Palm Beach

The Brazilian Court is the rare Palm Beach hotel that manages to be both genuinely luxurious and genuinely dog-friendly. This 1926 landmark sits one block from Worth Avenue and has hosted everyone from Gary Cooper to the Kennedys, but the real tell is how the staff treats your dog: they provide a custom bed, food and water bowls, treats at turndown, and a walking map of the neighborhood. No weight limit. The courtyard is lush and shaded — bougainvillea, fountains, the kind of quiet tropical elegance that Palm Beach does better than anywhere. The rooms are spacious, the restaurant (Cafe Boulud, Daniel Boulud’s outpost) is excellent, and the location gives you walking access to everything on the island. If you are staying on Palm Beach with a dog, this is the address.

The Colony is the most photographed hotel in Palm Beach — that unmistakable pink façade on Hammon Avenue has been an island landmark since 1947. The rooms are bright, playful, and decorated with the kind of confident whimsy that says old Florida without trying too hard. Dogs under 25 pounds are welcome with a $75 per stay fee, which is the significant caveat here: if you have a larger dog, this is not the play. But for small-dog owners, The Colony offers a genuinely delightful experience. The pool area is a scene, the rooftop restaurant (Swifty’s) is excellent for dinner, and the staff treats small dogs as part of the Colony aesthetic. Two blocks from Worth Avenue, a short walk from the Lake Trail.

If your dog exceeds the Colony’s 25-pound limit or you want a kitchen and a yard, the rental market in the greater Palm Beach area is surprisingly strong. West Palm Beach neighborhoods like SoSo (South of Southern) and El Cid offer charming bungalows and Mediterranean-style homes within walking distance of Clematis Street and the waterfront, and many are dog-friendly. On Palm Beach island, rental inventory is tighter and more expensive, but pet-friendly options exist if you book early. The advantage of a rental here is outdoor space — a fenced yard in the Florida sun changes the dynamic of the trip entirely. Check BringFido and VRBO with pet filters; confirm any weight limits and additional deposits directly with the owner.

The Lake Trail is the single best dog walk in Palm Beach. This 5.2-mile paved path runs along the western shore of the island, directly on the Intracoastal Waterway, from the north end near the Flagler Museum south toward Midtown. The views are extraordinary — yachts, the West Palm Beach skyline across the water, manicured estates to your right, and the kind of tropical light that makes every photograph look retouched. Dogs must be leashed, but the trail is wide, flat, and well-maintained, with enough room for bikes, joggers, and dogs to coexist comfortably. The morning hours are best: the light is golden, the temperature is tolerable even in winter-adjacent months, and the crowds are thin. Start at the north end near the Flagler Museum and walk south. This is the signature Palm Beach dog experience.

Since Palm Beach island’s beaches are off-limits to dogs, Singer Island is the move. Fifteen minutes north of Palm Beach, this barrier island has sections of beach where dogs are permitted on-leash, particularly near the Ocean Reef Park area. The sand is wide, the water is clear, and the crowd is significantly more relaxed than anything on Worth Avenue. Park at Ocean Reef Park (arrive early on weekends, the lot fills up) and walk north along the shore where the crowds thin. The water is warm year-round by Northeast standards, and the beach has that raw, uncrowded Florida feel that the island itself has polished away. Bring water for the dog — there are no concessions on the quieter stretches.

If your dog needs to run — really run — Okeeheelee is the answer. Located about 20 minutes west of Palm Beach in Royal Palm Beach, this is one of the best-maintained dog parks in South Florida. Separate areas for large and small dogs, double-gated entry, shaded benches, water stations, and more space than your dog will know what to do with. The park sits within the larger Okeeheelee Park, which also has walking trails, a nature center, and picnic areas. This is not a glamorous Palm Beach experience — it is a suburban dog park, and an excellent one. Come in the morning when the ground is cooler and the regulars are out. Pair it with a brunch stop at Coolinary Café on the way back to the island.

Dogs are not allowed inside the Flagler Museum (the Gilded Age mansion built by Henry Flagler in 1902), but the grounds and the surrounding streets are some of the most beautiful walking in South Florida. Cocoanut Row and the neighboring streets north of Royal Poinciana Way are lined with towering royal palms, manicured hedges, and the kind of quiet, moneyed architecture that defines the island. This is a walking route, not a destination — pair it with the Lake Trail for a full morning loop. The Flagler Museum’s exterior and gardens are visible from the path and worth the detour even without going inside. Best in the morning when the streets are quiet and the light is soft.

A great outdoor option for you and your dog.

A great outdoor option for you and your dog.

A great outdoor option for you and your dog.

A great outdoor option for you and your dog.

A great outdoor option for you and your dog.

A great outdoor option for you and your dog.

Check into The Olives at Prospect Park and let Ashton decompress — new smells, new room, give them 30 minutes to sniff everything. Then take an easy walk to Lake Trail to stretch legs after the drive. Nothing ambitious — just let Ashton set the pace. For dinner, head to Bice Ristorante. Request outdoor seating when you book and mention you are bringing a dog. Bring a portable water bowl and a chew toy to keep Ashton occupied while you order.

Start early. Grab coffee and head to Palm Beach Bicycle Trail Shop before the crowds — go before 9 am if it is a beach. This is Ashton's highlight of the trip, so let them lead. Brunch at Cafe Via Flora after. In the afternoon, explore Jupiter Dog Beach at a relaxed pace. Ashton will be tired from the morning — keep it mellow. Back to the hotel for a rest. Dinner at Five Guys — sunset seating if they have it. Ashton gets the best seat: under the table with a view.

Sleep in. Ashton earned it. Take a morning walk to Cinquez Park Dog Park — somewhere familiar feels right on the last day. Breakfast at Cafe Boulud. Request late checkout (most dog-friendly hotels are flexible about this). If you have time before heading out, Peanut Island Park is worth a quick visit. Take a final photo of Ashton in front of the hotel. You will want it.

Check into The Olives at Prospect Park and let Ashton decompress — new smells, new room, give them 30 minutes to sniff everything. Then take an easy walk to Lake Trail to stretch legs after the drive. Nothing ambitious — just let Ashton set the pace. For dinner, head to Bice Ristorante. Request outdoor seating when you book and mention you are bringing a dog. Bring a portable water bowl and a chew toy to keep Ashton occupied while you order.

Start early. Grab coffee and head to Palm Beach Bicycle Trail Shop before the crowds — go before 9 am if it is a beach. This is Ashton's highlight of the trip, so let them lead. Brunch at Cafe Via Flora after. In the afternoon, explore Jupiter Dog Beach at a relaxed pace. Ashton will be tired from the morning — keep it mellow. Back to the hotel for a rest. Dinner at Five Guys — sunset seating if they have it. Ashton gets the best seat: under the table with a view.

Sleep in. Ashton earned it. Take a morning walk to Cinquez Park Dog Park — somewhere familiar feels right on the last day. Breakfast at Cafe Boulud. Request late checkout (most dog-friendly hotels are flexible about this). If you have time before heading out, Peanut Island Park is worth a quick visit. Take a final photo of Ashton in front of the hotel. You will want it.

Check into The Olives at Prospect Park and let Ashton decompress — new smells, new room, give them 30 minutes to sniff everything. Then take an easy walk to Lake Trail to stretch legs after the drive. Nothing ambitious — just let Ashton set the pace. For dinner, head to Bice Ristorante. Request outdoor seating when you book and mention you are bringing a dog. Bring a portable water bowl and a chew toy to keep Ashton occupied while you order.

Start early. Grab coffee and head to Palm Beach Bicycle Trail Shop before the crowds — go before 9 am if it is a beach. This is Ashton's highlight of the trip, so let them lead. Brunch at Cafe Via Flora after. In the afternoon, explore Jupiter Dog Beach at a relaxed pace. Ashton will be tired from the morning — keep it mellow. Back to the hotel for a rest. Dinner at Five Guys — sunset seating if they have it. Ashton gets the best seat: under the table with a view.

Sleep in. Ashton earned it. Take a morning walk to Cinquez Park Dog Park — somewhere familiar feels right on the last day. Breakfast at Cafe Boulud. Request late checkout (most dog-friendly hotels are flexible about this). If you have time before heading out, Peanut Island Park is worth a quick visit. Take a final photo of Ashton in front of the hotel. You will want it.