How to Use Outsite to Travel Full Time in 2020: Where to Travel Each Month

The best places to travel in 2020 for digital nomads.

Published on
November 22, 2019

Why not give full-time slow travel a go in 2020? With 24 (and counting!) Outsite locations worldwide, there are plenty of options where you can colive and cowork in 2020, whether you want to be in the mountains, by the beach, or in a big city.

Outsite makes it easy to feel at home anywhere in the world, experience beautiful cities, and join a community of like-minded professional digital nomads. Here are some of the best times to visit our locations... although, we don’t really think there’s a bad time to visit any of them, either.

Where to travel in January

Swiss Alps

To experience a quintessential winter wonderland, head to the Swiss Alps in January. You’ll feel like you’re in a beautiful snow globe! Winter is technically low season for Switzerland, but if you want to ski, January is a great time to visit, because there will be no shortage of snow. Even if you’re not a skier, you can enjoy the delicious comfort foods (hello, cheese and chocolate) the region has to offer curled up by the fire for some relaxing down time at Outsite Swiss Alps - Davos Klosters.

If you are up for traveling a bit out of town, you can experience the incredibly unique International Hot Air Balloon Festival in Château-d'Oex. The festival will take place January 25th to February 2nd 2020. It’s not everyday that you have the chance to see a hundred colorful hot air balloons taking flight over the snowy Alps...and yes, you can ride in one, too!


San Juan, Puerto Rico

If you’d rather escape the winter than embrace it, head down to Puerto Rico for some Caribbean sunshine and Latin flavor. While January is usually Puerto Rico’s “coldest” month, temperatures are usually in the mid 80s, with lows of mid 70s. Sounds like good winter weather to us. You can hit the nearby beaches to sunbathe, snorkel, or surf. 

There are also a couple exciting events happening in January in San Juan. The San Sebastián Street Festival (Fiestas de la Calle San Sebastián, or abbreviated as San Se) is Puerto Rico’s largest and most fun festival. You’ll find live music, dance parties in the streets, local artisans selling goods, delicious food, and more. The 2020 dates are January 15th through 19th. At Outsite Puerto Rico - Old San Juan, you’ll be in the middle of all the action. 

Where to travel in February

Santa Teresa, Costa Rica

While you won’t be beating the crowds by traveling to Costa Rica in February (it’s technically high season) this is a great month to visit, for multiple reasons. First off, February is one of Costa Rica’s driest months, so you won’t have to worry about rain ruining your plans. If you’re trying to surf, the waves in Santa Teresa in February are a bit smaller and relatively consistent, which makes them great for beginners or intermediate surfers. The beach is easily accessible if you’re staying at Outsite Santa Teresa

Another big draw for people to visit Costa Rica in February is the Envision Festival, which will occur on February 17th through 24th, 2020. The festival is not in Santa Teresa – rather it’s a bit more south, nearby Uvita – but Santa Teresa is a great jumping off place to spend the first half of the month before making your way down to the festival. The festival has many aspects, including music, immersive art installations, yoga, and other wellness topics. Envision is also big on being sustainable and giving back to the community. 

Where to travel in March

Austin, Texas

The city always attracts a pretty cool crowd, but this amplifies even more when South by Southwest, AKA SXSW, comes around in March. This conglomerate of conferences and festivals is massive and really has something for everybody. There are live music performances by huge names in music (as well as up-and-comers) making up a music festival, a film festival, and a comedy festival. On top of all this entertainment, there are conferences, panels, and workshops on a variety of business topics ranging from everything from cannabusiness to climate and social action to tech. SXSW 2020 will be March 13–22, 2020.

Weather in Austin in March is also very comfortable. The beginning of Spring brings pleasant temperatures in the 70s, which allows for great outdoor activities like kayaking or stand up paddle boarding in bodies of water nearby Outsite Austin - Bouldin Creek

Where to travel in April

Bali, Indonesia

As you can imagine, Bali has blown up big time thanks to influencers and digital nomads. If you want to visit Bali at a time when the weather is likely to be best and crowds aren’t too crazy, aim to visit Bali in April. This month is the beginning of the dry season, so you’re going to avoid all the rainfall you might experience during the wet seasons. Also, this is low season for tourists, so you’ll be more likely to run into fellow digital nomads than families on holiday. 

Foodies can also have something to look forward to in April – the Ubud Food Festival. Indonesia’s best chefs and restaurateurs gather for this 3 day festival where you can attend cooking lessons, free events, and of course, taste some delicious food. It’s set to take place April 17th - 19th 2020. Ubud is a quick drive away from Outsite Bali in Canggu


Tulum, Mexico

April is a great time to visit Tulum if you want to avoid large crowds of tourists that typically flock to Tulum from December onwards throughout the winter. Also, April is just before the rainy hurricane season begins so you’re likely to experience less rainy days (and more perfect beach days!) Temperatures in April will be in the high 80s, perfect for tropical climate lovers to lounge on the beach and take lots of dips in the pool and/or ocean...which is a quick walk away from Outsite Tulum

April is also when Tulum holds its huge art and culture festival, Art With Me. There’s so much that goes on at this festival, including live music, art installations, sustainability talks, wellness workshops, and more. Bonus: some proceeds from ticket sales benefits “Care With Me” which is their environmental outreach and awareness program. This festival will take place April 22-26 2020. 

Where to travel in May

Santa Cruz, California

While you can typically find great waves all year long thanks to Santa Cruz’s location, May in particular is a great time to visit at catch some waves. Temperatures warming up from mid 60s to mid 70s lends itself to more pleasant surf days and beach strolls. All three of Outsite’s Santa Cruz locations are close to great surf breaks. Additionally, you can check out the annual Santa Cruz Longboard Surf Contest which takes place on Memorial Day weekend, which will be May 22nd to 24th 2020. This is the most famous longboard contest on the West Coast. 

If you’re more into on-land sports, you can join in on the Surfers Path Half and Full Marathon, for one of the most beautifully scenic runs of your life! You’ll run through the Monterey Bay coastline and pass many world renowned surf breaks.

Where to travel in June

Los Angeles, California 

While there’s certainly no bad time to visit Los Angeles (you’re pretty much always guaranteed sun and no rain), we love LA in June. You’ll experience comfortable weather of mid 60s to mid 70s. June is right before high season kicks in during July and August, when you’ll see a big uptick in tourists. This means, if you’re a surfer, you’ll have more space for yourself in the ocean! Waves are pretty consistent year round in Venice, and you can find breaks that are suitable for beginners or intermediate surfers. 

Culture wise, there’s a lot going on in LA in June. For example, June is LGBTQ pride month, and LA is a fun place to celebrate whether you’re a member of the LGBTQ community or an ally. There’s a huge parade and festival in West Hollywood thrown by LA Pride, which will take place June 12th-14th 2020. On top of the festival, there will be plenty of parties and events to attend all over town. 

If you’d like to network and sharpen your tech knowledge, you can attend Techspo LA June 10th-11th, a tech expo showcasing the next generation of technology & innovation. There’s also DigiMarCon West, a digital marketing conference, June 12th-13th. Both are held in Santa Monica. With 6 Outsite locations in Los Angeles, you’ll have no shortage of options for where to stay!


Biarritz, France

Europe is a lovely place to be in late spring/early summer, before the peak tourism season really begins. You will find the Basque coast beaches to be a bit less crowded in June than you would in July or August, which is a bonus whether you’re looking to surf or just kick back and chill. If you do want to surf, swells are pretty reliable in June, with breaks suitable for beginners and intermediate surfers (if you’re advanced and looking to surf some big waves, come here in the winter, instead!) During the month of June, you’ll also be able to watch some surf competitions in the birthplace of surfing in Europe! 

Also, there’s a festive party/street fair called Casetas which is a celebration of the beginning of summer. Many restaurants participate, there’s delicious street food, and live music...all with the beautiful backdrop of the Biarritz beaches. 

Where to travel in July

Lake Tahoe

There’s so much to do in Tahoe year round. The best time for you to go really depends if you’d rather enjoy snowy Tahoe or beachy Tahoe...but we’re partial to beachy Tahoe. South Lake Tahoe, where Outsite Lake Tahoe is, has plenty to offer in the summer months – swimming, hiking, kayaking, stand up paddle boarding, you name it! We particularly recommend stand up paddle boarding or kayaking in Sand Harbor where the water is perfectly crystal clear. 

As for entertainment, the summer is a perfect time for music lovers to visit. Harveys Lake Tahoe’s outdoor arena hosts a summer concert series annually featuring tons of big name musicians. The lineup for 2020 is not yet announced, but there’s sure to be some gems. There’s also lots of opportunity to check out free live music weekly at the Live at Lakeview concert series which takes place on El Dorado beach. Additionally, The Shop at Heavenly Village put on the The Heavenly Village Summer Concert Series, which includes free shows every Friday and Saturday throughout the summer.

Where to travel in August

Encinitas, California

Spending a summer month in one of the best surf towns in the world according to National Geographic? Yes please! August is a great month to visit Encinitas if you don’t love stiflingly hot summer days. Weather usually remains around the 70s, so you can enjoy your outdoor summer activities without getting too hot. 

The city of San Diego says its best surf season is August through November, so you’ll be arriving right on time to catch some great waves if you’re looking to surf. In Encinitas, you’ll likely find the most reliable waves at Grandview beach, which is just a few blocks away from Outsite San Diego - Encinitas Grandview. You’ll also be in town for the amateur surf contest series AM Slam Surf Series - Presented by Vans which typically occurs from June through September.  

Where to travel in September

San Francisco, California

Believe it or not, September and October are actually San Francisco’s warmest months, not July and August. September is also one of the driest months, so you can expect fewer rainy days than usual. Summer months are peak tourist season in SF, so by arriving in September, you’ll bypass a lot of that.

If you’re into startups, TechCrunch Disrupt SF is the original tech startup conference, and a must-do for tech entrepreneurs. You can learn from industry leaders and network with other conference goers. Startup founders can also enter The Startup Battlefield Competition, which has helped launched Fitbit and Dropbox! 

P.S. If you’re heading to Burning Man, you can actually take a bus service called the “Burner Express Bus” from Black Rock City right to SF. Burning Man 2020 will be August 30th to September 7th. Not a bad way to start off the month! 

Where to travel in October

Brooklyn, New York

October isn’t high season in New York, but it’s not necessarily low season either. The weather in October is brisk but not too cold yet. This fall month is a great time to experience Brooklyn and New York City as a whole. While the city as a whole may not have a whole lot of trees throughout, there are plenty of parks big and small where you can go to enjoy the colorful fall foliage, from lesser known McCarren Park in Williamsburg (close to Outsite Brooklyn - Williamsburg Grand) to Prospect Park to the world famous Central Park, which is an absolute must see in fall. 

Aside from the beautiful fall foliage and crisp air, Halloween in New York is epic. You will experience absolutely no shortage of Halloween parties and events leading up to the holiday and on Halloween itself. Dog lovers will be obsessed with the Annual Tompkins Square Halloween Dog of the biggest dog costume parades in the world. You’ll get to see hundreds of dogs in adorable costumes. What more could you want?! Stay tuned for the exact date of this parade in 2020. As for human costumes, the massive Village Halloween Parade is a sight to see. You can join in yourself, too, as long as you’re in costume. 


Ericeira, Portugal

Skip the crowds by heading to coastal town Ericeira in October instead of summer peak months. The surf is better in October, too! Even though it’s technically fall, you’ll likely be experiencing the same warm sunny days that the town sees in June. There are plenty of great surf spots in Ericeira, right nearby Outsite Ericeira. There are many other nearby beach towns great for surfers as well. Bonus: The warm October days allow for al fresco dining at the many delicious eateries around town.

Mid to end of October is also when the MEO Rip Curl Pro Portugal surf competitions usually occur in Peniche, which is about an hour away from Ericeira. 

Where to travel in November

Lisbon, Portugal

November is off season for Portugal, meaning less tourists hogging up space at all the cafes you’re trying to work from! Portugal’s mild climate means comfortable weather throughout November – not too chilly, not too hot. Average high temperatures will fall around the mid 60s. 

Aside from the benefits of visiting during low season, November is when the famous Web Summit – the largest tech event in the world – takes place. There are over 1,200 speakers and 11,000 CEOs. If you work in tech, startups, or digital media, this really is the place to be to network and learn. Web Summit 2020 will take place November 2-5. We have you covered for a central place to colive and cowork during Web Summit at Outsite Lisbon - Cais do Sodre

Where to travel in December 

Oahu, Hawaii

If you’re a surfer looking to surf the biggest waves the North Shore has to offer, head to Oahu in December. The months of November through April are surf season for the North Shore, where our two Oahu coliving locations are. December is a great time to go, as the season is already in full swing. Temperatures usually range from a toasty 79-83°F, with water temps around 72-80 °F, meaning you probably won’t even need to wear a wetsuit. 

Additionally, you can check out some really cool surf competitions, even if you aren’t a surfer yourself. For example, Billabong Pipe Masters is one of the most exciting surf competitions out there, where some of the world's best surfers come out to compete at the Banzai Pipeline. The 2020 Pipe Masters competition is tentatively set for December 8th through 20th. 

So, where is #1 on your itinerary? Make sure to check out our Instagram for live stories from Outsite locations!

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