The 10 Most Romantic Tours in North America

January 20, 2020
Jessica Padykula

Romance comes in many forms and can be found in many places. Maybe it’s a bottle of wine for two by a cozy fireplace, or maybe it’s an impromptu picnic on the beach just as the sun goes down. But something else that offers countless opportunities for romances – is travel. Travel is eye-opening, exciting, and often involves seeing and doing new things you may not have considered – all of which have the power to spark or deepen a romantic connection. Here at Urban Adventures, we are all about the power of travel to transform, whether it comes to romance or not. But since this is a post about romance, we want to point you in the direction of some of our most romantic tours in North America (tours that have even seen some proposals), just in time for Valentine’s Day!

San Francisco: Bridge and the Beach

Golden Gate Bridge
Take in epic views from the iconic Golden Gate Bridge | Photo by Urban Adventures

Our local guides have witnessed a few proposals during this San Francisco tour that will have you swooning over epic views. Start with a walk out onto Golden Gate Bridge and have your camera ready to capture the city’s stunning skyline. Follow that with a scenic hike along the coastline where you’ll be spotting sailboats gliding by and pelicans soaring overhead along the way. Add in a beach stop with time to put your toes in the surf and you have more than enough ingredients for a romantic afternoon.


Las Vegas: Private Las Vegas Wedding & Chapels Tour

Wedding chapel Las Vegas
Get the inside scoop on the world of Vegas weddings | Photo by Urban Adventures

If a wedding-themed tour doesn’t scream romance, we don’t know what does. Grab your other half and join a local guide to discover one of the world’s most famous wedding destinations, from its quirkiest chapels to the inside scoop on some of Sin City’s most famous weddings. And if that weren’t enough, one of our Las Vegas guides is a certified minister so if the spirit moves you, you can even incorporate your very own nuptials into this unique private tour made for romance.

Havana: Classic American Car tour

Classic American car Havana
Cruise the streets of Havana in a classic American car | Photo by Urban Adventures

Car loving couples (or even anyone excited at the thought or cruising the streets of Cuba in a classic car) will want to have this tour on their travel radar. Explore the city in style and feel the breeze on your face as you sightsee in a classic 1950s American convertible. Discover some of Havana’s top sights as you ride, and cap off your tour with a Cuban cocktail on the terrace of the famous Hotel Nacional.

New York: Private New York Times Journeys – Dumbo, the New Brooklyn

Brooklyn Bridge
Discover a new side of Brooklyn (and maybe a side of romance) | Photo via Pixabay

New York City is one of those destinations that often gets associated with romance. It’s a city of possibilities and opportunity where every neighbourhood has secrets to discover. In this case, our tour (curated by Urban Adventures and the New York Times), gives you an inside look at one of the city’s most intriguing districts: Dumbo. If you’re wondering where the romance lies, basically, it’s everywhere. From historic architecture and charming nooks, to breathtaking skyline views and cobblestone streets. Oh, and did we mention the chance to see the Brooklyn Bridge up close on a scenic ferry ride?

Los Angeles: Private Sips of Old Hollywood

Old Hollywood bar LA
Sip your way through a romantic tour of Old Hollywood | Photo by Urban Adventures

Step back in time to the golden age of Old Hollywood on a private tour perfect for ramping up the romance – and the glamour. Linger over a cocktail at bars once frequented by Charlie Chaplin, Marilyn Monroe and Ernest Hemingway while hearing stories of Hollywood’s fascinating history. In between sips, stroll along Hollywood Boulevard soaking up the atmosphere of a bygone era and discovering iconic bars, lounges, speakeasies, and mobster hangouts with more than a few secrets within their walls.

New Orleans: Private Cocktail Tour

New Orleans cocktail bar
Get a taste of New Orleans' thriving cocktail culture | Photo by Urban Adventures

Grab your nearest and dearest and get ready for a night on the town – New Orleans style! But forget tourist traps and generic restaurants. Romance here comes in the form of classy cocktails at historic bars and off-the-beaten-path hidden gems only locals know about. By the end of the tour, cocktail-loving couples will have an insider knowledge of the city’s famous drinking culture along with having sampled some seriously well-crafted libations.


Miami: Private Boat Adventure

Miami boat tour Urban Adventures
Find romance on the water in Miami | Photo by Urban Adventures

Romance awaits on a private boat tour that will have you seeing Miami in style, wind in your hair and sea spraying your face. Stop at a sandy caye for a relaxing dip, lounge on the beach, or just to admire the city skyline from a new perspective. Miami is a beautiful city and even more scenic from the water, something you and your plus one will discover as you enjoy your boat adventure for two.

Playa del Carmen: Rooftops and Cocktails of Mexico

Playa del Carmen rooftop bar
Discover some of Playa del Carmen's best rooftop bars | Photo by Urban Adventures

If relaxing at exclusive rooftop bars sipping tequila in the sun sounds like something with romantic possibility, you’ll want to think about taking this chilled out Playa del Carmen tour that takes you to not one, but three rooftop bars with gorgeous ocean views. Sip (and learn) about mezcal and tequila, learn to create your very own mezcal cocktail, soak up the sun, and snack on local dishes that pair perfectly with your beverages. Then at the last stop, an infinity pools awaits.

Washington: Private Craft Cocktail Tour

Washington DC cocktail bar
There are some seriously good craft cocktails to be had in Washington | Photo by Urban Adventures

Washington DC may not be the first city that comes to mind when you think about a thriving cocktail culture, but creative craft beverages can be found all over the city – and this private tour takes you and your other half to some of the best places to find them. Visit three of DC’s best cocktail bars to sip amongst locals while also learning about the city’s boozy history and how prohibition helped shape the city.

Philadelphia: Private Rocky Film Locations Driving Tour

Rocky filming locations tour
Grab your sweetie and run the Rocky Steps | Photo by Urban Adventures

Outside of the boxing ring and those nail-biting fight scenes, Rocky is, at it’s core – a love story. Sure, there’s a lot of other things going on, but Rocky’s relationship with Adrian is the movie’s heart and soul. So any fans of the film (especially those with romance on the brain) will be interested in this tour that covers filming locations from six of the seven Rocky movies, including those iconic steps where, it should come as no surprise, that our guides have seen multiple marriage proposals go down.

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