The Milwaukee Boat Line invites canines to join its crew for a 90-minute, adults-only cruise down the Milwaukee River to Lake Michigan. A featured attraction in the latest edition of our book, Ruff Guide to the United States, these pet-friendly voyages depart from the Milwaukee RiverWalk in the historic Third Ward district. The company’s Happy Hour tour combines upbeat music and rotating drink specials with gorgeous sunlit views of the city. Live narration is provided by entertaining tour guides and the captain. Snacks, soft drinks, beer and cocktails are available for purchase on board. After the tour, take a leisurely stroll along the scenic 3-mile RiverWalk, or head to Estabrook Beer Garden to enjoy a beer and bratwurst with your pooch.

Continue your relaxing Milwaukee vacation with Fido at The Iron Horse Hotel, a boutique property in a 100-year-old warehouse. Guests and their pups are invited to the hotel’s happy hour Wednesday through Friday from 4 to 6 p.m. in The Yard, a fun outdoor space with communal fire pits and cozy lounge furniture. Stay on a Wednesday and your pooch will enjoy his own Yappy Hour. The Yard is open Memorial Day through October. The Iron Horse Hotel allows two dogs of any size for an additional fee of $100 per stay.

Set sail with Fido on your very own tiki hut with Cruisin’ Tikis Key Largo. Bring your alcoholic beverage of choice as you cruise the Florida Keys on a 120-minute sunset tour. You can also bring snacks or dinner from Snook’s Bayside, where your tiki adventure begins. Choose to stay on the boat and enjoy the sunset, or ask your captain to drop anchor so you and your pooch can take a dip in the calm blue water. Bottled water, cups, a cooler of ice and a captain to guide your way are all provided.

Fido can enjoy his own daily Yappy Hour with a special pet menu during your stay at Baker’s Cay Resort Key Largo. You’ll both enjoy the views of Florida Bay from your private balcony, and your pup will receive an engraved pet tag, waste bags and a water bowl. You might even meet the Director of Pet Relations, Maya the Husky. Two pets with a combined weight up to 100 lbs are permitted for an additional fee of $75 per night.

Hop aboard the Horicon, a double-deck wooden yacht, and set sail with Lake George Cruises. The narrated, one-hour Happy Hour Historic Sightseeing Cruise will take two- and four-legged guests on an evening ride around the lake with gorgeous views of the Adirondack Mountains. Guests 21 and over can indulge in a complimentary alcoholic beverage while those under 21 will receive a soda, and everyone can enjoy a tasty cheese and cracker platter. Additional food and drinks can be purchased from the full cash bar. Your excursion might even include live music to get you dancing. After your journey around the lake, grab dinner with a waterfront view at Lake George Beach Club.

Spend the night at The Lake George Inn, located in the heart of town and within walking distance to most restaurants and attractions. Swim laps in the heated pool or unwind on the patio or sundeck. Dogs of any size are accepted for an additional fee of $15 per night.

There’s likely no better place to drink wine on a yacht than in California’s wine country. Sunset Kidd Sailing Cruises offers dog-friendly Sip & Sail happy hour and wine tasting cruises on select days. The 1.5-hour trip features a full bar with quality liquor, fine Santa Barbara wines and local craft beer, and happy hour specials including $5 margaritas and rum drinks. Sit back and feel the ocean breeze as your captain guides you through the American Rivera in Santa Barbara Harbor, where you’re likely to spot dolphins, sea lions and even whales. Sunset Kidd is currently operating private cruises by reservation, so call ahead to book. After your sail, stay in the harbor and dine on the fresh fish of the day or a pub steak on the patio of Breakwater.

After a full evening, walk your pup back to your room at Beach House Inn. The ambiance is perfect for relaxing by your room’s gas fireplace or in the garden courtyard. Two dogs of any size are welcome for an additional fee of $10 per pet, per night.

Choose between the “wild” or “mild” versions of the Sunset Cruise at Adventure Harbor Tours in Mount Pleasant, SC. Guests are encouraged to bring a cooler of food and drinks, adult beverages included, for this dog-friendly happy hour sail through Charleston Harbor. The Mild cruise is a 90-minute, semi-narrated, leisurely ride that takes place Tuesdays through Thursdays and on Sundays. The Wild cruise amps up on Friday and Saturday evenings and includes music, dancing and partying. Your “pawty” animal is welcome to join you but be advised it’s called “wild” for a reason. After the cruise, head to Red’s Ice House for a seafood dinner on the large deck.

Stay just outside of Charleston at SpringHill Suites by Marriott Charleston Mount Pleasant. In addition to the peaceful setting, you’ll also enjoy views of the famous Ravenel Bridge and be just a short drive from Mount Pleasant Memorial Waterfront Park. Two dogs of any size are permitted for an additional fee of $75 per stay.

Float away with Fido to a tropical paradise on Amelia River Cruises and Charters. Pack a small cooler and bring your favorite drinks and snacks for a two-hour Adult BYOB Cruise. You’ll set sail on the Bald Eagle from the Fernandina Harbor Marina as local musicians set the mood on board. Open a cold one for yourself, pour some water for your pup and relax as your captain leads the way through salt marshes and along wilderness beaches and historic river banks, spotting wildlife along the way. Once you’re back at the marina, grab a table on the patio of Brett’s Waterway Cafe and order the catch of the day.

Stay close to the water at Hampton Inn Amelia Island at Fernandina Beach. You’ll be within walking distance to dog-friendly Fernandina Beach and restaurants like La Mancha, which offers happy hour specials Monday through Thursday. Two dogs of any size are accepted for an additional fee of $75 per pet, per stay.

Climb on deck of Schooners Margaret Todd or Bailey Louise Todd and prepare for a beautiful sunset sail with Downeast Windjammer Cruise Lines. Beer and wine are available for purchase on board, and live folk, guitar, banjo or fiddle music will fill the air as you set sail in Frenchman Bay and enjoy beautiful views of Acadia National Park. You’re welcome to bring along snacks for you and your pup for this two-hour cruise. Afterward, grab dinner and one of many Maine-brewed beers on tap at Side Street Cafe.

Choose a dog-friendly room at Quimby House Inn & Spa and you’ll be within walking distance to many Bar Harbor restaurants and attractions. During your stay, pamper yourself with an on-site massage. One dog up to 100 lbs is allowed for an additional fee of $25 per night, and two dogs up to 100 lbs for $40 per night.

It will truly be a happy hour as you cruise Alexandria Bay with Fido on the 60-minute Sip N’ Sail Cruise with Uncle Sam Boat Tours. This sunset sail is an enchanting experience along the St. Lawrence River through the Thousand Islands at a time when the water is calm and the light is just right. Order beer or wine from the on-board bar, then find a bench on the top deck to watch the magic of the golden hour. Once you’re back on land, have dinner at The Spot Bistro & Patio, where your pup will be welcomed with treats and a bowl of water.

Book a cottage, chalet, bungalow or floating cottage at Swan Bay Resort & Marina, and allow your pet to run free in the on-site dog park. Then let Fido rest in the room while you grab a drink from the tiki bar with daily and weekly specials. Two pets of any size are welcome for an additional fee of $20 per pet, per night.

Ready for a Road Trip?

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