
Historic Uptown Vacations
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Where to stay in Historic Uptown

Pass-a-Grille
Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.
Historic Uptown Hotel Deals

RumFish Beach at TradeWinds
Loved it staff was incredible fav place in FL to go. Will be returning yearly
Reviewed on Apr 3, 2026

Wyndham Grand Clearwater Beach
It was better than we expected! Can’t wait to come back and bring our kids.
Reviewed on Apr 3, 2026

Hotel Tampa Riverwalk
I didn’t eat breakfast but did have dinner at their restaurant and it was subpar in my opinion. The hotel felt outdated, really old rickety elevator, and just didn’t ha
Reviewed on Apr 2, 2026
Frequently asked questions
Discover the most popular places to visit in Historic Uptown

John's Pass Village & Boardwalk
When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

Vinoy Park
While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Fort De Soto Park
Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.
Things to do

Sunset Celebration Cruise on Tropics Boat Tours

StarLite Majesty Evening Yacht Cruise Clearwater




