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DAY 1 Positioned on a peninsula along Tampa Bay , Boca Ciega Bay , and the Gulf of Mexico , St . Pete , as locals call it , holds the Guinness World Record for the most days of sunshine . During the 19th century , Tampa was a military center populated with forts and trading posts and became the cigar capital of the world . Cuban , Italian , and Spanish immigrants flocked to the area in the late 1800s and their influence endures today .
While each is a superlative solo destination , Tampa and St . Pete ’ s close proximity on Florida ’ s central west coast offers a two-for-one vacation : pristine Florida beaches and unrivaled art in St . Pete and European and Cuban-influenced culture and food in Tampa .
Begin in Ybor City , a historic neighborhood north east of downtown Tampa built around the Cuban cigar industry . Founded by Spanish cigar manufacturer Vicente Martinez Ybor , the area is registered as a National Historic Landmark .
Eat fresh Cuban bread , cafe con leche , and pastries at La Segunda Bakery . Opened in 1915 , the family-run Cuban bakery bakes around 18,000 loaves of bread daily .
Next , view exhibits on Ybor ’ s founding and the cigar industry and tour a restored casita at Ybor City Museum .
Then , walk to 7th Avenue , which is flanked by century-old red-brick buildings housing cigar shops , boutiques , and restaurants . Don ’ t be surprised to see chickens crossing the road — they ’ re descendants of the fowls that belonged to the neighborhood ’ s earliest residents .
Enjoy lunch at Columbia Restaurant , Florida ’ s oldest restaurant . Signature dishes here include the 1905 salad , named for the restaurant ’ s inaugural year , and the Ybor City-invented Cuban sandwich ( Spanish ham , Cuban mojo-marinated pork , Genoa salami , Swiss cheese , pickles and mustard on butter-brushed and -pressed Cuban bread ).
Walk off lunch with a stroll along the Tampa Riverwalk , then board a water taxi to sail Tampa Bay and possibly even spot dolphins . winter 2022 // 13