The perfect coastal New England road trip itinerary — and how to earn Hilton Honors points at every stop along the way

Some of my favorite books are set along the New England coast in Boston brownstones and small Maine harbor towns, but I've never actually been there myself. Living in Florida, I didn't realize how doable this road trip is. Boston to Portsmouth is about an hour by car, with another hour to Portland, Maine. So my husband and I packed up our bags and headed out to the Northeast to explore lighthouses, historical sites, local bookstores and of course, lobster rolls.But here's the thing about me: I am always thinking one trip ahead. Even when I'm planning one vacation, I'm always thinking of ways to save toward the next one. That's where the Hilton Honors American Express Surpass® Card comes in. It turns every stop, snack, gas fill-up, meal and souvenir into Hilton Honors™ points for my next dream trip — all for a $150 annual fee (see rates and fees).And right now, new Surpass cardmembers can earn 130,000 Hilton Honors Bonus Points, plus a Free Night Reward after spending $3,000 in purchases in the first six months of card membership. Offer ends Jan. 13, 2027. Terms apply.Here's how to plan a New England coastal road trip, with tips on how to use the Surpass Card to earn along the way.TPG editor road trip tip: Use the Hilton Honors American Express Surpass Card to plan and earnLAUREN WASSUM/THE POINTS GUYGas, snacks and quick lunch detours also add up: the Surpass card earns 6 points per dollar at U.S. restaurants, U.S. supermarkets and U.S. gas stations, to really make it worth your while on a road trip. The Surpass card includes complimentary National Car Rental® Emerald Club Executive® Status (enrollment in the National Car Rental Emerald Club through your American Express online account required to access Executive status, terms apply), so you can skip the counter when you land.When my flight arrived at Boston Logan International Airport (BOS), I went straight to the Executive area in the parking garage to choose my preferred vehicle.Where to staySurpass card editor tip: Automatic Hilton Honors Gold status gives you space-available room upgrades at select properties, daily food and beverage credits at select brands in the U.S. or complimentary continental breakfast at select brands outside of the U.S., an 80% bonus on base points earned during stays, and the fifth night free on standard room stays booked entirely with points.Boston, MALAUREN WASSUM/THE POINTS GUYTucked between downtown and Boston's historic North End, I stayed at Canopy by Hilton Boston Downtown, within walking distance of Faneuil Hall, Quincy Market and TD Garden.The hotel offers complimentary Canopy Bikes for registered guests to easily explore the city, and it's also steps from the T, Boston's subway system, to reach neighborhoods from Beacon Hill to Fenway Park. In general, there are plenty of Hilton properties across budgets to choose from in Boston based on your itinerary and budget, but a few other TPG-recommended properties include:Reward your inbox with the TPG Daily newsletterJoin over 700,000 readers for breaking news, in-depth guides and exclusive deals from TPG’s expertsBy signing up, you will receive newsletters and promotional content and agree to our Terms of Use and acknowledge the data practices in our Privacy Policy. You may unsubscribe at any time.Pennyweight Hotel Boston, Curio Collection by HiltonHilton Boston Park PlazaHampton Inn Boston Seaport DistrictPortsmouth, NHLAUREN WASSUM/THE POINTS GUYWhile visiting the historic coastal town of Portsmouth, you'll find lots of smaller properties to stay at. I made the Hilton Garden Inn Downtown Portsmouth my home base. Its Market Square location puts shops, restaurants, the waterfront and local galleries all within easy walking distance without overthinking the logistics. Nearby, Hampton Inn & Suites Portsmouth Downtown is another great option, offering a complimentary hot breakfast buffet daily before you set out on any excursions.Portland, METhe Longfellow Hotel is one of Portland's newer properties — an SLH Hotel with 48 boutique rooms. The hotel was designed with pared-back minimalism, custom furniture, even sleep-optimized beds and Loftie alarm clocks. The on-site Astraea Wellness Spa and gym make it easy to reset after several adventure-packed days on the road. Longfellow also offers amenities such as complimentary bicycles and casual dining at the Twinflower Café and the lobby bar, Five of Clubs.You can also find a second SLH property in Portland: The Francis, a restored 1881 Victorian mansion with 15 boutique-style rooms featuring original stained glass, intricate tilework and cast-iron fireplaces. For a room with a view of Casco Bay, the Canopy by Hilton Portland Waterfront is the pick.Surpass card editor tip: The Surpass card earns 12 points per dollar on purchases made directly with hotels and resorts within the Hilton portfolio. Plus, your entire trip works toward a free night reward that you can earn after spending $15,000 on eligible purchases with the card in a calendar year. It's redeemable at over 9,000+ Hilton properties, any night of the week, with no blackout dates.Where to eat and drinkSurpass card editor tip: 6 points per dollar at U.S. restaurants means every meal, from casual coffee to that fancy dinner, is contributing to your Hilton Honors point balance.Boston, MALAUREN WASSUM/THE POINTS GUYIt isn't easy to narrow down where you should eat in Boston, as there is no shortage of great restaurants, but a few stood out during my time there. For coffee and breakfast, Tatte Bakery and Cafe is the move with several locations around the city. Don't miss the Honey Halva Latte ($6.25) and pistachio croissant ($5.25).And of course, if you're craving lobster rolls, head over to James Hook and Co. There may be a line, but trust me, it's worth the wait. For dinner, head to the North End and visit Ciao Roma for their vodka pasta ($28). Their outdoor patio is in a courtyard across the street, making you feel like you are dining on an Italian side street. On the walk back, make it a point to stop at Modern Pastry to build your own customized cannoli.Portsmouth, NHLAUREN WASSUM/THE POINTS GUYThere are plenty of great eats in Portsmouth, but the restaurant I can't stop thinking about is Cure. You'll want to make a reservation before you leave on your trip. It's a cozy, intimate space that fills up fast. The menu changes seasonally, but order the Steakhouse Board ($55) if it's available and don't skip the crème brûlée ($12) for dessert. In the morning, walk to Elephantine for coffee and the most delicious chocolate almond croissant and breakfast sandwiches you can imagine. We went right when they opened up, and there was already a line, but believe me when I say it is well worth the wait.Portland, MELAUREN WASSUM/THE POINTS GUYWhen asking around for dinner recommendations in Portland, Duckfat came up again and again, so we made it a point to eat there, and I can confirm it lived up to the hype. They're known for their Belgian frites ($9), double-fried in duck fat until they're golden and crispy, and once you've had them cooked that way, you'll never be the same. If you're craving Italian, Via Vecchia hits the spot. The radiatori pasta ($35), made with Calabrian chili-braised pork, San Marzano tomato ragu, Parmigiano Reggiano cream and smoked pancetta, was absolutely heavenly.And when in Maine, you'd be remiss not to get a good old-fashioned lobster roll. Whether you like them hot or cold, Highroller Lobster is nonnegotiable and will serve you a lobster roll flight ($52), and each one can be topped with a different butter or mayo sauce. If taking a day trip to Kennebunkport, beeline it to the town's beloved Clam Shack for a classic cold roll ($31.95).Things to doSurpass card editor tip: Earn up to $50 Hilton Statement Credit each quarter for up to $200 per year on purchases made on the Surpass card directly with a property in the Hilton portfolio, including dining, resort charges and even spa services. For museum entrance fees, tours and souvenirs, you're earning 3 points per dollar on all other eligible purchases.Boston, MALAUREN WASSUM/THE POINTS GUYWalking the Freedom Trail is a must for any first-time visitor. The 2.5-mile route follows a red-brick path through 17 historic sites, from Boston Common and Paul Revere's House to the USS Constitution. Budget at least half a day to take it at a comfortable pace without feeling rushed.The highlight of my time in the city had to be my visit to the Boston Public Library. Opened in 1848, it was the first free municipal library in the United States. The stunning Renaissance Revival architecture is one of the few places in the U.S. that makes you feel like you've been transported to Europe. My favorite room was Bates Hall, a picturesque yet quiet reading space with a 50-foot barrel-vaulted ceiling and green lamps lining the entire hall. Speaking of books, I decided to commemorate my literary adventure by supporting two independent bookstores in the city: Beacon Hill Book Store in the Beacon Hill neighborhood and Brattle Book Shop in Downtown Crossing.Portsmouth, NHLAUREN WASSUM/THE POINTS GUYThe 10-acre waterfront Prescott Park is home to the beloved Prescott Gardens, which are beautifully maintained and worth a leisurely stroll. History buffs should also make time for the Strawbery Banke Museum, a living history museum spread across 10 acres of restored homes and buildings spanning 300 years of Portsmouth's history. Once you've explored the park, Market Square is where you'll want to spend your time. You can wander shops and go "deck hopping" as the locals call it, moving from one waterfront restaurant or bar deck to another to enjoy cocktails or mocktails, appetizers and scenic views.Portland, MELAUREN WASSUM/THE POINTS GUYBefore heading directly into Portland, stop in Kennebunkport and Ogunquit for an hour or two and explore the charm of these two port towns, each with streets lined with independent small shops and restaurants. In Ogunquit, walk Marginal Way, a 0.25-mile scenic coastal cliff walk accessible to most fitness levels, then head 20 minutes farther North to Kennebunkport to get some delicious artisanal ice cream at Rococo's for a sweet treat before arriving in Portland.After several days of driving and walking thousands of steps, my first stop in Portland was the Astraea Spa at the Longfellow Hotel. I treated myself to the Astraea signature massage ($245), which included warm Himalayan salt stones and a facial massage to relieve muscle tightness. Once I felt relaxed and refreshed, we ended our last day watching the sunset at the iconic Portland Head Light for some classic New England vibes.Bottom lineThis New England road trip finally brought some of the pages of my favorite books to life. And the Hilton Honors American Express Surpass Card made it easier to pull off than I expected. Complimentary National Car Rental Emerald Club Executive Status meant no waiting at the counter when I landed in Boston, and 6 points per dollar at U.S. gas stations and U.S. supermarkets meant every fill-up and snack run was working toward the next trip. Add in automatic Gold status, the up to $50 back in quarterly Hilton statement credits (which I used toward my Astraea Spa visit) and 12 points per dollar on Hilton hotel stays, and this road trip was helping me earn the whole way through.If a New England road trip has been on your list, there's no better time to start planning — and no better cards to bring along for the ride than one from the Hilton Honors card lineup, including the highest-ever welcome offer on the Hilton Honors American Express Aspire Card:Hilton Honors American Express Aspire Card: Earn 200,000 bonus points after spending $6,000 on purchases in the first six months of card membership. Offer ends Jan. 13, 2027. Terms apply.Hilton Honors American Express Surpass Card: Earn 130,000 bonus points and a Free Night Reward after spending $3,000 on purchases in the first six months of card membership. Offer ends Jan. 13, 2027. Terms apply.Hilton Honors American Express Card: Earn 70,000 bonus points and a Free Night Reward after spending $2,000 on purchases in the first six months of card membership. Offer ends Jan. 13, 2027. Terms apply.For rates and fees of the Hilton Honors American Express Surpass, click here.Terms apply to offers and benefits mentioned.