Niagara-on-the-Lake

Not to be confused with Niagara Falls, nearby Niagara-on-the-Lake, Ontario, is a charming storybook bed-and-breakfast village on the Canadian side which each summer hosts a world-famous theatrical festival in homage to the playwright George Bernard Shaw.

Stay at - The Oban Inn

Go shopping - up and down the streets of the village

Eat at - The Dining Room of The Oban Inn
Prince of Wales Hotel for afternoon tea
The Buttery
There are a number of local wineries with terrific restaurants - try Hillebrand Estates

Take side trips to - Niagara Falls, Toronto

Be sure to visit - The Shaw Festival
local wineries
Niagara Falls, if you're so inclined and have never been

Best time of year to go - When the Shaw Festival is on, April through October. I favor August.

Best things to buy - Shaw miscellany, books, British goods, tea, preserves, housewares, culinary, local souvenirs, wine

Best indulgence - Great seats for an evening performance of a favorite Shaw play, after an idyllic meal

Fly into - Toronto (YYZ) or Buffalo (BNIA)

Transportation - Rent a car. If you're coming from the US, remember you'll be crossing a border into Canada, and will need a current passport. There are taxicabs and horse-and-carriage operators in town. There is also a shuttle from Toronto airport to Niagara-on-the-Lake, if you'd prefer not to drive.

Oak Park

One of the loveliest and most liveable suburbs of the metropolitan Chicago area and an architect's dream, Oak Park is a few miles west on the Eisenhower, home of McDonalds' founder Ray Kroc, writer Ernest Hemingway and Prairie architect Frank Lloyd Wright, with the largest collection of Frank Lloyd Wright designed buildings in the world.



Stay at - The Carleton of Oak Park

Go shopping - Oak Park Avenue and Lake Street

Eat at - Philander's, The Carleton
Poor Phil's, The Carleton
Hemmingway's, The Write Inn

Take side trips to - downtown Chicago

Be sure to visit - the many Frank Lloyd Wright buildings in Oak Park
Hemingway Museum

Best time of year to go - April through October

Best things to buy - Local arts and crafts, antiques, furnishings, clothing

Best indulgence - An evening at Philander's with live music

Fly into - Chicago O'Hare (ORD) or Midway (MDW)

Transportation - Take suburban cabs from the airports, which have a flat rate to Oak Park. While in Oak Park, there are good local cabs available, and much of the downtown is very walkable. Elevated trains ("The L") runs right from downtown Oak Park to downtown Chicago and The Loop. Unless you've driven your own car to the Chicago area, you shouldn't need one, but rental cars are readily available at both airports and in the suburbs.

Kauai

Bali Hai, South Pacific, the quintessential pot of gold at the end of the island rainbow, the oldest, wettest, greenest, and arguably most beautiful of all the Hawaiian islands.


Stay at - Kauai Marriott Resort and Beach Club at Nawiliwili

Go shopping - north shore, south shore and Lihue
Be sure to shop at Kilohana Plantation for some great arts and crafts

Eat at - Gaylord's at Kilohana
Duane's Ono Char Burger
Duke's Canoe Club

Take side trips to - Oahu
Maui

Be sure to visit - Kilauea Lighthouse
Ke'e Beach
Poipu

Kauai Museum in Lihue
Hanalei
Princeville

Best time of year to go - February and March

Best things to buy - Ni'ihau shells and shell leis, art, Hawaiiana

Best indulgence - A helicopter ride over Mount Waialeale and along the Napali Coast. I recommend Jack Harter.

Fly into - Lihue (LIH)

Transportation - Rent a car at Lihue Airport. Kauai has one road which runs from the north shore to the south, with very few traffic lights in between, lots of covered bridges, and plenty of scenery. A car is the only way you'll get around, as public transportation is essentially non-existent.

Rome

The Eternal City, ancient and powerful, moving, filled with life, art, wonder, and the seat of Christendom.

Stay at - The Excelsior

Go shopping - Via dei Condotti
Via del Corso
Piazza Navona

Eat at -La Pergola
Trattoria Monti
L'Eau Vive
Imàgo at the Hotel Hassler

Take side trips to - Assisi
Florence
Hadrian's Villa and Villa d'Este
Castelgandolfo

Be sure to visit - St. Peter's
The Sistine Chapel and Vatican Museums
The Colosseum
The Catacombs
The Spanish Steps
The Seven Pilgrim Churches of Rome

Best time of year to go - Holy Week through September

Best things to buy - designer clothing, leather, art and antiques, wedding dresses, stationery, religious articles

Best indulgence - sitting on the rooftop of the Hotel Hassler at the end of the day gazing over the Eternal City

Fly into - Rome Leonardo da Vinci (Fiumicino) Airport (FCO)

Transportation - Get a private car and driver if you can. The Archeobus is a reasonably priced alternative for visiting Roman archeological sites. Watch out for gypsies if you're seeing the city on foot.

Sitka

Summer home of the humpback whale, once the capital of Russian America, home to the Tlingit, fur traders, artists and writers all spread out over Baranof Island and the Alexander Archipelago nestled under the shadow of Mount Edgecumbe, Sitka is a cultural and aesthetic goldmine for those who ply the waters of the Inside Passage.

Stay at - I recommend you visit Sitka as part of an Inside Passage Cruise, aboard Princess, Holland America or Regent Seven Seas

Go shopping - in town

Eat at -Ludvig's Bistro
The Channel Club

Take side trips to - Alaska Raptor Center
Fortress of the Bear
Sitka National Historic Park and Southeast Alaska Indian Cultural Center

Be sure to visit - St. Michael's Cathedral
Sitka Pioneer's Home
New Archangel Dancers

Best time of year to go - mid-to-late summer, up through Labor Day

Best things to buy - Fine Alaska clothing, souvenirs, artwork, jewelry, Native Alaskan art and culture, Russian-American art/icons and religious articles, gold, fish, books

Best indulgence - tendering in from ship to shore, with Mount Edgecumbe in the background in exquisite two-dimensional light and shadow as orcas play in Sitka Sound

Fly into - Sitka (SIT) if you're going directly there, otherwise fly to Vancouver (YVR) or Seattle (SEA) and take an Inside Passage Cruise

Transportation - If you are arriving by cruise ship, much of Sitka is walkable or transportation can be arranged by shore excursion. The Sitka Tribe of Alaska operates 'Sitka Community Ride,' an inexpensive community bus.

Buckhead

Stay at - The Ritz-Carlton Buckhead

Go shopping - across the street at Lenox Square Mall and Phipps Plaza

Eat at - The Dining Room and The Lobby Lounge, The Ritz-Carlton
Pano's & Paul's
Twist

Take side trips to - downtown Atlanta
CNN Headquarters
Underground Atlanta
The World of Coca-Cola

Be sure to visit - Lenox Square Mall
Phipps Plaza
take a drive through the gorgeous neighborhoods in Buckhead if you're able

Best time of year to go - spring and fall, but Atlanta is fairly temperate year-round. Buckhead is gorgeous in bloom.

Best things to buy - fashion, luxury items

Best indulgence - Hanging out in the Lobby Bar at the Ritz-Carlton after a full day of shopping (they serve a very credible afternoon tea if that suits your schedule). If you got your hair done at Vidal Sassoon while at Lenox Square, even better.

Fly into - Atlanta (ATL)

Transportation - You can entirely headquarter at the Ritz-Carlton in Buckhead, go shopping across the street at Lenox Square and Phipps Plaza, and do completely without a car. But if you feel you want one in Atlanta, rent one. MARTA runs throughout the metropolitan area, and taxicabs are good. The hotel has complimentary local transportation.

Key West

Stay at - Westin Key West Resort & Marina, and Sunset Key Cottages

Go shopping - in town, on Duval Street

Eat at - El Meson de Pepe (Cuban)
Latitudes on Sunset Key (take launch from the Westin)
Cafe Marquesa
Blue Heaven
Sloppy Joe's Bar and Hog's Breath Saloon

Take side trips to - Sunset Key
the rest of the Keys

Be sure to visit - Audubon House
Ernest Hemingway House
Key West Aquarium
Key West Butterfly and Nature Conservatory
Don't miss the Sunset Celebration every evening at sunset in front of the Westin

Best time of year to go - November through March

Best things to buy - Cuban and tropical souvenirs, Atocha coins, jewelry, tropical clothing, music, stationery, housewares, Audubon prints, art

Best indulgence - going to Sunset Key by motorlaunch from the Westin and having a leisurely lunch

Fly into - Key West (EYW), or Miami (MIA) and drive a car. High speed catamarans operate daily from a number of ports on the west coast of Florida, including Fort Myers/Fort Myers Beach/Naples/Marco Island.

Transportation - Much of Key West is very walkable. Unless you're planning to explore more of the rest of the Keys, you don't need a car, and can use the conch train, trolley, and taxis to get around.