Three Days: Anchorage

Planning a long weekend in Anchorage? Alaska’s largest city is the perfect gateway to stunning glaciers, abundant wildlife, scenic mountain views, and unforgettable outdoor adventures. From spotting moose in the city to exploring nearby national parks, Anchorage offers a mix of urban amenities and wilderness experiences. This three-day Anchorage itinerary highlights the best things to do, where to eat, and how to make the most of a weekend in Alaska’s most accessible destination.

Long Weekend: Havana, Cuba

Traveling to Havana offers a Caribbean experience unlike any other, blending vintage charm, rich culture, and a sense of stepping back in time. Beyond its beaches, Havana captivates with classic cars, historic streets, and the unique complexities of traveling under U.S. restrictions—making it an adventurous but rewarding destination, especially for American travelers.

Weekend Getaway: San Juan

Puerto Rico is an easy-to-reach Caribbean destination that blends stunning beaches, lush rainforest adventures, and vibrant city life. Visitors can hike through El Yunque National Forest, explore the historic streets of Old San Juan, and enjoy world-class rum and lively salsa nightlife—all in one trip. For travelers on the U.S. East Coast, flights to Puerto Rico are quick and often affordable with the right timing, making it a top choice for a Caribbean getaway, though prices can rival trips to Central America during peak seasons.

Quick Take: Fort Collins, Colorado

My hometown of Fort Collins, Colorado is a spot where I return often to re-discover a vibrant mix of outdoor adventure, craft beer, and Old Town charm. Whether you’re planning a weekend getaway, a day trip from Denver, or a stop on the way to Estes Park, FoCo blends the scenic Rocky Mountain foothills, Colorado State University’s energy, and a thriving food, art, and brewery scene for an unforgettable visit.

Four Days: Calgary

Explore Calgary’s vibrant Pride events, cozy neighborhoods, cultural highlights, and inclusive nightlife. But don’t miss the adventure and wilderness of Alberta’s Rockies and prairie—perfect for LGBTQ+ travelers seeking a blend of charm in the city and wild, natural exploration.

5 Van Life Lessons for LGBTQ Campers

Five of the van life lessons I’ve learned are key for LGBTQ travelers—from safe gay camping tips to finding community on the road. Read on for your next gay weekend adventure.

Weekend: Vancouver, B.C.

Escaping to Vancouver, B.C. for a weekend is a stunning mix of ocean and mountain views, a vibrant LGBTQ scene, and an inclusive vibe. From the rainbow crosswalks of Davie Village to craft breweries on the city’s Ale Trail, there’s no shortage of ways to soak up the culture, nightlife, and scenery. Add in queer-owned businesses, mild weather, year-round events, and easy access from major cities, and you’ve got the perfect recipe for a quick but unforgettable getaway.

Weekend: Bend, Oregon

Looking for an LGBTQ-friendly weekend getaway in the Pacific Northwest? Bend, Oregon delivers stunning mountain views, outdoor adventure, and small-town charm with a welcoming vibe. Known for its high desert landscape, this Central Oregon gem offers year-round sunshine, scenic hiking trails, river floats in the summer, skiing at Mt. Bachelor in the winter, and a thriving craft beer scene. Whether you’re escaping from Portland, Seattle, or beyond, Bend is a perfect long weekend destination for LGBTQ travelers.

Weekend: Chicago

Chicago is one of my favorite cities—especially in summer. From vibrant neighborhoods and lakefront strolls to LGBTQ events and street festivals, there’s always something happening. With friends in the city, I get to experience it like a local and play tourist when I want to.

Quick Take: Catskills

I loved the inclusive charm and nature of the Catskills and Andes, NY. It was a charming and welcoming blend of nature, art and food (and family) for a getaway that was surprisingly LGBTQ-friendly.