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Jill and David's Itinerary
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Key West Itinerary

Thursday, April 16

7pm - Mallory Square

David and Jill will be grabbing a bite and hanging out at this iconic social spot on the water in Old Town Key West, where local musicians, jugglers and other street performers entertain while even more creatives sell their artwork, crafts, photos and jewelry to the rest of us who're there to enjoy the sunset and a couple of margaritas. When the sun's gone, we'll undoubtedly head toward Duval Street to check out a few bars and all the crazies!

Friday, April 17

10:30am - Brunch at Pepe's, 806 Caroline Street

Pepe's is a landmark cafe that's been serving up great breakfasts and surf-n-turf since 1909, and we're gonna be there for eggs and mimosas to stave off the hangries until after that evening's wedding. Even if you aren't hungry, this is a place to say you visited while in Key West!

And we're buying the first round of mimosas and bloody Marys (your choice), so don't be late!

12:30pm - Wedding preps

jill and David will head to their rooms at L'Habitation Guest House to get ready for their 6pm wedding while everyone else checks out the sights of Key West.

5:30pm - Wedding first-look

A properly coiffed jill and tuxed David will rendezvous in the middle of Duval Street near L'Habitation for a dramatic first look. Photographer Barry Brown will be there to capture the moment in all its intensity as crowds of revelers and tourists photobomb the shot. Should be a blast!

6:00pm - Outdoor wedding ceremony at Hemingway Home

The wedding party (guys, then girls) will limo to the Hemingway for the vows, the rings, the kiss, the "hell-yeah!". This is what everyone's been waiting for, and Jill and David won't disappoint!

6:15pm - Formal photos outside the Hemingway

We'll be quick about it, but Jill and David want pics of everyone. So don't run off after the ceremony.

6:30pm - Drinks, food and live music by the Hemingway pool

You weren't thinking you'd be left to starve, did you? How about a taco station, a mac-n-cheese station, and some heavy hors d'oeuvres to go with those drinks? The place is ours til 9.

9:00pm - Hitting the town

More precisely, friends and family can hit the town. Jill and David will be saying goodnight ;)

Saturday, April 18

5:30am - Photoshoot on the beach

Barry wants to get some artsy golden daybreak photos of Jill and David on the beach in their wedding attire. There might even be a dress-trashing photo -- just not the dress Jill wore on Friday.

Saturday Group Adventure Options

8:30am - Snorkeling Adventure

Join Jill and David for a morning of snorkeling the coral reef located a short sail from Key West. This $41.25 Sebago Tours adventure includes snorkeling equipment, optional wet suits for a small additional fee, and should keep you occupied and amazed all Saturday morning. On the return sail, there's complimentary beer and wine to celebrate the experience.

The tour starts 8:30am at 205 Elizabeth Street, Unit I, between the Schooner Wharf Bar and the Conch Republic Seafood Company. The Sebago catamaran will shove off at 9:00am and will dock again at 12:30.

More info

11:30am - Glass-bottomed Boat Adventure

If getting up early to swim with the fishes isn't your thing, but you wouldn't mind seeing some, then a glass-bottomed boat ride over the coral reef might be perfect for you. The two-hour ride has check-in at 11:30 and departs at noon from the Margaritaville Resort & Marina, 241 Front Street.

More info

8:30am - Parasail Rides (hourly til 5pm)

So David and Jill gave parasailing a whirl in Cancun in 2018, and it's a total blast. Our ride was maybe 15 minutes long and super-gentle, and the view from 300 feet up is something you'll never forget. The Sebago Tours parasail rides depart hourly beginning at 9am (with check-ins 30 minutes prior) from Sebago's pickup location at 205 Elizabeth Street, Unit I, between the Schooner Wharf Bar and the Conch Republic Seafood Company.

More info

Saturday Evening Options

5:00pm - Dinner and Drinks at Blue Heaven

Reputed to be the best place to go in Key West for great local fare, and known for its offbeat atmosphere, Blue Heaven is where Jill and David will start the night. It's located at 729 Thomas Street, about a 10-minute walk from north Old Town. If you're there on time, we'll buy the first round of drinks!

More info

6:30pm - Catamaran Champagne Sunset Sail

If you'd rather take in a sunset aboard the 60' Sebago Flyer or Sebago Cubed catamaran, then choose this outing when you RSVP. You'll sail past Key West landmarks, sip on your included drink, and watch the ocean swallow the sun. It's a two-hour ride.

Check-in is at 6:00pm at 205 Elizabeth Street, Unit I, between the Schooner Wharf Bar and the Conch Republic Seafood Company. The catamaran will shove off at 6:30pm and will dock again at 8:30.

More info

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