Trip Itineraries for 2024

12 November 2023 - 25 mins read time
Tags: Travel

These are the trips I would like to do in 2024, and so I generated trip itineraries with GPT-4.

Overview

Itinerary for Hawaii Trip (February 2024)

Given your preferences and the fact that you’ll be working on weekdays during your 10-day February trip to Hawaii, I’d recommend choosing Honolulu on the island of Oahu as your home base for its central location, access to amenities, and blend of outdoor, cultural, and entertainment options.

Day 1 (Thursday): Arrival in Honolulu

• Fly into Daniel K. Inouye International Airport (HNL) in Honolulu Thursday evening.
• Check into your Airbnb in the Waikiki area, which offers a balance of accessibility, restaurants, and beaches.
• Have a quick dinner at a local restaurant such as Marukame Udon, known for its affordable and fast service.

Day 2 (Friday): Work + Evening Walk

• Breakfast at Tucker & Bevvy for some healthy options.
• Work during the day.
• In the evening, take a leisurely walk through Waikiki and enjoy beachside views. Alternatively, visit Ala Moana Beach Park.

Day 3 (Monday) to Day 6 (Thursday): Workdays with Evening Activities

• Breakfast: grab something quick from Island Vintage Coffee or a local cafe near your Airbnb.
• Workdays with a mix of affordable dinner options such as Ono Seafood for poke, The Pig & The Lady for Vietnamese fusion, or Rainbow Drive-In for local plate lunches in the evening.
• Explore local activities post-work: visit the Honolulu Museum of Art, take a historical walk around Iolani Palace, or catch a sunset from Magic Island.
• Look for evening concerts or events; check local listings closer to your trip’s date.

Day 7 (Friday): North Shore Adventure

• Breakfast at Kono’s Northshore for a hearty start to your day.
• Drive to the North Shore to appreciate Hawaii’s famous surfing beaches, like Waimea Bay and Sunset Beach.
• Visit the historic town of Haleiwa for shopping, art galleries, and lunch.
• Stop by Ted’s Bakery for some chocolate haupia cream pie, a local favorite before heading back to Waikiki.

Day 8 (Saturday): Koko Head and Hanauma Bay

• Early morning hike up Koko Head Crater for breathtaking sunrise views.
• Breakfast/Brunch after your hike: nearby options like Kona Brewing Company in Hawaii Kai.
• Spend the afternoon snorkeling and relaxing at Hanauma Bay Nature Preserve (remember to reserve your spot in advance due to conservation efforts).
• Dinner at a casual spot like Ono Hawaiian Foods back in Honolulu.

Day 9 (Sunday): Windward Coast + Cultural Experience

• Start with Leonard’s Bakery for their famous malasadas (Portuguese-style donuts).
• Drive to the Windward side and visit Kailua Beach or Lanikai Beach.
• Make your way to the Polynesian Cultural Center for an immersive cultural experience – check ahead for festival dates or special events.
• Enjoy an authentic Hawaiian dinner at the Polynesian Cultural Center, or head back to town and try Helena’s Hawaiian Food.

Day 10 (Monday): Submarine Tour and Farewell Dinner

• Have a quick breakfast at Café Kaila.
• Experience a unique Atlantis Adventures submarine tour off the coast of Waikiki.
• Work remotely in the afternoon if needed.
• For your farewell dinner, splurge a little at a nice restaurant such as Roy’s Waikiki or Hoku’s for high-end pacific cuisine.

Day 11 (Tuesday): Departure

• Spend your morning at leisure or enjoy a final swim at Waikiki Beach.
• A quick bite for breakfast, possibly at Bogart’s Café.
• Depending on your flight time, explore any last-minute shops or sights.
• Depart from Daniel K. Inouye International Airport back to Seattle Tuesday evening.

Remember that availability for accommodations and activities may vary, and making reservations in advance is crucial, especially during high season. Check festival schedules for any potential concerts and cultural events coinciding with your stay, and be flexible with your plans as weather conditions can sometimes adjust your itinerary. Enjoy the beautiful blend of nature, culture, and relaxation that Hawaii has to offer!

Trip Plan: Long Weekend in New York City, Late February 2024

Day 1: Arrival and Settling In

• Accommodation: For a central area to stay in that is convenient for both culture and dining, consider booking an AirBnB in the Lower Manhattan area, perhaps around Tribeca or the Lower East Side. This puts you in a good position to explore downtown attractions, access the subway for trips further afield, and find trendy breakfast spots.

• Breakfast Option: Jack’s Wife Freda (Lower Manhattan) - A beloved spot for American-Mediterranean inspired dishes.

• Exploring the Area: Spend your first afternoon walking around your neighborhood, perhaps heading to the High Line for a blend of nature, urban renewal, and public art.

• Dinner: Buddha Bodai Kosher Vegan Restaurant (Chinatown) – Affordable and unique, this spot provides a vegan twist on Chinese cuisine.

Day 2: Culture and Concert Day

• Breakfast Option: The Grey Dog (Nolita) - Casual, rustic-American café that is known for its solid breakfast menu. Fuel up here before a day of museum-going.

• Cultural Visits: Head to the Museum Mile on Fifth Avenue – visit The Metropolitan Museum of Art and the Guggenheim Museum for a dose of culture.

• Lunch: Try street food from the many food carts for an affordable bite; options range from hot dogs to halal to artisanal foods.

• Concert or Festival: Check local event calendars for late February concerts – venues like Lincoln Center, The Beacon Theatre, or Brooklyn Steel may have interesting acts. Alternatively, look for smaller music venues in the East Village or Williamsburg for more intimate concerts.

• Dinner: Patsy’s Pizzeria - Enjoy an iconic New York pizza at an affordable price.

Day 3: Sporty & Nature Day

• Breakfast at AirBnB: Shop local supplies the day prior and enjoy a homemade breakfast at your AirBnB to prep for an active day.

• Outdoor Activity: Weather permitting, hire bikes and cycle around Central Park, or, if you’re willing to travel further, head to the Hudson River Greenway.

• Lunch: Pack a picnic lunch from a local deli, enjoying the views and people-watching in Central Park.

• Visit a Sports Event: Check for any local games – from basketball at Madison Square Garden to ice hockey and even winter sports events in the area.

• Dinner: Xi’an Famous Foods (Multiple Locations) – Perfect for a quick, hearty, and budget-friendly meal.

Day 4: Local Neighborhood Exploration

• Breakfast Option: Russ & Daughters Café (Lower East Side) - Famous for their bagels and lox, indulge in a classic New York Jewish deli breakfast.

• Walking Tour: Book a walking tour of historic neighborhoods – consider the Lower East Side, Greenwich Village, or a Brooklyn neighborhood like DUMBO or Williamsburg.

• Lunch: Look for a local food market – Chelsea Market is a popular option for a diverse range of eats.

• Wrap Up: Finish your trip with a stroll through a local area you haven’t yet explored. SoHo or the West Village are great for window shopping and ambiance.

• Dinner: Taim (Multiple Locations) - Fast-casual spot renowned for its falafel and Mediterranean fare, ideal before heading back home.

Bookings and Reservations: Since you’re planning this trip and booking on November 25th, make sure to secure your AirBnB early as the good ones can go quickly. Also, book your museum tickets online to avoid queues, and keep an eye out for any special exhibitions. Check for concert tickets and sports events early as well to ensure availability.

Transportation: Consider purchasing an unlimited MetroCard for the duration of your stay to ease your travel throughout the city. It’s cost-efficient and reduces the hassle of buying single-ride tickets.

Weather: Late February can still be quite cold, possibly snowy, so make sure to pack warm clothes and good walking shoes for exploration. Layering is key to staying comfortable when ducking in and out of museums and restaurants.

Enjoy your trip!

A Trip to Chicago in Early March 2024

Accommodation: For a central area to stay in Chicago, consider booking an Airbnb in The Loop. This is the heart of downtown Chicago, with easy access to parks, museums, theaters, and public transportation. Alternatively, you could look at River North for a trendy area with many restaurants and shops, or Wicker Park for a more neighborhood feel with plenty of local charm.

Day 1 - Arrival and Exploration:

• Arrive in Chicago and check in to your Airbnb.
• Grab an affordable breakfast at “Yolk” – a popular spot with several locations that offer hearty breakfasts without breaking the bank.
• Spend the morning at Millenium Park, where you can see the iconic “Bean” (Cloud Gate sculpture) and enjoy the winter landscape.
• For lunch, try out “Portillo’s” for an authentic Chicago-style hot dog or Italian beef.
• In the afternoon, visit the Art Institute of Chicago and immerse yourself in culture.
• For dinner, check out “Lou Malnati’s Pizzeria” for some deep-dish Chicago-style pizza.

Day 2 - Nature and Museum Day:

• Start with breakfast at “The Bongo Room” for some inventive pancakes and a cozy atmosphere.
• Head over to the Field Museum or the Shedd Aquarium to indulge in natural history or marine life.
• Lunch can be enjoyed at “Manny’s Cafeteria & Delicatessen” for a classic Chicago experience with a wide variety of options.
• Spend the late afternoon walking along the Lakefront Trail if the weather permits for some fresh air and sporty activity.
• Dinner at “Girl & The Goat” for a trendier vibe, though reservations are recommended.

Day 3 - Neighborhoods and Concerts:

• For breakfast, enjoy “Wildberry Pancakes and Cafe,” famed for its signature pancakes and skillets.
• Take a walking tour of a Chicago neighborhood, like Wicker Park, to see a different side of the city with its cultural charm. Companies like Chicago Greeter offer free tours with locals.
• Lunch at “The Purple Pig” on Michigan Avenue – a place where you can enjoy a variety of Mediterranean small plates.
• If there’s a festival such as the Chicago Theatre Week in March, this would be a good day to enjoy a matinee show or performance.
• Dinner can be a more casual affair at “XOCO” by Rick Bayless, offering gourmet Mexican street food.
• End the day with a concert or live music at venues like the Chicago Symphony Center or House of Blues, depending on what aligns with your musical tastes. Check the schedule nearer the time for specific festivals or concerts happening during your visit.

Day 4 - Departure:

• Have a quick breakfast at “Do-Rite Donuts & Chicken” – don’t miss their artisanal donuts!
• Take a final stroll along the Chicago Riverwalk if time allows before heading back to pack up and check out.

Additional Tips:

• Chicago weather in March can be quite variable, so pack layers to prepare for cold, wind, and potential snow.
• Always check event schedules as they are released closer to your booking date for the latest information on cultural festivals and concerts.
• Public transportation on the “L” (Chicago’s subway system) is a reliable and affordable way to get around; consider purchasing a Ventra card for the duration of your stay.
• Use apps like OpenTable or Resy to make dinner reservations ahead of time, especially for popular spots.

Remember, booking your accommodation and making any necessary reservations should be done as soon as possible, and definitely before your stated booking date of November 25th, to ensure availability and potentially better rates. Enjoy your trip!

Trip to New Orleans: Late March 2024

Stay: For a central location in New Orleans that blends nightlife, culture, and proximity to many attractions, consider finding an Airbnb in the French Quarter or the adjacent Warehouse District. These areas are lively, full of character, and well-situated for exploring the city. The Garden District is also a charming option with its historic homes and tree-lined streets, offering a quieter base with easy access to the rest of the city.

Affordable Breakfast Options:

1. The Ruby Slipper Cafe - Known for its Southern breakfast staples and a variety of Eggs Benedict options.
2. Café du Monde - A must-visit for beignets and café au lait; bear in mind there might be a line, but it’s part of the authentic experience.
3. Surrey’s Juice Bar - Offers fresh juices and local farm-to-table fare with a focus on healthy eating.

Affordable Dinner Options:

1. Coop’s Place - Casual spot in the French Quarter with a reputation for some of the best value Cajun fare.
2. Dat Dog - Offers an array of gourmet hot dogs and sausages with unique toppings; it’s casual and great for groups.
3. The Gumbo Shop - Serves classic Creole dishes like gumbo and jambalaya at reasonable prices.

Activities for Sports and Nature Lovers:

• City Park - Explore one of the largest urban parks in the country. You can enjoy outdoor activities like jogging, biking, or paddle boating. The park is also home to the New Orleans Museum of Art and its adjacent sculpture garden.
• Kayaking on Bayou St. John - Rent kayaks and paddle through the serene waters of Bayou St. John, taking in views of the city from a different perspective.
• Audubon Park - Visit for running trails, the Audubon Zoo, and a picturesque golf course.

Cultural Attractions:

• French Quarter Walking Tours - Join a walking tour to learn more about the history and architecture of this iconic neighborhood.
• The National WWII Museum - A must-see for history buffs, this museum is an engaging and educational experience detailing the American experience in the war.
• New Orleans Museum of Art (NOMA) - Spend a few hours exploring fine arts in City Park.

Concerts and Festivals: Late March may coincide with some notable events in New Orleans:

1. Tennessee Williams/New Orleans Literary Festival (dates can vary) - A celebration of literature, culture, and the playwright Tennessee Williams, famous for “A Streetcar Named Desire,” set in New Orleans.
2. Buku Music + Art Project (dates can vary) - If it falls on the same weekend, this festival combines electronic, hip hop, and indie rock music with art installations and is a favorite among locals and visitors.
3. Wednesday at the Square - A weekly springtime concert series featuring local and regional acts, held at Lafayette Square in the Central Business District.

Be sure to check the exact dates for these events as they vary each year. Tickets or reservations for specific tours, restaurants, or events should be booked well in advance, especially if you’re visiting during a popular festival or concert series.

Please note that some events might be rescheduled, so you should keep an eye on local listings or official event websites for the most up-to-date information closer to your booking date. Enjoy your long weekend in New Orleans with friends, exploring the rich tapestry of culture, nature, and entertainment the city has to offer!

Weekend Trip to Victoria, British Columbia

Where to Stay:

Consider staying in the Downtown Victoria area. Downtown offers a convenient central location with easy access to many attractions, restaurants, and shops, as well as beautiful harbor views. Airbnb options in Downtown Victoria range from modern apartments to historic homes and will place you within walking distance of many popular sites.

Weekend Itinerary:

Friday:

• Arrival & Check-in: Settle into your Airbnb.
• Dinner at Fishhook at Mermaid Wharf: Enjoy a mix of Indo-French inspired seafood dishes in a casual setting.

Saturday:

• Breakfast at Jam Café: Indulge in a hearty breakfast. Arrive early as there could be a wait.
• Morning Activity - Sporty Nature Lovers:
  • Go for a hike in Goldstream Provincial Park to see waterfalls and lush forest.
  • Alternatively, rent bikes and cycle along the Galloping Goose Regional Trail.
• Lunch: Pack a picnic to enjoy in the park or along the trail.
• Afternoon Activity - Culture:
  • Visit the Royal BC Museum to explore natural and human history.
  • Take a self-guided walking tour of the heritage architecture around the city, including the BC Parliament Buildings, or join an organized walking tour.
• Dinner at Red Fish Blue Fish: Eat outdoors at this waterfront eatery famous for its fish and chips.
• Evening: Check for local concerts or festivals. The Victoria Conservatory of Music often hosts events and there might be a festival in town.

Sunday:

• Breakfast at The Village: Try one of their legendary brunch plates.
• Morning Activity:
  • Kayak or stand-up paddleboard in the Inner Harbour or along the coast with a tour.
  • Visit the Butchart Gardens – while not the peak season, it’s still a beautiful visit.
• Lunch: Have lunch at the Butchart Gardens café or return to the city for a meal.
• Afternoon:
  • Explore the local art galleries or the Art Gallery of Greater Victoria.
  • Discover Beacon Hill Park with its gardens, pathways, and coastline views.
• Dinner at Agrius Restaurant: A farm-to-table experience with organic and seasonal dishes.
• Departure & Check-out: Head home or to your next destination.

Known Festivals during that Time:

• Victoria Film Festival: While primarily in February, check if they have extended events or screenings.
• Cherry Blossom Festival: Depending on the season, you might catch the tail end of cherry blossom celebrations.

Additional Tips:

• Book activities and dinner reservations well in advance as Victoria can be quite busy in spring, especially for popular spots like Jam Café.
• Consult the Tourism Victoria website closer to your arrival date for up-to-date listings of cultural events, festivals, and concerts.
• Prices for tours and rentals may vary, so budget accordingly and book these in advance as well.
• Heritage buildings like Craigdarroch Castle provide a mix of culture and history if you’re eager for more exploration.

Itinerary for Alaska in July 2024

Stay: Anchorage

Anchorage is a central, well-connected city in Alaska that offers easy access to both natural wonders and city amenities. With a variety of AirBnBs available, you can find a place that suits the tastes of your group. It’s wise to book your AirBnB early, especially since July is a peak travel season in Alaska due to the mild weather and extended daylight hours.

Day 1: Arrival and Anchorage Exploration

• Breakfast: Arrive in Anchorage and grab breakfast at Snow City Cafe, known for its friendly atmosphere and delicious local foods.
• Morning activity: Visit the Anchorage Museum to appreciate Alaskan culture through art, history, and science exhibits.
• Lunch: Have a quick bite at a local food truck or café downtown.
• Afternoon: Take a walking tour of downtown Anchorage to learn about the city’s history and see some of its cultural landmarks.
• Dinner: Enjoy fresh seafood at Humpy’s Great Alaskan Alehouse which offers a casual setting and often features live music.

Day 2: Adventure in Nature

• Breakfast: Start your day with a hearty meal at The Rustic Goat, offering a variety of breakfast options to fuel your day.
• Morning & Afternoon activity: Head out for a hike on one of the many trails in the nearby Chugach State Park or opt for a wildlife viewing tour to spot bears, moose, and eagles.
• Lunch: Pack a lunch to enjoy during your outdoor adventure.
• Late Afternoon: Return to Anchorage. If time permits, visit the Alaska Native Heritage Center to learn about the indigenous people of Alaska.
• Dinner: Check out Moose’s Tooth Pub & Pizzeria for casual dining with delicious pizzas and local craft beers.

Day 3: A Day on the Water

• Breakfast: Grab a quick bite at Kaladi Brothers Coffee to start your day energized.
• Day activity: Take a day trip to Seward (about a 2.5-hour drive) and embark on a Kenai Fjords National Park cruise to see glaciers, sea life, and stunning coastal scenery.
• Lunch: Enjoy a meal included on most cruise tours or dine in one of Seward’s local eateries.
• Evening: After returning to Anchorage, rest or explore some local shops.
• Dinner: Try Ginger for some Pacific Rim cuisine and a pleasant atmosphere.

Day 4: Festival Fun and Departure

• Breakfast: Have brunch at Spenard Roadhouse to experience a local favorite.
• Morning: Depending on the festival schedule, Anchorage hosts various events like the Anchorage Market & Festival or summer concerts in July. Check the local calendar for events like Music in the Park, which are common in summer months.
• Afternoon: Before heading to the airport, take a stroll around Lake Hood, the world’s busiest seaplane base, and enjoy the serene environment and maybe catch a seaplane taking off or landing.

Affordable Dining Options: Food trucks and small local eateries often offer the best value for money. Look out for taco stands, seafood shacks, and other local favorites. Many diners and cafes also offer reasonably priced meals, perfect for travelers on a budget.

Cultural & Music Festivals: Check the Anchorage Events Calendar well in advance as festival schedules are usually announced early in the year. Common summertime events include the Anchorage Folk Festival, various Independence Day celebrations, and the Girdwood Forest Fair, a little further afield.

Booking Tips: Since Alaska’s summer season is very popular, and given you’re planning to book in February which is well in advance, be sure to secure your accommodations and any specific tours (like the Kenai Fjords cruise) early to avoid missing out on the best options and deals.

Enjoy planning your sporty, nature, and culture-filled Alaskan adventure!

Vancouver and Banff Road Trip Itinerary - August 2024

Booking in April 2024

Day 1-4: Vancouver, BC

• Central Area to Stay: Consider staying in the Kitsilano or Downtown Vancouver area since they offer easy access to beaches, cultural sites, and are relatively central for a variety of activities.
• Affordable Breakfast Options:
  • Breka Bakery & Café (various locations) - great for a light, budget-friendly start.
  • The Red Wagon Café – a hip location for hearty breakfasts.
• Affordable Dinner Options:
  • Banana Leaf – tasty and affordable Malaysian cuisine.
  • The Warehouse – a chain with a fun atmosphere and all meals at a great price.
• Sports and Nature:
  • Rent bicycles and ride around Stanley Park.
  • Hike the Grouse Grind or explore the Capilano Suspension Bridge Park.
• Culture: Visit the Museum of Anthropology or the Vancouver Art Gallery.
• Concerts/Festivals: Look out for the Vancouver Mural Festival which usually takes place in August, and enjoy live music and street art tours. Also, keep an eye on the schedules at the Orpheum Theatre or the Vancouver Symphony Orchestra for any outdoor summer concerts.

Day 5: Vancouver to Revelstoke (Optional Stop)

• Drive: Around 6.5 hours via the Trans-Canada Hwy/BC-1 E. Recharge in Revelstoke if needed.
• Recommended Area to Stay in Revelstoke: Near Victoria Road for easy access to local attractions.
• Activities in Revelstoke: Visit the Revelstoke Railway Museum, or if you’re up for it, enjoy some mountain biking.

Day 6-9: Banff, AB

• Central Area to Stay: For AirBnBs, look for places in the town of Banff itself or in nearby Canmore for more affordability, only a 20-minute drive away.
• Affordable Breakfast Options:
  • Wild Flour Banff’s Artisan Bakery Cafe – known for good coffee and baked goods.
  • The Whyte Wolf – an energetic spot for a health-oriented breakfast.
• Affordable Dinner Options:
  • Bear Street Tavern – a cozy tavern with great pizzas.
  • The Elk & Oarsman – a Banff favorite with approachable prices.
• Sports and Nature:
  • Hike the trails at Banff National Park, like Johnston Canyon or Sulphur Mountain.
  • Rent kayaks or canoes at Moraine Lake or Lake Louise.
• Culture: Take the Banff Gondola up Sulphur Mountain and visit the Banff Upper Hot Springs.
• Concerts/Festivals: Check out the Banff Centre for Arts and Creativity for any summer performances. The Banff Summer Arts Festival might be on, with a variety of shows and concerts.

Day 10: Banff to Jasper (Optional; Scenic Route)

• Drive: The Icefields Parkway (around 3-4 hours non-stop) – It is considered one of the most scenic drives in the world.
• Activities: Stop at the Columbia Icefield, Peyto Lake, and Athabasca Falls.

Day 11-12: Jasper, AB

• Recommended Area to Stay: Central Jasper to be close to shops and restaurants.
• Activities: Explore Jasper National Park, go mountain biking, or hiking.
• Culture: Visit the Jasper Yellowhead Museum and learn about the local history.

Day 13-14: Return to Vancouver

• It’s a long drive back from Jasper to Vancouver (about 9 hours). You may want to break it up with an overnight stay somewhere en route, such as Kelowna or Kamloops.

Additional Tips:

• Booking Accommodation: Book your AirBnBs as soon as your trip dates are fixed. August is a high-demand period, especially in places like Banff.
• Wildlife: Bring binoculars for wildlife spotting in the national parks.
• Weather: Even in the summer, mountain weather can be unpredictable. Bring layers and waterproof clothing.
• Parks Pass: Remember to purchase a Parks Canada Discovery Pass for access to national parks.
• Reservations: For activities and tours in national parks, book in advance to secure your spot.
• Concerts and Festivals: For the most current festival and concert information, check official tourism sites of Vancouver and Banff closer to your travel dates.
• Safety: Always carry bear spray when hiking in bear country and know how to use it.

By planning ahead and keeping these tips in mind, your road trip through Canada from Vancouver to Banff in August 2024 should be an incredible blend of nature, culture, and adventure. Enjoy your trip!

Prompt

Using the following prompt, we generated the trip guides above:

Please write a trip in 2024.
During the following time frame and at the following location:

<Insert a line from the table here>

Please suggest a central area to stay in that location. 
Most likely we will stay in AirBnBs.
Also suggest affordable breakfast and dinner options. 
Joy and I are sporty and nature lovers but we also really appreciate culture (museums, walking tours) as well as concerts (any known festivals during that time).

Please add any additional tips. 

Thank you!