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North America ยท 30 guides

North America Destinations

Road trip hubs, beach towns, and urban escapes across the US, Canada, and Mexico. Each guide includes neighborhood breakdowns and seasonal cost swings.

North America Updated Apr 2026

Austin, United States

A practical guide to eating, swimming, and hearing live music in a city that does all three better than almost anywhere in the country.

3-day itinerary 6 areas ~$175/day
North America Updated Apr 2026

Boston, United States

A neighborhood-by-neighborhood plan for first-timers who want to walk the history, eat the lobster rolls, and cross the river to Harvard without overspending.

4-day itinerary 6 areas ~$200/day
North America Updated Apr 2026

Cabo San Lucas, Mexico

A 4-day plan covering the swimmable beaches, the ones that will knock you down, the real cost breakdown, and why the quieter town up the road might be the smarter pick.

4-day itinerary 5 areas ~$200/day
North America Updated Apr 2026

Cancun, Mexico

A first-timer's guide to the Caribbean beaches, underground swimming holes, ancient pyramids, and $3 taco dinners that most all-inclusive guests never find.

5-day itinerary 4 areas ~$120/day
North America Updated Apr 2026

Charleston, United States

A practical guide to eating, walking, and learning in a city where the food is world-class, the history is complicated, and the humidity is non-negotiable.

3-day itinerary 5 areas ~$220/day
North America Updated Apr 2026

Chicago, United States

America's most underrated food city has a world-class transit system, a skyline designed by legends, and neighborhoods that reward the curious.

4-day itinerary 6 areas ~$195/day
North America Updated Apr 2026

Costa Rica, Costa Rica

A region-by-region guide to planning your first trip without overpacking your itinerary or overpaying for insurance.

7-day itinerary 6 areas ~$130/day
North America Updated May 2026

Cozumel, Mexico

The world's second-largest barrier reef is right here, the best tacos cost $3 at a counter two blocks from the plaza, and the Tulum day trip eats your entire port day for a 45-minute ruin visit.

3-day itinerary 3 areas ~$125/day
North America Updated Apr 2026

Denver, United States

How to drink craft beer at 5,280 feet, catch a show at the most dramatic concert venue in America, and avoid the headache that gets everyone on day one.

3-day itinerary 5 areas ~$195/day
North America Updated May 2026

Grand Cayman, Cayman Islands

No dock, no pier, just a tender boat and a 10-minute ride to an island where the beach is free, the water is see-through, and the bus costs $2.50.

3-day itinerary 3 areas ~$243/day
North America Updated Apr 2026

Honolulu, United States

A practical guide to eating, hiking, and swimming on an island where most tourists never leave the same two-mile strip of sand.

5-day itinerary 6 areas ~$250/day
North America Updated Apr 2026

Las Vegas, United States

A practical guide to eating, watching, and exploring a city that has quietly become one of the best food and entertainment destinations in the country.

4-day itinerary 5 areas ~$220/day
North America Updated Apr 2026

Los Angeles, United States

A practical guide to eating Korean BBQ at midnight, finding the beach that locals actually use, and spending less than you think in a city that looks expensive from the outside.

5-day itinerary 7 areas ~$220/day
North America Updated Apr 2026

Maui, United States

A 5-day plan that covers the beaches, the volcano, and the drive everyone talks about, plus how to pick between Kihei, Ka'anapali, and Wailea without overpaying.

5-day itinerary 6 areas ~$300/day
North America Updated Apr 2026

Mexico City, Mexico

How to eat, walk, and metro your way through one of the world's biggest cities without getting overwhelmed, overspending, or missing the colonias that make CDMX what it is.

5-day itinerary 6 areas ~$80/day
North America Updated Apr 2026

Miami, United States

A practical guide to the food, art, and neighborhoods that make Miami one of the most culturally layered cities in the country.

4-day itinerary 6 areas ~$230/day
North America Updated Apr 2026

Nashville, United States

The Broadway strip is 4 blocks. The rest of Nashville is where the city actually lives, eats, and plays.

3-day itinerary 6 areas ~$170/day
North America Updated May 2026

Nassau, Bahamas

Twelve cruise lines dock here, 5.6 million passengers walk through per year, and most of them see the same three blocks of Bay Street before reboarding.

3-day itinerary 4 areas ~$140/day
North America Updated Apr 2026

New Orleans, United States

A street-by-street plan for eating, drinking, and hearing live music in the city that invented all three as a lifestyle.

4-day itinerary 6 areas ~$165/day
North America Updated Apr 2026

New York City, United States

A local-tested route through Manhattan and Brooklyn that keeps you off the tourist treadmill and under budget.

5-day itinerary 6 areas ~$250/day
North America Updated Apr 2026

Oaxaca, Mexico

How to eat your way through Mexico's culinary capital for under $50 a day, plus the mezcal tasting etiquette that separates curious visitors from shot-taking tourists.

4-day itinerary 4 areas ~$55/day
North America Updated Apr 2026

Orlando, United States

A 5-day plan that covers the parks smartly, skips the tourist traps, and shows you the springs, neighborhoods, and food scene that make Orlando more than a theme park town.

5-day itinerary 5 areas ~$250/day
North America Updated Apr 2026

Portland, United States

A neighborhood-by-neighborhood plan for first-timers who want to eat well, browse vinyl, and understand why Portlanders refuse to use umbrellas.

3-day itinerary 6 areas ~$170/day
North America Updated Apr 2026

San Diego, United States

A neighborhood-by-neighborhood guide to the city where the weather is always good, the tacos are always cheap, and the beer is always local.

3-day itinerary 7 areas ~$200/day
North America Updated Apr 2026

San Francisco, United States

A neighborhood-level guide to a 7x7-mile city where the fog has a name, the burritos weigh two pounds, and every hill earns its view.

4-day itinerary 6 areas ~$280/day
North America Updated May 2026

San Juan, Puerto Rico

The cheapest international-feeling trip from the US mainland, where your phone works, the dollar is the currency, and the flight from New York is 3.5 hours.

3-day itinerary 5 areas ~$175/day
North America Updated Apr 2026

Seattle, United States

How to do Seattle on foot and light rail, eat the best seafood in the Pacific Northwest, and understand why nobody here uses an umbrella.

3-day itinerary 6 areas ~$220/day
North America Updated May 2026

St. Thomas, US Virgin Islands

Two cruise piers, the best snorkeling beach in the USVI, a 45-minute ferry to a national park island, and $1,600 in duty-free shopping allowance, all without a passport.

3-day itinerary 3 areas ~$258/day
North America Updated May 2026

Vancouver, Canada

How to make the most of your pre-cruise days on the SkyTrain and Seawall, eat $12 ramen in Richmond, and skip the $50 suspension bridge for a free one.

3-day itinerary 5 areas ~$120/day
North America Updated Apr 2026

Washington, United States

How to fill four days with museums that charge nothing, walk the entire National Mall without your feet quitting, and eat well in a city that thinks it is too important for good food (it is wrong).

4-day itinerary 6 areas ~$185/day

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