Working route + itinerary

Oct 1 – 3, 2026

Santiago

Arrive, buy the car, paperwork, gear — then leave the city south.

• Car · inspection · gear
• First days in Chile

Oct 4 – 5, 2026

Valparaíso

Pacific coast stop before turning inland toward the lakes.

• Hills · port · Pacific

Oct 6 – 9, 2026

Pucón

Lakes District — volcanoes, hot springs, and the start of wilder Chile.

• Volcanoes · lakes · hikes

Oct 10 – 14, 2026

Puerto Montt · Chaitén

Gateway to the Carretera Austral — ferry links and the road south.

• Puerto Montt
• Chaitén · Pumalín

Oct 15 – 21, 2026

Coyhaique · Río Tranquilo

Heart of the Carretera Austral — fjords, marble caves, and empty road.

• Coyhaique
• Puerto Río Tranquilo · Marble Caves

Oct 22 – 24, 2026

Cochrane

Far south on the Austral before crossing toward Argentine Patagonia.

• Carretera Austral endgame

Oct 25 – 29, 2026

El Chaltén

Fitz Roy country — hiking capital of Patagonia.

• Fitz Roy · trails · wind

Oct 30 – Nov 1, 2026

El Calafate

Perito Moreno and the ice before Torres del Paine.

• Perito Moreno glacier

Nov 2 – 7, 2026

Torres del Paine

The towers — one of the great trekking landscapes on Earth.

• W / O circuit · granite towers

Nov 8 – 13, 2026

Ushuaia

End of the road south — then board for Antarctica.

• Punta Arenas en route
• Ushuaia · embark

Nov 14 – 24, 2026

Antarctica

Antarctic Peninsula cruise — the southern geographical anchor.

• Peninsula · ice · wildlife
• Return to Ushuaia Nov 25–26

Nov 27 – 30, 2026

Bariloche

Turn north through the lakes after Antarctica.

• Lakes · Andes foothills

Dec 1 – 3, 2026

Mendoza

Wine country and the Andes wall on the way to Buenos Aires.

• Wine · mountains

Dec 4 – 7, 2026

Buenos Aires

City pause before the countryside and Paraguay.

• City · culture · rest

Dec 8 – 11, 2026

San Antonio de Areco

Gaucho country on the approach to Paraguay.

• Estancia · countryside

Possible ranch / gaucho days.

Dec 19 – 21, 2026

Santa Cruz

Enter Bolivia — lowland gateway before the highlands.

• First days in Bolivia

Dec 22 – 24, 2026

Sucre

White city and highland air on the way to Uyuni.

• Colonial city · altitude

Dec 25 – 28, 2026

Uyuni

Salar de Uyuni — the salt flat.

• Salar · southwest Bolivia

Dec 29, 2026 – Jan 3, 2027

La Paz · Copacabana

La Paz chaos, then Lake Titicaca at Copacabana toward Peru.

• La Paz
• Copacabana / Titicaca

Jan 4 – 16, 2027

Cusco · Machu Picchu

Inca heartland — Cusco, Sacred Valley, and a Machu Picchu trek.

• Cusco
• Machu Picchu trek
• Partly with friends

Jan 17 – 20, 2027

Arequipa

White city under volcanoes — Colca country nearby.

• Arequipa · Colca

Jan 21 – 24, 2027

Lima

Pacific capital pause before the Amazon.

• City · coast · food

Jan 25 – 30, 2027

Peruvian Amazon

Multi-day Amazon expedition — wildlife, isolation, maybe healing.

• Jungle expedition
• Wildlife · learning

Jan 31 – Feb 2, 2027

Huaraz

Cordillera Blanca stop on the way north to Ecuador.

• Mountains · high Andes

Feb 3 – 9, 2027

Quito · Cotopaxi

Ecuador’s capital and the volcanoes around it.

• Quito
• Cotopaxi

Feb 10 – 14, 2027

Baños · Cuenca

Waterfalls and a southern highland city before Colombia.

• Baños
• Cuenca

Feb 15 – 19, 2027

Cali

Back in Colombia — salsa city and the south.

• Friends · city energy

Feb 20 – 25, 2027

Medellín

Valley of eternal spring — friends, farm visits, city life.

• Medellín · friends · farm

Feb 26 – Mar 2, 2027

Bogotá

Capital highland pause before the Caribbean coast.

• Bogotá

Mar 3 – 16, 2027

Cartagena · Palomino

Caribbean Colombia — walls, beach, then the port for the car ship.

• Cartagena
• Palomino
• Port · Darién transfer prep

Mid-March 2027

Darién Gap · Panama City

Ship the car around the Darién; reunite in Panama City.

• RORO shipping
• Panama City · retrieve car

Flexible for shipping delays.

Mar 23 – 26, 2027

Boquete

Highland Panama — coffee country before Costa Rica.

• Boquete · hills

Mar 27 – Apr 7, 2027

Costa Rica

Caribbean coast, then La Fortuna and Monteverde.

• Puerto Viejo
• La Fortuna
• Monteverde

Apr 8 – 16, 2027

Nicaragua

Pacific surf, Ometepe island, and León.

• San Juan del Sur
• Ometepe
• León

Apr 17 – 23, 2027

Copán · Santa Ana

Maya ruins in Honduras, then into El Salvador.

• Copán Ruinas
• Santa Ana

Apr 24 – May 2, 2027

Antigua · Lake Atitlán

Colonial Guatemala and the volcano lake.

• Antigua
• Lake Atitlán

May 3 – 6, 2027

Tikal

Jungle pyramids before Belize.

• Tikal ruins

May 7 – 11, 2027

Caye Caulker

Belize Barrier Reef — last mainland Central America stop.

• Reef · island pace

May 12 – 15, 2027

Jamaica

Caribbean chapter opens — fly out from the mainland.

• Island hop begins

Car may stay secured on the mainland.

May 16 – 19, 2027

Dominican Republic

Santo Domingo — then east along the island chain.

• Santo Domingo

May 20 – Jun 5, 2027

Eastern Caribbean

Island hop: St Kitts, Antigua, Dominica, St Lucia, St Vincent, Barbados, Grenada.

• St Kitts · Antigua · Dominica
• St Lucia · St Vincent
• Barbados · Grenada

Jun 6 – 8, 2027

Trinidad

End of the Caribbean hop — then fly back toward Mexico.

• Trinidad & Tobago

Jun 9 – 14, 2027

Mexico City

Back on the mainland — food, history, and the long Mexican arc.

• CDMX

Jun 15 – 18, 2027

Oaxaca

Food capital of the south.

• Oaxaca · food · culture

Jun 19 – 22, 2027

Chiapas

Highlands and jungle on the way to Yucatán.

• Chiapas

Jun 23 – 27, 2027

Yucatán

Cenotes, Maya sites, and the peninsula.

• Cenotes · Maya history

Jun 28 – Jul 4, 2027

Northern Mexico · Texas

The long north run and the US border into Texas.

• Northern Mexico
• Texas / Southern USA

Jul 21 – 24, 2027

Upper Peninsula

Lake Superior country after Michigan.

• Pictured Rocks · Keweenaw

Jul 25 – 26, 2027

Chicago

Quick city stop heading west.

• Chicago

Jul 27 – 29, 2027

Badlands

Prairie and rock on the way to Yellowstone.

• Badlands · Black Hills nearby

Jul 30 – Aug 2, 2027

Yellowstone

Geysers, wildlife, and the Rockies approach.

• Yellowstone

Aug 3 – 6, 2027

Glacier National Park

Going-to-the-Sun country before crossing into Canada.

• Glacier · Montana

Aug 7 – 10, 2027

Banff

Canadian Rockies — lakes, peaks, Icefields approach.

• Banff · Lake Louise area

Aug 11 – 14, 2027

Jasper

Icefields Parkway north — quieter Rockies.

• Jasper · Icefields Parkway

Aug 15 – 20, 2027

Whitehorse

Yukon capital — long northern highway energy.

• Yukon · Whitehorse

Aug 21 – 23, 2027

Fairbanks

Interior Alaska — staging for Denali and the Dalton.

• Fairbanks

Aug 24 – 27, 2027

Denali

The mountain — then north on the Dalton.

• Denali National Park

Sep 4 – 10, 2027

Anchorage · Kenai

After the Arctic — enjoy Alaska without pressure.

• Anchorage
• Kenai Peninsula

Sep 11 – 15, 2027

Southeast exit

Exit buffer — then figure out what happens to the Chilean car.

• Southeast Alaska / exit
• Car: ship, export, or sell

Not part of the main climax.