O‘ahu, HI

Looking for a beach holiday destination with all the amenities of a big city? Oahu ticks the boxes with a coastline of beaches to catch the surf during the day and buzzy, hip hoods like Kaka’ako with its urban art murals and homegrown brewhouses (check out Aloha Beer Company and Waikiki Brewing Company) to explore by night.

When To Go ?
There’s no shortage of festivals taking place in busy Oahu. From marquee events like the Hawaii Food & Wine Festival in November and Duke’s Oceanfest in August to quirky ones like the Waikiki Spam Jam (March) and Kawaii Kon (April).

Maui, HI

Famed for its beautiful beaches, majestic volcanoes, and one of the most scenic drives in the world, Maui is regularly voted as one of the top islands in the world. A destination that offers a little of something for everyone, if you (and your crew) are into exploring the outdoors, you’ve come to the right place. Hike Haleakalā surrounded by native Hawaiian plants and animals, go surfing or kite surfing at Ho’okipa Beach and definitely make that trip down the Road to Hana.

When To Go ?
Maui isn’t just about the great outdoors, festivals like the Hawaiian Slack Key Guitar Festival pay tribute to this musical art form that originated in Hawaiʻi almost two centuries ago. June is also the month of the annual Maui Film Festival and the Wa’a Kiakahi Canoe Festival.

Kauai, HI

Arguably the most unspoiled of all the Hawaiian islands, Kauai (also known as the Garden Island) offers endless opportunities for groups to take an adventure break together, exploring unique natural wonders like the 11-mile Kalalau Trail, and hiking to pristine waterfalls like the Opaekaʻa Falls, and Waipoʻo Falls. The one-of-a-kind Napali Coast is not to be missed for its famed rugged coastline – viewable from Koke’e State Park, or from the comfort of a boat excursion.

When To Go ?
Get your fill of poke at the annual Kauai Poke Fest where 20 varieties of poke can be sampled, otherwise the Kōloa Plantation Days Celebration in July honors Kōloa’s multicultural heritage and the Kauaʻi Mokihana Festival in September features a highly celebrated hula competition performances and cultural workshop.

Napa Valley/Sonoma, CA

Is there a better way to take a vacation with friends than one centered around wine tasting? The vineyards of Napa Valley are easily explored over a long weekend where you can combine a Sip and Cycle tour of various vineyards with fun activities like hot air balloon rides and bottle blending sessions.

When To Go ?
There’s never a bad time to visit Napa Valley but for a first-hand look at what it takes from grape to bottle, visit during the harvest months of August through October where you’ll witness workers picking the best and ripest grapes off the vines.

Palm Springs, CA

Coachella isn’t the only reason to visit the desert oasis city of Palm Springs. The popular Los Angeles getaway has a lot going for it: amazing hikes (check out Tahquitz Canyon Trail and its hidden waterfall), jaw-dropping mountain vistas, being 10 minutes’ drive to the stunning Joshua Tree National Park, pretty mid-century architecture and loads of cool public art. Oh, and did we mention the food? Make reservations for Modern American eateries like 4 Saints and squeeze in a brunch or three at institutions like Cheeky’s.

When To Go ?
No doubt Coachella will be a big reason to plan a Palm Springs trip but there are loads of arts festivals like Modernism Week (held twice a year) and outdoor exhibits like Desert X featuring larger-than-life optical illusions and site-specific installations.

Central Coast, CA

California’s 350 miles of picturesque coastline from Los Angeles to San Francisco is a bucket list road trip that has to be experienced at least once. Cruising down Route 1 from North to South will bring you past charming towns like Monterey, Carmel, and Santa Barbara, and iconic sites like Hearst Castle, Morro Bay and Big Sur’s Julia Pfeiffer Burns State Park, all perfect places to make beautiful life memories.

When To Go ?
Depending on when you plan to visit, your trip could easily coincide with festivals like Chowchilla’s March Stampede and Cattle Drive, Modesto’s Graffiti Summer event in June, or the Big Fresno Fair in October.

Aspen, CO

Colorado’s mountain getaway may be famous for its après ski culture and world-class skiing opportunities on powder snow slopes but it also has a vibrant food and art scene that warrants dedicated attention. If you manage to tear yourself away from famous ski resorts like Aspen Mountain and Snowmass, there are also loads of opportunities to go snowshoeing, cross-country skiing or fishing and hiking.

When To Go ?
December to February is peak skiing season in Aspen but do consider booking a trip around hotly anticipated events like the Aspen Music Festival and the illuminating Aspen Ideas Festival in June.

Miami, FL

Luxe beachfront resorts, a glittering nightlife scene, and vibrant neighborhoods like South Beach, Little Havana and Little Haiti, Miami’s pastel-hued, art deco streets are a vibe. With year-round good weather, there’s never a bad time to visit (February gets pretty busy though) especially if you’re looking for a good party (check out Mynt, STORY, Hyde Beach and Nikki Beach) and a lot of beautiful people action.

When To Go ?
You don’t need to make an excuse to visit Miami but if you’re an art fiend, the world-class Art Basel in December is the place to talent-spot up-and-coming modern and contemporary artists. Down for a party? Visit in March in time for the Ultra Music Festival and Calle Ocho Festival.

Austin, TX

When a city earns a reputation as the “live music capital of the world” you know it’s an excellent choice to gather with fellow music lovers. Not sure which spot to hit? The Mohawk, The Parish, Austin Music Hall, and The Moody Theatre are some of the very best places to enjoy live music in Austin.

When To Go ?
Aside from March’s annual South by Southwest festival, make a note of the Austin City Limits Festival, the city’s second-largest music festival taking place every October.

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