From Girlfriend Getaways to Classic Family Reunions, Here’s How to Plan an Incredible Group Trip

May 10, 2019


Incredible Group Trip Locations and Tips

Whether you’re a seasoned traveler or are just dipping your toes into the world of wanderlust, it’s likely you’ll want to take a group trip at some point. Group trips are amazing ways to bond with family, friends, and even coworkers. All cliches aside, you’ll create the types of memories you simply won’t experience by opting to stay on your home turf. From the amazing photos and wonder to the foibles that inevitably happen along the way, group trips are a recipe for joy. Many group trips are well-established, such as family reunions and bachelorettes. As travel planners who specialize in curating experiences for smaller groups, we have also seen a crop of newer group trips pop up, such as girlfriend getaways just for the heck of it, or a much-needed post divorce-cation. Planning an incredible group trip is a great way to get over a hump in your life, shift your perspective, and generally broaden your horizons.

If you’re planning a group trip, know that it can be a lot of work (this is also why we do what we do!) You’ll have to balance multiple budgets, opinions, and of course make some compromises. While the end result is almost always magical, we know the planning can be stressful. It’s always a good idea to get some input from your group: are you looking for a nature-fueled escape? A cultural or urban adventure? Anywhere with a beach? Set some parameters, then get to planning!

We’ve curated a list below of the best locations and times of the year for planning an incredible group trip. While this isn’t an exhaustive list of the types of group trips or destinations, we’re sure it’ll spark some inspiration!

Family reunions

When: In general, summertime is the best time of year to consider for any trip that is highly likely to include children. Another option would be the winter holiday season, after Christmas and before or leading up to New Year’s. Family reunions can range from small, intimate gatherings to convention-like productions. First, you’ll need to consider the size of your family reunion and how organized you want it to be. If a lot of extended family or people who you haven’t seen in years are coming, organized activities will help break the ice and provide some structure so the group doesn’t

Location: If you’re in need of somewhere with a lot of space, consider a beach location where you can rent a large home or villa. You may also look into hotels that are friendly for group accommodations. Kiawah Island, SC, is one amazing option. The beaches are stunning, it’s very safe to bike, and it’s close to Charleston if you want to take an adventure as a family into town. Plus, it’s one of the most relaxing places on the East Coast.

As an international option, consider renting a home in Tuscany, Italy. Tuscan villas can run for surprisingly cheap rates! You can have space with a chef, a massive yard for children to play, and all the beauty you can imagine. Plus, it’s a great central location for day trips to Pisa or Cinque Terre!

Tuscan villa, photo by Beth Evans


Photo by Elias Kordelakos


When: You can’t always optimize the time of year for a bachelorette party as it’s likely to depend on your wedding, the bride’s needs, and occasionally, coordinating between the busy schedules of many women. That being said, when it comes to a bachelorette, it’s a great idea to avoid traveling to places during their peak season. It’ll be much easier to get reservations at restaurants when things aren’t jam-packed. We suggest a spring or fall bachelorette.

Location ~ Austin, TX is one of our favorite bachelorette locations and really has it all. From incredible dining options to a very fun bar scene, there are many reasons Austin reigns supreme as a destination for bachelorette (and bachelor!) parties. The tech-infused town in Texas’ Hill Country is teeming with young folks, as well. We love staying at Archer Austin, the only property with double king suites outfitted for the perfect girls getaway, including giant mirrors for getting ready and a convenient shower bar for shaving. (Shefari bonus: a special gift in room and on-site credit.) Consider an afternoon at Barton Springs or a day boating trip on Lake Travis for your crew. At night, be sure to stop in at Rainey Street, a formerly residential area converted to off-beat bars. We adore the whimsy of Unbarlieveable – a circus themed bar with a 2-story slide. Nashville and New Orleans are both runners-up for US-based bachelorettes.

As an international option, we love Tulum in Mexico for its mixture of nature-fueled activities, hip hotels, and incredible international DJs.

an incredible group trip is a great way to help your broken hearted friend heal
Heal your friend’s broken heart with an incredible group trip! Image by Kelly Sikkema


When: Literally any time. This is one of those trips that may be planned unexpectedly… As such, the location may be chosen to fit the time of year versus the other way around. Anytime you’re planning something post-divorce or breakup, consider self-care. It may be tempting to plan a blowout party trip, and that’s certainly an option. But we have some other types of trips in mind to help heal the heart.

Location: Santa Fe, NM. Sante Fe is simply stunning, and it’s one of those locations with a reputation for its healing vibes and natural beauty, aka the perfect divorce-cation spot. Nourish your spirit with a visit to the legendary Ten Thousand Waves Spa, a Japanese style spa that is pure zen. You can soak in the thermal baths, including private baths for your group or ones that are just for women. Follow it up with one of their lavish treatments and izakaya-style small plates at the onsite restaurant. Santa Fe is also known for its distinctive southwest architecture and art scene. Not only can you nourish your soul with the spas and land, but the galleries of Canyon Road will leave your crew (and broken hearted friend) feeling inspired and uplifted.

As an international option, you might consider Florence for its amazing food, inspiring art, and uplifting Italian culture.

Girlfriend getaways make for an incredible group trip

Girlfriend getaways

When: Anytime, but it can be fun to pick one or two weeks a year and make this an annual ritual!

Location: Tour some US Vineyards! As we’ve written about before, the US has some incredible wine country. You can pick a region and go from there. Consider, for example, a multi-day trip to upstate New York where you can rent an amazing cabin or Airbnb near the Finger Lakes for optimum bonding time. Plan some activities, and be sure to include at least a day or two of exploring the incredible vineyards. It’s a great way to leave any city hustle and bustle behind and really bond with your girlfriends. Plus, wine always wins.

As an international option, look to Medellin, Colombia! This is a great place to wander and discover a vibrant city and culture, all while bonding with your girlfriends. Medellin also has a vibrant international scene, so you never know who your single gal pals might meet!

If you’re looking for more inspiration, check out our Shefari signature destinations. We’re happy to help you curate the group trip of a lifetime!

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