10 Things You and Your Friends Must Try For an Unforgettable Summer

Is a vacation with friends coming up soon? Get ready to transform your summer into an unforgettable adventure with our ultimate guide to 10 must-try activities! Whether you're heading to a sun-soaked beach, setting out on a cross-country road trip, or enjoying a cozy cabin getaway, these unique and hilarious experiences are designed to turn every moment into a cherished memory.

Our handpicked activities include everything from outrageous dress-up challenges to inventive party pranks, ensuring that your time together is packed with fun and laughter. Perfect for group vacations, these ideas will not only spark joy but also deepen your connections through shared, unforgettable moments. Embrace the spirit of adventure and creativity as you dive into these exciting suggestions, each one guaranteed to add a memorable twist to your summer escapades.

Explore these fantastic ideas and discover how to make the most of your vacation with friends, ensuring that every day is filled with excitement, joy, and endless fun.

As you gear up for your vacation with friends, it’s time to think beyond the typical sightseeing and relaxation. This summer, why not infuse your trip with a series of unforgettable activities that will keep the laughter rolling and create stories you'll cherish for years to come? Our guide is packed with creative and slightly outrageous ideas that are perfect for adding a unique twist to your getaway.

From hilariously themed dress-up challenges to inventive party pranks, these activities are designed to bring out the best in your group dynamics and ensure that every moment is filled with joy and excitement. Each suggestion is crafted to break the ice, spark creativity, and enhance the fun factor of your vacation. So gather your friends, get ready to embrace some playful antics, and let’s dive into the first must-try activity that will kickstart your summer adventure!

1. Ugly Shirt Day

An Ugly Shirt Night is a fantastically fun and unconventional event where participants are encouraged to buy and wear the most hideously hilarious T-shirt they can find. The concept is simple but effective: each person in a friend group purchases an unappealing, often over-the-top shirt for someone else, and everyone is required to wear their new, less-than-stylish garment throughout the evening. The result is a night filled with giggles, photo ops, and endless amusement as everyone parades around in their intentionally awful attire.

This playful tradition takes the ordinary night out and turns it into a memorable experience packed with laughter and camaraderie. It’s all about embracing the goofy and celebrating the absurd. Ugly Shirt Night works perfectly for birthdays, casual parties, or even as a spontaneous outing with friends. The key to a successful Ugly Shirt Night is the shared humor and enjoyment that comes from seeing each other in the most ridiculous T-shirts imaginable. So, gather your friends, pick out your most outrageous shirts, and get ready for a night of uncontrollable laughter and fun!

2. Wig Night Out

Wig Night Out is a fantastically fun and unforgettable way to spice up your summer vacation with friends. The concept is simple: each person picks out a colorful, outrageous wig to wear for an entire night out on the town. The more vibrant and bizarre, the better!

Start by visiting a costume shop or browsing online to find the perfect wigs that reflect each person’s wildest hair fantasies. Think neon colors, wild styles, and lengths that defy gravity. Once everyone has their wigs, get ready for a night filled with laughter and unexpected adventures.

As you step out in your new personas, you'll instantly feel the carefree and playful energy that Wig Night Out brings. Head to your favorite bars, clubs, or restaurants, and watch as people react to your bold new looks. The wigs will undoubtedly become conversation starters, making it easy to meet new people and create hilarious memories.

Capture the night with plenty of photos and videos. The contrast between your usual selves and your wig-wearing alter egos will make for some priceless snapshots. Consider creating a theme for the night, like 80s rock stars, movie characters, or even famous celebrities, to add an extra layer of fun.

Wig Night Out is all about stepping out of your comfort zone, embracing a bit of silliness, and making the most of your time together. It’s a perfect way to bond with your friends, create unforgettable stories, and enjoy a night filled with laughter and spontaneity. Whether you're dancing the night away or simply enjoying each other's company, the memories made on Wig Night Out will be cherished long after the wigs are put away.

3. Faking a Bachelorette Party

Faking a Bachelorette Party is an outrageously fun and memorable way to add some extra excitement to your summer vacation with friends. The idea is to pretend that one of you is celebrating her last night of singlehood, complete with all the classic bachelorette party trimmings. This playful ruse not only allows you to create hilarious memories but also ensures a night filled with laughter, attention, and new connections.

Start by selecting who will be the “bride-to-be” for the night. The chosen friend can wear a sash, tiara, or veil to signify her special status. The rest of the group can dress in coordinated outfits or matching accessories to make it clear that you’re part of the bachelorette entourage. Props like inflatable rings, personalized T-shirts, and funny signs can add to the festive atmosphere.

As you hit the town, embrace the role-playing fully. Go to popular nightlife spots such as bars, clubs, or even a karaoke lounge, and let everyone you meet know about the “bachelorette” celebration. This will often lead to free drinks, special treatment from staff, and even random strangers joining in on the fun. Be sure to take plenty of photos to capture the hilarity of the evening.

To add to the authenticity, plan some classic bachelorette party games and dares. Create a checklist of fun and slightly embarrassing challenges for the “bride” and her “bridesmaids” to complete throughout the night. These can include tasks like getting someone to buy you a drink, finding a person with the same name as the groom, or dancing with a stranger.

The key to faking a bachelorette party is to let loose and fully immerse yourself in the role-play. Enjoy the thrill of pretending and the spontaneous adventures that follow. It’s a fantastic way to bond with your friends, meet new people, and create stories that will be talked about for years to come. By the end of the night, you’ll have experienced a unique and entertaining evening that’s perfect for a summer vacation highlight.

4. Inventing New Identities

Inventing New Identities is a playful and exhilarating activity perfect for making your summer vacation with friends truly unforgettable. The concept is to spend a day or night out where each person adopts a completely new persona, complete with an elaborate backstory and distinctive quirks. This creative exercise not only guarantees endless laughter but also fosters deeper connections and memorable experiences.

Begin by having each participant come up with their new identity. This could be a fictional character, an exaggerated version of themselves, or even a completely invented personality. Think of unique names, professions, and personal traits for each new persona. The more detailed and imaginative, the better!

Once everyone has their new identity, fully embrace the roles as you head out to explore your chosen destination. Act and interact with others as your new character would, maintaining your persona throughout the day or night. Whether you’re dining out, visiting tourist spots, or hitting the local nightlife, stick to your new identity and observe how it influences your interactions and experiences.

To enhance the fun, plan activities and challenges that align with your new personas. You might create a scavenger hunt where each clue requires you to perform a task related to your character, or engage in conversations and see how long you can maintain your invented story. Encourage spontaneous creativity and adapt your persona based on the situations you encounter.

The beauty of Inventing New Identities lies in the freedom to be as wild and imaginative as you like. It’s an excellent way to break away from the everyday routine and dive into a world of creativity and fun. This activity not only allows for hilarious moments and unexpected interactions but also deepens the bond among friends through shared adventures and laughter.

By the end of your identity-inventing escapades, you’ll have a collection of stories and memories that highlight the joy of stepping out of your comfort zone and embracing the whimsy of pretending. It’s a fantastic way to make your summer vacation truly stand out and provide a treasure trove of amusing anecdotes to reminisce about in the future.

5. Ugly Phone Case Swap

The Ugly Phone Case Swap is a delightfully entertaining activity that adds a unique twist to your summer vacation with friends. Inspired by the concept of Secret Santa, this game revolves around selecting and gifting hilariously ugly phone cases to your friends.

Here's how it works: Before your vacation begins, each participant draws a name from a jar or hat. This name corresponds to the friend who will receive the phone case they’ll choose for them.

Once everyone has drawn a name, the fun part begins. Over the course of your vacation, each person selects a phone case that they believe will delightfully surprise and amuse the friend whose name they drew. The key is to find a case that is as outrageous and entertaining as possible, adding an element of playful surprise to the activity.

On the first day of your vacation or at a designated moment, everyone gathers together to exchange their chosen phone cases. Each person presents their wrapped case to the friend whose name they drew, creating a moment of anticipation and laughter. The recipient unwraps the case and reacts to their new, often hilariously ugly phone accessory.

The fun doesn’t stop there. After the exchange, everyone is encouraged to proudly use their new phone case throughout the vacation. Whether you’re heading out for a day of sightseeing, hitting the beach, or enjoying a night out, flaunting your new phone case adds an extra layer of humor and camaraderie to your activities.

The Ugly Phone Case Swap is all about embracing the whimsical and playful side of your group dynamics. It’s a fantastic way to spark laughter, create memorable moments, and ensure that your summer vacation is filled with fun and unexpected delights. By the end of the trip, you’ll have a collection of amusing stories and hilarious photos showcasing the ridiculous phone cases and the joy they brought to everyone involved.

6. Crazy Face Paint

Crazy Face Paint is an exhilarating and whimsical activity that guarantees a day full of laughter and unforgettable memories with your friends. The idea is to transform your faces into vibrant works of art using bold and outlandish face paint designs. Whether you're planning a day out at a festival, a beach party, or just hanging out, crazy face paint adds a layer of fun and creativity that’s perfect for summer.

Start by gathering a selection of face paints in an array of bright and unusual colors. You can find these at costume shops, craft stores, or online. Choose paints that are specifically designed for skin use to ensure safety and ease of removal. You’ll also need brushes, sponges, and perhaps even glitter to add extra flair to your designs.

Before applying the face paint, gather your group and brainstorm a variety of wild and imaginative designs. This could range from whimsical creatures and abstract patterns to intricate, multi-colored designs. The more creative and bizarre, the better! Encourage everyone to choose a theme or character that excites them and aligns with their personal sense of fun.

Once everyone has their design in mind, it’s time to get painting. Set up a painting station with mirrors so everyone can see their progress. Spend time carefully applying the face paint, experimenting with different techniques and combinations. This process is as much about the fun of creating as it is about the final result.

After everyone is painted up, head out and show off your new looks. Whether you're hitting the town, attending an outdoor event, or simply strolling around, your crazy face paint will attract attention and spark conversations. Be sure to bring extra face paint with you, as it’s likely that strangers will want to join in on the fun and participate. You can set up a mini face-painting station and offer to paint others who are intrigued by your designs. This adds another layer of interaction and spontaneity to your outing.

Crazy Face Paint is more than just a creative outlet; it's a celebration of fun and spontaneity. It allows you and your friends to express yourselves in a unique way and enjoy a carefree day together. The laughter, the joy, and the vibrant memories created through this activity will make your summer vacation truly unforgettable.

7. Faking a Divorce Party

While faking a bachelorette party is a well-known and often tried prank, faking a divorce party is an even more unconventional and entertaining idea that’s sure to make your summer vacation memorable. The concept is simple yet surprisingly effective: stage a faux divorce party where the theme revolves around a humorous and dramatic celebration of "liberation" from a fictional relationship.

The charm of faking a divorce party lies in its novelty. Most people are familiar with the concept of pretending to celebrate a bachelorette party, but few have ventured into the realm of orchestrating a mock divorce party. This fresh take can provide a unique twist to your group’s adventures.

I know someone who decided to give this a try, and the results were eye-opening. According to her, the experience was both hilarious and surprisingly rewarding. She reported receiving a lot more free drinks compared to when she had staged a bachelorette party. This unexpected bonus came from the fact that people were intrigued and entertained by the unconventional theme of a divorce party.

The atmosphere at a faux divorce party tends to be even more jubilant and carefree than other themed gatherings. The playful notion of celebrating freedom and new beginnings can lead to an exuberant and fun-filled evening. Guests are likely to engage more, embrace the humor of the situation, and contribute to a lively party atmosphere.

To pull off a successful fake divorce party, make sure to create a few humorous elements and details that align with the theme. Think about incorporating cheeky decorations, amusing “divorce party” drinks, and playful activities that revolve around the idea of newfound freedom. Encourage guests to dress in exaggeratedly somber or hilariously celebratory outfits to enhance the comedic effect.

Overall, faking a divorce party can be a delightful and unexpected way to break from the norm and enjoy a night of laughter and camaraderie. It’s an opportunity to experiment with new party themes and enjoy a memorable experience with friends. So, if you’re up for a unique and amusing challenge, give a faux divorce party a try and prepare for an unforgettable time filled with joy, surprises, and plenty of laughs.

8. Creating a Vlog of Your Vacation

Making a vlog of your vacation can be an incredibly fun and memorable way to document your adventures, especially when you focus on capturing every interaction you have with strangers. This approach adds an exciting layer to your content, turning ordinary encounters into engaging and often hilarious moments.

To start, gather your vlogging equipment—such as a camera or smartphone with good video capabilities—and plan out your filming strategy. The idea is to film as many interactions with strangers as possible, turning everyday encounters into captivating stories for your viewers.

Begin by setting the stage for your vlog. Make sure to introduce your adventure, outlining your goal of capturing unique interactions with people you meet along the way. This sets the tone and lets your audience know what to expect.

As you go about your activities, be open and approachable. Whether you're visiting popular tourist spots, enjoying a local event, or simply hanging out at a café, make an effort to engage with people around you. Approach strangers with a friendly attitude and explain that you're filming a vlog. Most people will be intrigued and happy to participate in your video.

When you film these interactions, be sure to capture the spontaneity and authenticity of the moments. Record conversations, reactions, and any amusing or unexpected events that occur. This could include quirky anecdotes, interesting stories, or simply funny exchanges. The goal is to showcase the diverse and often humorous ways people interact in different settings.

Editing your footage will be crucial to creating an engaging vlog. Select the most entertaining and relevant interactions, and weave them into a cohesive story that highlights the variety of people you encountered. Add commentary or narration to provide context and enhance the viewer’s experience.

Publishing your vlog with a focus on these spontaneous interactions can turn your vacation footage into a dynamic and engaging piece of content. It offers viewers a glimpse into the unique and unexpected moments that arise when traveling and meeting new people. Plus, it’s a fantastic way to relive and share your vacation experiences with friends, family, and a broader audience.

In summary, filming every interaction with strangers during your vacation can transform a simple vlog into a lively and captivating documentary of your travels. It’s a creative way to capture the essence of your journey, celebrating the surprising and delightful moments that come from connecting with others.

9. Bar Hopping Competition with Challenges

Bar hopping with challenges is an exhilarating and interactive game designed to make your nights out with friends even more memorable. It combines the classic bar-hopping experience with fun, engaging tasks that add an extra layer of excitement and camaraderie to your evening.

Here's how it works: Before your night out, create a list of challenges that you and your friends will attempt at each bar you visit. Assign different point values to each challenge based on its difficulty:

- 1 point for easy challenges
- 5 points for moderate challenges
- 10 points for challenging tasks
- 15 points for very difficult feats

As you visit each bar, complete the challenges and document your successes. This could involve taking photos, videos, or simply recounting the experiences to your friends. The challenges are meant to be light-hearted and add a fun twist to your bar-hopping adventure.

At the end of the night, tally up the points based on the completed challenges and celebrate the victories with your group. You can create a fun recap of the evening with photos and stories of the most entertaining moments.

This bar-hopping game not only makes the night more engaging but also fosters group bonding and creates lasting memories of your fun-filled adventures. It’s a perfect way to add excitement and laughter to your outings, ensuring that your bar-hopping experience is anything but ordinary.

 

Example: 

1 point:

  • Start the night with a shot chosen by the bartender.
  • Order a cocktail you have never heard of.
  • Take a selfie with a stranger.
  • Take a selfie with a neon sign.
  • Order a drink using only charades to communicate.

5 points:

  • Play truth or dare with a stranger.
  • Take a shot with the bartender.
  • Trade accessories with someone.
  • Write your phone number on a stranger’s hand.
  • Take a photo with someone wearing the same color shirt as you.

10 points:

  • Ask the DJ to play your favorite song.
  • Create a conga line.
  • Get someone to buy you a drink.
  • Use the worst pickup line you can think of.
  • Convince a bartender to let you pour a drink.

15 points

  • Share a kiss with someone of the same gender.
  • Collect phone numbers from five different people.
  • Get a hickey from someone you just met.
  • Sneak into the VIP area.
  • Take a body shot off someone.

 

If you’re looking for another unique game with a point system, check out our Photo Scavenger Hunt designed for vacation. This engaging activity involves taking selfies with various items or scenes from a list, each selfie earning you points based on the challenge. Discover more about this exciting scavenger hunt and how it can add an extra layer of fun to your trip!

10. If You Break a Rule, You Take a Shot

The concept behind our "Ultimate Vacation Shot Rules" is to turn everyday moments into playful and memorable drinking game opportunities throughout your trip. Each rule dictates that whenever a specified action occurs (like crying, waking up last, or taking the longest to get ready), the person involved must take a shot. For example; Last person to wake up each morning takes a shot. This adds an element of surprise and fun to your vacation activities, whether you're relaxing at the beach, sightseeing, or partying at night.

To spice things up even more, before embarking on your vacation, everyone can predict who they think will have to take the most shots based on the rules. The person who predicts the most correctly gets to designate someone to take an extra "ultimate shot" at the end of the trip—a shot they can concoct themselves, making it a memorable finale to your vacation adventures. This concept ensures laughter, friendly competition, and shared moments that will make your vacation truly unforgettable. Cheers to fun times and lasting memories with friends!

As you wrap up your adventure through our guide of 10 must-try activities, we hope you're feeling inspired and excited to make the most of your upcoming vacation with friends. These creative and fun-filled ideas are sure to elevate your summer experience, transforming ordinary moments into unforgettable memories.

Whether you’re diving into outrageous dress-up challenges, pulling off clever party pranks, or simply embracing the whimsy of unique group activities, each experience is designed to add a special touch to your getaway. Remember, the key to an unforgettable summer is embracing spontaneity and enjoying every moment with your friends.

Thank you for exploring these ideas with us! We hope they bring joy, laughter, and a touch of adventure to your vacation. Here’s to a summer filled with incredible experiences and cherished memories. Have an amazing trip, and make sure to savor every moment with your friends!

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