Twice as nice: 2-for-1 vacation destinations

Welcome to Cheapflights

The simple way to find cheap flights and hotels from all your favorite travel companies

Does a buy one, get one free vacation sound too good to be true? Booking a BOGO bon voyage is easier than you might think. Many destinations offer an ideal opportunity to get two different vacations for the price of one, saving you money and time, with the bonus opportunity to check even more places off your ever growing travel bucket list.

Whether travelers choose to fly to a cheaper regional airport for a suburban escape, arrive in an adjacent town’s airport or pick a destination that offers multiple vacation options mere miles apart, there are dozens of destinations in North America that offer quick and easy vacays serving up double the fun.

We chose our favorite two-for-one vacation destinations offering two dramatically different experiences a quick train, bus or car trip away. These city combos are so intriguing you might find yourself booking a repeat trip.

New York City + Saratoga Springs, New York

Central Park
Get lost in Central Park. (Image: Jen Davis/NYC & Co)

There is an endless amount to see and do in the city that never sleeps. Whether you prefer taking in a Broadway show, dining at celebrity-filled, Michelin-starred restaurants and sipping craft cocktails at opulent city bars or would rather stroll Central Park and explore The Met before shopping in SoHo, there is something for everyone in NYC. Contrast the hustle and bustle of the Big Apple with a three-hour drive north to Saratoga Springs, N.Y., an idyllic town known for its summertime horse racing at Saratoga Racetrack. The picturesque countryside is also populated with farmers markets, breweries, museums and parks. Make sure to leave time for a relaxing dip in the hot springs at Roosevelt Baths & Spa within Saratoga Spa State Park.

Charleston + Hilton Head, South Carolina

Visit charming Charleston before your island vacation. (Image: Explore Charleston)

Combine a small city trip with an island vacation in South Carolina. Head to charming Charleston for a dose of Southern hospitality and fantastic food. The destination frequently tops the James Beard Foundation Awards with its long legacy as home to top chefs like chef Jason Stanhope of FIG Restaurant, Chef Robert Stehling of Hominy Grill and Chef Sean Brock of McCrady’s. Continue your culinary journey 95 miles south on Hilton Head Island, which boasts 250 restaurants. The tiny island also offers 12 miles of beautiful beaches, 24 golf courses and 350 tennis courses – all providing days of fun in the sun.

Washington, D.C. + Richmond, Virginia

The White House
Visit one of the most famous houses in the world. (Image: John Haslam, The White House, 1600 Pennsylvania Avenue; Washington DC via Flickr CC BY 2.0)

The U.S. capital is packed with museums, monuments and more. From visiting The White House to strolling the halls of the Smithsonian museums to learning about U.S. history, there are a plethora of options. Then hop a bus or train some 100 miles south to explore Richmond, Va. More than 7 million visitors head to the picturesque region each year to visit numerous Civil War sites, the Virginia Museum of Fine Arts, Henricus Historical Park, the James River, Lewis Ginter Botanical Garden and Kings Dominion amusement park.

Las Vegas, Nevada + Grand Canyon, Arizona

Las Vegas
Soar to new heights in Las Vegas (Image: Maverick Helicopters)

Known for spectacular shows, glittering lights and casinos, Las Vegas is a 24/7 playground in the desert. It’s increasingly become a family-friendly destination too, with impressive pools, family entertainment and attractions like gondola rides at The Venetian Las Vegas, Caesar’s High Roller, the world’s largest observation wheel, and Circus CircusAdventuredome, a climate-controlled amusement park offering 25 rides and attractions. When you’ve had your fill of Sin City, go explore the Grand Canyon. Travelers can drive four hours to the natural wonder or opt for a helicopter ride via Maverick Helicopters, which offers nearly a dozen helicopter excursions including its popular four-and-a-half hour Dream Catcher Sunset tour. Departing from Las Vegas, the afternoon trip flies over Nevada’s pristine desert landscape, red sandstone formations and, finally, the Grand Canyon, where the helicopter lands 3,500 feet below the West Rim on Hualapai Indian territory. After a brief photo op perched 300 feet above the Colorado River, visitors partake in a champagne toast and light snack before the return flight over Lake Mead, Fortification Hill and the Hoover Dam. Perfectly timed, the ride ends with a sunset flyover of downtown Las Vegas and the Las Vegas Strip.

Los Angeles + Santa Barbara, California

Hollywood sign
Say hello to Hollywood. (Image: Gary Leonard/Los Angeles Tourism & Convention Board)

With more than 300 days of sunshine annually in Los Angeles, Calif., most days are perfect for swimming, surfing and playing beach volleyball. If that’s for you, try Santa Monica State Beach or Will Rogers State Beach. While you are there, take time for a stroll on the Santa Monica Pier, a ride on the nine-story Pacific Wheel, a stop at one of the four weekly farmers markets and shopping at Santa Monica Place. Santa Monica is one of the classic California beach town options in the Los Angeles area. Get more glistening coastline in Malibu and Venice or head 15 miles into downtown Los Angeles. There City of Angels is perfect for getting multiple destinations, not only in one trip, but one city. Get even more from your California adventure by renting a car and driving north to Santa Barbara. While the gorgeous coastal city has a lot to offer, counter the busy LA scene with a relaxed West Coast wine tour. While Napa Valley and Sonoma may be the more frequented wine trails, Santa Barbara has an easily accessible and wide-ranging Urban Wine Trail with more than 20 tasting rooms amid a gorgeous, eclectic setting peppered with additional opportunities for art, culture and outdoor fun along the way.

Detroit, Michigan + Toronto, Canada

Take a two-for-one vacation to Toronto, Canada. (Image: Michael Gil, Toronto via Flickr CC BY 2.0)

There are more than 100 galleries at the Detroit Institute of Arts, enough art to fill an entire vacation itinerary, but don’t spend all your time in Detroit, Mich. there. Make sure to check out the Charles H. Wright Museum of African American History, which houses the world’s largest exhibit on African-American culture, and stroll the lively Greektown neighborhood. After exploring the Motor City, head northeast to Toronto, Canada’s largest city, via afour-hour car or train ride. Enjoy dim sum and browse the shops in the second largest Chinatown in North America before heading over to the Hockey Hall of Fame, home of the Stanley Cup. The museum has many interactive exhibits giving guests the chance to compete against animated versions of the sport’s greatest goalies, call game play-by-plays, watch 3-D films and see the Stanley Cup up close. If you’re not a sports fan, see Toronto from above at the CN Tower, where brave souls can walk along the top of the tower’s main pod 1,168 feet above the ground at the EdgeWalk attraction. Want to go to Canada but short on time? Windsor, Canada, a bustling city with plentiful parks, museums and breweries, is just eight minutes away from Detroit.

Orlando, Florida + a Caribbean cruise

Cirque Du Soleil
Run away with the circus in Orlando, Florida. (Image: Dynamite Studio, Inc.)

Orlando offers a variety of sun and fun vacations whether you’re traveling with kids in tow or looking for a more grown-up getaway. From family-focused theme park-filled days to adults-only golf and spa outings, there are plenty of options for travelers headed to central Florida. Double down on your central Florida vacay with a Caribbean cruise. Carnival Cruise Lines, Disney Cruise Line, Norwegian Cruise Line and Royal Caribbean International all offer three- to nine-day Caribbean cruises departing from Port Canaveral, just 45-minutes east of Orlando. Though there are 17 Caribbean destinations under a Zika virus travel alert, there are dozens more like the British Virgin Islands, Cayman Islands, Grenada, St. Lucia and Turks and Caicos Islands that are unaffected. Short on time? Victory Casino Cruises offers five-hour gaming cruises that depart twice a day.

Burlington, Vermont + Montreal, Canada

Burlington, Vermont
Book it to Burlington, Vermont. (Image: Jeff Turner, Burlington, Vermont via Flickr CC BY 2.0)

The picture postcard college town of Burlington in central Vermont is the perfect places for folks who enjoy the outdoors and fine foods. The completely walkable city boasts breweries, farm-to-table restaurants and a Waterfront Park where visitors can swim, kayak and paddleboard. Nearly 100 miles north, travelers can cross the border into Canada for a complete contrast. Montreal’s mesmerizing 18th-century buildings – home to quaint cafes, museums and souvenir shops – and predominantly French-speaking population will have you feeling like you are in Paris. Don’t miss the phenomenal food like local favorites Toqué! and Whisky Café in this riverfront city that boasts a higher concentration of restaurants than New York.

Seattle, Washington + Vancouver, Canada

See Seattle’s iconic spots. (Image: Ian Sane, Seattle via Flickr CC BY 2.0)

Located on the eastern shore of Puget Sound, there is much to see and do in Seattle’s 83 square miles. From fabulous family-friendly activities to great restaurants and offshore wineries, Seattle has a lot to offer travelers. Stroll the stalls and get lucky with Rachel the Pig at Pike Place Market, grab a cup of Joe at the original Starbucks and explore Seattle Center, home to some of Seattle’s most famous attractions, including the iconic 605-foot Space NeedlePacific Science CenterSeattle OperaPacific Northwest Ballet and Seattle Repertory Theatre. A three-hour drive north (or a slightly longer train ride that hugs the coastline) is Vancouver. Start with a 360-degree view of the bustling seaport city in British Columbia from 547 feet up at the Vancouver Lookout. Afterward, take a stroll through the Dr. Sun Yat-sen Classical Chinese Gardens, an elaborate garden built in 1986 using classic 14th-century methods.

Miami + Key West, Florida

Per Salomonsson, Sloppy Joe's Bar via Flickr CC BY-SA 2.0
Per Salomonsson, Sloppy Joe’s Bar via Flickr CC BY-SA 2.0

Miami is a perennially popular place to visit for many reasons. From strutting your stuff on Ocean Drive, admiring Art Deco architecture and tanning on South Beach to noshing on Miami’s must-try eats, like Cuban and creole cuisine, and dancing the night away in Miami’s top nightclubs, there is something for everyone in this Floridian hot spot. Offset the hectic Miami pace with an escape to the Conch Republic. Key West has a casual, quirky vibe that has quietly attracted visitors from near and far for decades. Whether you are biking through the Old Town neighborhood, populated with restored Victorian homes and cottages, taking an art walk on Upper Duval Street, eating seafood and key lime pie on weathered picnic tables or sipping piña coladas at the iconic Sloppy Joe’s Bar after a day at the beach, Key West is an ideal respite that seems a world away — even though it’s just 165 miles from Miami.

Main image: iStockPhoto/wundervisuals

Twice as nice: 2-for-1 vacation destinations was last modified: June 26th, 2019 by Lauren Mack
Author: Lauren Mack (163 posts)

Lauren Mack has traveled to 40 countries on five continents, including Cuba, New Zealand, Peru and Tanzania. For many years, she called China, and then Taiwan, home. Countries at the beginning of the alphabet, particularly Antarctica, Argentina and Australia are on her travel bucket list. Lauren is a multimedia travel and food journalist and explorer based in New York City.