IRELAND: Kenmare >> KillarneyDays Needed: 7
This lush green island has jaw-dropping scenery, a mystical history, and cozy pubs where you can listen to traditional music and enjoy a pint of Guinness. Concentrate on the southwest coast, Ireland's renowned Ring of Kerry.
Starting Point: Kenmare aka "The Jewel on the Ring of Kerry." Tour buses that frequent this route start in Killarney, so do the opposite for a traffic-free ride. Play a round of golf at the Kerry Golf & Country Club, go horseback riding, charter a boat to tour the coastline, or take a walk and enjoy the mesmerizing view. For lunch or dinner, head to La Cascade, the much-talked-about restaurant at Sheen Falls Lodge (from around $366).
Second Stop: Travel to the Iveragh peninsula, and make pit stops in Sneem, a small village of colorful houses, and Staigue Fort, a ring fort dating back to about 500 BC, to get a feel for the area and the people. End up at Waterville, "The Little Whirlpool," where you can fish, shop for local crafts, and tour various archaeological sites.
Where to Eat/Stay: Butler Arms Hotel (from around $89) is one of Ireland's best known family run hotels, and the only luxury stay in Waterville. At Fisherman's Restaurant (located in the hotel) all of the seafood is caught daily by, yes, local fishermen.
Third Stop: Halfway around the Ring of Kerry is Cahersiveen. Take a tour through the old Royal Irish Constabulary Barracks, built around 1871 (but recently restored). Leave enough time to take a boat trip to the Skellig Islands, a mystery rock formation eight miles off the West Kerry Coast that was once home to Celtic monks.
Where to Eat: Frank's Corner is a traditional Irish pub and a winner of the James Joyce award for its warmth and authentic Irish atmosphere. Each weekend it hosts live bands ranging from traditional Irish to modern pop.
Where to Stay: Iveragh Heights boasts large guest rooms with an ocean view. And it's just a four-minute walk from the center of town.
Final Stop: Killarney is tourist heavy, but incredibly scenic. Gaze upon Macgillycuddy's Reeks, Ireland's highest mountains; look out for Japanese Sika Deer and Red Deer in Killarney National Park; or surf and bask on the white beaches.
Where to Stay: Try Killarney Park Hotel (from around $505), a luxury, five-star hotel with a Victorian country house feel.
CALIFORNIA: Los Angeles >> NapaDays Needed: 10
There's something for everyone when you ride the Pacific Coast Highway. Our advice: take a leisurely mini road trip through Napa Valley -- a 30-mile stretch with nearly 400 wineries.
Starting Point: Los Angeles. Have drinks by The Standard's pool, dine at world-famous hot dog stand Pink's, shop at Fred Segal, pay a visit to the J. Paul Getty Museum.
Where to Stay: Get your beach on at celeb fave Shutters Hotel on the Beach (from $484).
First Stop: Big Sur lets you get up close and personal with Mother Nature. Catch a glimpse of California Gray Whales from the highway turnouts in late winter and spring; take a hike through Limekiln State Park, where redwoods and waterfalls abound; or rent a kayak for two.
Where to Eat/Stay: Deetjen's Big Sur Inn (from $110). The menu is top-notch with delicious selections like sweet potato soup and seafood-and-saffron risotto. Relax in romantic, cabin-like rooms nestled among the redwoods of Castro Canyon.
Second Stop: San Francisco. Visit great restaurants, funky neighborhoods, and Alcatraz -- not to mention the iconic Golden Gate Bridge.
Where to Stay: The Fairmont San Francisco (from $300), a historic hotel in posh Nob Hill.
Final Stop: Napa Valley. Drive north along Route 29, stopping at wine-making centers like Rutherford, home to Rubicon Estate, owned by Francis Ford Coppola. Enjoy picnics, hot air balloon rides, and browsing the boutiques of St. Helena.
Where to Eat: The French Laundry. Try the nine-course, splurge-worthy tasting menu ($210 per person) at this famed Thomas Keller eatery in Yountville.
Where to Stay: a most exclusive resort, Auberge du Soleil (from $500). Be sure not to miss the spa's amazing wine-based treatments including a warm grapeseed oil massage.
MEXICO: Cancún >> TulúmDays Needed: 7
With its turquoise beaches and sizzling nightlife, Cancún is known for being a spring break destination, but when paired with the Riviera Maya lesser-known spots -- quaint fishing villages, awe-inspiring Maya ruins, and ecoparks -- this route is a true tropical paradise.
Starting point: Cancún. Snorkel, scuba dive, or simply unwind with a few cold cervezas on one of the many white-sand beaches.
Where to Stay: The super luxe The Ritz-Carlton, Cancún with its Mayan-inspired spa.
Where to Eat: La Habichuela. Considered a "legend" in Cancún, the restaurant was once a private home and serves traditional cuisine (such as tampiqueña beef or chicken in mole). Be sure to book a table in the romantic garden.
Second Stop: Take a 45 minute car ferry from Punta Sam (a point north of Cancún) to sleepy Isla Mujeres. It may as well be a world away: quiet pink sandy beaches, clear waters, and a culture all its own. The islet, once a popular daytrip for tourists, has become a sexy secluded destination in its own right, with a handful of new boutique hotels and gourmet restaurants.
Where to Stay: The eight tranquil rooms at Casa de los Sueños -- or house of dreams, need we say more? -- each have ocean-view terraces and custom-designed furnishings that blend local Mayan décor with a Zen aesthetic (from $300).
Final Stop: Once you head back to the mainland, drive south on Highway 307 to local attractions including Playa del Carmen, a Caribbean-flavored village with charming boutiques and open-air cafés; Xcaret, an eco-theme park (snorkel among flamingoes, swim with dolphins); and Tulúm, ancient Maya ruins in a breathtaking cliff setting.
Where to Stay: Maroma Resort and Spa (from $480). If you can swing it, book one of the Sian Nah Suites, which come with ocean views, a spa area, a private plunge pool, and magazines!
-- Jill Fergus
See More: Europe + Africa , USA + Canada , Mexico, Baja + C. America