Best Guy Weekend Trips: The Ultimate Luxury Escape in the US & Canada

When it’s time for a high-end getaway with the guys, choosing the right destination makes all the difference. Whether you’re craving adventure, a golf retreat, fine dining, or just ultimate relaxation, these best guy weekend trips promise five-star experiences in the US and Canada. Here are 14 top luxury destinations that guarantee an unforgettable weekend.

 

1. Las Vegas, Nevada – The Ultimate Playground

(Best time to go: Year-round)

Sin City is synonymous with luxury, offering extravagant hotels, Michelin-starred dining, and world-class entertainment. The city’s vibrant nightlife, top-tier casinos, and exclusive pool parties make it a top destination for a lavish guys’ weekend.

• Stay: The Venetian Resort or The Wynn Las Vegas for lavish suites and VIP service.
• Do: Private poker lessons, bottle service at Omnia, helicopter rides over the Strip, and golf at Shadow Creek.
• Experience: VIP access to the hottest nightclubs, luxury car rentals, and exclusive whiskey tastings.

 

2. Miami, Florida – Beachfront Glamour & Nightlife

(Best time to go: November-April)

For sun, sand, and sophistication, Miami is an elite choice for a guys’ weekend retreat. Whether you’re soaking up the sun at a private cabana or hitting the exclusive clubs, the city delivers an ultra-luxurious experience.

• Stay: Four Seasons Hotel at Surf Club or Miami Beach EDITION for unparalleled luxury.
• Do: Private yacht charters, cigars in Little Havana, deep-sea fishing, and VIP club access.
• Experience: Private beach butler service, jet ski rentals, and rooftop cocktail tastings.

 

3. New York City, New York – The VIP Metropolis

(Best time to go: Year-round)

NYC offers an unbeatable mix of luxury, culture, and high-energy nightlife. From private speakeasies to rooftop cocktail bars with breathtaking views, the city caters to every kind of high-end traveler.

• Stay: The Peninsula New York or The Baccarat Hotel for indulgent suites.
• Do: VIP Broadway tickets, private whiskey tastings, behind-the-scenes tours of major sporting arenas, and helicopter tours.
• Experience: Exclusive shopping experiences, private chauffeur services, and cigar lounges.

 

4. Scottsdale, Arizona – Desert Golf & Relaxation

(Best time to go: October-May)

Scottsdale is a golfer’s paradise with luxurious accommodations and breathtaking landscapes. The city’s spa resorts and vibrant nightlife scene also offer plenty of options for relaxation and entertainment.

• Stay: Four Seasons Resort Scottsdale or The Phoenician for five-star service.
• Do: Golf at TPC Scottsdale, guided off-road desert tours, hot air balloon rides, or spa retreats.
• Experience: Custom golf club fittings, VIP spa treatments, and exclusive tequila tastings.

 

5. Montreal, Canada – European Flair with a Luxury Twist

(Best time to go: June-September, December for winter charm)

Montreal blends old-world charm with modern indulgences for a refined getaway. Its nightlife, luxury shopping, and unique fusion of French and Canadian culture make it a must-visit.

• Stay: The Ritz-Carlton Montreal or Four Seasons Hotel Montreal.
• Do: Whiskey tasting at Burgundy Lion, private cigar lounges, VIP club nights, and exclusive wine and cheese tastings.
• Experience: Private art gallery tours, tailored suits from renowned designers, and luxury car chauffeurs.

 

6. Aspen, Colorado – Elite Mountain Escape

(Best time to go: December-March for skiing, June-August for hiking)

Aspen offers year-round five-star experiences, from skiing to fly-fishing and beyond. The town is known for its exclusivity and celebrity clientele.

• Stay: The St. Regis Aspen or The Little Nell.
• Do: Hit the slopes in winter, go mountain biking in summer, or enjoy scenic gondola rides.
• Experience: Private ski instructors, luxury après-ski lounges, and helicopter tours.

 

7. Napa Valley, California – Wine & Culinary Perfection

(Best time to go: September-November, March-May)

A weekend of wine tastings, gourmet dining, and luxury accommodations in Napa is pure indulgence. The valley’s rolling vineyards and five-star service make it ideal for a laid-back yet upscale retreat.

• Stay: Stanly Ranch, Auberge Resorts Collection or Four Seasons Resort and Residences Napa Valley.
• Do: Private wine tours, hot air balloon rides, cooking classes with top chefs, or golf at Silverado Resort.
• Experience: Custom wine blending sessions, vineyard picnics, and sommelier-led tastings.

 

8. Jackson Hole, Wyoming – Rugged Luxury & Adventure

(Best time to go: June-September, December-March for skiing)

For an outdoorsman’s luxury escape, Jackson Hole offers high-end accommodations with endless adventure.

• Stay: Caldera House or Four Seasons Resort Jackson Hole.
• Do: Fly-fishing, guided wildlife safaris, or heli-skiing in winter.
• Experience: Exclusive horseback riding tours, hot springs retreats, and private wildlife photography tours.

 

9. San Diego, California – Coastal Luxury & Adventure

(Best time to go: Year-round)

San Diego combines a laid-back beach vibe with luxury experiences.

• Stay: The Lodge at Torrey Pines or Park Hyatt Aviara Resort, Golf Club & Spa.
• Do: Private yacht charters, surfing lessons, or golf at Torrey Pines.
• Experience: VIP brewery tours, exclusive deep-sea fishing trips, and custom cigar tastings.

 

10. Chicago, Illinois – The Sophisticated City Getaway

(Best time to go: May-October)

The Windy City is perfect for a luxury weekend with its renowned steakhouses, golf, and cultural attractions.

• Stay: The St. Regis Chicago or The Peninsula Chicago.
• Do: VIP rooftop cocktails, a private boat tour on the Chicago River, and golf at Medinah Country Club.
• Experience: Private art gallery tours, tailored suit fittings, and VIP entry to jazz lounges.

 

11. Lake Tahoe, California/Nevada – Alpine Luxury & Outdoor Fun

(Best time to go: December-March for skiing, June-September for lake activities)

A mix of winter adventure and summer relaxation.

• Stay: The Ritz-Carlton Lake Tahoe or Edgewood Tahoe.
• Do: Skiing, luxury lake cruises, or golf at Edgewood Tahoe.
• Experience: Exclusive après-ski parties, private cabin retreats, and guided backcountry experiences.

 

12. Toronto, Canada – The Luxe Urban Retreat

(Best time to go: June-September)

Toronto combines a cosmopolitan atmosphere with high-end hotels and nightlife.

• Stay: The Ritz-Carlton Toronto or The Four Seasons Toronto.
• Do: Private box at a Maple Leafs game, distillery tastings, and a rooftop helicopter tour.
• Experience: Private shopping experiences, cigar lounges, and luxury car services.

 

13. Nashville, Tennessee – Live Music & Southern Luxury

(Best time to go: March-May, September-November)

Nashville combines country music, fine dining, and luxurious accommodations for a perfect guys’ getaway. Experience the vibrant nightlife, private music sessions, and exclusive whiskey tastings.

• Stay: The Joseph or Four Seasons Nashville.
• Do: Private whiskey tastings, live music at the Ryman, exclusive recording studio experiences, or a VIP honky-tonk experience.
• Experience: VIP backstage passes, private distillery tours, and premium bourbon tastings.

 

14. Charleston, South Carolina – Southern Charm & Upscale Comfort

(Best time to go: March-May, September-November)

Charleston offers historic charm, excellent golf, and fine dining for a relaxing luxury weekend. Enjoy a blend of history, coastal beauty, and high-end hospitality.

• Stay: The Dewberry or Hotel Bennett for five-star Southern hospitality.
• Do: Private historic tours, golf at Kiawah Island, yacht charters, or oyster farm experiences.
• Experience: Exclusive carriage rides, luxury waterfront cruises, and custom bourbon blending classes.

 

Planning the best guy weekend trips

Looking for the ultimate guys’ weekend getaway? Whether it’s a milestone celebration or just a well-earned break, these top destinations deliver luxury, adventure, and VIP experiences with world-class accommodations and activities. From action-packed excursions to top-shelf indulgence, we’ll make sure your trip is nothing short of legendary.

Planning can be a hassle—let us handle it. Our expert Advisors will take care of every detail, so you can focus on having an unforgettable time. Contact us today for a quote or to start planning your next epic guys’ trip!