By travel writer Marco Monroy Robles.
Guys’ trips have evolved far beyond party weekends into sophisticated adventures which prioritize meaningful connections and personal growth. Discerning travelers now seek elevated bonding opportunities in luxury accommodations to create lasting memories. This guide will walk you through six of the best guys’ trip destinations where custom experiences mean you don’t have to stress over every detail.
6 TOP Guys’ Trip Destinations Worldwide: Where To Stay and What To Do
The first step to planning the perfect guys’ trip is finding destinations that are both adventurous and luxurious without the usual travel headaches. These six milestone celebration destinations give you the freedom to celebrate milestone achievements while creating the kind of memories that strengthen friendships for decades.
Cabo San Lucas, Mexico: Fishing, Golf, and Vibrant Nightlife
Cabo is Mexico’s premier destination for adventure sports and sophisticated relaxation. The incredible desert landscape contrasts with the sapphire ocean, where you can go on deep-sea fishing expeditions for marlin and dorado. You’ll also find championship golf courses designed by legends like Jack Nicklaus right by the Sea of Cortez.
When the sun sets, there’s no shortage of elevated nighttime experiences — Cabo is one of the best places for single men’s travel for a reason. World-class restaurants helmed by celebrity chefs compete with rooftop bars and exclusive beach clubs for your attention. The combination of Cabo’s outdoor adventure and luxury amenities is why Mexico is one of the best countries for a guys’ trip.
Big Sky, Montana: Rugged Adventures in a Refined Setting
Big Sky appeals to high-net-worth travelers who appreciate rustic charm elevated by world-class amenities. This Montana destination combines the raw beauty of the American West with the sophistication you expect in your accommodations and dining experiences. In winter, it’s one of the best places to ski in North America, while summer opens up backcountry adventures like horseback riding and zip lining.
The region’s luxury lodges and private mountain cabins blend beautifully with the mountains while still offering five-star amenities. Big Sky luxury accommodations range from ski-in, ski-out properties to riverside retreats. For those looking for the best guys’ trip destinations for outdoor adventures in the United States, Big Sky is the place to be.
Aspen, Colorado: Elevated Dining and World-Class Fly Fishing
Aspen is more than a winter ski destination — it’s an equally excellent choice for spring and summer guys’ trips. The town’s commitment to culinary excellence means your group will dine at world-class restaurants. The surrounding wilderness has some of Colorado’s best fly fishing and whitewater rafting opportunities.
The Roaring Fork Valley’s streams are packed with rainbow and brown trout. Experienced guides can arrange private access so you and your group can enjoy a part of the river to yourselves. Once you’ve had your fill of the outdoors, enjoy other Aspen experiences like wine tastings and private chefs’ dinners. This gem in the Elk Mountains is one of the best destinations for guys’ trips.
Lido Key, Florida: Tarpon Fishing and Coastal Leisure
Lido Key is the Florida Gulf Coast at its finest, where world-class tarpon fishing meets luxury living. The ocean and bay around this barrier island are great places to fish for the silver king. Experienced captains know the best spots to find these legendary fish.
Your days here will unfold at the relaxed pace of coastal living. Start your day with fishing in the morning, then relax on the beach in the afternoon. In the evening, enjoy dinner at restaurants by the waterfront known for their fresh Gulf seafood. Exclusive Florida beach vacations like this let your group experience the state’s natural beauty without the crowds that plague more commercial destinations.
This incredible guys’ trip destination is perfect for anyone who wants to fish and relax. You will return home with stories about battling 100-pound tarpon and memories of beautiful sunsets spent with your closest friends.
New York City: Icons and Endless Possibility
New York might surprise you as a guys’ trip destination, but this cosmopolitan city has experiences you simply won’t find anywhere else in the United States. You’ll spend your days exploring landmarks like Central Park and the Brooklyn Bridge. At dusk, relax at the city’s legendary rooftop bars as you take in sunset views, then head to world-class restaurants for the best meals and conversations.
Staying at a luxury residence in New York City in Midtown East puts you in the middle of this electric city. You can walk to Broadway shows that friends back home are still trying to get tickets for, then grab late-night cocktails at speakeasies that serve artisanal drinks.
St Andrews, Scotland: For Golf, Pints, and Stories That Last
Scotland is one of the best countries for guys’ trips centered around golf, aged Scotch, and unforgettable historic castles. And St Andrews is one of the holy grail destinations for serious golfers worldwide.
This ancient Scottish town is home to The R&A (one of golf’s governing bodies) and the legendary Old Course. You won’t find another location with such an intense connection to the sport’s history. The reverence you feel walking the same fairways as golf’s greatest champions is something you won’t forget, regardless of what the scorecard looks like.
Beyond golf, St Andrews has world-class whisky tastings at local distilleries and plenty of opportunities to stay in converted castles throughout the surrounding countryside. You’ll find many high-end accommodations in St Andrews, from historic properties within the town to historic estates overlooking the North Sea, giving your group both comfort and authenticity.
Once you’re here, you and your closest friends can share a dram of aged Scotch after conquering the Road Hole, recounting the day’s highs while planning tomorrow’s round. This experience is what makes golfing destinations one of the best locations for a guys’ trip.
Tips for Planning a Seamless Luxury Guys’ Trip
To make a guys’ weekend truly unforgettable, it helps to have every detail handled, so you can focus on time together instead of logistics. With Equity Estates taking care of the planning, from luxury residences to curated activities and concierge services, your group can enjoy a seamless experience while still leaving room for spontaneity.
Try following these tips when planning your next escape:
- Pick the right group: Six to eight people is usually the sweet spot for luxury accommodations and group activities. Smaller groups will let you have intimate conversations and will make deciding on activities and restaurants so much easier.
- Align expectations early: Ask your group about activity preferences and budget comfort levels before booking anything so everyone’s on the same page.
- Book professional services to elevate your experience: Private chefs and concierge services can really make a difference. These professionals handle all the details so you can sit back and enjoy your trip.
- Plan activities but leave room for spontaneity: Book tee times, fishing charters, tours, or restaurant tables for signature experiences, and keep other time blocks open for whatever comes up. The best memories sometimes come from unexpected activities.
- Choose accommodations that bring your group together: Properties with outdoor spaces and game rooms for everyone to gather are ideal for bonding. The right setting encourages the kind of conversation and shared experiences that make trips unforgettable.
LET EQUITY ESTATES Plan Your Guys’ Trip
The best guys’ trips come together when every detail reflects your vision — and it all starts with the right accommodations. All you need to do is pick the location, and we’ll handle the rest.
With everything taken care of, you can focus on what really matters: spending quality time with friends and creating lasting memories. Learn more by speaking with our Investor Relations team at 404.445.8501 or through online scheduling. In the meantime, explore our other stunning destinations waiting for you.
