The Joy Of Traveling Together
If there is one thing I can never get enough of, it's traveling with my favorite group of friends.
In 2024, my friend and client, Theresa, invited me to join her and her friends on a cruise. Little did I know that these ladies, our monthly get-togethers, and our shared adventures would become such an important part of my life. If you've ever considered traveling with a group of friends, take the leap and plan it. You won't regret it for a second. There's something special about experiencing the world with your people.
How To Build The Perfect Travel Crew
When choosing your travel group, look for friends or family members who are carefree, adventurous, flexible and genuinely love to travel. To begin planning, you can either work with a travel advisor or plan everything on your own.
In our group, Wendy and I take on the planning responsibilities. We work very well together, handling reservations, accommodations and logistics. The rest of the group is happy to contribute their share and let us manage the details.
Everyone brings unique skills, personality traits and experiences that enhance the group travel experience. Finding the right balance of personalities can make all the difference and create memories that last a lifetime.
An Orlando Stay And Caribbean Cruise With Friends
Our latest adventure included 12 women ranging in age from their 20s to their 70s. We come from all walks of life, including nurses, a hairdresser, retirees, a barista, a paralegal, an anesthesiologist and many other professions. We're a diverse group of women who proudly call ourselves the Accomplices & Alibis. Some are family, some are lifelong friends — and now we're all friends.
The ladies always add fun touches to our trips, including matching T-shirts, funny door magnets, glowing headbands and drawstring bags. They also seem prepared for every situation imaginable, carrying everything from sunscreen to first aid essentials. But the best thing they each bring is their sense of humor. I never laugh harder than when I'm with these women.
Our journey began in Orlando, Florida, with a stay at The Fountains. This resort has become a favorite home base for my family and friends whenever we visit Orlando. Conveniently located near major attractions, it's just minutes from SeaWorld® Orlando and approximately 15 to 20 minutes from Orlando International Airport, Walt Disney World and Universal Orlando Resort.
I booked two spacious Suites for our group. Our 2-Bedroom Suite slept eight, while our 3-Bedroom Suite accommodated 10. The Suites were clean, comfortable and equipped with everything we needed, including in-room laundry, full kitchens with dishwashers, and multiple bathrooms. Our group has become spoiled by the amenities offered at Hilton Grand Vacations and the former Bluegreen Vacations resorts, now part of the Hilton Grand Vacations portfolio.
Once we settled in, several members of our group quickly discovered the resort's multiple pools and the splash bar. Their favorite activity? Dancing poolside with bucket drinks in hand and enjoying the Florida sunshine. Many were perfectly content to spend the next couple of days relaxing by the water.
Meanwhile, my lifelong friend Lisa and I headed to one of my favorite Orlando shopping destinations, Orlando Vineland Premium Outlets, located just two miles from the resort. We also visited the Disney's Character Warehouse, where we found authentic Disney merchandise at deeply discounted prices. It's always an exciting treasure hunt.
The Fountains also offered plenty of convenient dining options. We loved the quesadillas at the Wakoola Bar & Grill and enjoyed delicious pizza delivered directly to our Suite from Flippers Pizzeria. The salads were excellent as well. I also can't forget to mention The Market, which proudly served Starbucks favorites and quickly became a daily stop for our group.
Unfortunately, we only had two days at the resort. We would have happily stayed longer.
Setting Sail For The Caribbean
Our next stop was Port Canaveral, where we boarded Carnival Vista for an eight-day cruise with four beautiful Caribbean destinations: San Juan, Puerto Rico; Grand Turk; Amber Cove, Dominican Republic; and St. Thomas, U.S. Virgin Islands.
Members can also use travel services through Hilton Grand Vacations to book cruise vacations, making it easy to combine resort stays with time at sea.
Carnival Cruise Line® remains our personal favorite thanks to its variety of destinations, lively entertainment and extensive dining options. Some of our must-visit spots on board include Guy's Burger Joint and Pig & Anchor Smokehouse. We're also big fans of Cucina del Capitano, where lunch is included at no additional cost.
Each evening, we gathered in the main dining room to enjoy dinner together, catch up on our day, and share plenty of laughs. One of the highlights of cruising is getting to know the waitstaff. Before long, they become part of the experience.
We sing, dance and have fun wherever we go. Our group often attracts fellow cruisers who stop by to chat, join in the festivities and occasionally ask to sit with us. None of that would be possible without the incredible waitstaff, who quickly become honorary members of Accomplices & Alibis on every cruise.
Memorable Moments From Each Caribbean Destination
St. Thomas, U.S. Virgin Islands
We sailed aboard a catamaran, enjoyed stunning coastal views, and snorkeled alongside sea turtles, barracudas and countless tropical fish. It was an unforgettable day on the water.
San Juan, Puerto Rico
We spent time wandering through Old San Juan, browsing local shops and visiting street vendors before exploring Castillo San Cristóbal, one of the city's most impressive historic landmarks.
Grand Turk
We enjoyed an excursion called Home Sweet Home, where we spent the day swimming in crystal clear waters, enjoying local cuisine, and soaking up the Caribbean sunshine.
Amber Cove, Dominican Republic
Although our planned excursion was canceled, I had previously visited this destination and highly recommend Monkeyland. Visitors can interact with adorable squirrel monkeys in a beautiful tropical setting, and several different tours include this unique experience.
Why Traveling With Friends Matters Most
We finished our cruise with a couple of relaxing sea days. Between an '80s Glow Party, afternoons on the Lido deck, games of euchre, evenings in the casino, and plenty of laughter along the way, we created memories that will last a lifetime.
As wonderful as the destinations were, this trip reminded me of something even more important: Travel is about the people you share it with. The beaches, excursions and adventures were incredible, but the friendships strengthened along the way are what made this journey truly unforgettable.
If you've been thinking about planning a getaway with your favorite people, don't wait. Gather your crew, choose a destination and start making memories together. You may discover, just as I did, that the journey becomes even more meaningful when shared with friends.
Key Takeaways
Traveling with Friends Creates Deeper Memories: Sharing new destinations and experiences with a trusted group can strengthen friendships and create lasting memories.
The Right Travel Crew Matters: Choosing companions who are flexible, adventurous and easygoing helps ensure a smooth and enjoyable group vacation.
Resort Stays Add Comfort And Convenience: Spacious accommodations, on-site dining and resort amenities provide an ideal setting for larger groups to relax and reconnect.
Cruises Offer Something For Everyone: From island excursions and entertainment to dining and downtime, cruises make it easy for travelers with different interests to enjoy the same vacation.
Shared Experiences Create Lifelong Memories: Whether exploring a new port, lounging poolside or laughing over dinner, the moments spent together often become the highlight of the journey.
FAQs
Q: What are the benefits of traveling with friends?
A: Traveling with friends allows people to share costs, create lasting memories, strengthen relationships, and experience destinations together in a fun and meaningful way.
Q: How do you choose the right group for a vacation?
A: Successful group travel often starts with choosing people who enjoy similar travel styles, communicate well and are flexible when plans change.
Q: What are the advantages of staying in a resort with a group?
A: Resorts offer convenient amenities, spacious accommodations, dining options and activities that allow groups to spend time together while still enjoying individual interests.
Q: Why are cruises popular for group vacations?
A: Cruises combine accommodations, dining, entertainment and multiple destinations into one trip, making them an easy and convenient option for groups with diverse interests.
Q: How can travelers make the most of a group getaway?
A: Balancing planned activities with free time, sharing responsibilities, and focusing on the experience rather than a strict itinerary can help create a more enjoyable trip for everyone.
