Nantucket Memorial Day Weekend Getaway

If you are looking for a surfing or sailing trip, summer wedding destination, beach getaway, or a visit to a historical town, the island of Nantucket is for you. Let’s not forget about beach hikes, lobster rolls, clam “chowdah,” and rows upon rows of beautiful, quaint, gray-shingled buildings. Did I mention that there are no traffic lights, fast-food restaurants, or big-box stores on the entire island?

Nantucket Logistics:

Depending on where you are coming from, there are several ways to get there:

1. Seasonal flights directly into Nantucket (ACK) (a must for fans of the 90’s sitcom Wings!)
2. Arrange transportation from the Boston Logan International Airport or the T.F. Green International Airport in Providence, RI to one of two available ferries out of Hyannis, MA.
3. Steamship Authority
4. Hyline Cruises

First, note that Hyannis, MA is 70 miles from Boston and 79 miles from Providence, RI, so you will need to arrange transportation to and from the airport.

Secondly, if you are bringing a car onto the island, just know that it’s expensive and car reservations book up by spring. The 2-hr Steamship Authority Ferry is the only ferry that transports cars.

Both Steamship Authority and Hyline Cruises offer 1-hour passenger service, but the high-speed Hyline ferry is routinely said to be the best option by everyone we spoke with from hotel managers to cottage owners. I found it to be a smooth ride even in rough seas, and it gets you to your destination in 1 hour.

There are several ways to get from Boston and Providence to Hyannis:

1. Rent a 1-way drop-off and pick-up car (Avis/Budget for Steamship or Thrifty Rent-A-Car for Hyline)
2. Try the seasonal CapeFlyer train connection
3. Hire a driver. We used Boston Executive Limo Services to arrange for pick-up in a suburban. Elite Car Services is another option.

Getting around on the Island:

While cars are allowed on Nantucket, it’s easy to get around on foot and bike or via shuttle, taxi, or ride-share. Easy Rider is my recommendation for bike rentals. They will deliver and pick up your bikes.

Nantucket is small and parking is limited. Walking, shuttles, and bikes are the recommended forms of transportation. That being said, while it was easy for us to walk into town or to Steps Beach from our Pilgrim Road cottage, several of our destinations required taxis. Maybe if the shuttles were running during our visit, it wouldn’t have been an issue. Most shuttles, including the airport shuttles, run approximately every 30 minutes for most of the season; from July until Labor Day, the Mid-Island Loop runs every 15 minutes, and the Miacomet Loop every 20 minutes. In hindsight, I think we would have benefited from renting a car. Nantucket Island Rent A Car came highly recommended.

Lodging:

1. Pilgrim’s Bliss House is a great spot for a generational trip. This was our lodging of choice. The location is within walking distance from Main Street, Steps Beach, and Jetties Beach. It is located in Cliff’s Neighborhood, one of the most sought-after neighborhoods because of its walkability to several prominent areas on the island.
2. Whale Watch is an ocean-front residential property on Nantucket that is famous for hosting weddings and large family gatherings. It is located in the secluded Tom Nevers neighborhood.
3. VRBO specializes in Nantucket rentals all over the island.
4. In-town hotels: The Nantucket Hotel and White Elephant.
5. The Wauwinet Hotel is located on the northeast end of the island and is Nantucket’s only Relais and Chateaux hotel. It’s an adults-only hotel and a 25-minute shuttle ride into town.
6. Cliffside Beach Club is the only lodging located directly on the beach. Cliffside is luxury lodging with limited availability (23 rooms).

Available Water Activities:

Please note that while the summer season starts Memorial Day weekend, the high season goes from the summer solstice to Labor Day weekend. Not all activities were available during our most recent Memorial Day weekend visit. It’s important to stay current on what’s open before visiting if certain activities are a must for you!

1. Surfing: With over 80 miles of beach on this little island, there are lots of surfing options (if you can handle the cold water!) We tried and loved the Nantucket Surf School owned by Gary Kohner. He opened the first Nantucket surf school and has grown the sport tremendously in the area. Sandbar surfing makes for a gentler experience compared to reef surfing. Your feet will thank you! We surfed on Cisco Beach. Although we never made it to Surfside Beach, we heard it was also great for surfing. Both beaches have food trucks during the high season for food and drinks.
2.  Critter Cruise: Off of Straight Wharf, families can board a one-hour Critter Cruise that travels a bit offshore to allow kids to fish, catch and handle crabs and lobsters, and take in harbor views.
3. Watch or partake in sailing races: The official beginning of Nantucket’s summer is typically heralded by the Figawi sailboat race on Memorial Day weekend.
4. Nantucket Community Sailing School: Group and private classes available for all levels. We regret this was not available during our stay. This year, programs do not open until Monday, June 27th.
5.  Sea Nantucket Paddle Sports: Kayak or SUP around the harbor. There are a few spits of beach that you can paddle up to for some good old-fashioned seashell hunting.
6. Fishing and whale watching charters: Looking at you, Shearwater Excursions, Sports Fishing ACK, and Bill Fisher Outfitters.

Available Land Activities:

1. Whaling Museum: I know it sounds boring, but it has received lots of recognition and positive reviews. The staff consisted of some great storytellers and the history of the island is fascinating. You also learn the background behind the names of many of the restaurants and roads. Great for history lovers.
2. Maria Mitchell Aquarium: Visit sharks, jellies, and other sea creatures here. You’ll see Maria Mitchell’s name all over the island; the scientist was a Nantucket native. Unfortunately, the aquarium was not open during our visit.
3. Dreamland Theater: Great for a rainy day. We all loved watching the new Top Gun movie, but we were sad to miss Daniel Tosh’s performance.
4. Bike and hike Nantucket: Nantucket has many beautiful miles of walking and biking trails.
5. Beach walks: We loved walking Steps and Jetties Beach. Although we frequented these beaches for logistical reasons (walking distance from our lodging), there are other great beaches.
6. Nantucket Ice Community Rink: year-round ice skating!

Nantucket Restaurants:

We found out the hard way that while high season doesn’t start until late June, Memorial Day weekend is a rowdy party weekend. But then, strangely, things slow down for a few weeks afterward. Plan accordingly: dinner reservations are encouraged where accepted. For example, we hit up Sandbar the Friday of Memorial Day weekend, and it was wonderful with a family-friendly vibe. Saturday and Sunday were different stories, with lots of inebriated patrons, a full bar, and music so loud that it wasn’t appealing to eat there. By Monday, the partiers had gone home and Sandbar was back to being one of our favorite restaurants.

The Restaurants we checked out in no particular order:

1. Sandbar at Jetties Beach: Quintessential beachfront restaurant with a great atmosphere and casual seafood menu.
2. The Galley: Beachfront restaurant with an upscale vibe. 2 course set menu. Not kid-friendly.
3. Millie’s Restaurant: Laid-back Tex-Mex and seafood specialist with Baja-style eats such as fish tacos, plus a patio and take-out window. About five miles west of town, Madaket Millie’s is a perfect place for family dinner, with yummy Mexican food, a grassy space to run around in, and even a few Shut the Box game boards (an island favorite) to entertain your group while you wait for food. An added bonus…there’s an ice cream stand at Millie’s Market for dessert.
4. Island Kitchen Nantucket: Fantastic breakfast/brunch spot. A focused menu of fresh, upscale American fare. Great atmosphere with inside and outside seating.  It’s right across from the local grocery store if you want to knock out some shopping post-meal.
5. Brant Point Grill (located inside the White Elephant Hotel): Select a table overlooking the harbor and indulge in succulent seafood, steaks, and choice selections. If you have a wait, let your tweens/teens run over to Children’s Beach and throw a ball around.
6. Bartlett’s Farm: Pick up groceries or enjoy lunch at this charming farm. While they sell wine and beer, you may not consume alcohol on their premises.
7. Cisco Brewers: A super place to unwind and listen to live music after a long beach day, Cisco Brewers is a magnet for families. Mom and dad can sample some brews, kids can get dinner and treats from food trucks, and everyone can enjoy live music with Bartlett’s Farm and wildflowers as a backdrop.
8. Lola 41: Great spot for a trendy crowd, and teen-approved per our cottage owner.
9. The Tavern and Gazebo: Great laidback lunch and happy hour spot if you are downtown by the wharf.

In Summary:

There is always something to do during Nantucket summers, so put on your Nantucket Reds (yes, it’s a thing) and be sure to check out this beautiful island. It is not to be missed. For those of you (like me) who are traveling from locales further south, it’s important to remember that the summer days in Nantucket are LONG! Our first morning there, we were surprised to wake up at 5:40am with the sun streaming in through the window. Pack an eye shade just in case the curtains in your room don’t completely block out the sunlight.

I will most fondly remember our long beach walks, our first cold water surf, the top-notch art galleries, and the abundance of great restaurants. I would love to come back in high season to give sailing a try and possibly extend my trip and check out some of the surrounding areas like Boston, Newport, or Martha’s Vineyard.