5 Travel Tips For Spontaneous City Trips

By Kate Bustillos

More travel, less planning. Traveling without an itinerary gives you the freedom to explore and really get to know a city vacation destination. Instead of rushing from one attraction to another, discover hidden gems at your own pace. Take time to engage with the local community and embrace the city at its most authentic. Some travel plans require a lot of effort up front, but that doesn’t have to be the case for every vacation. Spontaneous trips are a refreshing break from the pressure of planning the perfect vacation and a chance to incorporate more travel into your lifestyle. Try these five travel tips for your next city trip to make it a true adventure in wanderland.

1. Book Your Stay In A Walkable City

Some cities were designed with pedestrians in mind. Plentiful and well-planned walkways, bike lanes, and shop-lined streets make it easy for locals and visitors to wander their way around. Book your stay in the heart of downtown where a smorgasbord of shopping, dining, and entertainment venues are just outside your door.

Featured City Trip: New York City, New York

Ranked as the number one most walkable city in the U.S., New York City is a pedestrian paradise. Skip the bus tours and take a stroll. Whether you’re touring one of New York’s vibrant boroughs or heading to iconic Central Park, you’ll discover way more hidden gems, local landmarks, and unique photo-ops if you explore on foot.

Spontaneous City Trips

2. Eat Local

Avoid long lines and crowded chain restaurants. Instead, try local eateries and independent boutiques. Support the community and get an inside scoop on local favorites and events. Sample the artisan cuisine and expand your palate with signature dishes and flavors unique to the area.

Featured City Trip: Portland, Oregon

With a coffee culture centered around community and an affinity for locally-sourced food, this walkable city is a haven for coffee connoisseurs and foodies alike. Stop by one of Good Coffee’s convenient locations for a creative concoction and ask one of their friendly baristas for some sightseeing tips.

3. Buy A CityPASS

If traveling without an agenda feels too extreme, you can still save time and money with a CityPASS. Choose your own adventure from a curated selection of the city’s best attractions at a discounted price. Some restaurants and stores even offer additional discounts to pass holders.

Featured City Trip: San Francisco, California

Save up to 45% on admission to some of the city’s top attractions like San Francisco Zoo & Gardens, Aquarium of the Bay, and more. The San Francisco CityPASS is valid for 9 consecutive days, giving you the flexibility to explore selected attractions at your leisure.

4. Travel Off-Season

Traveling off-season is one of the best travel tips to try out. Save money and time by vacationing during off-peak months. During the off-season, accommodations and even restaurants are often cheaper. Less tourists means less crowds, so you can explore at your own pace. Visiting outside of peak season also creates opportunities for a more unique and authentic experience. It’s the chance to gain a more intimate perspective and see the side of a destination that most tourists miss.

Featured City Trip: Boston, Massachusetts

Boston enjoys all four seasons, each with their own benefits. Most tourists head to Boston during the summer, so for a chance to miss the crowds, but not the great weather, visit during the spring or fall. Of course, winter is the least popular travel time, so if you’re craving cold weather, try a winter weekend getaway. There are also tons of indoor attractions, like museums, aquariums, and more, so you can enjoy your stay while staying warm.

5. No Agenda, No Problem

When it comes to some vacations, think more like a traveler and less like a tourist. Tourists tend to follow predictable itineraries, moving from one crowded location to another, trying to check every “must-see” attraction off their list. But travelers know when to ditch the guidebook. Go where you want to go, not where you think you have to go. Immerse yourself in the sights and sounds of the city, instead of merely observing it.

Featured City Trip: Chicago, Illinois

Leave the guidebook behind and go where the locals go. Chicago has plenty of quintessential attractions from the Willis Tower to Navy Pier. But if skyscrapers and touristy sites aren’t your scene, there’s no obligation to follow the crowd. Instead, check out local favorites, like shopping and dining at Lincoln Park and the Lincoln Park Zoo, which offers free admission with a reservation.

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*These vacations are limited and subject to availability.

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