The Ultimate Engagement Guide: 28 Tips and Ideas for Planning the Perfect Proposal

Tips and Ideas for Planning the Perfect Tampa Bay Wedding Proposal | Amber McWhorter Photography

How to Pop the Question

“Proposals do take some planning, but try to make them as natural as possible! They will come across more authentic and meaningful if you are yourself. You’ll most likely be a little nervous, so it’s important to have details already in place: select a spot, (check the weather if it’ll be outside!), and have something in mind for right after whether it’s a surprise photo shoot or a gathering of friends and family.” – April Sherwin, NOVA 535

“The most important thing about proposing is that it be memorable, as it becomes a story to pass down. Try and propose while doing something you both love to do together. I got engaged while hiking, something we loved to do together! It was very memorable. Make sure, though, that it’s somewhere that you don’t have to worry about losing the ring. When buying the ring, remember to buy what you think your significant other will love, not what everyone else thinks you should buy. What’s right for one person may be off-putting to another.” – Dorelle Raphael-Fishkin, Brides N Blooms Designs

“Make the experience personal by incorporating elements unique to your personalities and relationship. This can mean partaking in a favorite activity, enjoying a favorite food, or including a personal decorative element. Enjoy hiking trails? Recall a memorable first date meal? Obsessed with Disney? Tie those details into your proposal, and it’s bound to be more special and memorable than a generic ‘fancy dinner’ or ‘holiday ring box under the tree.’ Also consider documenting the experience with a secret photographer or videographer, because just like a wedding, the experience flies by in a blur, and without someone to capture the moment your memory may get fuzzy due to emotions running high!” – Christi Winsor, Winsor Event Studio

“Maybe it’s a little old-fashioned, but I think it’s exceptionally meaningful to reach out to your partner’s parents and let them know your intention of marriage. Especially if your partner is a ‘Daddy’s girl,’ knowing that dad approves of you is a big deal. It also keeps your partner’s parents in the loop, and I believe sets you up to start your marriage off on the right foot in you future parent-in-law’s eyes. I also think it’s important to propose in a way that’s meaningful to your partner as opposed to doing what ‘everyone else does.’ If your partner is a quiet, shy person, they may not want to be proposed to in front of a large crowd. If family is super important to them, maybe it’s best to propose in front of family at Thanksgiving or Christmas. If your partner is obsessed with Disney, and maybe you’re not-so-much, perhaps bite the bullet and propose at Disney!” – Bonnie Newman, Bonnie Newman Creative

“Before you decide what to do for your engagement find out what’s important to the person you are about to propose to. Many clients that I have asked have said that having their family there is important to them. Have the ring ready and make sure you have asked for permission if that was a requirement. Get family or friends involved! They may have some great ideas for you. Have fun and be present! You love this person and hopefully, they are not expecting perfection. And if all of this sounds like you can’t handle it…hire a planner!” – Paulina Bartnicka, Amici’s Catered Cuisine

“Do something personal to the two of you: include a favorite date night location or a place with special meaning for both of you. Include favorite foods or adult beverages. Do your research and always have a Plan B. Proposing on the beach might sound like a great idea, but there’s a lot to consider. You have to deal with changes in the weather. You might not be able to have glass (champagne, glasses, or candles) on the beach. You’re also on display and might not have any privacy. You’re also out in the wide-open, so hiding a photographer, music, or even family can be challenging.” – Tammy Waterman, Special Moments Event Planning

“I always recommend doing the proposal on a random day! You are more likely to get a wonderful surprised reactions if you steer clear of holidays, birthdays, anniversaries, etc. Make sure your partner is wearing a nice outfit! They will forever hold a grudge if they are sporting loungewear in the photos.” – Heather Lorenz, The Birchwood

“Preparation is key! First off, make sure you are ready to get married: financially, emotionally, psychologically, etc. There are all types of marriage counselors, and they are all very helpful in asking the right questions to each of you before the life change. Asking someone to marry you is essentially taking a back seat to your own well-being and caring for another as much or more than yourself. You must be ready! Then, when it’s time to propose, make it a huge surprise!” – Brandon Wheeler, Gulf Beach Weddings

Favorite Tampa Bay Proposal Spots

“I think a proposal is such an intimate question and really a fork in the road and the location should be very intimate. My favorite is just in your living room, where it is just you and your spouse. Because after all, through life many times it is just you and your spouse. Your life partner.” – Michele Renee Zerda, Michele Renee the Studio

“The best proposal ‘spot’ is somewhere that is meaningful to you as the couple. Maybe it’s your first date spot, where you realized you wanted to spend your life with this person, or a previous vacation destination. You’ll want somewhere semi-private and quieter to make sure your partner can hear you and so you can hear their response! I love somewhere with a view as well!” – April Sherwin, NOVA 535

“One great spot for a proposal is North Straub Park in Downtown St. Pete! All of the trees, grass, winding sidewalks, and waterfront views make for a gorgeous background in photos. Once you put a ring on it, you can head across the street to The Canopy’s rooftop where you can surprise your partner with her family and friends!” – Heather Lorenz, The Birchwood

“Clearwater Beach! It is America’s number one beach for many years in a row. There are plenty of places to park and many opportunities for surprises. I believe the beach is perfect for couples who love nature and the beach. It is extremely budget-friendly which will leave you some budget for the perfect ring.” – Paulina Bartnicka, Amici’s Catered Cuisine

“There are several hotels with rooftop terraces along the gulf and the bay with spectacular views and sunsets. They also give you a tremendous indoor backup plan if you need one and can help you through details like dinner or additional services. Hyatt Regency Clearwater Beach, The Wyndham Clearwater Beach, and Marriott Rocky Point all have great rooftop locations. The Clearwater Aquarium has some beautiful options that can include dolphins. The Grand Hyatt Tampa has a private beach location that can offer you some better options than a public beach. Wedding planners have all the resources you need and can develop creative ideas for planning a proposal.” – Tammy Waterman, Special Moments Event Planning

“It depends on the way you plan the surprise proposal. I have had couples ‘book a session’ and then in the middle of it, the photographer gives the cue for the proposal, and SURPRISE! If it is completely a secret, meaning there is no actual photography session planned, choose a location that is somewhere not too isolated. If it is just the couple and then someone casually off in the distance, it may seem odd, but if it is a place that typically has other people, it will seem less noticeable. With these reasons in mind, I think the beach or a park is a perfect place for a proposal. I wouldn’t choose a very packed beach or park, but one that has some people.” – Amber McWhorter, Amber McWhorter Photography

“Anywhere on the beach in the Tampa Bay Area or Panhandle just prior to sunset. Florida sunsets are literally world-renowned. If you choose a weekday/weeknight you will have more privacy.” – Brandon Wheeler, Gulf Beach Weddings

“No matter where you propose, make sure it’s somewhere that has special meaning to the pair of you! Whether it’s a favorite spot on the beach, or your go-to kitchen nook for weekend pancakes and crosswords, selecting a space that holds sentiment will ultimately add to the experience.” – Christi Winsor, Winsor Event Studio

Should I Hire a Photographer/ Videographer to Capture Our Engagement

“Capturing video of such a moment can be such an amazing heirloom to have! The key difference between a friend using an iPhone, and a professional videographer is audio and video quality. As professional videographers, we can hide a microphone in your shirt and be able to capture high-quality audio of your partner’s reaction and yours as well! If you end up hiring the same videographer to capture your wedding, we can even use the footage and audio from the proposal in the storyline of your wedding film. Imagine showing your future children and grandchildren that film!” – Bonnie Newman, Bonnie Newman Creative

“Hire a professional photographer for your proposal because they will be able to provide you with high-resolution images that you can keep forever. They know where to hide, how to pose, how to capture the perfect angles, etc. If you just let your friend document it, your photos probably are on a phone, not high-quality and could deteriorate over the years leaving you with not the best photos of this important milestone in your life.” – Amber McWhorter, Amber McWhorter Photography

“Hiring a photographer/videographer for this most memorable occasion helps to keep the memory alive! Most people are alone when they get engaged, what better way to share the ‘moment’ than with a photo or video of the event?” – Dorelle Raphael-Fishkin, Brides N Blooms Designs

“All photographers absolutely love love, it’s in their DNA! But they are also great at putting their emotions aside and getting down to business, which is capturing that one perfect moment! Friends and family are great to celebrate with afterward, but they may be too emotional and excited to focus on the task at hand. Leave it to someone who has been there and done it countless times before!” – April Sherwin, NOVA 535

Bonnie Newman Creative

“It’s so important to hire a professional photographer/videographer for the proposal because they truly know the best angles to capture! Also, since they would be a ‘stranger’ to your partner, it would be less suspicious for them to be around as opposed to a friend.” – Heather Lorenz, The Birchwood

“Similar to a wedding, the proposal experience flies by in a blur, and without someone to capture the moment, your memory may get fuzzy due to emotions running high! To avoid raising suspicion, many photographer and videographers offer ‘secret coverage’ where they document the proposal from afar, allowing for more privacy.” – Christi Winsor, Winsor Event Studio

“You need to hire a professional photographer and videographer for the engagement because these are the milestones in your life that you want to remember forever. You don’t want some shaky cell phone video to look at in 20 years!” – Paulina Bartnicka, Amici’s Catered Cuisine

“Hiring a professional photographer and videographer gives you someone who might be less conspicuous than a friend or family member, and you can be sure they won’t miss a shot! This is not a moment you want to trust to your smartphone.” – Tammy Waterman, Special Moments Event Planning

Favorite Locations to Celebrate after Your Engagement

“We love when couples enjoy a celebration with friends and family immediately after the proposal, so consider planning a group function to coincide with your engagement. This may be a secret gathering of friends at your home when you return from your proposal experience or it could be a restaurant reservation that serves as an excuse to get all dressed up and out of the house, aiding in your proposal surprise.” – Christi Winsor, Winsor Event Studio

“The Canopy at the Birchwood is the perfect spot to celebrate after the engagement! Since it’s a rooftop lounge, you can hide friends and family members up there without being seen from a distance. Once the elevator doors open, everyone can yell “Surprise!” – Heather Lorenz, The Birchwood

Outdoor Terrace Wedding Feasting Table at St. Pete Wedding Venue The Birchwood | Intimate Micro Wedding Elopement COVID Styled Shoot | Fall Autumn Wedding Inspiration | Hotel Terrace Reception with Canopy String Lights Orange Copper Wedding Table Linens | Gold Beaded Glass Chargers with Napkin and Menu Card and Gold Flatware | Wedding Centerpiece with Orange White and Peach Roses
Shauna and Jordon Photography | The Birchwood

“My favorite place to celebrate after an engagement would be at Tommy’s Tiki Bar at the Hilton Clearwater Beach. You can have some cocktails to celebrate while having your feet in the sand.” – Paulina Bartnicka, Amici’s Catered Cuisine

“My favorite locations to celebrate an engagement are somewhere where the couple can enjoy and celebrate their moments together. If you propose on the beach or at a park, you can plan a little surprise picnic with some champagne. If you aren’t feeling a picnic vibe, you can make reservations at a place that you both love. It is important to include moments and locations that you will hold close to you forever.” – Amber McWhorter, Amber McWhorter Photography

MEET THE EDITOR

Marry Me Tampa Bay editor, Anna Coats, created Marry Me Tampa Bay in 2012 to showcase the area's best local weddings and vendors. She has been featured as a wedding expert on the national talkshow Daytime, Fox13, ABC Action News, Great Day Tampa Bay, and Bay News 9 (now Spectrum).

NOVA 535

NOVA 535

Avila Golf & Country Club

ALOFT/ ELEMENT TAMPA MIDTOWN

Organic Boho Modern White and Brown Rooftop Wedding Ceremony Flowers with Peach Roses, Gold Leaves, Feathers, and Ghost Chairs | Tampa Bay Wedding Florist Monarch Events | Planner and Designer UNIQUE Weddings + Events | Venue Aloft/Element Midtown | Photographer and Videographer Bonnie Newman Creative | Rentals A Chair Affair

BELLWETHER BEACH RESORT

St. Pete Beach Wedding Venue Bellwether Beach Resort Aerial View

The Vault

The Godfrey Hotel

Renaissance Tampa International Plaza

Hyatt Regency Clearwater Beach

Red Mesa Events

Lifelong Photography Studio

Creative Bride and Groom Wedding Portrait with Veil Blowing in Wind | Tampa Bay Wedding Photographer Lifelong Photography Studio

Carrie Wildes Photography

dewitt for love

Modern Dramatic Unique Asymmetrical Red Wedding Bridal Bouquet with Ranunculus Tulips Protea Roses Anemone and Amaryllis | Dewitt for Love Photography

LIMELIGHT PHOTOGRAPHY

Tampa Bay Wedding Photographer | Limelight Photography

Breezin’ Weddings

Florida Bride and Groom Romantic Portrait Under Whimsical and Lush Circular Floral Arch with Pampas Grass, White and Blush Pink Roses, Hydrangeas and Greenery, Bride in Full Length Veil | Tampa Wedding Planner Breezin' Weddings | Wedding Dress Isabel O'Neil Bridal | Wedding Hair Femme Akoi | Waterfront Wedding Venue Tampa Yacht and Country Club

Coastal Coordinating

UNIQUE Weddings & Events

Parties a la Carte

Special Moments Event Planning

Modern, Garden Inspired Wedding Decor, Blush Pink Floral Wall and White Draping, Gazebo, Outdoor Dance Floor, Long Feasting Tables. Rose Gold Chiavari Chairs, Floral Curly Willow Arches | Tampa Bay Wedding Planner Special Moments Event Planning | Tampa Bay Wedding Florist Gabro Event Services | Tampa Bay Wedding Rentals A Chair Affair

Truly Forever Bridal

Michele Renee The Studio

Elite Events Catering

Graingertainment

Longboat Key Club

Beso Del Sol

Isla del Sol Yacht & Country Club

The Poynter Institute

The Don CeSar Hotel

Hotel Zamora

Postcard Inn

Hotel Alba

PARADISE SPRING

Paradise Spring | Tampa Bay Wedding Venue Private Estate

LAKE LODGE

The Lake Lodge Wedding Venue | Lake Thonotosassa Tampa Area Wedding Venue

amber mcwhorter photography

Spaghetti Strap Casablanca Ivory Simple Slip Wedding Dress Bridal Gown | Light Blue Grey Groom Suit | Outdoor Bride and Groom Beach Portrait at Tampa St Pete Florida COVID Destination Elopement Beach Wedding Ceremony | Neutral White Ivory and Greenery Bridal Bouquet | Amber McWhorter Photography

Luxe Light Images

Gulf Beach Weddings

Elope Tampa Bay

Tampa Bay Wedding Elopement Planning | Elope Tampa Bay

eventfull weddings

Tampa Bay Wedding Planner EventFull Weddings

Lynn’s Catering

Amici’s Catered Cuisine

Sweetly Dipped Confections

Bella Bridesmaid

ADORE BRIDAL

Lifelong Photography Studio | The Current | Adore Bridal Hair and Makeup

A&P Designs

Grant Hemond & Associates

Grant Hemond and Associates | Tampa Bay Wedding DJ

breezin' entertainment

St. Petersburg Wedding DJ Breezin' Entertainment

A Chair Affair

outside the box

Tampa Bay Bride and Groom Cheers in front of Champagne Wall, Greenery Boxwood Bubbly Wall Rental, Bride Holding Vibrant Jewel Toned Floral Bouquet with Bright Pink Roses, Ivory, Purple, and Blue Flowers | Florida Wedding Planner Breezin' Weddings | South Tampa Outside The Box Event Rentals