Where to climb in the winter
-If Zwift or the Peloton are not cutting it for you, consider traveling to one of the few areas on earth where you can get outside and up with varying options and a fair chance of good weather. In our experience, here are some of the best places to travel to and ride outside during winter.
Tenerife, Canary Islands

The total rainfall for November through March is 7" at the northern end of the island and 3.5" at the southern end. While the winter is very mild compared to most other bike climbing destinations, it is also the low season, making it the least expensive time to visit Tenerife. Many pro teams train here during the winter which is a strong testament to its value for those of us bent on cycling outdoors during the winter.
Hawaii

Haleakala, Maui; Waipoli, Maui; Mauna Loa, Big Island;
Kaloko, Big Island; Mauna Kea, Big Island (middle photo).
Some of the world's and US top bike climbs are on the Island of Hawaii (Big Island) and Maui. The weather on the north side of of both Maui and the Island of Hawaii is mild year round, although you can encounter snow at the higher elevations on and off through the winter on Mauna Kea, Mauna Loa, and Haleakala. However, at least you can have a fighting chance to get to the top of each during the winter, almost always for Mauna Loa and Haleakala which are 3,000-4,000' lower than Mauna Kea.

While the Big Island and Maui are not the second safest destinations during winter, we rank them #2 because they can be climbed the majority of days during the season, they are epic, and they are more challenging than any of the other winter cycling climbing venues.
Death Valley

There are four Top US Bike climbs plus several other really good ones in Death Valley. While early spring and late fall are the ideal times to ride in Death Valley, there is only a total of 1.5" of rain during the five months beginning in November through the end of March. However, beware that it does get cold there -- often in the 40s and occasionally into the 30s.