The Real Deal: Round-trip airfare, five nights' accommodations, local transportation, some meals, and sightseeing tours, from $1,529 per person—plus taxes of about $86.
When: Oct. 31, Nov. 21, 2008; add $10 for Nov. 7; $220 for Sept. 12, 26, Oct. 3, 17; $250 for Sept. 5, 19.
Gateways: New York City; add approximately $75 for Boston; $135 for Chicago; $193 for Houston; $208 for Miami; $279 for Seattle; $358 for L.A.; additional gateways are available.
The fine print: Five breakfasts, one dinner, airline fuel surcharges, all transfers, transportation in an air-conditioned motor coach, entrance fees as per the itinerary, and the services of an English-speaking tour manager and local guides are included. The package also covers tours of the Prado Museum in Madrid, the baroque Plaza Mayor in Salamanca, the Jerónimos Monastery in Lisbon, and the Our Lady of the Rosary Basilica in Fátima. Air taxes and fees are an additional $86, and there's a $5 charge for restaurant gratuities. Based on double occupancy; single supplement is $314. Read these guidelines before you book any Real Deal.
Book by: No deadline; based on availability.
Contact: Gate 1 Travel, 800/682-3333, gate1travel.com.
Why it's a deal: According to a recent search on Kayak, the lowest multi-city fares (NYC-Madrid, Lisbon-NYC) for departures on October 31 start at $737, including taxes (Air France or Continental). For an additional $883, including all taxes, Gate 1 covers airfare as well as the five-night hotel stay, breakfast daily, one dinner, all transportation and transfers, some sightseeing tours, admission fees, and the services of English-speaking tour guides.
Trip details: The package includes multi-city airfare, arriving in Madrid and departing from Lisbon, on a major carrier such as Air France, American, Delta, Iberia, or Northwest, and five nights' accommodations.
You'll begin in Madrid, with two nights at the 158-room Hesperia Emperatriz in the commercial district near the shops and restaurants of Paseo de la Castellana. The hotel makes a great jumping-off point for exploring all reaches of the city—it's only 100 yards from the Gregorio Maroñón metro station, less than a mile from the Nuevos Ministerios metro station, and 1.9 miles from the Atocha Railway station.
The package covers a morning sightseeing tour of Madrid, which takes you along the Gran Via through the Opera District and Plaza de Colón to the Royal Palace. You'll also pass by Puerta Del Sol Plaza and Plaza de España, which has a monument dedicated to "Don Quixote" author Miguel de Cervantes, before arriving at the Prado Museum (admission is included). For an extra $58 per person, you can tack on a guided tour of El Escorial, a nearby 16th-century monastery/palace/mausoleum erected by King Philip II.
Leaving Madrid, you'll travel west, stopping in both Segovia and Ávila, a walled city where St. Teresa's order of the Carmelites was founded, before reaching Salamanca. This portion of the package includes an orientation tour and a visit to the baroque Plaza Mayor. You'll spend the night at the 144-room Hotel Monterrey, a short walk from the Plaza Mayor and the historic city center.
Then continue along the Serra da Estrela mountain range to Portugal, with a stop along the way at the Our Lady of the Rosary Basilica in Fátima (a city where apparitions of the Virgin Mary are said to be common). You'll wind up in Lisbon, where your base for two nights is the 350-room Hotel Mundial in the Baixa Pombalina district, not far from the Rossio train station. A tour of Lisbon hits sights like the Tower of Belém, the tomb of Vasco da Gama at Jerónimos Monastery, the Avenida da Liberdade, the Monument to the Discoveries, and Alfama, a cobblestoned former fishermen's quarter.
You'll also have some free time to explore the city on your own. If you prefer the guided-tour approach, you can always add a half-day excursion to nearby Sintra for $52 per person.
Not ready to leave? You can extend your stay in Lisbon for an additional $117 per night at Hotel Mundial, or book pre-tour nights in Madrid for $148 per night at the Hesperia Emperatriz.