Naples, Florida

Located in Southwest Florida, Naples is a dog lovers’ paradise that’s beloved for its calm Gulf waters, epic sunsets and sophisticated restaurants and shops. Dapper dogs and their owners regularly stroll Fifth Avenue South or Third Street South, which are dotted with stores that leave water bowls outside and dog-friendly restaurants like The Continental fitted with al fresco patios. There’s even a cute dog-themed art installation along Third Street South.

Pups can play and run free at the Naples Dog Park, and if you want to sightsee together, Naples Botanical Garden allows guests to bring their dogs to the gardens on Sundays and Tuesdays from 9 a.m. to 11 a.m. Advance registration is required.

Where To Stay

At Naples Bay Resort & Marina, pet owners love the spacious accommodations, including one- and two-bedroom suites, and private balconies where dogs can sunbathe. Pick a suite that overlooks Naples Bay or the marina. While your dog chills back in the room, guests have access to the private Naples Bay Club, five pools (including one with a lazy river), five restaurants and a spa.

Newport, Rhode Island

Known for its Gilded Age glories, Newport, Rhode Island is a destination by the sea where dogs can live their best lives. A top activity for you and your leashed pup is walking the famous 3.5-mile Cliff Walk, which weaves by glitzy mansions and the crashing waves below. Another scenic spot for shopping and strolling (and grabbing a lobster roll) is Newport’s bustling waterfront at Bowen’s Wharf. Grab a craft beer at Newport Craft Brewery, which allows dogs on the patio, rooftop deck and large lawn, or make a stop at dog-friendly Frosty Freez for soft serve and a frozen pup treat. You can’t visit nautical Newport without getting on the water, and some boat outfitters like Sea Newport allow well-behaved dogs on board.

Where To Stay

With a laid-back feel, canine guests at Wayfinder Newport are greeted by the friendly staff who are often ready with treats. The boutique hotel features spacious rooms and suites decked out in a coastal motif, which means comfortable spaces for cuddle time with your dog. Nearby green spaces make dog walks easy, including the trails at Miantonomi Memorial Park, located behind the hotel.

Vail, Colorado

Colorado is calling, and Vail is a mountain resort town where dogs can be part of the active mountain lifestyle, especially in summer and early fall when the leaves change colors. Vail Village, which looks like a scene ripped from a Bavarian village, is pedestrian-only and it’s common to see people popping in shops with their dogs. Leashed dogs can join their owners on trails like the Upper Piney River Trail, which ends at a cascading waterfall, and locals love Bighorn Park for its pond where dogs can take a cool dip. It’s easy to find welcoming restaurants with outdoor seating, like longtime pub Bart and Yeti’s in Lionshead Village, named for famous local dogs—and friendly dogs can hang on the patio of Vail Brewing Company while you enjoy a beer flight.

Where To Stay

The family-owned Tivoli Lodge is nestled slopeside in Vail Village and its own resident mascot, a friendly chocolate lab named Racer, is always on hand to welcome guests. This peaceful escape has 65 rooms with cozy fireplaces and features panoramic mountain or village views. Soak up the mountain air and scenery from their mountainside hot tub, cruise around on electric bikes, and take advantage of easy access to chairlifts and Gondola One at the base of the mountain.

Chatham, Massachusetts

Situated on Cape Cod in Massachusetts, Chatham is a quintessential New England town that’s extremely dog friendly. Many stores on Main Street welcome well-behaved dogs to pop in while their owners shop or grab an ice cream to share. When you’re craving lobster or fresh fish, Mac’s Chatham Fish & Lobster allows dogs to join owners at their outdoor picnic tables. Paws in the sand? While dogs are not allowed on most beaches during summer, leashed dogs can saunter Jackknife Harbor Beach before 9 a.m. and after 6 p.m. In the off-season, from September 16 through April 30, dogs are generally allowed at all town beaches.

Where To Stay

You don’t have to sacrifice five-star luxury when traveling with your dog at Chatham Bars Inn. The iconic resort sits on 25 acres with a private beach and has its own fleet of boats for everything from whale-watching tours to sunset cruises. There are plenty of places to walk your leashed dog on the sprawling property, so everyone can enjoy the scenery and salty air.

Explore more pet-friendly hotels and destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.