Join a Monsoon!

Journey with the core staff of The Monsoon Diaries on our premier-level tours to destinations we’ve never been. These trips are our signature expeditions designed to push the limits of travel (aka monsooning).

Headliner Trips (Monsoons)

Our signature headliner trips, aka monsoons, designed and led personally by Calvin and his fellow monsooners.

Destination Start End Year Details
Oct: Camping / Robbinsville, NJ Oct 3  Dec 5 2025 $60: Robbinsville, NJ
Dec: Yemen Dec 2  Dec 6 2025 $4495: Optional extension to Niamey, Niger on Nov 30, and then Cairo → Seiyun → Shibam → Wadi Doan → Tarim
Dec: Killington, VT Dec 19  Dec 21 2025 $420: Killington, VT
Jan: Park City, UT Jan 19 Jan 25 2026 $1495: Park City, UT
Spring: The Alps Mar 25 Apr 3 2026 $1190-$3050: Alpe d’Huez, France (TOMORROWLAND WINTER) to Zermatt, Switzerland
Apr: Paraguay Apr 20 Apr 26 2026 $945: Asunción, Trinidad
Jun: The Trans-Canada Highway June TBD June TBD 2026 $2590: 18 days – Halifax, Prince Edward Island/Charlottesville, Bay of Fundy, Fredericton, Quebec City, Ottawa, Toronto, Sault Ste Marie, Thunder Bay, Winnipeg, Saskatoon, Edmonton, Banff, Vancouver, Victoria
Jul: Tomorrowland 2026 Jul 23 Jul 28 2026 $1600: Tomorrowland 2026
Kaliningrad & Lithuania Jul Jul TBD $590 USD: Kaliningrad, Vilinius, Trakai
Extreme Oz Aug Aug TBD $1890 USD: Southern Australia, Tasmania
Aug-Sept: Pacific Island Hopping II: Auckland Base Aug Sept ?? TBD $3950: New Zealand, Niue, Cook Island, New Caledonia, Wallis and Futuna

 

Partner Trips

We’ve designed some of these ourselves, we’ve led trips there before, and now we’re offering them again with the help of our travel friends & partners around the globe!

Destination Start End Year Details
Extreme Philippines Apr 18 Apr 25 2026 $800 USD, 4 nights, 5 days: Manila – Angeles – Laoag – Batac – Vigan – Manila
May Day In Cuba Apr 30 May 7 2026 $900 USD, 7 nights, 9 days: Havana-Trinidad-Cienfuegos-Santa Clara-Havana-Viñales (optional)
Colombia May 11 May 18 2026 $1295 USD, 8 nights, 9 days: Bogotá – Santa Marta – Sierra Nevada National Park – Cartagena – Medellín
Palawan Island Hopping Sep 30 Oct 09 2026 $845 USD, 8 nights, 9 days: Manila – Palawan Islands – Manila
Christmas in Myanmar Dec 20 Dec 27 2026 $910 USD, 6 nights, 7 days: Yangon – Bagan – Mandalay – Nyaungshwe – Kalaw – Yangon

 



“Anytime” Trips (Trips On Demand)

Whenever you want to go, these destinations are offered all year-round, anytime you want (weather depending), on demand! We’ve set them up so you can just pick your dates and we’ll take care of the rest!



Destination Details
Unknown UAE $175 USD: Dubai, Sharjah, Ajman, Umm Al Quwain, Fujairah, Ras al Khaimah, Madha, Nahwa, optional day trip to Khasab (Musandam Oman) and/or Abu Dhabi – September to May weekends only. Maximum of 4 people per group.
Australia & New Zealand $1250-3700 USD: Sydney, Brisbane, Cairns, Great Barrier Reef, Uluru, Melbourne, Auckland, Rotorua, Wellington, Christchurch, Queenstown, Milford Sound
Antarctica $5550 USD (starting price) per person, various itineraries from Antarctica Peninsula to South Pole
The Baltic Crescent $750-1400 USD per person, various itineraries that include Denmark, Norway, Sweden, Finland, Estonia, Latvia, and Lithuania
Cuba $60 USD (starting price) per person, various itineraries including Havana-Trinidad-Cienfuegos-Santa Clara-Viñales
Private Palawan Island $200-$245 USD per night (group rate) or $895 USD per person for 1 week (sample price) of planned activities
Southern Africa $1850 USD per person, various itineraries that include South Africa, Namibia, Botswana, Zambia, Zimbabwe,
Lesotho, Swaziland, Mozambique