Where to Go on Vacation with Your Boyfriend: Our Top 4 Picks

The best cities for you and your BF to cozy up in

Get out your sharpie and circle October 3rd on your calendar – it’s National Boyfriend Day. And yeah, we get it; it sounds kind of made up. But National Boyfriend Day is the real deal, you guys. And what better way to celebrate than planning a trip just for your BF?

Want to know the best cities to head to for a vacation with your boyfriend? Check out our four top choices for some couples’ fun!

• Key West, FL

  Year-round warm weather, world-class fishing, and legendary watering holes. What won’t your boyfriend love about Key West? And located just 90 miles south of Miami, you can even make it a two city getaway!

  Key West’s warm turquoise waters are ideal for all sorts of aqua activities: snorkeling, scuba diving, kayaking, and more. Or you can just be lazy with a beach-side mojito, we won’t tell.

  Make the most of Key West’s laid-back island vibe by booking a B&B in the charming historic district (aka Old Town). You’ll be walking distance from restaurants, shops, bars, and Ernest Hemingway’s famed 6-toed cats.

  Best Vacation with Your Boyfriend If: you’re flip-flop wearing beach lovers.

• New York City, NY

  Looking for a bit of excitement? Head over to “The City that Never Sleeps” for the ultimate city-life couple’s trip!

  There’s so much to do in NYC that we can’t possibly get to all of it. But here’s our favorite tip: skip the overcrowded climb to the top of the Empire State Building and head over to the Top of the Rock instead. It’s not quite as tall, but here’s the thing: you get an amazing skyline view that includes the Empire State Building. Super cool!

  If the way to your boyfriend’s heart is through his stomach, you’re in luck! Greek, Indian, Italian, Dominican, pizza, pastrami – whatever your BF’s favorite food, you’ll be sure to find it in NYC. You’ll walk it off in Times Square, promise!

  Best Vacation with Your Boyfriend If: you’re urbanites.

• San Francisco, CA

  San Francisco and its surrounding cities are some of the most beautiful – and fun! – places to go on a couple’s trip. And your boyfriend will think so, too, if you plan out some San Fran fun!

  First up: Alcatraz – aka “The Rock.” Once the world’s most famous prison, its cells are now open for tourists. Ferry over and keep your phone handy for some seriously Insta-worthy views of San Francisco. When you return, explore Fisherman’s Wharf and treat your boyfriend to some of the city’s best seafood.

  Another can’t miss: a side trip to Muir Woods. Just a 35-minute drive from San Francisco and you’ll be staring up at some of the largest, oldest trees in the world. And, bonus: you get to drive over the Golden Gate Bridge. If you rent a car and have extra time, don’t miss Sausalito and Tiburon on the way back.

  Best Vacation with Your Boyfriend If: you want to explore the west coast.

• Yellowstone, WY

  We know: technically, it’s not a city, but the country’s first national park makes for such an amazing couple’s trip that we had to include it!

  Yellowstone is famed for its geysers, especially Old Faithful and Steamboat. But there’s a ton more to do there. You can go boating on Yellowstone Lake, check out the aquatic rainbow at Grand Prismatic Springs, and marvel at the wildlife (bison, elk, wolves, and more).

  You can stay onsite, either camping or in cabins. But if you really want to score points with your boyfriend, head over to uber-cool Cody. Just a short drive from Yellowstone, this is the ultimate Wild West City, founded by Colonel William F. Cody. Yep, that’s Buffalo Bill! Rodeos, log cabins, and the hotel built by Buffalo Bill himself are all part of Cody’s fun.

  Best Vacation with Your Boyfriend If: you’re ready for a western adventure.

Since you’re planning this vacation as a treat for your boyfriend, make it as easy as possible for him. Instead of asking him to haul bags around the airport, ship your luggage to your hotel or Airbnb with LugLess. All your boyfriend has to do is hop on and off the plane with you, with nothing to hold but your hand. Awwww!