The Bahamas were favored by President Franklin Delano Roosevelt for fishing expeditions. Besides the crystal-clear water and sandy beaches, the beloved islands are known for excellent deep-sea and bonefishing, and claim 50-plus record catches. With near-constant events and competitions, experienced guides, fishing lodges, and charter boats, there's no shortage of places to cast a line. Hotels in the Bahamas average out to around $127 per night, depending on the season. 

Best freebie: The Glass Window Bridge, which connects Eleuthera's Gregory Town and Lower Bogue, is the narrowest point on the island — and perhaps the most photogenic. The strip of rock, just 30 feet wide, draws a thin line between the deep blue, roaring waves of the Atlantic Ocean and the calm, turquoise-green waters of the Exuma Sound.

President Theodore "Teddy" Roosevelt visited this scenic Rocky Mountain town during a three-week bear-hunting trip in 1905. Book the Roosevelt Suite (rates at Hotel Colorado average out to about $170 per night, depending on the season) — the room where the President stayed — at the Hotel Colorado, which is now a National Historic Landmark. The confluence of the Colorado and the Roaring Fork rivers are also known for white-water rafting, fly-fishing, and cave tours. 

Best freebie: The three-mile Hanging Lake Trail is not for the faint of heart.  Due to the sometimes-dicey drops, the forest service has carved steps into the rock and installed hand railings, but it is still steep. But the view alone is worth it: The majestic teal-colored lake, surrounded by waterfalls, looks surreal amidst the Colorado mountains.

When you see those classic photos of John F. and Jackie Kennedy sailing with wind-blown hair, you're looking at the waters off of Cape Cod. The quaint village of Hyannis Port is the Kennedy family's most beloved retreat. The town features miles of sandy shores, delectable fried seafood, and, of course, sailing excursions around the peninsula. Hotels in Hyannis Port average out at about $124 per night, depending on the season. 

Best freebie: Catch a Cape Cod Baseball League game. The collegiate summer league comprises ten teams, which star top-level talent before they go pro. Plus, the games offer a convivial picnic-like atmosphere. Grab a hot dog, roll out a beach blanket, and enjoy the summer night.

Each winter since 2008, President Barack Obama and his family jet to the sleepy town of Kailua, 12 miles northeast of Honolulu (where Obama was born). To replicate the retreat, rent the Winter White House, the five-bedroom beachfront home where they spent Christmases (rates from $3,500 per night, depending on the season). Spend your days doing exactly what the First Family did while vacationing here: Exercise, snorkel, gold, and, of course, indulge in shaved ice at Island Snow. 

Best freebie: One of the best things about Oahu is the abundance of free scenic hikes. Lanikai Pillbox is an easy, family-friendly hike (think flat pathways and gradual inclines), which offers views of the Kailua coastline all the way down to Lanikai and the Mokulua Islands (the Mokes) off shore. All in all, the Lanikai Pillbox takes about one hour round-trip.

The historic Little White House on Key West hosted President Harry Truman for 175 days during his tenure in office back in 1946. Today, you can tour the house where Truman and his go-to guys enacted bills, prepared budgets, and even composed the State of the Union address. Other presidents, including JFK and Jimmy Carter, have also roamed the halls of Little White House. Hotels in Key West average out to about $300 per night, depending on the season. 

Best freebie: West Martello Tower & Botanical Garden is set within the ruins of a never-completed Civil War-era fort, which were almost torn down in 1949. Fortunately, thanks to US Congressman Joe Allen and the Key West Garden Club, the site is now flush with vibrant, beautifully-maintained trees and flowers overlooking the Atlantic Ocean. However, although the entrance is free, donations are encouraged.

This long-time celebrity sanctuary hosted Bill, Hillary, and Chelsea back in the '90s when they were America's First Family. Biking, kayaking, and fishing are all popular pastimes here, and miles of sandy beach make for great sunbathing. If you need a break from the sun, just buy an ice cream cone and stroll past historic homes and charming seaside shops. It’s easy to see why the Clintons came back again and again. Hotels on Martha's Vineyard average out to about $300 per night, depending on the season. 

Best freebie: Bike to the Aquinnah Cliffs (formerly known as Gay Head), which were carved by glaciers millions of years ago. See the cliffs up close from Moshup Beach, or follow the trail to the top of the cliffs to catch a glimpse of Gay Head Light and nearby islands.

After retaining his seat in Congress during the 1972 general election, Gerald R. Ford retreated to Montego Bay, Jamaica, where the soon-to-be president and his wife, Betty, were photographed lounging on the beach, deep-sea fishing, and napping on their chartered boat. Today, you can enjoy the same spectacular surroundings and laid-back vibe at one of many luxe resorts nearby. Hotels in Montego Bay average out to about $235 per night, depending on the season. 

Best freebie: Explore the remains of Fort Montego, which was built in the 1700s to defend Montego Bay from pirates, the Spanish, and the French. Afterwards, follow the “Hip Strip,” which transforms into a street party at night, complete with loud Jamaican music, food vendors, and drinks.

Santa Barbara's allure was not lost on Ronald Reagan. He bought what came to be known as the "Western White House" — the 688-acre Rancho del Cielo (also dubbed "Reagan Ranch"), overlooking the magnificent Santa Ynez Valley and the Pacific Ocean. Though the general public can't tour the ranch, Santa Barbara's idyllic wineries, bucolic landscapes, palm-fringed beaches, and gourmet fare will inspire you just the same. Hotels in Santa Barbara average out to about $248 per night, depending on the season. 

Best freebie: Spend an afternoon at Santa Barbara's historic and highly photogenic courthouse. Head to the top of the 85-foot clock tower for a breathtaking view of the city. After, be sure to stop in the Mural Room to see a show-stopping depiction of the city’s history across 6,000 square feet of wall space. End your visit by strolling through the courthouse's colorful gardens.

Franklin D. Roosevelt first retreated to this rural town (an hour-and-a-half south of Atlanta) in 1924 hoping to find a cure for polio, which he was diagnosed with three years prior at age 39. Eight years later, just before his inauguration, he built a modest six-room cottage that's been kept intact since his death there in 1945. Rich with Southern charm, Warm Springs is home to quaint antique stores and B&Bs. Hotels in Warm Springs average out to about $95 per night, depending on the season.

Best freebie: Tour the Roosevelt Warm Springs Institute for Rehabilitation, a 940-acre campus with historic buildings located at the eastern edge of Pine Mountain (both self-guided and guided tours are available). Before you go, spend some time exploring the F.D. Roosevelt State Park, which is home to more than 40 miles of verdant hiking trails.