Bachelor Party in Bend, Oregon - 4 Days Itinerary

• Day 1: Bend Ale Trail and Outdoor Excursions
  Start your day with a brewery tour of Deschutes Brewery and then stroll leisurely through the Old Mill District. Before breaking for lunch, make sure to check out the Les Schwab Amphitheater schedule for live music. In the afternoon, spend some time exploring Pilot Butte State Park, which offers panoramic views of the city, and end the day with a bonfire and a hike at Shevlin Park.
  
• Day 2: Casual Fun on the Water and the Bachelor Night
  Rent a stand-up paddleboard or a kayak to explore the Deschutes River, and then head back to town for a gourmet lunch at Ariana Restaurant. In the evening, enjoy a private poker night with a bartender and a hostess at the Wild Ride Brewing.
  
• Day 3: Thrill-Seeking Adventures and a Relaxing Night
  Get the adrenaline pumping with a whitewater rafting trip on the Deschutes River. Afterward, refuel at Jackson's Corner Eastside with some hearty comfort food. In the evening, experience indulgence at Kanpai Sushi, Teppanyaki & Bar for teppanyaki, sushi and sake.
  
• Day 4: Golfing Day and Leftovers
  Spend the morning playing golf at Tetherow Golf Club and then head to the Bend Brewing Company to sample some brews before lunch. Finish the day by catching the sunset at Mount Bachelor, just a short drive away from the city.
  

Time and Costs Estimates

• Deschutes Brewery (2 hours, $20)
• Les Schwab Amphitheater (2 hours, $30)
• Pilot Butte State Park (2 hours, free)
• Ariana Restaurant (2 hours, $100)
• Wild Ride Brewing Poker Night (4 hours, $300)
• Whitewater Rafting Trip (4 hours, $150)
• Jackson's Corner Eastside (2 hours, $60)
• Kanpai Sushi, Teppanyaki & Bar (2 hours, $80)
• Tetherow Golf Club (4 hours, $200)
• Bend Brewing Company (2 hours, $40)
• Mount Bachelor (2 hours, $50)

Total Estimated Costs: $1050

Transportation

You can easily get around Bend using rideshare apps such as Uber and Lyft, or by renting a car. Renting a car is recommended for excursions outside the city. There are several rental car options conveniently located at the airport. Expect to spend around $40-$80 per day on car rentals, and roughly $15-$20 for rideshare apps for shorter trips. Bend is a walkable city, so feel free to get some exercise by walking to and from your activities.

Useful Tips

If you have more time, consider visiting nearby attractions such as the Newberry National Volcanic Monument or Smith Rock State Park. If you have less time, prioritize activities based on your preferences and consider cutting some less important activities. Also, be sure to pack hiking boots and appropriate outdoor clothing as some activities involve outdoor exploration. And finally, be sure to drink lots of water to stay hydrated.

Airports

Bend, Oregon's airport is the Bend/Redmond Airport (RDM), which is located in Redmond, Oregon, about a 20-minute drive from downtown Bend. RDM serves several airlines including Alaska Airlines, American Airlines, and Delta Airlines, and has regular daily flights to cities such as Seattle, Portland, San Francisco, Los Angeles and Salt Lake City.