrs RT — note: road closed past Mile 43 due to Pretty Rocks landslide repair, check 2026 status)
ALLSpot grizzlies, caribou, Dall sheep, moose, possibly wolves. Hop off bus to walk anywhere
EVEDinner in Healy (49th State Brewing — Magic Bus from Into the Wild is here)

Book bus tickets the moment they open (early Dec for next summer — likely already needs booking). Bring binoculars, a packed lunch, and layers. Only ~30% of visitors actually see Denali itself — Denali makes its own weather.

Day 8 Mon, Jun 8

Denali — Hike & Flightsee

Hike Flightseeing

AMHike: Savage River Loop (2 mi flat, easy wildlife) or Mount Healy Overlook (5.4 mi, 1,700 ft, big views)
PMFlightseeing + glacier landing from Talkeetna or Kantishna — Sheldon Air Service, K2, Talkeetna Air Taxi. Land on Ruth or Kahiltna Glacier
EVESled-dog kennel demo at park HQ (free, ranger talk + huskies)

If yesterday's bus didn't deliver Denali views, today's flight will. 2 hrs in a Cessna or Otter circling the south face — best money spent on the trip.

Day 9 Tue, Jun 9

Denali → Anchorage

Drive ~5 hrs Anchorage

AMSlow morning, last Denali viewpoint stop
MIDDrive south. Lunch in Talkeetna or Wasilla
PMArrive Anchorage. Bike the Tony Knowles Coastal Trail (rentals downtown — sunset moose & beluga sightings)
EVEDinner: Marx Bros Cafe (splurge) or Snow City Cafe

Alternative: Take the Alaska Railroad Denali Star one-way back (8 hrs, dome car). Drop the rental in Denali, retrieve in Anchorage — costs more but is its own experience.

Day 10 Wed, Jun 10

Anchorage Day — Matanuska Glacier Trek

Ice trek Day trip

AMDrive to Matanuska Glacier (~2 hr each way, scenic Glenn Hwy)
MIDGuided ice trek with MICA Guides — walk on the glacier, blue ice, crevasses (3–4 hrs)
PMBack to Anchorage. Flattop Mountain trailhead for sunset (7-mile views over Cook Inlet)
EVELast dinner: 49th State or South Restaurant. Pack up

Matanuska is the only glacier in AK you can drive to and walk on. Skip if you're glacier-fatigued — substitute Anchorage Museum + Flattop + a relaxed evening.

Day 11 Thu, Jun 11

Anchorage → Boston

Travel day

AMReturn rental car. Snow City Cafe for breakfast if time
MIDFly ANC → BOS (red-eye works well — sleep on the plane)

Iceberg & Glacier Experiences

Bear Glacier Kayak

Liquid Adventures · Seward · $500–800

Helicopter or water-taxi into a hidden lagoon filled with icebergs the size of houses. The headline kayak experience in Alaska.

Aialik Bay Kayak

Sunny Cove · Seward · $400

Water-taxi to Aialik Glacier, paddle right up to a calving tidewater glacier. Seals on bergy bits, full day.

Kenai Fjords Cruise (8.5 hr)

Major Marine · Seward · $200

Calving Northwestern or Aialik Glacier, orcas, humpbacks, puffins, sea otters, sea lions. Hot lunch included.

Matanuska Glacier Trek

MICA Guides · 2 hr from Anchorage · $130

Walk on the glacier — crampons, blue ice, crevasses. Drive-up access, no boat needed.

Exit Glacier — Harding Icefield

Kenai Fjords NP · Free · 8 mi RT

One of the great day hikes in North America. Climb to the edge of a 700-square-mile ice sheet.

Portage / Byron Glacier

1 hr from Anchorage · Free

Easy stop on the Seward Hwy. Boat tour out to Portage Glacier face, or short walk to Byron Glacier ice cave.

Wildlife

Denali Transit Bus

Denali NP · $40 · all day

Best wildlife viewing in the state — grizzlies, caribou, Dall sheep, moose, wolves. Hop off anywhere.

Alaska Wildlife Conservation Center

Portage · $20 · 1 hr

Rescued bears, moose, wood bison, lynx. Easy stop on the way to Seward.

Beluga Point

Seward Hwy · Free

Pull-off on Turnagain Arm. Beluga whales chase salmon up the inlet on incoming tides — check tide tables.

Bear Viewing — Lake Clark

Floatplane day trip · $900

Splurge add-on: fly to Lake Clark NP for guided coastal brown bear viewing. Bears feeding on sedge in June.

Flightseeing

Talkeetna Air Taxi — Denali Grand Tour

Talkeetna · 2 hr + glacier landing · $550

The classic. Circle the south face of Denali, land on a glacier in skis. Pick a clear day.

Sheldon Air Service

Talkeetna · similar · $500

Smaller operator, deep Denali history (Don Sheldon was the original mountain pilot).

Seward Helicopter

Seward Helicopter Tours · $400

Add-on if you skip Bear Glacier kayak — fly over the Harding Icefield, optional dog-sled landing.

Add-Ons & Backup Days

Hatcher Pass

1 hr from Palmer · Free

Alpine tundra, old gold mine (Independence Mine SHP), wildflowers. Easy half-day from Anchorage.

Whittier — 26 Glaciers Cruise

Phillips Cruises · $200

Alternative to Kenai Fjords. Drive through the one-lane Anton Anderson tunnel, cruise Prince William Sound.

Alaska Railroad — Denali Star

Anchorage ↔ Denali · $200+

Dome cars, slow scenic ride. Use one-way to swap out a driving day.

Spencer Glacier Whistle Stop

Train-only access · $100

Take the train to a trailhead, paddle a small lake of icebergs, train back. Cult favorite.

At a glance

Dates: Mon Jun 1 – Thu Jun 11, 2026 (11 days)
From: Boston (BOS)
To: Anchorage (ANC)
Daylight: ~19 hrs in June. Sunset Anchorage ~11:30 PM, Denali ~midnight
Weather: 40s–60s°F. Rain likely. Snow possible at altitude
Driving: ~1,000 miles total. Rent SUV/AWD for peace of mind
Time zone: AKDT — 4 hrs behind Boston
Cell: Verizon best in AK. Spotty in Denali, none past mile 30 in park
Cash: Cards everywhere. ~$100 cash for tipping guides

Lodging plan

Anchorage (Nights 1, 5, 9, 10)

4 nights total

South Addition Airbnb or Hotel Captain Cook downtown. Easy car drop on departure day.

Seward (Nights 2, 3, 4)

3 nights — same place

Seward Windsong Lodge, Harbor 360, or a downtown VRBO. Walkable to harbor.

Denali (Nights 6, 7, 8)

3 nights — same place

Denali Bluffs, Grande Denali, or Healy cabins. Healy is cheaper and has 49th State Brewing.

Booking priority (do this first!)

Flights BOS↔ANC — June is peak. Book 3+ months out.
Denali transit bus — sells out fast.
Bear Glacier kayak (Liquid Adventures) — limited slots.
Kenai Fjords cruise — 8.5 hr Northwestern Glacier tour.
Lodging in Seward & Denali — both fill up by spring.
Rental car — AK rentals get expensive late.
Flightseeing — flexible, can book 1–2 weeks out and watch weather.

Things to actually book — links

Liquid Adventures (Bear Glacier kayak)

liquid-adventures.com

Search "Bear Glacier" — pick the helicopter add-in for the iconic shots.

Sunny Cove Sea Kayaking

sunnycove.com

Aialik Glacier full-day or Resurrection Bay half-day.

Major Marine Tours

majormarine.com

The 8.5-hour Northwestern Glacier cruise.

Denali Park Bus

reservedenali.com

Transit bus to Toklat or Eielson (depending on road status). Grab the earliest morning departure.

Talkeetna Air Taxi

talkeetnaair.com

Denali Grand Tour with glacier landing.

MICA Guides (Matanuska)

micaguides.com

Glacier trek — the standard 4-hour is plenty for a first ice walk.

Alaska Railroad

alaskarailroad.com

Denali Star, Coastal Classic to Seward — book Goldstar for the dome car.

Turo / Avis (rental)

turo.com / avis.com

Pick up at ANC, return at ANC. AWD SUV recommended.