How to plan the ultimate trip
My name is Mishana Sturdivant and I run Tad Bit Rad Travels. The purpose of this blog is to share tips, tricks, and recommendations to empower my readers to travel efficiently and unapologetically. The best way that I travel as efficiently and unapologetically as possible is proper planning. In this post, I will walk through my process of planning a trip from start to finish.
Deciding Where to Go
The first step is deciding where to go. I encourage you to be open-minded with your destination options. The more open-minded you are, the easier it will be to find a deal. I allow the deals to dictate my travels (sometimes!). I use tools such as Google Flights and Skyscanner in incognito mode so that my constant searches won’t change the price of flights. I search several destinations that I’m interested in visiting to see when’s the cheapest time of the year to fly there. Or if I have a month in mind, I will search several cities to fly to from my local airport in the month that I have in mind to find the cheapest option.
If you don’t have the time or patience to search for deals on your own, you can consider following organizations that will do the work for you. For example, I follow Secret Flying for error fare deals. Secret Flying searches the internet for deals on flights that are priced incorrectly. If you book the flight before the airline can catch their mistake, they must honor the price. I also follow Going.com, formally Scotts Cheap Flights. Going.com sends flight deals from your preferred airport on a reoccurring basis and will keep you in the know of flight deals.
Maybe you already know where you want to go and when? Some of my travels are like this. For example, I know I want to be in Portugal for Afronation at the end of June, now I must find some affordable flights. I use tools like Skyscanner and Hopper to find the best time to book flights. Be aware. I never book directly from Skyscanner or Hopper. You can if you prefer, they often offer deals and discounts. However, I recommend only searching for deals with Skyscanner and Hopper and then booking directly with the airline. It’s more flexible in case you must make changes to your flight, or your flight gets canceled, you’re able to work directly with the airline. If you book through Hopper or Skyscanner or any other third-party site that offers flights, the airline will direct you to them to receive refunds, changes, or cancellation compensation.
Flights Booked, Now What?
Accommodations are next! Booking accommodations are my favorite part of trip planning. The hard part (finding flights) is over and now it’s starting to set in that we have an official trip on the calendar! Personally, if I’m planning a group trip and others in the group chat haven’t purchased their airline tickets yet, they are not confirmed for the trip! I don’t care what deposit they sent in or what hotel preferences they have. They are not confirmed until the flights are booked. If I’m traveling solo, it’s even better because now I can start looking for accommodations that fit my preferences.
What matters to you regarding accommodations when you travel? That’s the first thing you should consider before you start searching for accommodations. Considering somewhere to stay can be overwhelming when you have thousands of options. Here are a few things you should consider when narrowing down your accommodation options:
1. Budget – How much are you willing to spend a night?
2. Location – Do you prefer to stay in the city center? What landmarks or tourist attractions are you sure you want to visit? Consider staying close to those activities if possible. If not, consider staying in a central location where intercity travel isn’t too far or expensive. Have you looked up the best/worst neighborhoods to stay in when visiting your destination? Where’s the nightlife? Where’s a walkable neighborhood that has cafés, restaurants, and other hotels?
3. Type of Accommodation – Do you prefer to just stay at Hotels or Airbnb/Rental Properties? Long-term stays or hostels? Need multiple rooms for a big group?
4. Non-negotiables – What are your non-negotiables? These are the must-have amenities that you need for every trip such as complimentary breakfast, airport shuttle, hotel restaurant or bar, 24 Hour room-service and/or reception, central air-conditioning and/or heating, Beach Access, Private Bathroom, child bed, etc.
When using hotel/rental property aggregators like Booking.com, Expedia, Delta Vacations, Trip Advisor, hotels.com, etc, adjust the filters to get a more specific list of options aligned to your preferences. I have never booked hotels via Expedia, Trip Advisor, hotels.com, etc. But I am a huge fan of booking through booking.com and Amex Travel. I get a ton of benefits and discounts booking through these third parties vs. directly with the hotel. However, I would be recommending price-checking both the third-party site that you are booking with and the hotel’s site for the best price. Sometimes, the hotel will offer a better price or offer additional amenities to book direct like a hotel credit, late check-out, or a bottle of wine (depending on the hotel). I’ve received those specific rewards in the past by booking directly on the hotel’s site after finding the option on Booking.com. Please note that if you book via the third-party site, you will have to contact their support when needing to make hotel changes (date changes, room type changes, reimbursements, and cancellations).
Airbnb offers filters to find your preferences and flexible options to pay. If you are open to hotels and rental properties, I suggest a price comparison to see which is more affordable or if they are priced similarly. Some hotels can be found on Airbnb and sometimes are slightly cheaper on one site than the other.
If you’re interested in hostels or long-term stays, you can adjust the filter settings in Booking.com, Airbnb, and Hostel World to find the best according to your preferences.
Flights and Accommodation are Booked, and now it’s time for activities.
At this point, you can decide if you’re the type of traveler who would rather book activities, and dinner/lunch reservations when you arrive or if you’re like me and want to have a plan before you board your flight. I would recommend doing some research on your destination to see if planning is necessary. Some destinations are better off reserving activities upon arrival, and some that are in peak season and have popular activities that tend to sell out months in advance. A quick Google search on what to do and when to book will give you a better idea of how to proceed. For example, I booked a two-week summer trip to Italy last year. I planned each day down to the hour, made dinner reservations every night, and booked all activities in advance. All I had to do once I hopped off the plane was show up on time for everything. The trip was relaxing and one of my favorite travel experiences. I visited over 10 cities, rode many buses, trains, and taxis, stayed at five hotels/Airbnb, and didn’t have to wait at all for any of the popular restaurants that we visited. On the flip side, I visited Tulum with a friend a year or so ago and all we had booked was our rental car, hotel, and flights. For everything else, we just went with the vibe. We had a great time. Matter of fact, when I’m staying at an all-inclusive resort, I never book activities until I check into the hotel. I would recommend booking in advance if your group is big or complex.
Here are a few tips for finding the best activities.
1. Search blogs of travelers who have visited your destination. If you have a favorite blogger, find their guide. If not, search “Best Things to do in (Destination)”. This old hack has never failed me. I usually check multiple blogs and reviews to build a list of activities that I’m interested in. You can also search “Must Do activities in (Destination)” and “Most Unique activities in (Destination)
2. Find Tours on Get Your Guide, Viator and Eventbrite – search your destination and dates and see what options you have. I like to support local businesses, so I use GYG and Viator as an aggregator to see what’s possible. Then I search those specific types of tours on Google to see if any local tour guides have their website that I can book through. Sometimes when you book directly with the tour guide, the price is cheaper or you’ll get additional benefits.
3. Consider Tours hosted by your Hotel – Excursions hosted by your accommodations can provide convenience because they may arrange transportation as well. This option can be more expensive depending on your accommodations. However, if you’re staying at a local hotel, the excursions are curated by locals and will offer must-do experiences when visiting their destination.
4. Contact your Airbnb host for their recommendations – Some people will wait until they check in to ask for local recommendations, but what if you are visiting Italy during peak season? You may be too late! ;) Use the messaging feature in Airbnb to contact your host to ask for recommendations from a local’s perspective. Many hosts are excited to share their recommendations. They may have guides pre-prepared.
5. Use Google Maps to see what’s near your Accommodations - Search the address of your accommodation and select the options “Show restaurants near me”. It will provide a list of close by restaurants with their website and reviews to check out.
Get Organized!
Now, put it all together and what do you have? A fully planned trip! How do you stay organized? It doesn’t matter if I’m traveling solo or within a group, I will have a Google doc that breaks down the itinerary day by day. This helps me identify gaps in my trip. This also allows me to easily share my itinerary with other members of my travel group or family so they know when/where I am in case they need to contact me. Your itinerary can be as detailed as you would like. I will post an example of one of my trip itineraries for your reference.
In short, to plan your next trip, break it down in this order: book flights, accommodations, and then activities. Stay organized in a tool that allows you to make dynamic changes and share with others. Most importantly, figure out what works best for you. Once you figure that out, you can apply it to every trip you plan in the future! The more you do it, the better you can get at it and hopefully, the less time it will take. Good Luck!
