Truckland Vacations from $664
Book a Hotel + Flight or Car together to unlock savings
Your Truckland Vacation
Lock in a Truckland vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Hancock, which is great for watersports, views and walking. A trip to Truckland is an excellent opportunity to do a bit of sightseeing. Be sure to visit renowned attractions like Lynn Hall Memorial Park, Sanibel Island Lighthouse and Bunche Beach. A couple of quick clicks is all it takes to put together the perfect Truckland vacation on Expedia.
The Latest Truckland vacation packages
Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa
$918
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,011 reviews)
So nice to have the benefit of being able to enjoy both the beach side and bay side.
Reviewed on Aug 31, 2026
Casa Ybel Resort
Mid Island
$972
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (412 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on Aug 30, 2026
Wiggins Pass Chalet
$718
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (284 reviews)
I would especially like to highlight the wonderful service we received from Alyssa. She was incredibly sweet, attentive, and kind throughout our experience. She made us feel very welcomed and well taken care of. Alyssa truly went above and beyond, and her excellent service made our experience even more enjoyable. Thank you, Alyssa!
Reviewed on Aug 30, 2026
What to do in Truckland
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
$55
per adult
Fort Myers Beach Sunset and Dolphin Watching Cruise
$63
per adult
100% of travellers recommend
Truckland Hotel Deals
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
20091 Summerlin Road Fort Myers FL
Fully refundableReserve now, pay when you stay
$79 nightly
$88 total
Sep 17 - Sep 18
Total with taxes and fees
8.2/10 Very Good! (1,323 reviews)
"It’s a good choice."
Reviewed on Aug 31, 2026
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$223 nightly
$248 total
Sep 15 - Sep 16
Total with taxes and fees
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$183 nightly
$204 total
Sep 28 - Sep 29
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Truckland Vacation Packages
Truckland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Southwest Florida Intl. Airport (RSW) |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | Barbara B Mann Hall, Sanibel Harbour Beach and Imaginarium Hands - On Museum |
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Frequently asked questions
How much does a Truckland vacation package cost?
Offering excellent value package deals from $664 on Expedia, you'll be pleasantly surprised at how much a vacation to Truckland costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Truckland?
March, April and October are great times to look for cheap Truckland vacation packages. Choosing to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Truckland?
Generally, a handful of days is enough to go to the main attractions during your Truckland vacation. However, if you'd like to have some time to rest or take day tours, consider extending your itinerary.
How to find the best Truckland package deals?
Start your search for a Truckland package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Truckland package deal right away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Truckland getaway off to a flying start.
Is it cheaper to book a Truckland vacation as a package?
You can enjoy significant savings on your next Truckland getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Truckland?
If you have your Truckland vacation dates confirmed, book early to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Truckland?
- Choose your travel dates: What you'd like to do in Truckland and your favorite season can help you decide when to get away.
- Set your budget: Consider costs like flights, meals and transportation when working out how much to put aside for your trip to Truckland. Then, choose a property that suits your budget, whether that's a low-cost option or a more upscale retreat.
- Use our trip planning tool to explore Truckland: Research every part of your trip to Truckland with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Decide your trip length: Think about how long you'd like to spend discovering Truckland. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Truckland vacation package that brings all your bookings together.
- Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Truckland has to offer. Find all the incredible things to do in Truckland in Truckland with our dedicated activity guide.
Does Expedia offer Book Now, Pay Later Truckland vacation packages?
Set off on your dream getaway to Truckland with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snag great deals before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.