In 2018, my older sister, Kelsey, came to visit me in New York. Our plan was initially just to spend time in the city, but we ended up deciding last minute to explore a small beach town in New Jersey. Neither of us had been to this state before, let alone this quaint coastal town, but this trip created some of my most cherished memories with Kelsey. It sparked my love for traveling with my sister, and I will always be thankful for that experience.

Following our New Jersey escapade, sister trips became a regular occurrence, and now, there’s no other vacation I’d rather take (or anyone else I’d rather travel with). We’ve explored various destinations, including a mountain resort in Aspen, a condo in Chicago, a high-rise in downtown Denver, a desert hotel in Scottsdale, and a waterside property in the Hamptons.

Each trip we embark on seems to surpass the previous one, not because the destination is better, but because our bond keeps growing stronger. We could visit a remote cabin and still manage to have an incredible time. These moments with my sister are what I live for, and if you have a close sister, you likely understand how special it is to have one-on-one time together. Continue reading for a guide to planning your own sister trip.

Source: Kara Thompson

How to Plan a Sister Trip

Below, you’ll find tips on organizing your own sister getaway, including destination ideas, activities, and itinerary suggestions.

Start with the logistics

Choosing a destination is the key factor in planning any vacation. Some of my favorite sister trips with Kelsey occurred in cities that I hadn’t initially considered. While popular tourist spots can be enjoyable, there’s something uniquely special about selecting a less mainstream destination.

When planning your sister getaway, explore smaller towns you wouldn’t typically visit with a larger group. Traveling with your sister allows you to explore new destinations together, making it the perfect opportunity to check off some unique places from your list.

Don’t overschedule activities

While it’s essential to outline some activities for your trip, I recommend leaving some flexibility in your schedule. You never know what unexpected experiences you might encounter at your destination. Allowing room for spontaneity can lead to memorable moments.

Create a stellar dining list

My sister and I are food enthusiasts and enjoy exploring the bar and dining scene together. We often visit a bar before or after dinner, leading us to meet locals and fellow travelers. Collaborate on researching restaurants for your trip and designate someone to make reservations to streamline the process.

Be open to the unexpected

The most unforgettable experiences often occur unexpectedly. Embrace spontaneity during your sister trip, whether it’s engaging with locals or adapting plans on the fly. Stay open-minded for memorable adventures.

Pack something fun

Consider bringing a small surprise for your sister on the trip to add excitement. On our last Scottsdale trip, I surprised my sister with quirky sunglasses, which became fun photo props and enhanced our desert and poolside vibes.

Source: Kara Thompson

18 of the Best Destinations for Sister Trips

Explore unique destinations beyond the typical spots like Nashville or Austin for your sister trips. These out-of-the-box locations offer vibrant dining scenes, cozy accommodations, and plenty of activities to enhance your getaway:

  • Asheville, North Carolina
  • Cape May, New Jersey
  • Charleston, South Carolina
  • Chicago, Illinois
  • Dallas, Texas
  • Denver, Colorado
  • Hamptons, New York
  • Miami, Florida
  • Middleburg, Virginia
  • Napa Valley, California
  • New York, New York
  • Newport, Rhode Island
  • Philadelphia, Pennsylvania
  • San Diego, California
  • Savannah, Georgia
  • Scottsdale, Arizona
  • Seattle, Washington
  • Washington, D.C.

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