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Explore curated travel guides, itineraries and custom travel planning services for Boston. Whether you are spending 4 days in Boston or 2 weeks in Boston, Thatch guides and itineraries can help you make the most of your trip with curated Boston recommendations by locals and travel experts. Explore what to eat in Boston, the best things to do in Boston and the must sees in Boston. From a long weekend in Boston to a trip of a lifetime, let Thatch local experts help you plan the perfect vacation.

Find a local Boston expert
to plan your trip

Leandra Rivera

Lives in Boston, MA, USA

✈️ Let's Adventure Together Hi there, my name is Leandra and I have a passion for experiencing the world through travel. More than that, I have a deep desire to show others how easy and EMPOWERING travel can be, no matter your budget. I specialize in solo travel, taking the road less traveled, and cultural immersion. There is power in seeing the world, don't be afraid to harness it. Xx Leandra

Adventure • Backpacker • Female Solo • Budget • History • People & Culture • Romantic • Wine • Road Trip • Slow Travel

$45 Consultation Call

$15 Custom Guide

$50 Custom Itinerary

Cortney Van Wilpe

Lives in Boston, MA, USA

Exploring new cities one meal at a time🥖😋 My passion for people, culture, history, and food has brought me to Thatch to share my experiences with you ✨ I have professional experience in attaining higher education abroad while simultaneously making time to travel and enjoy my host country. I am here to help you maximize your educational experience while spending the weekends exploring the your new home and the surrounding cultures and countries. The best way to get to know a city is to eat your way through it! My curated travel guides help you travel on a budget and hone in on the experiences that await you. I am available for consultations to aid the student visa process and talk through the scholarships and loan opportunities that are available to you based on your individual needs. You can get in touch with me via email cvanwilpe@outlook.com to start planning all your travel dreams today💌

Adventure • Foodie • Female Solo • Budget • History • People & Culture • Wine • Digital Nomads • Coffee

$20 Consultation Call

Casey the All American Road-Tripper

Lives in Portland, Maine, USA

Hey there! I'm Casey, an ex-van lifer originally from Florida, now based in Portland, Maine. I'm passionate about road trips and believe that the journey matters just as much as the destination. My road trips are designed for those who crave the open road and have the endurance for long drives. I've explored the East Coast, Utah, Arizona, California, and traveled the length of Route 66, all from the comfort of my converted van. My store features road trip itineraries, city guides, and van life tips and tricks, all based on my personal experiences. Every guide and tip in my store has been personally tried and tested by me, so you can trust that the recommendations are solid. If you're planning a road trip in the US, I'd love to help out!

Adventure • Female Solo • Van Life • Budget • Family • Camping • Road Trip

$25 Consultation Call

$50 Custom Guide

$60 Custom Itinerary

DIY your trip to Boston with guides
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Lucas and Kelsey

The Ultimate Northeast Road Trip Itinerary

This Ultimate Northeat Road Trip guide is an accumulation of over 65 HOURS of research and planning. I have always wanted to go to this area during the Fall and I finally was able to make this dream a reality. I have taken all of my research and expertise and compiled this itinerary into a great 10-14 day road trip guide. You can spend less time or more time on your trip based on your needs. This itinerary has over 60 plus stops including places to hike, sights you can't miss, the best places to stay, the best places to eat, great photo stops, and much more. You won't have to spend hours upon hours trying to figure out where to go or what not to miss. This is your one-stop shop to be fully prepared to make this the trip of your dreams. If you follow this guide I promise you this will be a trip of a lifetime and you will see some amazing experiences. If you want to take your own route that's fine use this as a great start to plan your epic adventure. You can't go wrong. Tag us in the photos you take - we'd love to see your experience! @thejourneyest2016

Digital Nomads • Backpacker • Car-free • Couples • Family • Female Solo • Pets • Adventure • Budget • Camping • Coffee • Foodie • Outdoors • Road Trip • Photography • RV • Van Life • People & Culture

$15.00

4.0

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Jack and I spend half of our honeymoon in Boston, here are some of our favorite places we visited!

History • Foodie • Coffee • Wine • People & Culture

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Katie Howerton

2023 Travel Journal

I went into 2023 with a huge appetite for travel but very few plans to do so. Little did I know London was on the horizon, and while my annual anniversary trip was much tamer than usual in humble Huntsville AL, I was so glad to do a solo Disney World trip (again), take my girls on the road for the first time to Louisiana, and have lots of Tennessee day trips in between. Enjoy this travel journal of 379 (!!!) places, including: 🖼️ 64 Museums, Gardens, and Attractions ☕️ 53 Coffee Shops 🍽️ 82 Restaurants, Bakeries, Bars, and Food Trucks 🛏️ 29 Hotels, Bed & Breakfasts, and Airbnbs ✨ and a whole bunch more! Scroll to the bottom for my favorites of the year!

Couples • Family • Architecture • Art • Budget • Coffee • Foodie • History • People & Culture

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Reasons to visit

Boston

Discover the Best Areas to Explore in Boston

Boston, a city brimming with historical charm and contemporary vibrance, offers a rich tapestry of experiences for travelers. From cobblestone streets to world-class museums, this iconic New England destination is a treasure trove of attractions.

The Freedom Trail

Tracing the roots of American history, the Freedom Trail is a 2.5-mile red-brick path that takes you through 16 significant historical sites. Immerse yourself in the storied past of the United States as you visit the Boston Common, Paul Revere's House, and the Old North Church. Each landmark offers a glimpse into the revolutionary spirit that shaped the nation.

Beacon Hill

Beacon Hill, with its gaslit streets and Federal-style row houses, is one of Boston's most picturesque neighborhoods. Wander through charming alleyways like Acorn Street, often cited as one of the most photographed streets in America. The area is also home to the Massachusetts State House, with its iconic golden dome, offering a perfect blend of history and architectural beauty.

Back Bay

Back Bay is renowned for its stunning 19th-century architecture and upscale shopping. Stroll down Newbury Street, a haven for fashionistas and foodies alike.

Boston

Rich history, iconic landmarks, diverse neighborhoods, and vibrant cultural scene, ideal for history buffs and urban explorers.