Tips for Vacationing With Friends

It’s Saturday night, and you’ve gathered with your closest friends. Suddenly, you have the idea to cruise the Mediterranean, just you and your pals, and realize you’re speaking out loud. Is it merely the wine talking, or is traveling with friends a good idea? 

As long as you choose the right people, traveling with friends can be an incredible experience. Imagine checking off bucket-list destinations alongside people who understand and cherish you — what could be better than that?

While a trip with friends may seem easy to throw together — after all, you have plenty in common — you’re still individuals with different wants and needs. These differences can make some aspects of traveling a bit more challenging than traveling solo.

Still, with the strong bonds you share and positive mindsets, you can overcome common obstacles and have a trip of a lifetime. In this post, we’ll help you start the planning process with tips on how to have a vacation with your friends.

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Why Travel With a Group of Friends?

Do you have friends you’ve known for a long time, but you’ve never taken a trip with them before? If you’re not sure if you should hit the sea, road or sky with your best friends, consider the following benefits of friend-centric travel.

  • You’ll create lasting memories: Whether you’re snorkeling in Aruba or touring wineries in Greece, it’s bound to be more meaningful if you include friends. Even restful moments feel more special with friends, like watching the sunset over the sea. Meaningful experiences create lasting memories that you and your friends can cherish and maybe even laugh about long after the journey has ended.
  • You can support each other: If you’ve ever traveled before, you know things don’t always go as planned. If you feel overwhelmed by a delay or other unexpected event, your travel companions will be there to uplift you and help you stay grounded. Likewise, if a friend needs some reassurance, you’ll be available to offer your support. 
  • You’ll strengthen bonds: Have you fallen out of touch with some of your closest friends?Traveling is one of the best ways to reconnect and strengthen your friendships. When you’re away from the daily grind, you can finally spend quality time with your friends, talking, sharing, learning, exploring and connecting on a profound level. As the saying goes, “Friends who travel together stay together.”
  • You can have a planning party: Planning a trip with friends is exciting and a good excuse to get together. Savor the exhilaration of exploring your travel dreams together, envisioning where you’ll go and what you’ll do. Though you’ll need to choose a destination eventually, dreaming and planning is part of the fun, especially with your best friends gathered around.
  • You’ll stay youthful: Do you have friends you’ve known for years, maybe even decades? Traveling with longtime friends can make you feel like you’re back in college or high school before life became filled with responsibilities. When you visit new places with old pals, you’ll laugh, reminisce and get in touch with your younger self again.
  • You’ll all be safer: Exploring new cities or wilderness areas is safer with friends, especially if you plan on wandering off the beaten path or roaming at night. You’ll also have the freedom to do more than if you were alone. So, if you’ve always wanted to tour pubs in Dublin or go hiking in Alaska, you can make your dreams come true and have peace of mind at the same time.
  • You’ll complement each other: Is one of your friends an expert map reader? Is another bilingual? Each of you brings unique skills and talents when you travel, making it so much easier to get around, communicate with locals and immerse yourself in a new culture — which is one of the highlights of traveling.
  • You can take heartwarming photos: Posing in front of the Trevi Fountain or at the top of Mount Etna is even more fun with friends by your side. You’ll have many opportunities to take pictures with your friends as you travel, which will warm your heart and make you smile for many years.
  • You’ll still have time alone: Traveling with your friends doesn’t mean you’ll need to spend every waking minute together, and you’ll still have opportunities to catch up on “me time” throughout your journey. When you have time to recharge your battery, you’ll appreciate every moment with friends even more.

Tips for Taking a Vacation With Friends

Are you already packing your bags with sunscreen and bathing suits? We understand you probably can’t wait to escape the everyday routine and get some much-needed relaxation. Still, you’ll want to consider a few tips before booking your trip.

1. Discuss Travel Goals

Before you and your friends catch the next flight to Barcelona, take time to talk about your travel goals. What does each person hope to accomplish on their vacation? Do half of your friends want to focus on relaxing, spending most days with cocktails in hand? Is the other half eager to satisfy their appetites for culture, even if it means getting lost in a foreign city?

Some of your friends might be craving lazy days, while others might want nonstop action. It’s essential to get everyone’s preferences and goals out in the open before you start planning. By having an honest discussion about each person’s hopes and dreams, you can prepare for a satisfying journey. 

2. Address Different Habits

Everyone has different habits that can impact how they travel. For instance, one friend might be a morning person who’ll want to start each day early, and another one a night owl who will wish to sleep in every day.

Your friends also might have specific routines they follow rigorously, even when they’re on vacation. Maybe they want to work out before they start the day, or perhaps they like to take short naps to recharge. Find out what your friends need to feel comfortable and happy during the trip, and plan accordingly.

3. Talk About Costs

Discuss how you’ll share expenses, including paying for restaurants, accommodations, transportation and other costs, before you plan. Will you divide everything equally? Or will you take turns paying for meals or activities? Knowing how you’ll split expenses will prevent uncomfortable moments and will allow you all to focus on the journey.

Plenty of digital tools are available to help your group handle bills, like Splitwise and Venmo. You might also appoint someone to be in charge of tracking expenses and payments to prevent confusion.

4. Leave Room in the Itinerary

It’s essential to have an itinerary to help guide the trip and fit in everyone’s travel priorities. However, you’ll also want to leave some wiggle room in your itinerary and avoid packing too many things into one day. By avoiding a crammed schedule, you and your travel companions can feel more at ease and less pressured to be on the go constantly.

With that said, there may be some things you’ll want to book in advance and build your day around. For example, if there’s a world-renowned restaurant you’re all excited to try, ensure someone makes a reservation as soon as possible, especially if you’re traveling during the summer, which is generally peak season. The same applies to in-demand tours or excursions your group wants to take. If you book specific activities in advance, you won’t have to worry about missing your top sights.

5. Consider a Cruise

Going on a cruise is an excellent way to travel with friends stress-free. After you book the cruise and any excursions you wish to take, the planning process is pretty much over. You and your friends can get on board and enter vacation mode instantly. You don’t have to worry about how you’ll get from one destination to the next or spend time figuring out where you’ll eat.

You’ll also get to experience various ports to satisfy the different personalities in your group and have access to exciting shore excursions, such as culturally immersive guided tours and rare wildlife experiences. And, when you’re at sea, you can relax with friends sipping cocktails on the deck or enjoy some alone time and treat yourself to room service. When you take a cruise, you and your friends will feel like royalty as you sample some of the world’s most desirable places. Could it get much better?

6. Set Aside Personal Time

Even if you’re traveling with your best friends who you feel completely comfortable around, everyone should still have some private time to themselves every day. Try to reserve a half-hour or hour every day to spend time alone and unwind during your vacation. Maybe you’ll go for an early-morning swim each day, or write in your journal every night before bed — whatever helps you recharge. When you reunite with your friends for more adventure, you’ll feel refreshed and ready to embrace the journey ahead.

7. Be OK With Doing Your Thing

Do your friends want to spend the day shopping, but you’d prefer to visit a local history museum? Or maybe you’re looking forward to relaxing on the beach, but your pals have their hiking boots on, ready to go? If you have items on your must-see list that your traveling companions would rather skip, or if you’re not in the mood for a given activity, consider exploring on your own for a day. When everyone agrees that it’s OK to split the group or do some things alone, no one has to sacrifice their top activities. You can catch up with your friends at lunch or dinner and exchange stories.

8. Get Enough Sleep

Ensure everyone gets enough sleep during the journey, so you can all feel your best and make the most of each day. To help promote restful shut-eye, talk about your sleeping habits before planning your trip, especially if you intend to sleep in the same room with friends. For example, can you only sleep with a fan on? Do you snore? Make sure your roommate is aware of any potential issues before booking a room together. You might decide it’s worth the extra cost to get a private room.

9. Use a Travel Professional

Working with a travel professional can take the pressure off your group to plan all the details. A travel planner will compose an itinerary that meets your group’s needs and budget, while arranging elements like accommodations and transportation. These services can be beneficial if you need to coordinate flights for friends who live far away, so you can all get together simultaneously. A travel professional can also recommend tours, excursions and other activities your friends may enjoy.

For example, at Windstar Cruises, our Vacation Planners can suggest exciting excursions that suit your group in some of the most scenic places in the world. Do you consider yourselves chocolate aficionados and beach addicts? We’ll help you plan an unforgettable chocolate tour in the Caribbean. Are you trying to please the history buff in the group as you plan your journey to the South Pacific? We might suggest a historical park overlooking the ocean, providing stunning views and plenty of context.

Overall, if you want to leave the legwork to someone else and keep stress levels minimal, using a travel planner is the way to go.

10. Take Tons of Photos

Be sure to pack your camera and prepare to take an array of photos during your vacation with friends. Take pictures of friends posing in front of natural scenery or historical landmarks. Capture special moments indoors, like sharing paella with locals in Spain or sipping aperitifs at a glamorous restaurant in Monaco.

Remember to get candid shots to catch little moments worth remembering, and don’t forget to include yourself in some photos. If you’re more comfortable being in snapshots rather than taking them, ask a friend to be the group photographer. Though no one should spend every moment looking through a lens, you’ll treasure the pictures when you return home. You may even want to throw a post-trip celebration to gather with your friends, share the photos you all took and reminisce about the time you had.

Plan Your Friendcation With Windstar Cruises

Vacationing with friends is something every world traveler should try at least once. With the memories you’ll create and stories you’ll have to share, you’ll be glad you gave it a chance. If you take a cruise with your travel companions, you can enjoy stress-free planning, attentive service and a vibrant mix of destinations and excursions.

At Windstar Cruises, we invite you and your friends to step aboard our small, uncrowded ship and prepare for an unforgettable journey. We’ll ensure each of you feel pampered and tended to as we sail you to must-see destinations, from exclusive harbors to dazzling ports. You’ll also enjoy extraordinary onboard amenities to enhance your voyage, from world-class dining experiences to comfortable, elegantly furnished staterooms. When you travel with Windstar, you can leave all your worries behind and let us manage the details.

Contact us today to learn more about a group cruise, or browse our destinations to get inspired.

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