Launch the Next Chapter of Your Love Story at Sandaway Suites & Beach

Oxford, Maryland, is famous for its timeless coastal elegance and breathtaking sunsets—the very qualities that drew Hollywood right to our shores! Our quaint town served as a key filming location for the romantic comedy Failure to Launch, starring Matthew McConaughey and Sarah Jessica Parker. Just as the movie characters sought a change of scenery to find their next chapter, Sandaway Suites & Beach offers the perfect, secluded stage for you to launch yours.

Behind the Scenes: The Day Hollywood Came to Oxford

The film crew didn't just casually pass through Oxford—they lived here! To create the perfect scenes for Failure to Launch, the production team essentially transformed key parts of the town for several weeks of shooting.

While the bulk of the film was shot in New Orleans, the most visually charming and pivotal scenes required Oxford’s unique seaside atmosphere. Filming was tightly scheduled for locations like Bachelor's Point, The Masthead at Pier Street, and the local Oxford Boatyard, with work also taking place at Cutts & Case Inc.

The Famous Yacht Scene:

One of the most memorable scenes shot right here at the Oxford Boatyard features Matthew McConaughey's character, Trippe, trying to impress Sarah Jessica Parker's character, Paula, by taking her out on a luxury yacht. In classic romantic comedy style, the moment is ruined when the actual boat owner shows up and unceremoniously kicks them off—a hilarious snapshot of the film’s central conflict!

A Major Production:

This was no small affair! The film, directed by Tom Dey (Shanghai Noon) and produced by Scott Rudin (The Truman Show), brought a cast and crew of about 170 people to Oxford. Many worked on the hit movie Wedding Crashers the previous year, highlighting that Hollywood consistently chooses Talbot County for its perfect romantic backdrops. It took extensive preparation, including "peel painting" boats to temporarily change their look for the cameras.

Live Like the Film Crew

During the weeks of filming, the large cast and crew needed quiet, comfortable accommodations close to the water. Our very own Sandaway Suites & Beach had the distinct pleasure of hosting some of the film crew right here on our secluded, romantic property.

When you choose Sandaway, you are literally choosing the same idyllic, waterfront charm that Hollywood producers selected for a major romantic film. Imagine the inspiration that sparked on the very lawn where you could say "I do" or pop the ultimate question!

Your Romantic Oxford "Failure to Launch" Location Tour

While you’re here launching your own love story, why not enjoy a little local sightseeing? You can plan a charming, romantic walking tour right from Sandaway to visit some of the key spots in Oxford featured in the movie. It’s the perfect way to spend an afternoon capturing fun, film-inspired photos together!

Shooting locations in Oxford, Maryland included in the Failure to Launch movie production intineray were Bachelor’s Point, Oxford Boatyard, Masthead at Pier Street (Now Doc's Sunset Grille), and Cutts & Case Shipyard.

1. The Iconic Dock Scenes (Now Doc's Sunset Grille):

   • What you saw: Many of the most memorable boat and dock scenes, including where they filmed the dockside restaurant what is now "Doc's Sunset Grille" and Oxford Boatyard.

   • Your tour moment: Take a sunset stroll down these historic piers. Imagine the cinematic moments that unfolded against the Chesapeake Bay backdrop and recreate your own romantic scene looking out over the water.

2. The Town Charm (Historic Oxford, Maryland):

   • What you saw: The picturesque, historic streets and charming homes in the main part of Oxford served as the backdrop for numerous scenes.

   • Your tour moment: Walk hand-in-hand down Morris Street. Admire the beautiful architecture and imagine yourselves as the stars of your own romantic comedy while enjoying the town's tranquil atmosphere.

3. The Sailing Views (The Montages):

   • What you saw: The beautiful shots of sailboats gliding on the open water, which emphasize the breezy, romantic lifestyle, were captured right here on the Tred Avon River and the Choptank River.

   • Your tour moment: These views are best enjoyed right from the comfort of Sandaway's private beach and waterfront lawn! Relax in an Adirondack chair with a drink and watch the sailboats go by, taking in the same panoramic, cinematic water views the filmmakers sought out.

Your Success Story Starts Here

Don't suffer from a "failure to launch" your romantic plans! Sandaway Suites & Beach offers the seclusion, beauty, and intimacy needed to make your proposal or intimate wedding absolutely unforgettable. We are the perfect Hollywood-approved launchpad for your next great adventure.

• A Private Beach for "I Do"s: Our exclusive, secluded beach is ideal for a heartfelt proposal or a stunning, intimate waterfront ceremony.

• Romantic Suites: Our adult-only suites are designed for pure relaxation and reconnection, offering water views and a peaceful escape.

We offer specialized Romance and Proposal Packages to help you craft the perfect moment without any stress. Let us take care of the details while you prepare to launch into the most exciting chapter of your love story!

Visit Sandaway Suites & Beach official wedding page for Sunset Ceremony or Proposal Packages https://www.sandaway.com/weddings/

 

Trailer Summary: Failure to Launch (2006)

The trailer for Failure to Launch quickly sets up the central, humorous conflict:

• The Problem: Trippe (Matthew McConaughey) is 35 years old and still lives at home with his parents, who are desperate for him to move out [00:25].

• The Solution: They hire Paula (Sarah Jessica Parker), a professional "motivator," to start a romantic relationship with Trippe, boosting his self-esteem until he is ready to leave the nest [00:36].

• The Complications: Paula is an expert at creating a relationship that will eventually push him away (she details her strategy for a first date, including ordering a huge dessert and talking about old boyfriends [00:55]). However, she soon realizes she genuinely likes Trippe, and the line between the professional arrangement and real feelings starts to blur [01:49].

• The Stakes: The parents and Paula's team start to panic as the relationship deviates from the plan, leading to a race against time and a final realization that Trippe must conquer his fear of love and launch after Paula [02:05].