Write a Love Letter to Pensacola, Enter to Win a Pensacola Vacation!

Through our From the 1500s, With Love campaign, we’re celebrating more than 250 years of history and the moments that make Pensacola so special. Maybe it was a beach sunset you still think about, a family vacation that became a yearly tradition, or the destination you chose to call home. Whatever your story looks like, we want to hear it. We’re inviting you to write your love letter to Pensacola in 500 words or less for a chance to win a Pensacola vacation for four valued at $2,500!

LODGING
A three-night stay for four at The Hilton Pensacola Beach in a junior suite
DINING EXPERIENCES
PENSACOLA EXPERIENCES
$150 gift card to Restaurant IRONAn inshore fishing charter with Hot Spots Charters
$150 gift card to Flora-BamaA dolphin cruise with Frisky Mermaid Boat Tours
$150 gift card to The Wharf Fish & Oyster Co.Passes to Fast Eddie’s Fun Center
$150 gift card to Union Public HouseA daytime sailing cruise with Condor Sailing
$100 gift card to The Hideaway Beach BarPasses to Historic Pensacola
$100 gift card to O’Riley’s Irish PubA special gift basket from Renfroe Pecan Company valued at $80
$25 gift card to Bamboo Willie’s


How to Enter

Complete the contact form below and tell us why you love Pensacola in 500 words or less. Select submissions may be featured across Visit Pensacola’s marketing channels as part of the From the 1500s, With Love campaign.

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(500 characters max)

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Bonus Entry! Upload a photo or single video clip of your favorite memory

Complete the contact form below and tell us why you love Pensacola in 500 words or less. Select submissions may be featured across Visit Pensacola’s marketing channels as part of the From the 1500s, With Love campaign.

NO PURCHASE NECESSARY. The Visit Pensacola “Love Letter to Pensacola” Sweepstakes begins on 05.13.2026 and ends on 06.30.2026 at 11:59:59 p.m. CST. Open to legal U.S. residents residing in the 48 contiguous United States and Washington D.C., age 21 or older at time of entry. Limit one (1) entry per person per letter. An additional single entry may be earned through uploading a photo or video in addition to a letter. Void in Alaska, Hawaii, and where prohibited. Winner is responsible for travel expenses not specifically included in the prize package. Prize partners and experiences are subject to change. See Official Rules for full eligibility requirements, prize details, and complete terms. Sponsor: Visit Pensacola, 1401 E. Gregory Street, Pensacola, FL 32502.

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From the 1500s with Love: Discover Pensacola, America’s First Settlement, During America’s 250th Anniversary

As the nation prepares to celebrate America’s 250th anniversary, Pensacola offers a chance to explore a story that began centuries before 1776. Founded in 1559 as America’s First Settlement, Pensacola’s history began more than two centuries before the nation declared independence. Today, the Pensacola Bay Area invites visitors to explore more than 465 years of culture, resilience, and discovery, including historic landmarks and museums to the beaches, waterways, and neighborhoods that define the destination.

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