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The Celestial Railroad enjoyed a brief run in late-1800s Florida, linking the hamlets of Jupiter and Juno with stops along the way at freight stations named Venus and Mars. It went bust by the turn of the century, but the winter town of Jupiter took off. Today, Jupiter is one of the wealthiest and most exclusive winter retreats in the state with some of the biggest names in show business among its residents. Celine Dion, Burt Reynolds and Perry Como have all called it home. With gorgeous beaches, memorable dining and an all-around luxe vibe, Jupiter makes the perfect weekend getaway.

What to Visit

An outstanding way to structure a visit is to grab the Passport to Jupiter ( It can be downloaded as a mobile app, requested in the mail or picked up from the Town Hall or Jupiter Community Center. The passport includes more than 70 fun stops and activities, and it’s great for exploring both Jupiter’s hidden gems and better-known landmarks.

Don’t miss the stately Jupiter Inlet Lighthouse (500 Captain Armour’s Way, Jupiter; 561.747.8380; Officially lighted in 1860, the beacon played a key role in saving ships from the reefs and shoals that run along the coast. Keepers tended the lighthouse until it became automated in 1987. Today visitors can tour both the lighthouse and its museum, including climbing to the top.

Where to Eat

The Square Grouper Tiki Bar (111 Love St., Jupiter; 561.406.6417; is one of the most recognizable joints in Florida. It was the setting for the music video for the hit country song “It’s Five O’Clock Somewhere” by Jupiter Island resident Alan Jackson and Jimmy Buffett. The Square Grouper is a 21-and-up establishment with live music seven nights a week. It has an easy-going atmosphere with no dress code, no reservations and nothing to get in the way of its beachy, boozy vibe.

For a luxury dining option, reserve a table at 1000 North (1000 US-1, Jupiter; 561.570.1000;, the glamorous waterfront establishment that counts Michael Jordan as one of its partners. The menu features upscale American regional cuisine with a focus on steaks and seafood. Guests can enjoy a meal inside the stunning dining room, on the al fresco terrace or at the luxuriously appointed tavern. The Club Lounge, however, is for members only.

Where to Stay

For those seeking a traditional hotel experience, the Wyndham Grand (122 Soundings Ave., Jupiter; 561.273.6600; offers upscale rooms and suites on Jupiter’s Intracoastal Waterway. Its poolside bar is a prime spot for frozen daiquiris.

For a more personalized and unique experience, the area has incredible short-term rentals. Try the River House on the Loxahatchee from Airbnb. The vintage coastal property was built in 1962 and majorly renovated in 2021. It overlooks the Loxahatchee River and includes amenities such as a hot tub and private beach. Or look for tastefully renovated mid-century bungalows in the exclusive Jupiter Inlet Colony. Many come with pools and water views, and celebrity sightings are no extra charge.

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