The Summer Packing & Travel Guide

In our experience, the best summer trips are the ones that require little in the way of planning ahead, without forfeiting the option to actually do and see a lot. The following destinations are easily accessible and offer plenty of opportunity to both stay put and explore (plus, freedom for the little ones to connect with nature). And in the spirit of minimal effort, we compiled easy packing lists to accommodate all three.

San Juan Islands

The obvious draw of the San Juan Islands, which are a convenient ferry ride (or sea plane trip) from Seattle, is the landscape—the verdant green islands, views of nearby mountain ranges, and pebbled beaches are a stunning backdrop. And while it can absolutely make for a cozy romantic getaway, the opportunities for exploring make it a bucket-list spot for families: Kids love camping, whale-watching, and hanging out on the beaches, plus there’s plenty to discover in the cozy harbor towns (lighthouses, fish markets, and even an adorable little alpaca farm). Bonus: As other summer destinations reach scorching heats, cool Pacific breezes keep the San Juans moderate from Memorial Day through Labor Day.

Stay

Leanto

360.298.1684

Leanto operates several campsites on Orcas Island, each one outfitted with a canvas lean-to plus a real mattress, bed, and picnic table, with wool blankets and checkered tablecloths that look straight out of Moonrise Kingdom. The result? All of the good parts of camping (remote landscape, crackling fire, fresh air, family bonding) without any of the tiresome planning and packing.
Friday Harbor House

130 W. St., Friday Harbor | 866.722.7356

Accommodations in the San Juans are notoriously rustic, but if camping’s not your jam, book a room here. Friday Harbor House has simply outfitted rooms that center around the gorgeous view of the bay that you’ll have right off the porch. They also have a lovely little restaurant and easy walking access to this quaint fishing town.

Shop

Griffin Bay Bookstore

155 Spring St., Friday Harbor | 360.378.5511

Nestled into adorable Friday Harbor and identified by a gold-lettered sign, Griffin Bay Books is every bit the small town bookstore. There’s a cute coffee shop inside, and it’s a great place to hide out if there’s unpredictable weather.
Girl Meets Dirt

208 Enchanted Forest Rd., Eastsound | 360.375.6269

Girl Meets Dirt’s traditional preserves are a beautiful homage to Orcas Island’s unique history of orcharding. Founder Audra Lawlor moved to her “farmette” after leaving a Wall Street job in the downturn, and hasn’t looked back since. You can pick up her preserves (all made with island fruits) at gourmet shops around the country, but she reserves the small-batch specialty stuff for the island. The shop is open weekdays from 9am-5pm, but you can also call ahead to arrange a tasting—the jams make great souvenirs, and she also sells a gorgeous little selection of home goods like hammered copper pots and wooden serving boards, which are also made locally.

Eat

The Place Restaurant & Bar

1 Spring St., Friday Harbor | 360.378.8707

This charming restaurant is positioned right along the harbor, so ask for a window table and enjoy the view of the water and surrounding islands while you eat. The menu is packed with local, organic produce and sustainably harvested seafood from the harbor.
Tops’l

1 Front St., Friday Harbor | 360.378.2922

Tops’l is right next door to the local docks, so the chefs visit them daily to pick up the freshest seafood around. In addition to the classic crab, salmon, and cod, they’re expert at handling some of the area’s more unusual catches, like uni and sea cucumbers.

Do

Pelindaba Lavender

45 Hawthorne Ln., Friday Harbor | 360.378.4248

The cool thing about Pelindaba (besides, um, that it’s a lavender farm) is that the owners are outspoken community members, advocating for organic, responsible cultivation of the San Juan Islands. When you visit, you can walk through the fields before picking up some soap or lavender oil, which is all made on-site—there’s lavender lemonade for the kiddos, too.
TerraTrek

40 Spring St., Friday Harbor | 360.378.4223

Everyone comes to the San Juans for the gorgeous landscape, and there’s probably no better way to see it than by bike, which is fast enough to cover serious ground, but slow enough to take in the drama of it all. Terratrek handles the bookings and/or campsites (depending on your trip) and provides kayaks at key moments, so you can also explore the marine environment up close.

Packing List

Cape Cod

From the shingled homes and fresh lobster to beaches that look like something out of a children’s book, there’s something about the Cape that feels so very American (and makes it a perfect place to celebrate the 4th). The most difficult part of the whole trip—unless, of course, you’re an every-summer loyalist—is picking just one of these adorable New England towns to shack up in.

Stay

Chatham Bars Inn

297 Shore Rd., Chatham | 508.945.0096

This oceanside resort, complete with tennis courts, spa, and a fleet of charter boats, has been around for over a century and luckily, the main house has retained its understated glamour even after several updates. Whether you’re staying in the original main house or the newer stand-alone cottages or spa suites, the vibes are distinctly Cape Cod, with huge paned windows (a good chunk of the rooms have ocean views), plush beds, and shades of blue. The property is operational year-round and the deserted beach (the hotels sits on a private stretch) and ample roaring fireplaces make it an unforgettable stay off-season.
Wequassett Resort & Golf Club

2173 Rte. 28, Harwich | 508.432.5400

Nestled into a particularly picturesque nook of Pleasant Bay, this unapologetically grand resort is top-notch through and through—everything from the manicured lawns to private cabanas to the four stellar on-site restaurants has been meticulously thought out. There’s a world-class golf course, tennis, and an adults-only pool, but the real action is, as to be expected, at the beach, where you and the kiddos can take sailing lessons among other watersports and activities. Accommodations-wise, choose between sprawling rooms in the main house, rustic cottage-style suites, or a sprawling private villa.

Shop

John Derian Company

Law St. (back of 396 Commercial St.),
Provincetown | 508.487.1362

Entirely worth a day trip from anywhere else on the Cape, John Derian’s telltale mix-and-match style is on full display at his teeny Provincetown outpost, which happens to sit just steps from his summer home. Once you’re done picking through the intricate serving platters, paperweights, and cake stands in all their découpage glory head over to Nor’East Beer Garden for a dozen of the freshest Wellfleet oysters and a cold one or two. Staying overnight? With its insane ocean views and excellent restaurant, the centuries-old Red Inn is your best bet.
Wellfleet Drive-In Theater Flea Market

51 State Hwy., Rte. 6, Wellfleet | 508.349.0541

During the summer season, the Wellfleet Drive-In Theater grounds become a sort of meeting spot for the entire community. At night, it functions as an old school drive-in theater and during the day plays host to an adorable kids playground and miniature golf course. On the weekends, the space morphs into a sprawling flea market with dozens of stalls devoted to everything from kitschy Cape Cod memorabilia to one-of-a-kind antiques.

Eat

The Glass Onion

37 N. Main St., Falmouth | 508.540.3730

In the land of never-ending seafood, this fine-dining spot in Falmouth is where you go for a really great steak, a veggie-rich salad, or house-made ravioli (though there is a good chance that it will be stuffed with lobster). With its pane-glass windows and exposed-beam ceilings the setting is both romantic and unintimidating—to up the wooing factor, spring for a bottle from the excellent wine list.
Moby Dick’s Restaurant

3225 Rte. 6, Wellfleet | 508.349.9795

Just-caught seafood is Cape Cod’s claim to fame and if you’re only here for a few days, having a turkey sandwich for lunch just doesn’t feel right. Moby Dick’s, which has been family-operated since the 80’s, has the quaintness of a clam shack and the menu of a full-on restaurant, meaning that you can order an oyster platter, steamed lobster, and grilled fish in addition to the basics like chowder and fried clams. It’s also one of the few spots around with a respectable gluten-free offering.

Do

Chatham Lighthouse Beach

While you really can’t go wrong with any of the beaches along either Cape Cod Bay or the Atlantic Ocean side, this particular one, at the foot of a historic lighthouse, is unique in that you can swim (or wade) out to a beautiful sandbar where locals like to set out picnics and barbecues. While the surf can be too intense for the littles to handle on certain days, the beach is great for long seal-spotting strolls and shell-collecting expeditions. Fair warning: parking can be a pain, so consider biking.

Photo: Flickr
Lighthouse Mini Road Trip

Starting at Chatham and driving up the cape to the Easternmost tip of Provincetown—and stopping at the historic lighthouses along the way—is an iconic New England experience. While some are closed to the public, many will have staff on hand to share historically significant tidbits and even take you for a look inside. Best of all, there’s no need to pack a lunch: Each town you’ll pass will have plenty of can’t-go-wrong seafood shacks to choose from, where you can also always find the requisite soft-serve.

Packing List

Santa Barbara

At a little under two hours outside of L.A., Santa Barbara’s beachside perch and breathtaking mountain backdrop make it an easy choice for the kind of long weekend that calls for both relaxing and exploring. Although it’s a small city—and therefore, very easy to navigate—every element of an ideal summer getaway is well represented, starting with a classically West Coast beach and ending with really stunning vineyards.

Stay

San Ysidro Ranch

900 San Ysidro Ln., Montecito | 805.565.1700

Inarguably, this is one of our favorite hotels in the world. Set against the Santa Ynez Mountains, on an olive and lavender tree-studded estate that was originally built as a citrus farm in the 19th-century, you’ll find 41 secluded bungalows. Each cottage comes equipped with a fireplace, private patio (many have outdoor hot tubs and rain showers), and wonderful extras, like heated bathroom floors. It is definitely romantic (i.e., leave your four kiddos at home).
The Biltmore Santa Barbara

1260 Channel Dr., Montecito | 805.969.2261

The oceanside Four Seasons in Santa Barbara is every bit as gorgeous as you’d want it to be. Their signature pool, over 160 feet long, overlooks the Pacific Ocean, and is surrounded by 31 private cabanas, which you can rent for a day of total, semi-secluded relaxation. Also on the main deck: a wading pool for the kids. Although you may feel like you’re at a remote resort, the Biltmore is still close to downtown—so it’s easy to head there for a dinner out. And Montecito’s main drag is just a few blocks away.

Shop

Upstairs at Pierre Lafond

516 San Ysidro Rd., Montecito | 805.565.1503

A rambling warren of rooms devoted to everything from coffee table books, to Mini Rodini onesies, to Il Bisonte wallets and Paul Smith socks—this is one of those spots where you can easily (and happily) pass the better part of an hour, and emerge with about 80 potential gifts.
Jenni Kayne

525 San Ysidro Rd., Montecito | 805.309.0560

If you only go to one shop while in the area, make it Jenni Kayne’s beautiful Montecito outpost for home and kids, which feels like an adorable little house with soaring ceilings and rustic, whitewashed decor. The offering is classic Jenni Kayne: completely timeless and entirely effortless. She also has a women’s boutique in the same complex.

Eat

Finch & Fork

31 W. Carrillo St., Santa Barbara | 805.879.9100

Fresh, California cuisine meets American classics at Finch and Fork, where the dishes are prepared simply (think only a few select ingredients each) to perfection. There are different daily specials (i.e. burger and beer, pork and cork) and just-caught seafood on the menu. Although the brunch line-up is particularly awesome, this is a solid choice for any mealtime.
The Lark

131 Anacapa St., Santa Barbara | 805.284.0370

Tucked inside the beloved Santa Barbara Fish Market, this indoor-outdoor restaurant is named after the overnight train that’s serviced this part of California for the first half of the last century (which also explains the vintage train booths). As evidenced by the generous portions of comfort food staples like deviled eggs, roasted chicken, and ribs (all locally sourced, all delicious), the menu is designed to encourage sharing.

Do

Santa Barbara Museum of Art

1130 State St., Santa Barbara | 805.963.4364

Santa Barbara is a hotbed of creatives, and so it’s no surprise that the Santa Barbara Museum of Art has a deep and wonderful collection: Established in 1941, they have everything from Chagalls and Kandinskys to Rauschenbergs and Monets. Which is all a backdrop to their lineup of excellent lectures, exhibits, and events, as well as lots of activities geared towards kids.
Stolpman Vineyards

2434 Alamo Pintado Ave., Los Olivos | 805.688.0400

Tucked away on an outcropping of limestone, this family-owned vineyard focuses on Syrah and Roussanne grapes, which they tend through sustainable and natural dry farming techniques. They take just as much care post harvest, using native fermentation techniques whenever possible. If you can, book a private tour of the vineyard—incredible—or, next best thing, visit one of their tasting rooms (in Los Olivos and Lompoc).