Island beach with palm trees

How to Plan a Trip With Friends

Have you and your friends decided it’s time to plan a getaway? Nothing beats exploring exotic places and cultures with your favorite travel companions. When you travel with friends, you get to create vivid memories, strengthen bonds and laugh together as you let loose. Also, the planning process is a lot more fun when you’re gathered with friends around snacks, wine and a pile of travel brochures anticipating freedom and relaxation.

Unlike traveling solo, a group trip also requires careful planning to ensure everyone has a great time. In this post, we’ll share tips to help you plan an unforgettable journey with friends. You’ll enjoy the process, and best of all, the trip!

Tips for Planning Group Travel

It’s fun to share a sense of wonder with friends as you roam a medieval castle or hike through a rainforest. Whatever your interests, the following tips will help make planning a breeze, even if you all have different interests.

1. Appoint a Leader

The first step to planning a group trip is to appoint a leader. The leader will do most of the planning, like booking the accommodations and making reservations. Whoever you choose to be the leader should be organized, patient and have time to take charge. Having a leader will streamline the process and keep it confusion-free.

2. Plan Early

Generally, the earlier you can start planning a group trip, the better. This way, you’ll have more time to handle any cancellations or schedule changes. You’ll also have a better chance of finding deals and group discounts on accommodations, tours and other details. Lastly, you’ll want to make arrangements early if you’re planning on traveling to a popular destination during the summer or holidays, want your choice of cabins if you’re taking a cruise, or have a specific itinerary in mind. Ideally, you’ll want to plan six months to a year in advance, especially if you’ll be traveling internationally.

Plane flying over a city

With that said, you won’t want to plan too early when it comes to booking your flight. Experts agree that you’ll get the best deal on flights if you book one to three months in advance because prices typically increase a week or two before departure. So, if you book your flight too soon, you might pay a higher price.

If you and your friends decide you can’t wait half a year to soak up tropical sunshine, don’t despair. You can book a trip on a whim, and you may even be able to find some last-minute deals. Just know you might not get the room or cabin you want, and be willing to be flexible with your plans.

3. Choose a Destination Together

Perhaps the most critical aspect of the planning process is choosing a destination everyone will enjoy. Some of your friends might dream of spending an entire week lounging on a beach, while others might wish to explore museums and other cultural attractions. Consider the following factors to help you decide where to go:

  • Goals and interests: What does each person hope to accomplish by traveling? Do some want to relax, while others want to explore? You can find a destination that satisfies everyone’s needs. For example, with our Classic Caribbean cruise, beach lovers can kick back on the shore while adventurers take a snorkeling tour. If you all share a common interest, like a love of cooking, you might consider a culinary-themed cruise — it’s all up to you and your pals. The key to a happy trip is to make sure everyone’s expectations are clearly defined from the get-go.
  • Fitness level: Make sure you and your friends discuss your fitness levels and what you can handle. For example, you wouldn’t want to book a hiking tour if one person isn’t comfortable climbing a mountain. Find activities you can enjoy together, and also be open to experiencing some activities separately if necessary.

    Coastal city near the ocean

  • Budget: Budget is a significant part of the trip, and you’ll all have to be on the same page when it comes to accommodations, travel expenses, dining and excursions. While one person’s budget may allow them to explore Africa for a month, another person may only be able to afford a weekend getaway. Talk about budget openly and how much each person is willing to spend.
  • Length of trip: Consider how many days each friend can spare for traveling, as this will affect your destination choice. For example, if someone in the group can only take a five-day vacation, it doesn’t make much sense to plan a trip to China. Generally, a week-long vacation is a good amount of time for group trips, unless you and your friends share the same travel style.
  • Type of accommodations: Make sure everyone has the same expectations regarding accommodations, and one person isn’t planning a camping trip while another is booking rooms at a five-star hotel. Ideally, you’ll want to find accommodations that suit everyone’s comfort level and budget and provide easy access to a variety of dining, entertainment and recreational options.
  • Time of year: Decide what time of year you all wish to travel and how the season affects the destination and budget. For instance, most people travel during the summer, which means you’ll pay higher prices and face larger crowds if you take a summer trip. However, vacationing during the summer may also provide opportunities to attend a range of festivals and events,

     and you may enjoy nicer weather depending on where you go. Gather your travel friends and discuss what’s most important regarding the season.

Remember, if you can’t all agree on the same activities, try to find a destination that meets everyone’s needs in some way, and be comfortable with doing your own thing now and then. If you can’t do everything together while on vacation, you’ll have lots of fun stories to share when you meet up for dinner.

4. Create a Checklist

Getting organized is a great way to take the stress out of any planning process. When it’s time to plan your group trip, create a checklist of all the items you need to take care of before you embark on your journey. Make sure to share the checklist with your travel companions so everyone can prepare for a safe, healthy and stress-free voyage. You can use online tools like Google Docs so people can add to the checklist when needed and stay updated.

Here are critical items to add to your pre-trip checklist, which will ensure you don’t forget any crucial steps.

Items to pack

Open suitcase with personal belongings

Make a list of travel must-haves and share it with friends. This will include items to pack that suit your destination, such as:

  • Appropriate clothing: Pack clothing and accessories with the destination and season in mind. This may include bathing suits, sunglasses and flip-flops.
  • Toiletries: Don’t forget toiletries like sunscreen, a toothbrush, toothpaste, insect repellent, floss, deodorant and personal hygiene items.
  • Equipment: Plan to bring a camera, chargers and headphones.
  • Fun items for the group: Consider packing a deck of cards, board games or movies to enjoy each other’s company between excursions. You might create a playlist to add background music to the fun. Create a playlist together by asking friends to add five or ten songs to the list.

Passports and Visas

No one wants to forget their passport at home. If you plan to enter another country, you’ll need a passport. Depending on where you go and the length of your stay, you may also need a visa. For example, you need a visa to enter China, but not for a week-long trip to Mexico.

You’ll want to check this information as soon as possible. If someone in the group needs a passport, it takes six to eight weeks to process. You can find out if you and your friends need a visa by researching your destination at the U.S. Department of State website.


If you’re heading abroad with your pals, make sure to research currency and the currency exchange process for the places you plan to visit. Although you may plan to use a credit card for most of your purchases abroad, it’s recommended to carry a little cash in the local currency for small purchases, such as tips, snacks or souvenirs. The best way to receive cash in the local currency is to withdraw money from an ATM once you arrive, and avoid airport kiosks or exchange booths, which typically charge higher fees. If you’re concerned about having cash on you before you arrive, see if you can purchase currency from your bank before you depart.

If you are going on a cruise with friends, you likely won’t need cash for your time spent on the cruise ship. Most of your expenses will be included with the initial cost, and many ships run on a cashless system. With that said, cash might come in handy when you’re exploring different ports for tipping drivers, waitstaff or tour guides. Generally, plan for each person to have between $5 and $20 per day for a cruise. Also, don’t forget to call your bank and credit card companies a week or two before you leave to let them know you’ll be traveling.


Another vital item to add to your checklist is immunization. It’s recommended to get vaccinated four to six weeks ahead of time if needed because some vaccines require multiple doses or take time to be effective.

To find out if you and your travel companions need vaccines, visit the Centers for Disease Control and Prevention (CDC) website, and search for your destination. It’s also a good idea to meet with your doctor before the trip to discuss your itinerary. Depending on where you’re going and what you plan to do, some vaccines may not be necessary, while others can help prevent a health issue.

Person receiving a shot in the arm

Ports and Excursions

If you’re going on a cruise, aim to research ports early in the planning process, and be ready to book shore excursions a month or two before you depart. Also, consider how you’ll get to and from excursions once you arrive at each port. Planning and booking excursions ahead of time will ensure you and your friends don’t miss out on activities you really want to experience.

5. Make Time to Relax

If you start to feel overwhelmed during the planning process, take a deep breath and remember what it’s about — relaxing and having fun. There’s no need to pack the itinerary full with activities — make sure to save room for downtime. When it comes to group travel, there are no rules, as long as everyone’s happy. In other words, if someone wants to sleep in late while someone else wakes up early to go for a swim, it’s no big deal.

The Best Way to Plan a Group Vacation

Because a group trip requires careful planning, you may want to hand it over to professionals and save yourself the effort. One way to do this is to consider taking a cruise with your friends. A cruise is a great way to travel with friends, whether you’ve known your pals for decades or met a few months ago. When you sign up for a cruise, you don’t have to worry about finding shore excursions or determining who’s going to cook dinner. You also don’t have to worry about anyone getting restless. Friends can comfortably do their own thing while onboard, and meet up later to enjoy each other’s company.

Lastly, cruise ships often go to desirable destinations like tropical beaches and scenic European ports where there’s sure to be something to please everyone. When you go on a cruise, your job is to relax, enjoy delicious food and let your worries melt away while the captain and the crew take care of the rest.

Start Planning Your Group Trip With Windstar Cruises

If you’re ready to plan an unforgettable voyage with friends, we’re ready to accommodate everyone in your group at Windstar Cruises. Come sail with us, and we’ll take care of the details. Our cruises include all meals in all of our venues, 24-hour room service, all non-alcoholic beverages, live music, cooking demonstrations, watersports equipment and more. Our goal is to make guests comfortable, pampered and delighted as they sail to the world’s most breathtaking destinations. In addition, our excursions offer authentic, culturally rich experiences you and your friends will talk about for years to come.

To start planning a life-changing voyage, browse our cruises and destinations today. For a completely stress-free experience, call a Windstar Vacation Planner who will take care of every detail to meet your needs, from the flight to excursions.

Boat on the water

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