Twenty stays, and the first one matters most: Dunns Josephine is Black-owned in Overtown, fifteen suites named for Black icons, walking distance to Red Rooster and the Lyric. From there it is the Peebles-rebuilt Royal Palm on South Beach, Faena's red velvet in Mid-Beach, Arlo's rooftop over Wynwood and the 1926 Biltmore in Coral Gables. Every price band, every neighborhood.
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Black-owned boutique hotel in the heart of Overtown, with fifteen suites named for Black icons and a gallery downstairs. Walk to Red Rooster, the Lyric Theater and Lil Greenhouse Grill. This is the address if you want to stay inside the story.
Pip’s Tip Black-owned, 15 suites named for Black icons
R. Donahue Peebles rebuilt this 1939 Art Deco landmark and reopened it in 2002 as the first full-service luxury hotel owned, developed and managed by African Americans. Two pools, a private beach, and a piece of Miami Beach history that took sixty years to come back around.
Pip’s Tip R. Donahue Peebles' landmark rebuild
Owned by RLJ Lodging Trust, founded and chaired by BET's Robert L. Johnson. Two pools, direct beach access and a quieter stretch of Collins well north of the South Beach noise, the value play on the sand.
Pip’s Tip Black-founded and Black-led ownership (RLJ)
The most literary hotel on Ocean Drive, with a poetry program, a rooftop, and a piano bar running live jazz nine times a week without ever charging a cover. Stay here and you never have to leave the building for a good night.
Pip’s Tip Live jazz nine times a week, no cover
Gold, red velvet and a gilded skeleton in the courtyard. The Faena Theater downstairs runs cabaret and live shows that are worth booking on their own, and the beach club out back is the best-run in Mid-Beach.
Pip’s Tip The red-velvet Faena Theater
The white-curtain hotel that defined a whole era of South Beach is finally back after six years dark. Rose Bar, the pool with the underwater music, and the long lobby walk that still works exactly the way it did.
Pip’s Tip Reopened 2026 after a six-year rebuild
A Spanish-village hotel that opens directly onto Española Way, which puts you a two-minute walk from the cigar bar and the salsa. Guests-only rooftop pool and rooms that feel handmade rather than branded.
Pip’s Tip Right on Española Way
A cheerful, well-kept Mid-Beach hotel across the street from the sand, with a courtyard pool and none of the attitude. The room rate leaves money for the rest of the trip, which is the whole point.
Pip’s Tip Best-value beach block in Mid-Beach
Private rooms and shared rooms around a garden that contains the Broken Shaker, one of the best bars in the country. Cheap to stay, expensive to leave, nobody makes it past the courtyard on the first night.
Pip’s Tip Home of the Broken Shaker
The first hotel to open in Wynwood, with a rooftop pool, a good bar and the murals starting at the front door. Monthly afrobeats nights up top and Dante's HiFi four blocks away.
Pip’s Tip Wynwood's first hotel, rooftop pool
A 1921 furniture showroom turned hotel, built around Zaha Hadid's Elastika sculpture in the four-story atrium. Design District shopping downstairs, a rooftop upstairs, and one of the few genuinely beautiful buildings on the mainland.
Pip’s Tip Zaha Hadid's Elastika in the atrium
The 1925 Miami National Bank building, restored down to the vault door, in the middle of downtown. Walkable to Jolene, Over Under and The Corner, the rooftop bar is temporarily closed, so plan the night elsewhere.
Pip’s Tip The 1925 Miami National Bank building
Sugar, the Asian garden bar on the fortieth floor, is one of the best rooftops in the city and it's an elevator ride from your room. Below it, Brickell's cigar rooms are a five-minute walk in three directions.
Pip’s Tip Sugar on 40 is upstairs
Small smart rooms, a very good lobby, and cloudM on the nineteenth floor with the Brickell skyline in the windows. The best price-per-location in the neighborhood by a distance.
Pip’s Tip cloudM rooftop on 19
A small, well-designed hotel a few blocks off Calle Ocho with Terras on the roof. Walk to Ball & Chain, Café La Trova and three cigar factories without ever getting in a car.
Pip’s Tip Terras rooftop upstairs
A jungle of a hotel in the middle of Coconut Grove, all balconies and greenery, with the Sipsip calypso rum bar and pool deck on six. The Grove's best room, and quieter than anything on the Beach.
Pip’s Tip Sipsip rum bar on the sixth floor
A 1926 National Historic Landmark with a bell tower, a golf course and a pool so big it once hosted alligator wrestling. Old Miami at its most confident, and ten minutes from Armstrong Jazz House.
Pip’s Tip 1926 landmark, the enormous pool
Across from the University of Miami with a rooftop pool bar and a Caribbean-leaning kitchen downstairs. Easy Metrorail access into downtown, which matters more in Miami than people expect.
Pip’s Tip Orilla rooftop, across from UM
Big suites, two rooftop pools and a stretch of Surfside beach where nobody is trying to sell you anything. The move when the trip is about the water rather than the night.
Pip’s Tip Two rooftop pools, quiet stretch of sand
Thirty-six holes, a water park with slides, a full spa and enough restaurants that you can go four days without repeating. The family and golf-trip answer, twenty minutes north of the Beach.
Pip’s Tip Golf, water park and a full spa
Black-owned in Overtown, fifteen suites named for Black icons and a gallery downstairs, the address if you want to stay inside the story.
Group rates when the family travels. Members hear first.
Stays are one chapter of Pip's Lifestyle, find the lounges, rooftops, brunch spots and the Domino Club below.
